Читать книгу Rising Star: The Making of Barack Obama - David Garrow J. - Страница 11

Back in Chicago, Obama continued his almost weekly discussions with Greg Galluzzo, who told numerous organizing colleagues that Barack was “really special.” But even though Greg spent more time with him than any other person in Barack’s workday world, he knew almost nothing of Barack’s home life, and he met Sheila Jager only once in passing.

The young couple’s first nine months of living together had melded two intensely busy lives into an increasingly cloistered relationship where Sheila saw almost no one from Barack’s day job, and Asif was their only regular contact in Hyde Park’s graduate student community. Barack’s heavy smoking was a regular topic of comment within DCP, and Reformation Lutheran pastor Tyrone Partee nicknamed him “Smokestack.” Sheila said that at home, “he actually introduced me to smoking, so we smoked like chimneys together.” She wanted a cat, and after Barack relented, “Max” joined their household and became a less-than-fully-welcome presence in Obama’s life. “He drove Barack crazy because the cat would always pee” in their one large houseplant.

Sheila recalls the early months of 1987 as a time when she witnessed a profound self-transformation in Barack. “He was actually quite ordinary when I met him, although I always felt there was something quite special about him even during our earliest months, but he became someone quite extraordinary … and so very ambitious, and this happened over the course of a few months. I remember very clearly when this transformation happened, and I remember very specifically that by 1987, about a year into our relationship, he already had his sights on becoming president.”

This change in Barack encompassed two interwoven themes: a belief that he had a “calling,” coupled with a heightened awareness that to pursue it he had to fully identify as African American. The “ ‘calling’ had more to do with developing a sense of purpose in the world,” Sheila later explained, and even two years earlier, Genevieve Cook had sensed an incipient presence of the same thing. She remembered thinking that “all along he had some notion of testing his own mettle and potential for greatness, and that it was as much about that personal journey as it was finding the best way to effect the maximum positive social change. Those two aspirations, the personal and the heroic,” were “melded from very early on.” Yet by early summer 1987, Barack’s understanding of his “calling” was as “something he felt he really had no control over; it was his destiny,” Sheila explained. “He always said this was destiny.”

By then, Barack had gotten to know Al Raby and John McKnight, whose political roots lay in the civil rights struggles of the 1960s, and he had a relationship with Jeremiah Wright, whose theology sprang from that same soil. Barack had also developed an acquaintance with Emil Jones, a savvy politician, and he had witnessed at close range the charm and aura Harold Washington possessed even in a nondescript storefront. But as Sheila experienced and reflected upon what occurred, she realized the stimulus for Barack’s transformation lay not in one or another precinct of black Chicago, but in the disparaging evaluation he had received from her father back at Christmas. “After that visit, and over the course of spring ’87, he changed—brooding, quiet, distant—and it was only then, as I recall, that he began to talk about going into politics and race became a big issue between us.” Once “we got back from California,” Barack “became very introspective and quiet,” Sheila recalled. “I remember very specifically that it was then he began to talk about entering politics and his presidential ambitions and conflicts about our worlds being too far apart.”

Meanwhile, “the marriage discussion dragged on and on,” but it was affected by what Sheila describes as Barack’s “torment over this central issue of his life,” the question of his own “race and identity.” The “resolution of his ‘black’ identity was directly linked to his decision to pursue a political career,” and to the crystallization of the “drive and desire to become the most powerful person in the world.”

Eight years later, Obama would say that through organizing “I think I really grew into myself in terms of my identity,” and that his community work “represented the best of my legacy as an African American.” It had allowed him to feel that his “own life would be vindicated in some fashion,” and his immersion in black Chicago gave him “a sense of self-understanding and empowerment and connection.” Obama’s daily experiences on the Far South Side had reshaped him. “I came home in Chicago. I began to see my identity and my individual struggles were one with the struggles that folks face in Chicago. My identity problems began to mesh once I started working on behalf of something larger than myself.” He also explained that organizing had “rooted me in a specific community of African Americans whose values and stories I soaked up and found an affinity with.” And most specifically, “by the second year,” he told one interviewer, “I just really felt deeply connected to those people that I was working with.”

Sheila was convinced that “something fundamentally changed” inside Barack during the first half of 1987 that had transformed him into a “powerfully ambitious person” right before her eyes. “We lived so cut off from everyone else” that no one else was privy to her perspective, and Barack’s ability to “compartmentalize his work and home life, to the extent that the two worlds were never brought together physically” or in any social setting, meant that their increasingly stressed and intense relationship existed as “an island unto ourselves.”

In later years, Obama once said that his experiences in Chicago had “converged to give me a sense of strength.” At an expressly religious event, he cited Roseland as where “I first heard God’s spirit beckon me. It was there that I felt called to a higher purpose.” Sheila caviled at that, saying she “would not call him religious. Perhaps spiritual is a better description” of the man she lived with. “Barack was definitely not religious in the conventional sense. He talked about God in the abstract, but it was mostly in terms of his destiny and/or some spiritual force.”

Early in the summer, Barack’s older brother Roy visited Chicago and met Sheila briefly, but Barack went alone to the Chicago home of his maternal uncle Charles Payne for his nephew Richard’s high school graduation. His sister Maya had just completed her junior year at Punahou, and she wanted to visit a number of mainland colleges before submitting her applications. Ann Dunham was attending the Southeast Asian Summer Studies Institute being held at Northern Illinois University, west of Chicago in DeKalb, so she and Maya arrived in Chicago before Sheila left to see her parents in California and make a brief initial research trip to South Korea.

This was the first time Barack and Ann had seen each other in eighteen months, and Ann had gained a tremendous amount of weight and now seemed “very matronly.” She had not made much headway on her Ph.D. dissertation, in part because she had spent half of 1986 in the Punjab, working as a consultant for the Agricultural Development Bank of Pakistan. But her analysis was coming together, and one of her closest academic colleagues described her conclusions in words that echoed what her son had learned from John McKnight. “Anti-poverty programs … only reinforce the power of elites” and “it is resources and not motivation that poor villagers lack,” in Indonesia as elsewhere. Once Ann’s summer institute was complete, she would return to Pakistan for three more months of work. Barack’s close friend Asif Agha recalled playing volleyball out at Indiana Dunes during Maya’s visit, and Jerry Kellman remembers Barack bringing Maya along to a barbecue at Jerry’s home. During this trip, Maya wanted to see the campuses of the University of Michigan and the University of Wisconsin, where Asif spent much of the summer studying Tibetan.

Early in the summer Barack decided that he and Sheila should acquire a new Macintosh SE computer, which had debuted just three months earlier. “It was the latest model and very fancy,” Sheila remembered, and as with their rent, Barack happily footed the bill. “Barack said we both needed it,” and they each used it a lot, but when it first arrived, Barack had no idea how to operate the mouse. A call to Asif resulted in the dispatch of Asif’s other best friend, Doug Glick, a fellow linguistic anthropology graduate student who quickly showed Barack that you do not hold the mouse up in the air.

By the end of June, with Sheila away from Chicago and Asif up in Madison, Barack and Doug on several weekends made the three-hour drive up to where Asif was housesitting in some Wisconsin professor’s lakefront home. Obama years later would publicly joke that he had had “some fun times, which I can’t discuss in detail,” on those visits and “some good memories,” but Glick clearly remembered the long drives in Barack’s noisy Honda. Barack was “just a regular guy,” an “incredibly friendly guy” with “a great sense of humor.” During the road trips, Barack talked “about wanting to write the great American novel…. I spent an awful lot of time in the car with him. These are long drives, he can talk,” and “he doesn’t shut up.” At least once Obama mentioned an interest in law school, but he rarely talked about his DCP work. “I never heard him talking about community work and public service as the driving force of who he was.” Sometimes “I’m making fun of him,” asking, “ ‘If I whisper “shut up,” will you hear it with those ears?’ ” But Barack clearly had “tremendous intelligence, tremendous charisma,” and indeed “a certain kind of aura to him,” Glick thought. Doug, like Asif, felt that “Barack is not that black,” but it also seemed as if “he was ideologically loaded a little.”

During one drive, Glick recounted, “we had a god moment. The strangest thing that has ever happened to me in my life happened with him.” Every trip included a pit stop to get gas and pick up something to drink, and on one occasion Barack was “sitting in the car in the driver’s seat” with the window open as Doug returned carrying snacks and bottles. “I tripped. The Snapple goes flying…. We both watch as it hits the ground, breaks like an egg, goes up through the air, goes through the window and both of the things land on his legs face up.” Yet somehow Obama was completely dry. “We’re never going to forget that,” Barack said to Doug. “Religions start at moments like that.”⁵²

In Chicago, the battling intensified over the Southeast Side landfills and their toxic impact on nearby residents. The Sun-Times published a six-part, front-page series of stories titled “Our Toxic Trap” which focused on CID, the Metropolitan Sanitary District’s (MSD) “shit farm” just north of Altgeld Gardens, and older, more mysterious dumps like the Paxton Landfill. Hazel Johnson was quoted on the “nauseating stench” of sewage sludge permeating Altgeld and said, “it smells just like dead bodies.” In response, the state legislature created a special joint committee to investigate the problems, and the MSD’s board pledged its own study after an angry public meeting during which Johnson called one African American MSD commissioner an “Uncle Tom.” After a large illegal dump was discovered in a remote corner of Auburn Gresham, four city sanitation workers who were excavating the waste for transfer were “overcome by noxious garbage fumes” and hospitalized.

On June 30, WMI’s Mary Ryan proposed to Chicago’s city council that if the city would set aside its existing moratorium on landfill growth, WMI would move forward with an “economic and community development assistance program” that could be a huge “ ‘catalyst’ toward revitalizing” the entire Southeast Side. But Ryan’s proposal only intensified the fury of local activists like Marian Byrnes, Vi Czachorski, and Hazel Johnson over a possible deal between the city and WMI to expand landfill capacity. “Perhaps Washington is Vrdolyak in disguise on dump issues,” James Landing, the chairman of the Lake Calumet Study Committee (LCSC), told his fellow allies.

With a new and energetic Chicago chapter of the international environmental group Greenpeace eagerly joining in, Southeast Side activists prepared for a July 29 blockade of all dumping at CID. A large rally drew media coverage, and a dozen or more Greenpeace members and local activists would chain themselves together to CID’s entrance gate to block waste trucks from entering the landfill. By the morning of the twenty-ninth, DCP’s Dan Lee, Cathy Askew, Margaret Bagby, Loretta Augustine, Betty Garrett, and Obama joined the protesters. Cathy recalled years later, “He led that. He led that in the background. He had to be there to bail them out.”

The day was “beastly hot,” one young Greenpeace member remembered, and “wearing a media-friendly buttoned-down shirt” became a sweaty mistake. But the blockade was a grand success. The Daily Calumet reported that a crowd of 150 people gathered and said it was “the largest environmental protest in years.” As many as a hundred waste trucks were backed up on the nearby expressway and unable to enter CID, as protesters chanted, “Take it back!” They blocked the entry gate from 10:00 A.M. until midafternoon. One photo caption said: “Wearing a gas mask, Deacon Daniel Lee of the Developing Communities Project … makes a point about odors and toxic wastes.”

Some reporters lost interest as the day dragged on, and the next morning’s Sun-Times erroneously reported that “there were no arrests.” Leonard Lamkin, an East Side activist who joined the chain-in, said that “when the media went away, that’s when they made the arrests.” Hazel Johnson and Marian Byrnes were among the sixteen participants taken into custody, and the women remained jailed for six hours even though the men were released in less than two. Scott Sederstrom, the young, overdressed Greenpeacer, thought “it was almost an act of mercy by the Chicago police to take us into their air-conditioned precinct house for booking…. The Cubs game was on TV in the station” and comments about baseball leavened the fingerprinting process. “As a further act of generosity, they let me stay in the air-conditioned area watching a little more of the game” instead of moving Sederstrom to a holding cell. Given the Cubs’ all-too-typical performance, though—they were trailing 10–0 by the seventh-inning stretch—interest in the game understandably waned. Weeks later the charges were dropped against defendants who agreed not to enter any WMI properties for one year.⁵³

Before the summer ended, Hazel Johnson and Marian Byrnes staged three more protests near the CID entrance, taking care not to get arrested. They also testified before the special joint legislative committee, chaired by Emil Jones. Assisting Hazel was a thirty-five-year-old black man who had just returned to Chicago after working toward a master’s degree at Harvard University’s Kennedy School of Government and who had earlier won a Rhodes Scholarship to attend Oxford University in England. Like Jones, Melvin J. “Mel” Reynolds was eyeing a challenge against incumbent U.S. congressman Gus Savage in the spring 1988 Democratic primary, and both men—like Savage—were eager to raise their profiles among district residents angry over authorities’ inability to take meaningful action against the Southeast Side’s multiple toxic threats.

Several months earlier, Harold Washington had elevated Howard Stanback to an influential post as his assistant in charge of the city’s infrastructure. An African American economist, Stanback had taught at New York’s New School for Social Research until he came to Chicago as Maria Cerda’s deputy at MOET. His new appointment made him the mayor’s primary adviser on Chicago’s landfill crisis, and in late summer 1987, Stanback gave Washington a memo that laid out the city’s options. Chicago had done “very little towards developing and implementing alternatives to dumping,” making the city almost completely dependent on landfill availability. The only solution was “the O’Brien Locks property currently owned by the Metropolitan Sanitary District,” but using that property would mean lifting the moratorium and incurring a huge uproar from Southeast Chicago.

Stanback gave the mayor two options for how to proceed. One would be to convey the land to WMI, to whom “the site is probably worth $1 billion,” and in order “to neutralize opposition to lifting the moratorium,” WMI would contribute sufficient funds to the surrounding neighborhoods, just as Mary Ryan’s outreach efforts envisioned. Stanback believed that this could succeed, even with WMI’s “negative image,” and that this was superior to the second option, which would involve the city itself operating a landfill on the O’Brien Locks property. Stanback believed political opposition would be higher to this scenario because it would not include WMI’s contributing to community revitalization projects. “Operating a landfill is not a business the City should enter,” Stanback recommended.

One Saturday, Stanback drove to South Chicago to meet Bruce Orenstein at UNO’s East 91st Street office. Also there that morning was DCP’s Barack Obama, whom Bruce had asked to join them. Stanback described the city’s thinking regarding the landfill and WMI’s proposal, but he also explained that Washington wanted to be sure that WMI’s big gift would not be controlled by the Southeast Side’s traditional power brokers, particularly South Chicago Savings Bank president James A. Fitch, a longtime backer of mayoral rival Ed Vrdolyak and the dominant figure in the four-year-old Southeast Chicago Development Commission (SEDCOM). If a deal could be cut with WMI, the mayor wanted his allies—such as UNO, with whom Washington had worked in close alliance for four years—to take charge of the windfall.

“Barack in particular, his eyes got so bright,” Stanback remembered. “He said, ‘This can be one of the biggest community development coups of all time.’ I said, ‘You’re right,’ ” but UNO at present had no development capacity. “We agreed that nothing was going to happen anytime soon,” Stanback recalled, but “we agreed in principle” that UNO, DCP, and the city would closely coordinate as discussions moved forward. When Fitch then wrote to another Washington aide, budget director Sharon Gist Gilliam, to initiate a discussion of lifting the moratorium to allow for WMI’s use of the O’Brien parcel, Gilliam waited twelve days before sending Fitch a cold, rude reply stating that she had given his letter to Stanback.⁵⁴

For Obama, the late summer of 1987 was a busy and intense time. Throughout July, his hourly consultations with Greg Galluzzo were more than weekly, but from August forward the two men met only twice monthly, as Greg began having ninety-minute or longer sessions with Johnnie Owens almost weekly. One weekend, Barack met Ann and Maya in New York, where Maya was looking at Barnard College and Ann was visiting friends before returning to Pakistan via London. A rooftop photograph shows Ann and Barack with several of her anthropologist friends, including Tim Jessup, who had first met Barack in Jakarta four years earlier and had seen him again in Brooklyn in 1985 with Genevieve. Barack stayed with Hasan and Raazia Chandoo in Brooklyn Heights, playing basketball nearby with Hasan and walking across the Brooklyn Bridge into Manhattan.

Hasan recalled that “by that time he knows for sure he wants to be a political person,” and Beenu Mahmood, then a lawyer in Sidley & Austin’s New York office, remembered the visit similarly. “By that time he was very clear that he was going into politics” and “it was very clear that law would be the vehicle for getting into politics for him.” Several nights Raazia cooked dinner, but one thing had most definitely changed: by 1987 Barack never again “partied” as he had so many times in 1984 and 1985. Hasan recalled Barack mentioning how brutally cold Chicago winters were and also remembers him describing the time he and Johnnie had to duck behind a car when they heard gunfire nearby in Palmer Park. Raazia, five years younger, found “Barack a little bit arrogant”—just “intellectually arrogant,” Hasan interjected—“so I didn’t want much to do with him.”

Obama was back in Chicago by the end of the second week in August, and he may or may not have seen a prominent headline in the Defender that would have reminded him of an influential relationship from earlier in his life: “Frank Davis Dead at 81.” During Sheila’s midsummer visit home, she told her mother much of what Barack had said to her in recent months, and Shinko Jager in turn recounted Sheila’s comments to Mike Dees, the family’s closest friend, who had met Barack months earlier during the Christmas holiday. Barack’s marriage proposal still loomed, and “if Sheila went with Barack, she would have to follow his lead. He wanted to be president.” Shinko remained opposed to the marriage, “but she never gave a reason,” Mike recounted. “I was against it because I thought they were two ambitious people, and I knew they wanted their own separate careers, and he was talking about being president, which I thought was a little strange” for a twenty-five-year-old community organizer. But there was also something more, something Barack had begun to articulate to Sheila. “There was a problem there,” Mike recalled. “He was concerned if he was going to take the steps to the presidency with a white wife.”

One August Friday, Sheila joined Barack for the trip to Asif’s summer house in Madison. Sheila was “very quiet” and slept in the back of the car most of the drive, but an unusual tension was present. By Saturday morning, the problem broke into the open, and Barack and Sheila kept pretty much to themselves upstairs. But according to someone there that weekend, “it’s the summer … these houses are old. You’d die if you closed windows. Everything is open.” From morning onward “they went back and forth, having sex, screaming yelling, having sex, screaming yelling.” It continued all day. “That whole afternoon they went back and forth between having sex and fighting.”

Others remember “moving around to the other side of the porch just to be able to talk.” It “was a long weekend” and “an incredibly unpleasant one,” one person recalled. “It was so stressed and tense.” Barack tried “to be more social about it,” and “they came down a few times to grab a beer, to eat,” but “then they went back up to scream or fight.” Sheila was “a very sweet person … very mild-mannered,” and “certainly exotic” in her looks, but “shy and withdrawn” that “extremely emotional” weekend.

“They called truces here and there, but it kept popping back up” that Saturday afternoon, as “she screamed and they fought.” Sheila’s voice came through loud and clear: “That’s wrong! That’s wrong! That’s not a reason,” she was heard saying. As the others talked quietly, the explanation of what they were hearing was shared: Barack’s political destiny meant that he and Sheila could not have a long-term future together, no matter how deeply they loved each other. But she refused to accept his rationale: “the fact that it was her race.” It was clear—audibly clear—that “she was unbelievably in love with him,” that “the sex for her was the way to bring it back.” Barack “was very drawn to her, they were very close,” yet he felt trapped between the woman he loved and the destiny he knew was his. According to one friend, Barack “wasn’t black enough to pull that off and to rise up” with a white wife.

Sunday afternoon Barack drove them south to Chicago, with Sheila again napping in the back seat. “Thank god it’s a crappy car that made a lot of noise!” A quarter century later, Sheila had almost no recollection of going with Barack to Madison, but she unhesitatingly characterized their relationship as “a very tumultuous love affair.” No matter how others saw Obama, “the Barack I knew was not emotionally detached, in control, and cool,” she stressed. Instead, Barack was “a very passionate, sentimental” and “deeply emotional person,” indeed “the most overwhelmingly passionate and caring person I ever knew.”

In Barack’s workday world, Cathy Askew, the white single mother of two half-black daughters, witnessed most starkly Barack’s newly articulated racial identity. With a new school year about to begin, Cathy told Barack about what she considered a perplexing and offensive racial conundrum: although the Chicago Board of Health said her daughters were black, their school in West Pullman wanted to count them as white. Cathy rejected this binary view of racial identity—“50-50 is a good term”—and expected biracial Barack to agree. She was astounded when he rejected any middle ground, especially since he had spent most of his childhood in a predominantly “hapa” world. But he did. “He said, ‘Well, there comes a time when you have to pick a side, you have to choose a side,’ ” Cathy remembered him saying. And Barack repeated it: “You have to choose.”

More than a decade later, Barack again gave voice to the sentiment he had expressed to Cathy. “For persons of mixed race to spend a lot of time insisting on their mixed race status touches on a fear” that a darker complexion is innately inferior to a lighter one, and too many nonwhite people are “color-struck…. There’s a history among African Americans … that somehow if you’re whitened a little bit that somehow makes you better, and that’s always been a distasteful notion to me,” perhaps ever since seeing that magazine story one day in Jakarta. “To me, defining myself as African American already acknowledges my hybrid status,” and “I don’t have to go around advertising that I’m of mixed race to acknowledge those aspects of myself that are European … they’re already self-apparent, and they’re in the definition of me being a black American.” Any other mind-set intimated racism. “I’m suspicious of … attitudes that would deny our blackness.”⁵⁵

Fred Hess knew well ahead of time that September 1987 would witness a train wreck of historic proportions for Chicago Public Schools. The board of education needed to negotiate new contracts with multiple unions, most important the Chicago Teachers Union (CTU), and in midsummer, Hess had told the board that it could afford to offer a pay increase of 3.5 percent to teachers. Instead, the board announced a three-day reduction in the upcoming school year, thereby cutting teachers’ pay by 1.7 percent. The CTU demanded a 10 percent salary increase, and Superintendent Manford Byrd asserted that CPS could afford no raise at all. Hess labeled that claim “a bunch of bull,” and on September 4, four days before schools were to open, more than 90 percent of CTU members voted to strike.

The strike began on September 8, with Hess warning the Sun-Times that “it’s going to be a long strike because it looks like it has turned into a question of principle,” especially for Byrd. In a subsequent op-ed in the Tribune, Hess denounced “an administration that insists on adding central office administrators while cutting other employees’ salaries.” More than 430,000 students were out of school, and on September 11 a large group of parents and students from sixteen community groups picketed CPS headquarters, with the group’s spokesman, Sokoni Karanja, telling the news media that “our children are victims of a school system that is failing to educate them.”

Karanja was a forty-seven-year-old African American native of Topeka, Kansas, who had earned a Ph.D. from Brandeis University in 1971 before moving to Chicago’s historic Bronzeville neighborhood, joining Trinity UCC, and founding a family-aid organization he christened the Centers for New Horizons. Nine months earlier, Karanja had become the Woods Fund’s first black board member, but this September 11 was significant because it illuminated the deepest social and political chasm in black Chicago: African American families with children in heavily minority public schools were fighting against a system made up of 41.6 percent black administrators and 47 percent black teachers.

Those numbers explained why Harold Washington had been so ambivalent four months earlier when he seemingly embraced school reform. The city’s public schools provided middle-class salaries and middle-class status to thousands of black Chicago families, while at the same time they were shortchanging tens of thousands of black students. The human toll was staggering: more than 40 percent of African American men in Chicago in their early twenties and 35 percent of young African American women were unemployed, many of them lacking basic job skills because the CPS had not offered them real schooling.

“Our education system is in shambles,” Rob Mier, Washington’s economic development commissioner, publicly acknowledged. “We’re producing a legion of functional illiterates.” Some critics described “a vicious circle of incompetence,” with CPS hiring teachers who had graduated from weak nearby state universities, which enrolled mainly ill-prepared graduates of Chicago high schools. As Fred Hess kept emphasizing, the abysmal state of public education in Chicago was the result not of a lack of resources, but instead of their dramatic misallocation: during the 1980s, “the number of central office administrators rose by 29 percent while the number of staff members in the schools rose by 2 percent.” By 1987, CPS’s central bureaucracy had reached an astonishing thirteen thousand employees.

On Thursday, September 17, two hundred angry parents picketed outside Harold Washington’s Hyde Park apartment building while others targeted the homes of Governor Jim Thompson, new board of education president Frank Gardner, and CTU president Jacqueline Vaughn. The next morning more than a thousand parents and children picketed outside CPS headquarters, but as the strike moved into its third week, neither the board nor the union were showing any signs of compromise. Superintendent Manford Byrd, furious at Fred Hess’s disparagement of CPS’s central administration, wrote his own op-ed for the Tribune, claiming that the system’s fundamental problem was “the extraordinary special needs of most Chicago public school students.”

That remarkable assertion—a school superintendent labeling the majority of his system’s children as “special needs” students—laid bare the deep class divide within black Chicago between middle-class professionals and “those people.” As Hess later explained, again echoing John McKnight’s analysis, Byrd’s explicit articulation of a “deficit model of ‘at-risk’ ” children revealed the attitudes of administrators “whose jobs depend on the existence of a pool of ‘at-risk’ students as clients.” Unable to see that students might bring strengths to school, CPS bureaucrats could not imagine that Chicago’s schools, “rather than the students themselves, might be to blame for students’ lack of success,” Hess explained. Only by reallocating power from CPS headquarters to local schools so as to “reemphasize local communities rather than large, hierarchical bureaucracies” could meaningful educational improvement be attained.

While most parents and community groups were angry with the CTU as well as the board, UNO simply backed the teachers’ demands. As the strike entered its third week, the parents’ groups, with support from Anne Hallett at Wieboldt and input from Al Raby, came together as the People’s Coalition for Educational Reform (PCER). On Thursday, October 1, in what the Tribune called a “dramatic confrontation,” a predominantly black group of PCER representatives, many of whom were close allies of Harold Washington, told both the board and the CTU that a 3 percent raise must be agreed upon to end the strike. First the board, overruling Byrd, and then a reluctant CTU, bowed to the coalition’s demand, and on Saturday morning it was announced that schools would reopen on Monday. Nineteen days of classroom time had been lost in “the longest public employee strike in Illinois history.”

On Sunday, Harold Washington summoned Casey Banas, the Tribune’s education reporter, to his Hyde Park home. The mayor wanted everyone to know he understood the significance of the parents’ protests. “Never have I seen such tremendous anger and never have I seen a stronger commitment on the part of people” to make Chicago a better city. But Washington also did not want to alienate the black educators Manford Byrd represented. “There’s no discipline in many homes. There’s no stimulus in many homes. And even though the educational structure is a poor substitute to supply what the family is not supplying, it must be done,” the mayor declared. He said he would personally lead a new, far more inclusive iteration of his Education Summit to reform Chicago’s public schools. It would begin the next Sunday at the University of Illinois’s Chicago Circle campus (UICC). “We’re going to have a massive forum,” Washington promised.⁵⁶

Obama and DCP had remained entirely on the sidelines throughout the protests against the shutdown. On the Monday of the strike’s final week, and after three months of trying, Barack finally had an appointment with Harold Washington’s top policy adviser, Hal Baron, to pitch his Career Education Network plan to the mayor. It was entirely thanks to John McKnight that Baron consented to see Obama, despite education aide and Roseland native Joe Washington’s negative attitude. “I did it purely as a favor to John McKnight,” Baron recalled. “John was just so high on him…. I think John wanted me to get him a meeting with the mayor, but he pestered me and I finally did a meeting with him myself.” Joe Washington joined Baron in Hal’s City Hall office, but Barack’s presentation was anything but persuasive. Baron remembers it as “cocky standard Alinsky bullshit” and “very glib.” He also recalls Obama saying, “ ‘We’ve got Roseland organized.’ ” After Barack left empty-handed, Joe Washington told Baron what he thought: “That guy doesn’t know shit about Roseland.”

Far more fruitful for Obama was his relationship with John McKnight. Barack’s reactions to now two years of immersion in the macho, conflict-seeking world of Alinskyite organizing—including his first year with Jerry Kellman, dozens of hours with Greg Galluzzo, and his warm, almost brotherly relationship with fifteen-years-older Mike Kruglik—had drawn him toward McKnight’s alternative vision of human communities. At least twice Barack drove up to McKnight’s second home in Spring Green, Wisconsin, west of Madison, for weekend-long discussions. He was the only young organizer other than Bob Moriarty with whom McKnight had developed a truly personal relationship, and one weekend Barack brought Sheila along with him. Jerry, Greg, Johnnie, Mary Bernstein, Bruce Orenstein, and Linda Randle would all remember meeting Sheila a time or two, usually by chance in Hyde Park or at her and Barack’s apartment on South Harper. “She’s a cutie,” Bruce remembered, but virtually never did Barack seek for anyone in his workday world to meet or know the woman with whom he lived. Mike Kruglik never laid eyes on her.

But one Friday Barack drove north with Sheila, and McKnight remembered Barack calling him from the Penguin, a working-class bar in nearby Sauk City, to say that his shabby Honda had broken down. John drove in to pick them up, and Barack introduced him to Sheila, whom McKnight thought was “absolutely stunning.” The regulars at the Penguin “must have been pretty surprised when that couple walked in,” McKnight suggested.

That weekend, like others, was spent mostly “talking about ideas,” McKnight recounted. Barack had a “set of things he was concerned about that he didn’t think he could talk with Kellman or Greg about that was outside the true faith.” McKnight, as a longtime Gamaliel board member, knew how “absolutely rigid” Greg was about the Alinsky model’s view that the way to make people “feel powerful was their anger,” instead of feeling “powerful because of their contributions.” Barack was deeply averse to anger and confrontation, and therein lay his difficulty with the attitude that Alinsky organizing sought to inculcate in its young initiates. McKnight remembered these discussions were “mostly my … responding to him about questions he had,” with McKnight talking about how his asset orientation differed from the “really true faith people” like Greg. McKnight had just written a powerful new paper, “The Future of Low-Income Neighborhoods and the People Who Reside There,” addressing what he termed “client neighborhoods.” Anyone who had spent time in Altgeld Gardens would have appreciated McKnight’s analysis. Such areas are “places of residence for people who are not a part of the productive process” and “have no hopeful future.” What was needed was “a new vision of neighborhood that focuses every available resource upon production.” In a sentence that reached directly back to the quintessential lesson of the 1960s’ southern freedom movement, McKnight insisted that for a group like DCP, “it is the identification of leadership capacities in every citizen that is the basis for effective community organization.”

As McKnight and Obama continued to talk throughout 1987, what became “very clear to me was that I was talking to a young man who had not bought the true faith,” McKnight remembered, one who had come to realize that Alinskyism “is ultimately parochial” and offered no prospects whatsoever for attaining large-scale social change. As the best historian of Chicago racism, Beryl Satter, would incisively note, Alinskyism’s “insistence on fighting only for winnable ends guaranteed that” community organizing “would never truly confront the powerful forces devastating racially changing and black neighborhoods.”

McKnight’s long-term impact on Obama would be profound, irrespective of how much Barack later remembered of their conversations or how few commentators were knowledgeable enough to hear the readily detectable echos. “If you want to see an intellectual influence on Obama’s thinking, it’s John McKnight,” citizenship scholar Harry Boyte told one Washington audience two decades later. “A lot of things started in part through John McKnight,” observed Harvey Lyon, a Gamaliel board colleague whose political roots also reached back to the 1960s. Stanley Hallett, an influential urban development pioneer, a onetime theology school classmate of Martin Luther King Jr., and the husband of Wieboldt’s Anne Hallett, was also deeply influenced by McKnight. For Hallett, directing public funds to service poor people’s professionally identified needs is “money spent to maintain people in a condition of dependency,” Hallett told one interviewer. Progressive public officials needed to stop “looking at people in terms of their problems instead of their capabilities.”⁵⁷

The People’s Coalition for Educational Reform issued its demands in advance of the mayor’s Sunday, October 11, summit. Calling for local school-based management, greater parental involvement in schools, a requirement that 80 percent of students perform at or above grade-level standards, and deep cuts in CPS’s huge central bureaucracy, PCER made clear its student-centered focus: “We do not want cuts to affect anyone providing direct service to students.” On Sunday, almost a thousand people packed UICC’s Pavilion as the mayor slowly made his way through the crowd. The Tribune described the almost four-hour program as having a “town-meeting atmosphere,” and called it “the most remarkable gathering to focus on the Chicago public schools in at least 25 years.” Washington proclaimed that “a thorough and complete overhaul of the system is necessary,” promised to appoint a fifty-member parent/community advisory council within two weeks, and pledged to present a unified reform plan within four months.

Washington soon convened the first meeting of his Parent Community Council, promising it would begin holding neighborhood forums before the end of November. The city’s most influential biracial coalition of business leaders, Chicago United, also shared its own school reform plan with the Tribune. Angry at Manford Byrd for his arrogance and disinterest in meaningful change, Chicago United had adopted the belief of Fred Hess and Don Moore that the best path toward improved student performance was through parental and community control of local schools. Patrick J. Keleher Jr., Chicago United’s public policy director, said, “we think the leadership could be found” and that organizations such as UNO could recruit and train interested parents.⁵⁸

At the same time, Barack’s DCP work remained often frustrating. Some Saturday mornings he met with the Congregation Involvement Committee at Rev. Rick Williams’s biracial Pullman Christian Reformed Church, while he and Johnnie Owens also met with two Chicago State University (CSU) professors who had just started a Neighborhood Assistance Center. The only result of that was Barack being invited to join a CSU-sponsored panel at a mid-October conference on “Developing Illinois’ Economy.” One of his fellow panelists, CSU’s Mark Bouman, addressed “the spectacular fall of big steel,” and another speaker was Chicago Tribune business editor Richard Longworth, who had written so forcefully about Frank Lumpkin’s efforts on behalf of Wisconsin Steel’s former workers. Whatever Barack contributed to the session was unmemorable, for Longworth, looking two decades later at a photograph of himself and Obama sitting side by side, had no recollection of the event whatsoever.

In Roseland, significant economic development news came from the low-profile Chicago Roseland Coalition for Community Control (CRCCC), a twelve-year-old organization that had successfully followed through on the interdenominational protests against Beverly Bank that Alonzo Pruitt and Al Sampson had mounted seven months earlier. When the bank announced plans to open a new branch in suburban Oak Lawn, the little-known Community Reinvestment Act (CRA) of 1977 allowed CRCCC to petition the Federal Deposit Insurance Commission (FDIC) to block that expansion. Three years earlier Beverly Bank had stopped making home mortgage loans, leaving it vulnerable to FDIC enforcement of the CRA’s community service requirements that proscribed disinvestment in older neighborhoods. Advising and guiding CRCCC’s strategy was the similarly low-profile Woodstock Institute, a nonprofit fair-lending organization created in 1973 by five founders, three of whom were John McKnight, Al Raby, and Stan Hallett. Woodstock vice president Josh Hoyt, an organizer who previously had worked under Greg Galluzzo and Mary Gonzales at UNO’s Back of the Yards and Pilsen affiliates, brought the Beverly situation to the attention of U.S. Senate Banking Committee chairman William Proxmire’s staff, and Proxmire wrote to FDIC chairman William Seidman. Soon Beverly Bank was in negotiations with CRCCC president Willie Lomax, and the national American Banker publicized the tussle. By mid-September Beverly had agreed to commit $20 million worth of loans to low-income Far South Side neighborhoods over the next four years and to open central Roseland’s first ATM. “We made use of some tools of the law to get the bank here,” the courageous Lomax told the weekly Chicago Reader’s excellent political reporter Ben Joravsky. “We had to play hardball.”⁵⁹

The “tools of the law” were increasingly on Barack’s mind by October 1987. Going to law school had been a possibility for years, ever since his graduation from Columbia. His grandmother more than once had spoken of a career in law and then a judgeship, and Barack had never seen his work as a community organizer as something long term. He had mentioned going to law school in passing to several people in recent years—IAF’s Arnie Graf being one—and early in 1987 Barack had heard a National Public Radio interview with Supreme Court justice William J. Brennan Jr. Brennan told NPR’s Nina Totenberg that the guarantees in the Constitution’s Bill of Rights are “there to protect all of us” and to “protect the minority from being overwhelmed by the majority.” Barack would later recall what he termed “the wisdom and conviction” of Brennan’s words.

Barack’s embrace of his “destiny,” as he described it to Sheila, had quickened his thinking for the last six months. Kellman’s move to Gary had left DCP entirely in Barack’s hands until he had been able to hire Johnnie Owens, but once Johnnie was on board, Barack’s references to law school—to Sheila, to his close friend Asif Agha, to Asif’s friend Doug Glick on their long drives up to Madison and back—became far more frequent. Early that fall Bobby Titcomb, Barack’s closest Hawaii friend, passed through Chicago, and he remembers Barack talking then about wanting to get a law degree. Asif left Chicago in early November for six months in Nepal, and one October evening, not long before he left, he went to Barack and Sheila’s apartment on South Harper. “We used to cook dinner for each other a lot,” said Asif, and that evening Barack was out on one of his several-days-a-week runs along Hyde Park’s lakeshore. “I was sitting with Sheila in the kitchen, and he walked in all sweaty,” wearing shorts, and “I remember him saying something about his law school essay, and that he had been mulling it over for many days, maybe weeks.” Mary Bernstein remembered Barack mentioning it to her as well. He had cited Harvard in particular to Asif—“his dad went to Harvard,” Asif remembered, “so he had some interest in Harvard” and “that was his first choice.” Asif had not heard what Barack had told Sheila about a “destiny,” but after two years of weekly conversations, he knew Barack “was an ambitious person.”

Several weeks earlier, Jerry Kellman told Obama about a conference titled “The Disadvantaged Among the Disadvantaged: Responsibility of the Black Churches to the Underclass.” It would be held in late October at Harvard Divinity School in Cambridge, Massachusetts, and Barack agreed they should go. The weekend of “study, reflection, and worship,” as the divinity school’s dean termed it, for the two hundred attendees began on Friday evening with a sermon by Samuel D. Proctor, pastor of New York’s Abyssinian Baptist Church and one of the most famous living black preachers. Proctor’s sermon “chilled us,” one listener recounted, with its description of “the ordinary terrors of normal life in Harlem.”

Saturday morning featured a powerful and provocative lecture by Philadelphia congressman and clergyman William H. Gray. “Will we have a two-tiered society of the haves and the have-nots … or will we have a society … that allows people to move from the underclass on up?” Gray asked. For black Americans, “education is an absolute essential,” as the record was clear: “no education, no advancement,” and “blacks with no education have very little hope” of bettering their lives. Gray did not shy from naming other ills. “The leading cause of death among young black males is black-on-black crime. That’s us. Superfly selling drugs and coke in our community is not someone else. It’s us. Those who are mugging us, raping us, and robbing us are not coming from somewhere outside. It’s us. The teenage pregnancy problem is not the white man’s problem, it’s our problem…. You cannot ever escape poverty with children having children.”

Two sets of four concurrent workshops bracketed a lunchtime lecture by sociologist William Julius Wilson. After the workshops ended, Jerry and Barack took a walk around the Harvard campus. “We didn’t spend a lot of time with other people at the conference,” Kellman recalled, “just with each other.” During their stroll, Barack told him that he was applying to law schools. Kellman remembers Barack saying, “ ‘I owe it to you to let you know as soon as I can,’ ” and Kellman recalls being “very surprised.” Kellman also remembers Barack saying he did not think that community organizing was an effective means for attaining large-scale change or a practical method for influencing elected officials who potentially could. Years later Obama described his thoughts similarly, saying that “many of the problems the communities were facing were not really local,” and that he needed a better understanding of how America’s economy worked “and how the legal structure shaped that economy.” He also “wanted to find out how the private sector works, how it thinks.” By “working at such a local level” he had learned that problems like joblessness and bad public schools were “citywide issues, statewide issues, national issues” and he wanted to “potentially have more power to shape the decisions that were affecting those issues.” In a subsequent interview he would specifically cite decisions that “were being made downtown in City Hall or … at the state level.” He had been able to get “outside of myself by becoming a community organizer,” but the experience also had taught him that “community organizing was too localized and too small” to offer significant promise to those it sought to empower.

Saturday night’s dinner speaker was Children’s Defense Fund president Marian Wright Edelman, who one listener said presented a “terrifying analysis” and emphasized the need for “an ethic of achievement and self-esteem in poor and middle-class black children.” Sunday morning the symposium concluded with a sermon by Harvard professor and pastor Peter J. Gomes, who worried that after two days of “some pretty depressing statistics, some very grim predictions, some very sobering analyses” the discussion had become “so intimidating, so daunting as to lead to paralysis rather than action. With more conferences like this, one will be terrified of thinking about any form of response.” But Gomes believed the weekend’s clear message was that “money, programs, and advocacy alone will not solve the problems of the underclass.” Instead, a consensus had identified “despair as the root and fundamental disease: despair, the loss of hope, the loss of any sense of purpose, or worth, or direction, or place,” an analysis all too true to someone familiar not only with Altgeld Gardens but also Chicago’s Far South Side high schools.⁶⁰

Back in Chicago on Monday, Barack wrote a congratulatory postcard to Phil Boerner, who had announced his upcoming marriage to his longtime girlfriend Karen McCraw. “Life in Chicago is pretty good,” Barack wrote. “I remain the director of a community organization here, and I’m now considering going to law school. Makes for a busy life: not as much time to read and write as there used to be. Seeing a good woman, a doctoral student at Univ. of Chicago.”

The next weekend was the beginning of Gamaliel’s third weeklong training at suburban Techny Towers, with about sixty trainees joining the network’s usual roster of trainers: Greg, Mary, Peter Martinez, Mike Kruglik, Phil Mullins, Danny Solis, and Barack. David Kindler now worked under Mike at SSAC in Cook County’s south suburbs, and Kindler brought his Quad Cities friend Kevin Jokisch to the early November training. “Who you brought to training was a reflection of your ability as an organizer,” Kindler explained, and Jokisch already had hands-on experience.

“Barack was always a great trainer,” Danny Solis remembered. “He had a presence.” After sitting in on two of Obama’s sessions, Jokisch agreed. “Barack was totally in control without appearing to be in control…. His sessions flowed, were all lively, and engaged participants. He drew people out, had them tell their stories in the context of the session he was leading. His style was different than many of the other trainers. Most of the trainers were aggressive, in-your-face types.” In contrast, “Barack and Mary Gonzales had a very similar way of moving, speaking, drawing people out, utilizing humor, and probably most importantly being trusted by those in the room.”

Most nights some of the trainers adjourned to an Italian restaurant and bar just down the road. “Obama showed up twice to have beers with us. The after-hours sessions were very lively,” Jokisch recalled. “Most of the debates were around politics and politicians,” with Barack jumping in. Phil Mullins remembers how Barack “saw the limitations of just pure community organization” and asked, “How do you get at these bigger issues?” Given Gamaliel’s IAF worldview, that meant Barack “was kind of out there on his own,” and he was “constantly asking himself what he actually thinks about something,” another colleague recalled. Phil, like Kindler, also knew that among all the organizers, Barack’s real relationship was with Kruglik. “That’s the tighter person-to-person relationship” for Obama, more so than Jerry or even Greg, Mullins recounted. It was “more personal,” because as everyone could see, “Kruglik’s a warmer personality.” Given his Princeton undergraduate education, plus his graduate school history background, Kruglik’s intellectual depth and acumen were unique among the Gamaliel network. He also possessed an uncommonly superb memory.

By November 1987, Mike and Barack had known each other well for more than two years, and with Mike Barack could be spontaneous and frank to a degree he rarely was with other organizing colleagues. Even a quarter century later, Mike remembered some of what Barack said to him that week. Barack’s time in Roseland had placed him “in the armpit of the region, as far away from the center of power as you can get,” and he saw a prestigious law degree as the first step on the road to true power. Mike disagreed, telling Barack not to leave organizing and instead to commit himself to building a citywide network of organizations broader than UNO’s set of community groups, a network so sweeping that it would represent the fulfillment of what King and Al Raby had hoped the 1966 Chicago Freedom Movement would become.

Barack demurred. A top law school would give him entrée to the corridors of power. “I can learn from these people what they know about power,” and a legal education would allow him to understand “financial strategies and banks and how money flows and how power flows. Then I can come back to Chicago and use that knowledge to build power for ordinary people.” But Barack was imagining more than just building a powerful network of community groups, Mike recalled. “He said to me, ‘I’m going to become mayor of Chicago. I’m thinking I should run for mayor of Chicago.’ ”

Barack believed that Chicago’s mayor was the most powerful of any U.S. city’s, one who with widespread grassroots support could begin the rebirth of neighborhoods like Roseland. “ ‘At the end of the day, the question is, How do we lift people out of poverty? How do we change the lives of poor people, in the most profound manner?’ That’s what he was interested in,” Kruglik recounted.

And by November 1987, Barack had a specific political template in mind. “Harold was the inspiration,” Mike recalls. “Obama saw himself in a very specific way as following in the footsteps of Harold Washington … following the path to power of Harold Washington.” Ever since the mayor’s appearance at the opening of the Roseland jobs center, Barack’s attempts to win direct access to Washington had foundered. “It’s almost like he was saying to himself … ‘I’m limited by the power of Harold Washington the mayor. Therefore the answer is, I’ll be Harold Washington.’ That’s what happened,” Kruglick explains. “The Harold path was to become a lawyer, become a state legislator, become a congressman, then become mayor. That’s the Harold path.”

Barack was “fascinated with Washington,” Mike believed, and “replicating Washington step by step” was his game plan. “That was in his mind. He talked about that.” Barack “was constantly thinking about his path to significance and power,” and “Harold Washington inspired him to think about becoming a politician.”⁶¹

The next Thursday was the launch of what Barack and DCP were now calling the Career Education Network’s “Partnership for Educational Progress,” a label borrowed at least in part from Chicago United’s blueprint for improving the employment skills of public high school graduates. Ever since DCP’s May decision to make education and particularly high school anti-dropout efforts a priority, Barack, Johnnie, and top DCP education volunteers like Aletha Strong Gibson, Ann West, and Carolyn Wortham had been in contact with Far South Side high school principals and guidance counselors and with officials at both Olive-Harvey College and Chicago State University. Thanks to Al Raby, who had just left his city human relations post so he could work for school reform at a newly founded consultancy called the Haymarket Group, Barack had recently met reform proponents Patrick Keleher, of Chicago United, and Sokoni Karanja.

In a fall proposal Obama would submit to multiple funders, he wrote that “the condition of the secondary school system called for a wider and more intensive campaign than we originally envisioned.” But beyond the initial $25,000 that Emil Jones had obtained from the state board of education, CEN’s only other support would be an additional $25,000 that the Woods Fund would soon officially announce.

Ever since early summer, Obama had met ambivalence among DCP’s congregations about forcefully targeting the sorry state of Chicago’s public schools. He later acknowledged that “every one of our churches was filled with teachers, principals, and district superintendents,” or, as UNO’s Phil Mullins more pungently yet properly put it, “if you removed every education bureaucrat from Reverend Wright’s church, it would go under.” Barack spent much of the last months of 1987 trying to expand DCP’s base by approaching the pastors of largely Protestant, and mainly Baptist, Greater Roseland churches. He realized that these congregations “have had no direct involvement in the issues surrounding the public school system,” and DCP wanted to enlighten them about “the need for broader reform in the school system.” Jerry Kellman knew that Mary Bernstein’s father, a senior Teamsters official, was a close colleague of Robert Healey, a former Chicago Teachers Union president who was now head of both the Chicago Federation of Labor and the Illinois Federation of Teachers. Mary arranged for Obama to meet with Healey, but Healey had no interest in aiding a movement that would empower parents.

Roseland’s five high schools were in sorry shape. One study revealed, “High school students in Roseland are testing more than ten percent below the city-wide average,” and that average was more than 30 percent below grade-level norms. The dropout rates at the two weakest schools, Harlan and Corliss, were rapidly increasing. Corliss’s principal published an essay in the Journal of Negro Education describing her efforts to combat “gang activity and vandalism,” “low teacher morale,” “disrespectful attitude and behavior of students,” and “student apathy and high failure rate” at her school. Julian, named after the pioneering black chemist Percy Julian, was considered to be the best of the five, but the principal there, Edward H. Oliver, still had a serious problem with ganglike female “social clubs.”

A crowd of three hundred showed up for CEN’s November 17 kickoff rally at Tyrone Partee’s Reformation Lutheran Church. The Defender covered the event, where DCP announced it would begin offering tutorial and counseling services at both Holy Rosary and Reformation in early 1988 to students referred by Carver, Fenger, and Julian high schools. Olive-Harvey College president Homer Franklin as well as Chicago State University vice president Johnny Hill pledged their institutions’ assistance, and Chicago United policy director Patrick Keleher said that his organization would arrange for employment internships.⁶²

Barack was also keeping up with the city’s landfill crisis. When the U.S. Environmental Protection Agency issued a report attributing the South Side’s poor air quality to highway traffic and wood-burning stoves without mentioning landfills, the Tribune said that UNO’s Mary Ellen Montes “laughed when told of the EPA’s findings. ‘That’s crazy. Wood-burning stoves? Are there any left?’ ” Then the Sun-Times revealed that the Paxton Landfill had been operating without the necessary permits since 1983. The newspapers had a field day at the Washington administration’s expense, but mayoral aide Howard Stanback remained focused on the O’Brien Locks issue.

On November 16 South Chicago Savings Bank president Jim Fitch convened an initial meeting of all interested parties, ranging from South Deering’s Foster Milhouse to Bruce Orenstein and Mary Ellen Montes from UNO and hard-core landfill opponents Marian Byrnes and Hazel Johnson, who did not like anything they heard. Four days later Lake Calumet environmentalist James Landing distributed a letter warning that the Washington administration “is making prodigious attempts” to win over opponents of a new O’Brien Locks landfill.⁶³

On Wednesday morning November 25, the day before Thanksgiving, a Chicago Tribune headline announced “948 School Jobs Axed for Teachers’ Raises.” In order to meet the pay raises in CPS’s new union contracts, 167 elementary school teachers had been terminated. Then, at 11:01 that morning, Harold Washington collapsed with a heart attack in his City Hall office. The sixty-five-year-old mayor was seriously overweight, and attempts to revive him were unsuccessful. An official announcement was delayed for more than two hours, but word that Washington had died spread rapidly throughout the city, with tearful crowds gathering outside City Hall.

“Mayor’s Death Stuns City” read one headline the next day. Black Chicago’s loss was especially painful and heartfelt. Seven months earlier, when Washington was reelected, the Tribune editorialized that “he has been a symbol more than a leader,” but he was also the greatest “symbol of black empowerment” the city had ever seen. Only with his April 1986 erasure of Ed Vrdolyak’s city council majority had Washington truly become Chicago’s mayor, and as one Tribune story poignantly declared, “Washington’s legacy is not what he did, but what he was on the verge of doing.”

The next morning the Tribune lauded Washington as “a symbol of success and dreams realized for people who felt they had little reason to dream, let alone achieve,” while again noting that “his tangible record of accomplishments is a short list.” Economic development commissioner Rob Mier would write that “many of his goals and plans remained unfulfilled or barely started.” Mier also recognized that Chicago’s loss was greater because Washington had “died at the peak of his power.”

Tribune reporter John Kass highlighted how Washington had been “an incredibly charismatic leader,” but one of Washington’s most fervent early backers identified the mayor’s greatest mistake. “He took the power to himself, almost like Mayor Daley” in earlier decades, “and the political maturity of black politics stopped while he increased his power.” White 49th Ward reform alderman David Orr, who became interim mayor upon Washington’s death, had articulated the underlying problem months earlier: “There’s a large group of black aldermen … who don’t support reform but who have to vote with the mayor because he’s so popular in their wards.” By tolerating rather than purging those black aldermen who professed to support him while nonetheless remaining fully loyal to the Democratic party machine, Washington had advanced “his own political self-interest at the expense of institutionalizing his reform movement,” wrote historian Bill Grimshaw, the husband of Washington’s top political aide, Jacky Grimshaw.

The enormity of Washington’s failure became clear within the first hours after his death, as his city council majority sundered into two angrily hostile camps. Washington’s true supporters rallied behind the mayor’s council leader, 4th Ward alderman Tim Evans, with whom Barack and DCP’s Altgeld asbestos protesters had met eighteen months earlier. Washington’s opponents eagerly reached out to the black machine aldermen, who now controlled the balance of power in a political world where they no longer had to bow to a singularly charismatic leader. Washington’s political base “unraveled immediately after he was pronounced dead,” John Kass wrote, and Rob Mier also rued “the immediate collapse of his political coalition.”

Over the Thanksgiving holiday weekend, the two factions warred publicly as Washington’s body lay in state for a fifty-six-hour around-the-clock wake in the lobby of City Hall. Monday night at the UICC Pavilion where Washington had hosted his Education Summit just seven weeks earlier, his official memorial service turned into a political rally for Evans. Yet the only votes that would count were those of the fifty city council members, and by Tuesday morning, there was little question that 6th Ward black machine alderman Eugene Sawyer would become Chicago’s next mayor thanks to Washington’s hard-core opponents plus at least five black aldermen who would support Sawyer over Evans.

As Tuesday night’s council meeting convened, a crowd of thousands stood outside City Hall, chanting “No deals” and “We want Evans.” Clownish behavior marred the council’s proceedings as protesters mocked black Sawyer allies like 9th Ward alderman Robert Shaw, and Sawyer was not formally elected as Harold Washington’s successor and sworn into office until 4:00 A.M. Wednesday.

In skin color Gene Sawyer was just as black as Harold Washington, but as the angry crowd well knew, Chicago now had a completely different mayor than the one it had just buried. When Sawyer was asked by a historian some months later about Washington nemesis Ed Vrdolyak, his answer highlighted the chasm: “He’s a fun guy!”⁶⁴

“I loved Harold Washington,” Barack blurted out years later when asked what he had thought of the mayor. He once wrongly but perhaps wishfully stated that in 1985 “I came because of Harold Washington,” and at another time, he mused that “part of the reason, I think, I had been attracted to Chicago was reading about Harold Washington.” There was no doubt that Washington, or more precisely Washington’s treatment at the hands of the Vrdolyak majority during Barack’s first nine months in Chicago, contributed in some degree to Barack’s own embrace of a resolutely black racial identity. “Every single day it was about race. I mean every day it was black folks and white folks going at each other. Every day, in the newspapers, on TV, in meetings. You couldn’t get away from it,” Obama later recounted. “It was impossible for Harold to do anything.”

Upon his arrival in Chicago, and throughout all of his Oxy and Columbia years prior to Jesse Jackson’s 1984 presidential run, Barack had been “skeptical of electoral politics as a strategy for social change,” he later acknowledged. “I was pretty skeptical about politics. I always thought that the compromises involved in politics probably didn’t suit me.” Jerry Kellman, Greg Galluzzo, and the Alinsky tradition of organizing certainly did not teach respect or admiration for elected officials. But watching Washington week after week, even if he had never been physically closer than in that nondescript Roseland storefront eight months earlier, had fundamentally changed Barack’s mind. “You just had this sense that his ability to move people and set an agenda was always going to be superior to anything I could organize at a local level,” Obama explained in 2011.

In his own telling years later, Obama was in that angry, chanting crowd outside the city council chambers that Tuesday night, witnessing what he called Washington’s “second death.” Yet even at the time he wrote that, Barack understood Washington’s fundamental error, just as Bill Grimshaw had explained it. “Washington was the best of the classic politicians,” Obama told an interviewer. “But he, like all politicians, was primarily interested in maintaining his power and working the levers of power. He was a classic charismatic leader, and when he died, all of that dissipated. This potentially powerful collective spirit that went into supporting him was never translated into clear principles, or into an articulable agenda for community change,” Obama rightly stated in words that would echo painfully two decades later. “All that power dissipated.”

Yet in those last weeks of 1987, Washington’s death strengthened Barack’s belief that now was the time to leave DCP for law school. He had “a sense that the city was going to be going through a transition, that the kinds of organizing work that I was doing wasn’t going to be the focal point of people’s attention because there were all these transitions and struggles and tumult that was going on in the African American community,” he recalled in 2001. “So I decided it was a good time for me to pull back” and attend law school.

Barack’s long-pondered personal essay was finished, but completing his application required soliciting letters of recommendation as well. Al Raby was a recognizable name to anyone who knew the history of the 1960s, and Michael Baron had given him an A for his senior year paper at Columbia, the most serious piece of coursework Barack had ever tackled. Now working at SONY, Baron readily agreed to write a letter. But Baron’s knowledge of him was now more than four years dated, so Barack also went to see John McKnight, asking him to keep their conversation confidential, especially from Greg and Mary. “Would you write me a letter of reference? You’re the only professor I know.” McKnight immediately said yes, but asked Barack what his plans were. “I want to go into public life. I think I can see what can be done at the neighborhood level, but it’s not enough change for me. I want to see what would happen in public life” and “I think I have to go to law school to do that.” McKnight questioned whether Barack understood how fundamentally different life as an elected official would be from that of an organizer. While the latter was quintessentially an advocate, “my experience is that legislators are compromisers,” McKnight observed, people who synthesize conflicting interests. “You want to go into a world of compromise?” he asked. Barack responded affirmatively, saying, “That’s why I want to go into public life” and to pursue a role quite opposite that of a confrontational Alinsky organizer. “It’s clear to him he’s making a decision that that’s not the way he’s going,” McKnight remembered. “He left for a different mode of seeking change.”⁶⁵

With Gene Sawyer uncomfortably ensconced in City Hall, the Parent Community Council’s ten public forums were surrounded by uncertainty. At the first one, Chicago United’s Patrick Keleher reiterated the business community’s demand for dramatic reforms, and at the third Sawyer pledged “my commitment to the Washington reform agenda.” In response, Manford Byrd protested that CPS’s “many needy students” meant that any improvement in schools’ performance would require “major additional funding” for more teachers, counselors, and, of course, “other professionals.” DCP’s Aletha Strong Gibson told one reporter that the reform movement would be undeterred by the mayor’s loss. “Harold Washington did not move the community. The community moved Harold Washington,” she declared. “It is incumbent upon us to keep our voices raised. We have to take back ownership of the schools.”

Sawyer also inherited Chicago’s landfill problem, with Howard Stanback seeking to quickly explain the city’s O’Brien Locks strategy to the new mayor. Environmental activist James Landing realized that Washington’s death would not alter the situation, and even he wondered whether the opponents should give up and join Jim Fitch’s effort to agree on what the Southeast Side neighborhoods should demand from WMI. Senator Emil Jones’s special legislative committee concluded its investigation by ruing “the lack of one centralized authority to address all environmental problems” in the area, but also bluntly acknowledging that continuing Chicago’s ban on landfill expansion “is irresponsible unless the city is able to implement a successful citywide waste-disposal plan” through massive recycling.

At DCP, Barack and Johnnie were preparing the CEN tutoring program to start in early 1988, in both Roseland and Altgeld, undeterred by the December murder of an eighteen-year-old Gardens youth by five fellow teenagers, all members of the infamous Vice Lords gang. Weeks earlier Barack had asked Sheila to go with him to Honolulu for the Christmas holidays so that his relatives could meet her, the first time Barack had ever introduced a girlfriend to his family.

Madelyn had just turned sixty-five, and a year earlier had retired from the Bank of Hawaii. Stanley, almost seventy, was now retired too. Ann Dunham, still struggling to complete her dissertation, told her mentor Alice Dewey how much she was looking forward to meeting Sheila, and Sheila would always remember how exceptionally warm Ann was to her throughout the couple’s visit to Honolulu. Ann was fascinated that Sheila had written her master’s thesis on Claude Lévi-Strauss, and Sheila remembers the two of them “talking about that thesis, my time in Paris, and my work at Chicago.” Ann was “genuinely very interested and warm and inquisitive. She was extremely generous with us and treated Barack with reverence. She really admired him and thought the world of him.”

Even though Ann and Sheila liked each other very much, Sheila felt that Ann was not in favor of her and Barack getting married. She wondered if Ann “sensed what we already knew, that we were too isolated and would sophisticate each other.” Sheila was especially struck by how everyone in Hawaii—Gramps, Toot, Maya—called Barack either “Bar” or “Barry.” In Chicago, only Asif used “Barry.” When Sheila called him “Barry for fun one day, just because everyone else was calling him that name,” Obama’s reaction was unforgettable. “He got so angry at me. Irrationally furious, I’d say. He told me that under no circumstances was I ever to use that name with him.” Perhaps Obama had some deep boy-versus-man association to the two names, but Sheila understood that he “was very sensitive about this aspect of his life and wanted me walled off from it—like a lot of other things in his life.”⁶⁶

Back in Chicago, the mayor’s Parent Community Council moved toward recommending that each Chicago public school be controlled by a locally elected governing board, but without Harold Washington present to embrace its conclusions, school reformers started arguing over which of several just slightly different proposals should be introduced in the state legislature. DCP participated tangentially, following UNO’s lead, with Danny Solis in charge and Johnnie Owens rather than Barack following developments most closely.

In late January Barack wrote to Phil and Karen Boerner to apologize for missing their wedding, and updated them on his plans: “I’ve decided to go back to law school this fall—probably Harvard.” At the end of the month, Barack also wrote to Anne Hallett at Wieboldt to submit DCP’s 1988 grant application, but he gave no indication that he might be leaving DCP anytime soon. He wrote that “DCP has come a long way in the past year,” most notably in hiring Owens, “someone with both the talent and background to become a lead organizer in his own right.” Because of DCP’s “success with the education issue … we have the potential in the coming year to become a truly powerful advocate for change not only in the area, but citywide,” Barack boastfully asserted. “Whether we fulfill that potential will depend on two things: how well we parley the Career Education Network into a vehicle for organizing parents and community, and whether the relationships we have established with the major Black churches in the South Side translate into their making a full commitment” to DCP by contributing financially so that the organization could begin to wean itself from outside funders. “If we succeed, I envision us having 30 new churches involved by the end of 1988.”

That was optimistic, because Obama’s ongoing efforts to connect with dozens of black pastors had garnered polite conversations but few enlistments. If CEN was to grow beyond a small pilot program in which DCP housewives tutored dozens of high school students in a trio of church halls, funding was necessary for “significant expansion of the program by the State Legislature.” Barack also still hoped that Olive-Harvey could reallocate resources “to create a comprehensive job training program with specific emphasis on Public Aid recipients and with the outreach and satellite facilities necessary to target the Altgeld Gardens population.”

DCP would soon hire a CEN project coordinator, thanks to Emil Jones’s state money and the Woods Fund, and hoped to approach major corporations through Chicago United. Barack’s success at fund-raising had let him raise his own salary to $27,250 and Johnnie’s to $24,000. Ideally Olive-Harvey would foot the bill to house CEN, but expanding the program for the 1988–89 school year depended on state board of education officials and state legislators.

Obama believed that “parents and churches” were “the most crucial ingredients” for “a long-term process of educational reform.” Gamaliel and Don Moore’s Designs for Change, now a top player in the citywide school reform movement, could be asked to provide parental training. The city’s community colleges were responsible for vocational and general educational development (GED) training, but their actual track record was even worse than that of Chicago Public Schools. “Only 8 percent of the 19,200 persons enrolled in GED preparation classes in 1980 actually received certificates,” Barack had discovered, and “only 2.5 percent of those enrolled in City College basic education programs end up pursuing additional vocational or higher education.” Instead, just as at CPS, “funds go into central administrative tasks rather than student instruction.”⁶⁷

Barack’s church-recruitment efforts continued throughout the winter of 1987–88. One successful visit was to a small church on West 113th Street just across from Fenger High School. Thirty-two-year-old Rev. Alvin Love had arrived at Lilydale First Baptist Church four years earlier, inheriting an “elderly congregation” that was “comfortable sitting and doing nothing.” Love wanted to “get this congregation engaged in their community,” and he was happy when Obama “just walked up to the door and rang the bell” and asked if Love would tell him what he thought Roseland needed. Love, like other pastors before him, asked Barack which church he belonged to. Love warned Barack that his standard response—“I’m working on it”—wasn’t going to be acceptable to all black clergymen. Barack invited Love to a box-lunch gathering of other interested pastors, and he was slowly beginning to expand DCP’s ties to freestanding Protestant congregations.

The clergymen with whom Barack was having the most contact, however, were not involved at all in DCP. One was Jeremiah Wright at Trinity United Church of Christ, whom Barack continued to visit on a regular basis. Barack also began speaking with Sokoni Karanja, a longtime Trinity member whom he had met through Al Raby when Karanja emerged as one of the most outspoken African American voices calling for school reform. Barack “was trying to think about ministers and how to organize ministers across the whole city—African American ministers—because he felt like the power that was needed for the community to get its just due was through that,” Sokoni remembered. “He was trying to think about churches and how to organize the churches.” Barack also told Sokoni about his plan to attend law school. “One of the things I notice is that a lot of these politicians get in trouble because they don’t know the law,” Barack commented. Becoming a politician was indeed his goal. “He was talking about becoming mayor of Chicago,” Sokoni—just like Mike Kruglik—remembered. “We had a lot of conversations about it,” and “that’s what he emphasized to me. It sounded like a good idea.”

The other church Barack visited frequently was St. Sabina. DCP members like Cathy Askew, Nadyne Griffin, and Rosa Thomas knew Barack “was a big admirer of Father Pfleger,” but Cathy’s fellow St. Catherine’s parishioner, Deacon Tommy West, saw the most of Barack at St. Sabina. One of St. Sabina’s wintertime ministries involved a tangible outreach to the homeless, many of whom lived in the relative warmth of Lower Wacker Drive, the underground level of a downtown Chicago roadway. “We brought clothes and food down there for them,” West explained. “My wife made corn bread” and “minestrone soup.” One evening Barack joined Tommy and Mike Pfleger for the trip downtown. “He was with us underground, feeding the homeless,” West recounted. “Lower Wacker—I remember him going to that with us,” Mike agreed. Tommy also remembered Barack saying he was about to go back to school. He “told me when he went down to Wacker Drive with us and we had the soup and the coats.” Tommy had asked why, and he recalls Barack saying, “I just get tired of getting cut off at the pass” by government officials, and “I need some other stuff. I’ve got to go. This is something I have to do.”

But one day in those early months of 1988, Barack went with Mike Pfleger and Tommy West on a different sort of outing. Years later Barack would say that “the single most important thing in terms of establishing” safe neighborhoods “is having a community of parents, men, church leaders who are committed to being present and getting into the community and making sure that the gangbangers aren’t taking over, making sure that there’s zero tolerance for drug dealing.” In 1988 Pfleger shared that sentiment as strongly as anyone could, and he had adopted an interdiction technique that was nonviolent direct action at its most aggressive: walking into a known drug seller’s home in clerical garb, asking if he could use the bathroom, then grabbing whatever narcotics he could and heading for the toilet. Only “a very small group” of men accompanied Mike on such drug raids, and Tommy West—wearing a deacon’s collar—was a regular participant.

Pfleger cannot remember Barack going with him on such a sortie, although “he very well may have.” But Tommy West recalls Barack’s involvement with great clarity. “One time he went with us to this drug dealer’s house, and Father Mike grabbed up the guy’s drugs and ran in the washroom—first he asked the guy, could he use the washroom,” and once in there Mike “dropped it and flushed it, and the guy pulls out his pistol. I said, ‘Look, put that up. He’s a priest—you don’t want to hurt him. Use it on me.’ He said, ‘No, he’s the one who did this.’ I said, ‘Don’t touch him. That’s God’s man. You don’t want God to be down on you the rest of your life. Leave him be and try to find you somewhere else.’ He said, ‘I think I will, because I’m ready to kill him.’ So Barack said, ‘Woo.’ ” Mike Pfleger looked calmly at his colleagues. “I’m doing God’s work. God is taking care of me.”

“He was around for that one,” Tommy affirmed. “That was the first time I remember him going inside of the drug dealer’s home with us to see what Father Mike did.” Then, with the dealer still holding his gun, Tommy again asked the man to leave: “ ‘then we can get out of here.’ ” The dealer did take his gun and leave, and as the raiding party exited as well, “everybody was kind of shook up,” Tommy West recalls with considerable understatement.

Barack had developed significant relationships with Mike Pfleger and Jeremiah Wright, just as he had two years earlier with Bill Stenzel and Tom Kaminski. But at home on South Harper, Sheila Jager never heard a single word about any of them, or about institution-based religious faith. “I don’t think Barack ever attended church once while we were together,” and he “certainly was not religious in the conventional sense,” Sheila reiterated. Barack “never suggested going to church together,” and “I had no awareness of Jeremiah. He certainly never mentioned him to me.”

Barack’s closest Hyde Park male friend, Asif Agha, remembers their conversations similarly. “I always assumed he was an atheist like me.” Barack “had no interest in religion” and knew “nothing about Islam.” Asif’s friend Doug Glick, Barack’s companion on all those long summer drives to and from Madison, bluntly concurred. “I do not believe he believes in Jesus Christ.” Asif states the trio’s consensus succinctly: Barack “did not have a religious bone in his body.”

In Barack’s daily life with Sheila, “he didn’t tell me a whole lot about” who he was dealing with in his work, Sheila explains, “although he did bring a lot of their ideas home.” Barack “never compartmentalized ideas, which we discussed freely.” At home “we spent a great deal of our time discussing/talking about all sorts of things, which was one of the things I liked so much about him.” And, just like at DCP, Barack “was also a very good listener.” Yet “we lived a very isolated existence,” and even their immediate neighbors at 5429 South Harper barely remember either Barack or Sheila.

One longtime older resident had no recollection at all, and custodian Joe Vukojevic, who lived directly across the hall from Barack and Sheila, only remembered being introduced to Barack’s mother Ann during her summer 1987 visit. Barack and Sheila’s immediate upstairs neighbors, John Morillo and Andrea Atkins, thought Joe the janitor was “a very nice guy” but “practically never” saw Sheila or Barack. They would remember the unusual name on the mailbox, and saying hi to Sheila, but Barack was “just another guy doing laundry” in the basement laundry room.⁶⁸

On January 31, the Daily Calumet reported that South Chicago Savings Bank president Jim Fitch was privately brokering talks to allow Waste Management to use the O’Brien Locks site as a new landfill in exchange for a $20 million community trust fund. Fitch then called for another gathering of neighborhood representatives at 7:30 P.M. Monday, February 8, at his bank to discuss “the structure of the community trust.” Since the Daily Cal story “events have been evolving rapidly,” Fitch explained, and “conversations with Waste Management have continued.”

UNO’s Bruce Orenstein and Mary Ellen Montes had previously attended Fitch’s conclaves, but now they grew concerned. If UNO and the city’s Howard Stanback hoped to have the community fund managed by mayoral allies, they could not allow Fitch to continue driving the conversation with WMI. Bruce and Lena called on Fitch at his bank in advance of the meeting and told him he lacked the authority to have this gathering because he had not been involved in the fight to stop the landfills. Bruce recounts telling him, “We think you’re undermining our agenda, you’re undermining the agenda of the community, the wishes of the community.” Bruce and Lena “really asked him to stop,” but Fitch was no rookie at power politics. He recognized their raw grab for control and brusquely dismissed them.

Orenstein next called Barack to ask for DCP’s support in a confrontational move straight out of the Alinsky-style community organizing playbook. Local print and broadcast journalists were notified, a press release was prepared, and late Monday afternoon prior to the scheduled meeting, Barack, Loretta Augustine, and other DCP members drove to UNO’s office on East 91st Street, less than two blocks from Fitch’s South Chicago Savings Bank. “We met there, we practiced,” Bruce remembered. “Barack and I and Mary Ellen and Loretta have devised this thing,” and shortly after 7:30 P.M., Mary Ellen led a column of more than one hundred participants, including some children, out the door and down the street toward the bank’s second-floor conference room. The goal was “to let Fitch know in no uncertain terms he does not represent the will of the community on this issue,” Bruce recounted. “We just wanted to tell him that in front of everybody else who was around the table,” including UNO and DCP’s old friend Bob Klonowski, pastor of Hegewisch’s Lebanon Lutheran Church. Bruce remembered the group very quietly “walking up the stairs and being actually quite nervous,” for “it was quite a confrontational approach to things.”

But with Mary Ellen in the lead, the “ambush”—as the Daily Cal’s front-page headline the next day called it—worked to perfection. “Mary Ellen led the charge and we walked in and the camera lights went on,” Bruce recalled. “Barack and Loretta and the TV cameras and the Chicago Tribune” reporter Casey Bukro all followed Lena into the conference room. “Everybody looks up” as Mary Ellen approached Fitch. “Tonight we publicly take the position ‘No deals Jim Fitch, no deals Waste Management,’ ” Lena proclaimed. “We will fight you every step of the way.” As a confrontational leader, “she was fantastic,” Bruce knew. “Then we turned on our heels and walked out.” It was a “very memorable action,” even “a hoot of an action,” and from Bruce’s perspective, Barack had shown no discomfort with these tactics: “I certainly think he enjoyed it.”

UNO and DCP’s press release claimed that “We are diametrically opposed to any ‘buyoff’ deal … with Waste Management,” while acknowledging that “communities are due substantial reinvestment.” A simultaneous one by Howard Stanback on behalf of the mayor’s office was deceptively titled “City Reaffirms Landfill Moratorium” and asserted that “Waste Management is misleading the public if they suggest that they are in a position to acquire O’Brien Locks for landfilling.”

As Bruce Orenstein told the Daily Calumet, “If Waste Management gets ahold of that property, out the window goes any protection for the community.” The real issue was not the fate of the O’Brien Locks acreage, whose future looked preordained, but who on the Southeast Side would control whatever community trust fund would receive the $20 or $25 million that Waste Management was clearly willing to pay. Only Hegewisch News editor and community activist Vi Czachorski gave readers a clear understanding of what was happening. “Montes wants a landfill at the O’Brien Locks,” directly across the Calumet River from Hegewisch, and in exchange, she gets “a trust that UNO would operate” rather than Jim Fitch and other traditional Vrdolyak loyalists. But UNO’s Alinskyite “ambush” not only infuriated Fitch’s nascent coalition, it also angered the trio of hardcore landfill opponents—Jim Landing, Marian Byrnes, and Hazel Johnson—who had been reconsidering their own position. Within a week, they were picketing outside Chicago’s City Hall, clear evidence that Bruce and Barack’s strategy of blowing up Fitch’s negotiations had torpedoed any prospect of achieving a community-wide consensus.

For Barack, all this tussling created a fundamental personal tension. He had made clear to John McKnight that he rejected the confrontational politics of the Alinsky tradition, even though he had just helped lead an action that was so pugnacious it had made even the hard-bitten Orenstein nervous. It unquestionably was the “most confrontive meeting he had ever been involved in,” Bruce acknowledged, and “left to his own devices, I don’t think he would have designed an action like that.” True enough. What then accounted for so stark a contradiction?⁶⁹

A weekend or two after the South Chicago ambush, Barack took Sheila to see a movie that had debuted the Friday before the Fitch action: The Unbearable Lightness of Being, an adaptation of Czech writer Milan Kundera’s 1984 novel. Set in Czechoslovakia in the years leading up to the Prague Spring of 1968, the film featured three leading characters: Tomas, a young doctor, his partner Tereza, and his additional lover Sabina. The movie was not necessarily loyal to the spirit of Kundera’s book, and, at almost three hours’ length, it had not been praised in prominent reviews in the Chicago Tribune and the New York Times. The Tribune’s critic wrote that “the film has no vision and no life,” and warned that it “is likely to be incomprehensible to anyone who hasn’t read the novel.”

Vincent Canby’s Times review was more revealing. Tomas, played by Daniel Day-Lewis, lived a compartmentalized life, with “one part of his mind” analyzing something while another “part that’s outside it criticizes” the first. Tereza, played by Juliette Binoche, “falls profoundly in love with” Tomas “without knowing anything about him.” In turn, “Tomas is drawn against his will into commitment to Tereza,” yet with Sabina, played by Lena Olin, he indulges in “a passion for … sex that excludes serious emotional commitment … while always remaining a little detached.” Tomas “remains committed to Tereza, though still unfaithful.” The film conveyed “an accumulating heaviness” accentuated by its “immense length.”

Almost a quarter century later, Sheila Jager described the film as an indelible memory, explaining that it could offer “some insight into our relationship…. Although Barack did not fool around (not that I know of), I remember being powerfully moved by that film when we saw it together because Tomas and Tereza’s relationship seemed to so uncannily mirror the dynamics of our own—Tomas’s ‘neurosis’ like Barack’s ‘calling.’ ” She believed that perhaps was “why I reacted so hard when I saw that film. Because it was mirroring reality in an eerie sort of way, and I somehow understood what was happening even if I was unaware of what was going on. I remember feeling so trapped and suffocated back then, just like poor Tereza and her cheating husband. I’ll never forget that feeling of desperation, and wondering what I was going to do. I remember him telling me how he wished he could take me to the countryside and live with me,” just as Tomas does with Tereza, “but he couldn’t do that, no matter how much he loved me,” because his destiny inescapably must trump love. “I always knew that I couldn’t marry him,” yet in those early months of 1988, Sheila never doubted Barack, in part because something happened between them, something Barack subsequently never spoke about.

Barack was also close with the almost thirty-year-old Mary Ellen Montes—Lena—and he told her too about the vision of his future that otherwise he had only shared with Sheila. “He wanted to be the president,” Lena explained. “He used to say that his goal was to be the president of the United States.” Their ambitions were mutual. “By the time I met Barack, I was thinking about politics as well, with aspirations of being the mayor.” Lena told him, “I could see myself being the mayor of the city of Chicago. That’s where I’d want to end it, and his thing was oh no, he wanted to go on to be the president.” While Barack had told Mike Kruglik and Sokoni Karanja that being mayor of Chicago was his ultimate goal, Lena firmly declared, “That’s not what he’s telling me.”

Lena understood their similar trajectories. “You start to feel and realize your potential, so as you’re growing in this arena, why wouldn’t you think about those things? … That’s why I thought about the mayor,” and for Barack “it’s because of what he realized as he’s growing in the public arena and realizing his potential.” She knew that getting a law degree was “absolutely” his first step toward electoral politics. Across those months, “our conversations—they were real. They were genuine, sincere conversations about ourselves and what we wanted to do, what we were doing, what we were thinking of.” Lena knew Barack lived with someone. “I hear of her,” Lena explained. “Asian woman.” No, “I never met her…. I remember him saying she was Asian.” What did Barack tell Lena about that relationship? “He gave the impression that they lived together more because of convenience—they both needed a place to stay.”

Barack’s diminution of his life with Sheila to Lena was reminiscent of how he had characterized it to Phil Boerner eighteen months earlier: “winter’s fast approaching, and it is nice to have someone to come home to,” given his “mortal fear of Chicago winters.” After years of distancing himself from his mother, Barack’s identification as African American—not international, not hapa, not biracial—was now complete. This transformation had been immensely aided by his exposure to and ease with strong black women like Loretta Augustine, Marlene Dillard, Aletha Strong Gibson, and Yvonne Lloyd, but this success came at a high price, one visible only in the light of the distance, the unknowable distance, that was always impenetrably there. That distance, that lightness, would extend well beyond 1988.⁷⁰

Two days after the action against Jim Fitch, a remarkable, substantive victory was announced by attorney Tom Geoghegan: Navistar, the renamed International Harvester, would pay $14.8 million to Frank Lumpkin and twenty-seven hundred other surviving former Wisconsin steelworkers. The largest individual payment would be $17,200, though Frank, with a better-protected pension, would receive only $4,000.

No one in Chicago doubted that Frank deserved the most credit for this achievement, and the ex-workers approved the settlement in an overwhelming vote of 583 to 75. But Frank was never someone to pat himself on the back. “It is a victory of sorts,” he told the Daily Cal. “It was the best we could get, and that’s the way everyone who voted for it felt. But we appreciate the feeling that the little guy has won and that giants can fall.” Tribune business editor Richard Longworth wrote a wonderful tribute to Frank, describing him as “an amazing man … who is probably as close to a saint as Chicago has these days.” Tom Geoghegan is “the only other real hero,” a commendation underscored when James B. Moran, the federal judge handling the Wisconsin litigation, publicly praised Tom’s “dedication,” “professionalism,” and “modesty in seeking fees.” Frank also represented the last of a dying breed: at South Works hardly seven hundred men were still working, and Republic LTV was down to 640. Maury Richards would soon be reelected as Local 1033’s president, but even as dedicated a steelworker as Maury was beginning to wonder what his next career would be.⁷¹

By mid-February, UNO, hoping to take the lead in Chicago’s fractured school reform movement, distributed a twenty-nine-page proposal to compete with a much more detailed plan championed by Don Moore’s Designs for Change, Sokoni Karanja, and Al Raby from Haymarket. DCP was listed as an organizational backer of UNO’s plan, but no DCP member was among the twelve names credited with preparing the document. Danny Solis, Peter Martinez, and Lourdes Monteagudo, an elementary school principal now working closely with UNO, were among them, as was an education professor at the University of Illinois at Chicago, Bill Ayers, who had arrived there six months earlier and met both Danny and Anne Hallett the previous fall. Acknowledging that “good schooling is an expensive proposition,” the UNO proposal called for the hiring of an astonishing 14,563 additional educators for Chicago’s elementary schools, at a cost of $442 million. UNO envisioned an annual CPS budget increase of $584 million, and called for a $481 million increase in state funding to support it.

On February 18, the same day that the Sun-Times gave the proposal prominent coverage, UNO and DCP brought busloads of members to a school reform hearing at board of education headquarters, but the overflow crowd intimidated officials and the meeting was adjourned. Soon a third major plan, this one backed by Fred Hess’s Chicago Panel, Gwendolyn LaRoche from the Chicago Urban League, and Patrick Keleher from Chicago United, joined the confusing fray. DCP concentrated on getting its Career Education Network off the ground, with Obama and Owens hiring an African American woman in her early thirties, Cassandra Lowe, who had been working as a college recruiter for nearby St. Xavier University, to oversee it. By early March, afternoon counseling sessions for fifty or so high school students were finally under way at Reformation Lutheran and at Our Lady of the Gardens. Asked about DCP’s 1987–88 change from an employment emphasis to its new concentration on secondary schooling, Owens explained that “the focus shifted to the more fundamental question of preparing people for jobs in a changing society.”⁷²

By the end of February, Barack had to decide both about law school and about making his long-mulled trip to Kenya before the fall 1988 academic year began. His sister Auma had returned home from Heidelberg and would eagerly host a midsummer visit.

Barack later would write that he applied to Harvard, Yale, and Stanford, but he also applied elsewhere, including to Northwestern University’s law school, right in downtown Chicago. Acceptance letters had arrived from both Harvard and Northwestern, but with one huge difference: Harvard’s financial aid package would require him to take out loans of well over $10,000 a year, while Northwestern’s offer, the Ronald E. Kennedy Scholarship, would allow him to attend a top-twenty law school in Chicago for free. Debating his choice of school, Barack asked Jean Rudd and Ken Rolling at the Woods Fund about attorneys from whom he could seek advice. Jean’s husband Lionel Bolin was a descendent of a famous African American family, a 1948 graduate and now a trustee of prestigious Williams College, and a successful broadcast executive who, after serving in the U.S. military, had graduated from low-cost New York Law School. Woods Fund board member George Kelm, a low-key civic activist, had been managing partner of a prominent Chicago law firm, Hopkins and Sutter, before becoming president of the Woods family’s Sahara Enterprises investment firm.

Barack “was trying to make a strategic choice about which school,” Jean Rudd recalled, and Jean and Ken remember Barack telling them about Northwestern’s full-scholarship offer. George Kelm was a Northwestern Law School alumnus and a past president of its alumni association, and he strongly advised Barack against attending Harvard. Northwestern was so interested in persuading Barack to accept its Kennedy Scholarship, named after an African American faculty member who had died four years earlier at the age of forty-two, that the admissions office asked the law school’s dean, Robert W. Bennett, to speak with Obama. “The admissions people came to me and they said, ‘We’ve got a fantastic prospect for this scholarship’ ” and “ ‘we want you to try to talk him into taking it,’ ” Bennett recounted. “Barack was brought to my office” and “I tried to talk him into taking this Ronald Kennedy Scholarship.” Bennett was a 1965 cum laude graduate of Harvard Law School, and Barack was “the only applicant that the admissions people ever” asked him to help recruit during a full decade as dean.

Neither Kelm and Bennett’s efforts nor the full three-year scholarship were sufficient to outweigh Barack’s belief in his destiny. Harold Washington had graduated from Northwestern’s law school, and only once had a Harvard law graduate become president—Rutherford B. Hayes, in 1877. Northwestern law alumni had been major party presidential nominees five times, but William Jennings Bryan was a three-time loser and Adlai Stevenson had lost twice. It would be a costly decision for Barack—a cumulative difference of more than $40,000—but his choice was evidence of how deeply he believed what he so far had shared only with Sheila and Lena.

The only person in Barack’s workday world, other than Lena, to whom he spoke about leaving was Johnnie Owens, whom he had recruited to DCP with at least half an eye toward this decision. Johnnie remembered the moment clearly. “I didn’t have a clue until one day he asked me, ‘Are you ready to lead?’ I’m like ‘What do you mean? What are you talking about?’ ‘I’ve been accepted at Harvard Law School,’ ” and he would be leaving DCP to attend its three-year J.D. program. “And I’m like ‘What?’ ” Owens remembered, for there had been no prior indications that Barack was contemplating such a future. “Nothing. Absolutely nothing: about applying, that he was interested, anything like that. And so he began explaining to me how he’d been struggling with the thought of maybe going into the ministry versus law school.” Neither Sheila nor Lena ever heard him talk about the ministry, but as Johnnie remembers it, Barack “said he had ideas and thoughts about going into the ministry and that he had actually talked to Reverend Wright about some of this.”

Barack asked Johnnie to succeed him as DCP’s executive director, promising not only to work with the members on the transition, but also to introduce Owens to the trio of women who were DCP’s most important funders: Jean Rudd at Woods, Aurie Pennick at MacArthur, and Anne Hallett at Wieboldt. Owens agreed, but several weeks passed before Barack was ready to tell DCP’s volunteer leaders about his upcoming move.⁷³

On March 5, ten days before Democratic ward-level and congressional primary elections across Chicagoland, the Chicago Tribune reported that Waste Management had fired two managers at its SCA chemical waste incinerator at 11700 South Stony Island Avenue for repeatedly disconnecting air-monitoring devices designed to measure the facility’s destruction of highly toxic PCBs. WMI insisted that the misconduct “did not threaten health or safety,” but Marian Byrnes, Hazel Johnson, and congressional candidate Mel Reynolds picketed the plant, demanding it be closed. Metropolitan Sanitary District officials pulled back from a plan to dump eighty thousand cubic yards of sewage sludge in a wetlands property five blocks south of SCA.

Howard Stanback, Bruce Orenstein, and Barack were working on plans to have Mayor Sawyer attend a postelection March 17 rally at St. Kevin to announce publicly the city’s strategic alliance with UNO and DCP regarding landfills. On Election Day, four African American ward committeemen who were allied with Sawyer were defeated, an unsurprising verdict on the process that had made Sawyer Harold Washington’s successor. Two successful challengers were forty-eight-year-old educator Alice Palmer in the 7th Ward, who defeated organization loyalist William Beavers in a virtual landslide, and young West Side activist Rickey Hendon in the 27th Ward. Another winner, in a South Side state representative contest, was 8th Ward precinct captain Donne Trotter, who a year earlier had turned out such an impressive victory margin for Harold Washington at London Towne Homes. One of the few challenges to a Sawyer loyalist that failed was Salim Al Nurridin’s 9th Ward committeeman contest against Bill Shaw, whose twin brother Bob, the 9th Ward alderman, bizarrely alleged that Salim operated a harem full of welfare recipients. Only slightly more uplifting had been Emil Jones and Mel Reynolds’s unsuccessful challenges to incumbent 2nd District congressman Gus Savage.

When the Tribune reported that the thirty-six-year-old Reynolds had voted only twice since he turned twenty-one, Reynolds claimed that plotters had altered his voting records. Tribune political reporter R. Bruce Dold commended Reynolds for running “a surprisingly effective first-time campaign” and praised him as “a walking role model for black achievement.” But when the votes were tallied, Reynolds received only 14 percent, Jones 24 percent, and Savage won renomination with just 53 percent.⁷⁴

Stanback, Orenstein, and Obama carefully scripted the St. Kevin evening rally where Gene Sawyer would eagerly agree to UNO and DCP’s demand for a new mayoral task force to study the city’s landfill options. Unlike Jim Fitch’s committee, this new group would be heavily stacked with UNO and DCP loyalists. Howard, Bruce, and Barack jointly drafted Sawyer’s remarks, and then both organizers, along with Lena and Loretta, met with Sawyer, Stanback, and other mayoral aides at City Hall. A young assistant to Stanback, Judy Byrd, remembered being struck by Barack, who “spoke with such command and such clarity.” This was in stark contrast with Bruce’s impression of the new mayor. “I remember in that meeting talking to Sawyer,” Orenstein said, “and feeling like no one’s there, no one’s home.” Yet the central trio worked exceedingly well together. Bruce found Barack “very collaborative and very easy to work with,” and was repeatedly impressed by how Barack made sure that his top leader was never ignored or left out: “he was looking out for Loretta.” In addition, “Stanback’s a full partner. I remember Stanback saying at the time that he’s never had a more collaborative relationship with a community organization, and he really appreciated it.”

At Stanback’s insistent urging, Orenstein also tried to convince some hard-core landfill opponents like Marian Byrnes to take part in the new process, but Byrnes realized that this was all leading to two predetermined ends: a new landfill at O’Brien Locks that the city desperately needed, and a $20 to $25 million community trust funded by Waste Management that would be controlled by UNO and DCP, not Jim Fitch and the wider community.

Angry but determined, Marian, Hazel Johnson, and others picketed St. Kevin that evening, distributing a no-more-landfills flyer that invoked the title and featured song from the Eyes on the Prize civil rights documentary that had aired a year earlier. UNO members tried to obstruct the leafleting, and when Hegewisch News editor Vi Czachorski, a UNO opponent, tried to enter the basement, UNO’s Phil Mullins physically blocked her. “As I descended St. Kevin’s stairs, Mullins put his arms across the narrow stairway and said ‘You can’t attend this meeting.’ I tried to continue, crowds pushed. Mullins said ‘I’m getting the police. I’ll charge assault!’ ” Czachorski wrote in the next issue of her weekly newspaper. “I left.”

UNO and DCP’s own dueling flyer demanded that Sawyer name a new task force “made up entirely of residents who live in communities affected by landfills.” Only such a group can “take this issue out of the backrooms and into the light of day.” DCP also distributed a statement in Loretta Augustine’s name denouncing “backroom deals that ram landfills down the communities’ throats and send the enormous profits from such dumping into corporate and city coffers.”

As a crowd of more than six hundred filled St. Kevin’s basement, Orenstein paced nervously while Barack was “relaxed and cool.” Sawyer carried with him a briefing memo summarizing the remarks that Loretta and Mary Ellen would make as well as his own speech, typed out in large, bold capital letters. A seven-piece mariachi band provided entertainment as multiple TV camera crews set up their equipment. DCP president Dan Lee and St. Kevin pastor George Schopp joined Loretta, Lena, and the mayor on the stage.

DCP’s Loretta Augustine opened the meeting. “We, as residents, have had no control over what has happened in our community. We are tired of being victims. We are taking control of our own community.” Then Lena spoke, followed by Sawyer. “Waste disposal and landfill decisions will no longer be made in the back room, at a table full of politically connected financial opportunists,” the mayor read, his text sounding far more like Bruce Orenstein than Gene Sawyer. “Whatever happens here will be because you decide.”

With Lena and Loretta flanking the mayor, Lena then took charge of the traditional IAF-style colloquy with Sawyer, just as she had with Harold Washington almost five years earlier on that same stage. UNO and DCP had encouraged their supporters to be boisterous, and one reporter called the crowd “raucous.” Lena enjoyed her role to the hilt, and she began reciting the formal demand that the mayor appoint a new task force within ten days. She warned Sawyer to “be careful how you respond because this is an angry group of people tonight.” The mayor stuck to his script and pledged full acceptance of UNO and DCP’s demands. At that point, Lena turned to the cheering crowd and declared, “I’m going to take it for granted that we will have all the power we want!” As one veteran organizer later remarked, five years as a quintessential Alinsky leader had made Mary Ellen Montes into “one of the most macho women I had ever met.”

As the gathering concluded, Bruce and Barack were ecstatic about the meeting. But UNO and DCP’s Alinsky-style power grabs—first blowing up the Fitch talks, then bringing a sad sack mayor to heel before an excited crowd—had fractured the Southeast Side community. Bruce, Lena, and Barack had succeeded in infuriating and alienating the local business leadership and the true environmentalists, two groups that just weeks earlier had been prepared to join forces in a true community consensus. Ed Vrdolyak quickly put Sawyer on notice, objecting to the city allowing UNO and DCP to control negotiations with Waste Management: “For certain community organizations who without question do not truly represent the vast majority of homeowners, residents, and taxpayers to submit their community buyout (sellout) wish list is totally and completely wrong.”

But Vrdolyak’s public protest bore no political fruit, and a week later, Sawyer and Stanback announced a new sixteen-member Task Force on Landfill Options: Mary Ellen Montes led a group of five UNO supporters, including Father George Schopp; five other appointees were DCP members: Loretta Augustine, Dan Lee, Marlene Dillard, Margaret Bagby, and Father Dominic Carmon. Bob Klonowski was another ally, and no more than three appointees, including Marian Byrnes and Hazel Johnson, were likely dissenters. It was hard to imagine a more politically unrepresentative group.⁷⁵

In late March Barack announced his upcoming departure. He went to see Loretta first. “He told me he was leaving and he needed to go back to school.” Most DCP members learned the news at a meeting where Barack spoke of a smooth transition to Johnnie Owens as his successor. Dan Lee recalls that “I wanted to cry” and “we all got teary-eyed…. He was like a brother.” Tommy West called out, “No, you can’t go,” but they all realized that Barack’s potential reached well beyond Roseland. “We hated to see him go,” Yvonne Lloyd remembered. “It was very sad,” but they all appreciated, as Betty Garrett explained, that “if he could better himself, then we wanted him to go.” Barack remembered overhearing Yvonne remark how different he seemed now than he did on that August day two and a half years earlier when Jerry Kellman had first introduced him. “He was just a boy. I swear, you look at him now, you’d think he was a different person.” Of course, in many ways indeed he was.

Cathy Askew was the most emotional about Barack’s announcement. “I was really upset,” she recalled. “I thought we were friends.” Barack remembered Cathy expressing her disappointment and saying. “What is it with you men? Why is it you’re always in a hurry? Why is it that what you have isn’t good enough?” Yet they all understood how frustrating the past year had been for Barack. “For the leader or organizer who feels expected to bring some change and improvements to the community, the day-to-day litany of roadblocks and resistances makes it hard,” one close observer of Chicago organizing wrote that spring.

Marlene Dillard had watched Barack experience repeated setbacks while always trying to hide his disappointment from DCP’s members. The outreach to Local 1033 at Republic LTV had gone for naught, the efforts in Altgeld Gardens had led to little, and only now was a tiny version of CEN getting under way. Again and again, “I always felt that it was a disappointment to him.” Whenever she and Barack visited a funder like Woods, “he was trying to project how great we were doing.” Then, “when we were leaving,” he would turn to her and apologize for his braggadocio: “Well, we’re trying.” Overall, “I think it weighed very heavy on him…. He was leading people, and he was getting nowhere.” Indeed, Marlene came to believe “that he felt ‘If I could just become the mayor of Chicago, I would be able to do this.’ ”

Ernie Powell saw the same thing. “I think Barack got a little frustrated with that, and he felt like he had to get into the seat of power.” The DCP pastors who interacted regularly with Barack understood likewise. With CEN operating out of Reformation Lutheran, Tyrone Partee saw Barack almost daily and remembered him saying, “I’m going to law school.” Barack knew Tyrone was from a political family, and to him, Barack was “clear that he wanted to go into politics. ‘I believe that’s what I’m called to do.’ ” Alvin Love was caught off guard by Barack’s announcement, but he realized Barack was “frustrated with the speed of change” and had concluded that “there might be a better way to do” things.

Barack went to see both Rev. Eddie Knox at Pullman Presbyterian Church and Rev. Rick Williams at Pullman Christian Reformed Church in person. With Knox, Barack presented Harvard as an opportunity he was pondering, and Knox smilingly replied, “There isn’t much to think about.” Harvard was such “a golden opportunity” and Knox believed “You’re going to go far.” Rick Williams reacted similarly. “I’m happy for you,” Rick remembered saying, “but I’m also sad, because this kind of work needs people for the long haul, people like yourself.” Rick understood Barack’s hope of building a truly large, multicongregational alliance to pursue educational reform and employment opportunity all across Chicago, but, just as Jeremiah Wright had sought to explain a year earlier, bringing people and churches together behind such an agenda was far more complicated than Barack could imagine. Rick told Barack that Harvard was “a wise decision” and wished him well. “You are going to do more for more people getting a law degree from Harvard than you would do here.” Barack had “a passion for making life better for lots of people,” Rick remembered, and to do that, “you’ve got to have power.”

Barack also visited Emil Jones at his office on 111th Street. No elected official had done more for Barack and DCP, and Jones said he was sorry to see him go. To Jones as to others, Barack emphasized that there was no question he would return to Chicago after law school. He called Renee Brereton and other CHD staffers to tell them, plus organizing colleagues like Linda Randle. Barack apologized to Howard Stanback for pulling up stakes during their landfill effort. Stanback was surprised by Barack’s choice. “ ‘Why are you going to Harvard?’ He said, ‘Because I need to.’ I said, ‘Are you coming back?’ ” to which Obama said, “I’m absolutely coming back.”⁷⁶

Barack, Loretta, and Yvonne Lloyd all attended Lena’s thirtieth birthday party, but by early April, there was not much to celebrate regarding UNO and DCP’s position in the Southeast Side’s landfill war. Anger at Sawyer’s new task force was white hot, especially in Hegewisch, just across the Calumet River from the O’Brien Locks site. Hegewisch News editor Vi Czachorski asked Howard Stanback, “Why should UNO decide if there will be a landfill in our backyard?” and Marian Byrnes, Hazel Johnson, and three allies called the task force unrepresentative and called on Mayor Sawyer to disband it. That group held its first public hearing at St. Kevin on April 7, and this time UNO’s critics made it into the basement meeting room, mocking cochairwomen Lena Montes and Loretta Augustine with chants of “No deals,” the same slogan Lena had used during the Fitch ambush two months earlier.

The Daily Cal reported that Loretta defended the panel’s “makeup and goals” as a “positive development for the community and said the mayor had pledged to abide by the task force’s findings,” with its report due at the end of May. “The panel approved reopening discussions with Waste Management,” with Lena declaring, “What is different about it is that it will be talked about in open hearings, not behind closed doors.” But when old foe Foster Milhouse rose to speak, “Montes quickly closed” the meeting.

The Daily Calumet editorialized against any reopening of negotiations with WMI, and UNO’s opponents advocated for a popular referendum vote against landfill expansion on the upcoming fall general election ballot in Southeast Side wards. One week later, the task force convened its second hearing at Our Lady of the Gardens gymnasium in Altgeld Gardens, where the tumultous Zirl Smith meeting had occurred two years earlier. Father Dominic Carmon, a task force member and Our Lady’s pastor, remembered that Barack “was there listening,” as at the previous St. Kevin session too. Howard Stanback, Jim Fitch, and WMI’s Mary Ryan all spoke to the panel as a crowd of 125 chanted “No more dumps.” For the first time, Stanback publicly acknowledged that the city did want the O’Brien Locks site to become a new landfill. Mary Ryan said WMI would immediately place $2 million into a community trust fund, with similar sums to be added every year, and it would give up title to two other parcels of land, including the marshland just below South Deering whose vulnerability had led Harold Washington to impose the initial landfill moratorium. That was followed by numerous single community members who spoke fervently against the deal. In the days that followed, the Daily Cal kept up a regular drumbeat against the task force. “Why study something no one in the community wants or asked for?” political columnist Phil Kadner queried.

As the UNO–DCP landfill gambit drew more and more flak, the task force’s third hearing, scheduled to take place at Bob Klonowski’s Hegewisch church, was postponed and moved to Mann Park’s field house. When it finally convened, Klonowski welcomed the crowd in a calm tone, but, according to Vi Czachorksi, when a city representative again explained why O’Brien Locks was the best option available, “500 angry, frustrated people shouted down the city proposal of a new landfill.” The meeting “ended abruptly when Mary Ellen Montes lost control, stating ‘This has turned into a war.’ ” Declaring that “It doesn’t appear we can conduct this in a civilized manner,” she dissolved the hearing, leaving the entire UNO–DCP–Stanback strategy in tatters. The mayor’s office named several additional task force members and postponed its reporting date until later in the summer, but the entire venture was now dead.

Years later, Bruce Orenstein acknowledged that his and Barack’s game plan had gone entirely awry. When “we make ourselves the center of authority … we make ourselves the target” for large numbers of Southeast Side residents who for years had been opposed to the city using their neighborhoods as a dumping ground. Orenstein mused that if Harold Washington had not died, perhaps the O’Brien Locks deal with Waste Management could indeed have netted the community a $25 million trust fund, just as he, Obama, and Stanback had envisioned. But Gene Sawyer had no public stature as mayor. “With a very strong mayor” like Washington, a successful outcome was highly plausible, but “now we have a very weak mayor.”⁷⁷

During April’s landfill warfare, Gamaliel held its fourth weeklong training at Techny Towers, and Barack drove out there for several days’ sessions. By then, everyone knew he was leaving. Mary Gonzales was “pretty upset” when she heard, and David Kindler recalled thinking: “there goes one of our best and brightest.” Kindler’s friend Kevin Jokisch remembered telling Greg Galluzzo that Gamaliel would certainly miss Barack, with Greg responding, “We held on to him about as long as we were going to. Barack will probably end up being a United States senator.”

One evening that week, Barack drank beer with Mike Kruglik and talked about what he wanted to do after law school. “Obama is talking about his vision for a very powerful, sweeping organization across black Chicago, of fifty to 150 congregations, that would be highly disciplined, highly focused, professionally organized,” Mike remembered. “This vision … had such a claim on his mind” and Barack was explicit about “coming back to Chicago after Harvard and reengaging in community organizing in a more powerful way.”

Barack was thinking ahead in part because Ken Rolling and Jean Rudd at Woods had decided to fund and commission a series of articles about community organizing in Illinois Issues, the state’s premier public policy journal. Barack accepted an invitation to write one, but a quick deadline loomed. He had decided that he would travel to Nairobi to see Auma and meet the other members of his Kenyan family, but before that he wanted to spend at least three weeks on his own touring the big cities of Europe. Thus he needed to write his article before he left Chicago in late May. His essay would document how his thinking had evolved. Recent African American activism, Barack wrote, had featured “three major strands”: political empowerment, as personified by Harold Washington; economic development, of which black Chicago had seen very little; and community organizing. Barack argued that neither of the first two “offers lasting hope of real change for the inner city unless undergirded by a systematic approach to community organization.” Electing a black mayor like Washington was “not enough to bring jobs to inner-city neighborhoods or cut a 50 percent drop-out rate in the schools,” though such a victory did have “an important symbolic effect.”

At the community level, “a viable organization can only be achieved if a broadly based indigenous leadership—and not one or two charismatic leaders—can knit together the diverse interests of their local institutions.” Barack claimed that DCP and similar groups had attained “impressive results,” ranging from school accountability and job training programs to renovated housing and refurbished parks. Those assertions echoed what Marlene Dillard had heard Barack boast about during their visits to DCP’s funders, yet when he wrote that “crime and drug problems have been curtailed,” he was making his wishfulness give way to fantasy. It was true that “a sophisticated pool of local civic leadership has been developed” thanks to DCP’s recruitment and training efforts, but he admitted that organizing in African American neighborhoods “faces enormous problems.” One was “the not entirely undeserved skepticism organizers face in many communities,” as he had experienced; a second was the “exodus from the inner city of financial resources, institutions, role models and jobs,” as he had seen all too well in Roseland and especially in Altgeld. Third, far too many groups emphasized what John McKnight called “consumer advocacy,” and demanded increased services rather than “harnessing the internal productive capacities … that already exist in communities.” Lastly, Barack declared that “low salaries, the lack of quality training and ill-defined possibilities for advancement discourage the most talented young blacks from viewing organizing as a legitimate career option.”

Barack also argued that “the leadership vacuum and disillusionment following the death of Harold Washington” highlighted the need for a new political strategy. “Nowhere is the promise of organizing more apparent than in the traditional black churches,” if those institutions would “educate and empower entire congregations and not just serve as a platform for a few prophetic leaders. Should a mere 50 prominent black churches, out of the thousands that exist in cities like Chicago, decide to collaborate with a trained organizing staff, enormous positive changes could be wrought in the education, housing, employment and spirit of inner-city black communities, changes that would send powerful ripples throughout the city.”

Barack ended his essay on a revealingly poetic note, writing that “organizing teaches as nothing else does the beauty and strength of everyday people.” When the entire series of Illinois Issues articles was subsequently republished in book form, one reviewer quoted that sentence as the single most powerful statement in the entire volume. But another of Barack’s sentences about organizing was the most revealing of all, for when he wrote that through their work “organizers can shape a sense of community not only for others, but for themselves,” he was publicly acknowledging the self-transformation he had experienced in the homes and churches of Greater Roseland.

As early as his second year at Oxy, Barack had felt “a longing for a place,” for “a community … where I could put down stakes.” The idea of home, of finding a real home, “was something so powerful and compelling for me” because growing up he had been a youngster who “never entirely felt like he was rooted. That was part of my upbringing, to be traveling and always … wanting a place,” “a community that was mine.” His “history of being uprooted” allowed Barack to develop in less than two years what Sheila knew was “his deep emotional attachment to” Chicago, one that was almost entirely a product of Greater Roseland, not Hyde Park.

“When he worked with these folks, he saw what he never saw in his life,” Fred Simari explained. “He grew tremendously through this,” through what he acknowledged was “the transformative experience” of his life, through what Fred saw was “him getting molded.” Greg Galluzzo saw it too and said that Barack “really doesn’t understand what it means to be African American until he arrives in Chicago.” But, working with the people of the Far South Side, Barack “recognizes in them their greatness and then affirms something inside of himself.” Through “the richest experience” of his life, through discovering and experiencing black Americans for the first time, Barack “fell in love with the people, and then he fell in love with himself.”

Years later, Barack admitted that “the victories that we achieved were extraordinarily modest: getting a job-training site set up or getting an after-school program for young people put in place.” And he also knew that “the work that I did in those communities changed me much more than I changed the communities.” Ted Aranda, who had worked for Greg and in Roseland before Barack and whose Central American heritage made it possible for him to be accepted as black or Latino, came to the same conclusion as Barack. “I’m not sure that community organizing really did that much for Chicago,” he reflected. “I don’t know that we had any really tremendous long-term effect.” But Greg, looking back on a lifetime of organizing, understood the great fundamental truth of Barack’s realization: “it’s the people you encounter who are the victories.” For Ted, the disappointments and frustration of organizing radicalized him. A quarter century later, deeply devoted to Occupy, Ted was driving a cab. Greg understood as deeply as anyone that “the great victory of the whole thing is Barack himself.”⁷⁸

In mid-April, the Spertus museum, part of a historic Jewish cultural center on South Michigan Avenue in downtown Chicago, opened a seven-week exhibit depicting the 1961 trial of Adolf Eichmann, the Nazi henchman who had played such a central role in the anti-Semitic effort to exterminate European Jews. The centerpiece of the exhibition was a continuous film of the trial, supplemented by large photographs and illustrations of newspaper stories plus Jewish artifacts documenting the culture that the Nazi Holocaust had sought to destroy.

The Tribune publicized the opening, and then, less than three weeks later, a front-page Tribune story revealed that anti-Semitism was alive and well even in Chicago’s City Hall: “Sawyer Aide’s Ethnic Slurs Stir Uproar,” read the headline of a story about mayoral assistant Steve Cokely, who had recently delivered four “long and frequently disjointed” lectures under the auspices of Louis Farrakhan’s Nation of Islam (NOI). Tapes of them were on sale at an NOI bookstore, and while anti-Semitism lay at the center of Cokely’s often incoherent ramblings about a “secret society,” he also called both Jesse Jackson and the late Harold Washington “nigger.” Even worse, it was revealed that Mayor Sawyer’s office had known about the recordings for more than four months, and three weeks earlier representatives of the Anti-Defamation League had met with Sawyer about the lectures. But Cokely was still on the mayoral payroll.

Well-known Catholic monsignor Jack Egan labeled Cokely’s retention a “travesty,” but a number of prominent black aldermen defended Cokely. Danny Davis, a supposed reformer from the 29th Ward, called Cokely “a very bright, talented researcher with an excellent command of the English language.” The 9th Ward’s Robert Shaw, citing voters he knew, said, “I don’t think it would be politically wise for the mayor to get rid of Mr. Cokely.” But the Tribune published a blistering editorial, denouncing Cokely as “a hate-spewing demagogue” and “a fanatic anti-Semite” and also lambasting Davis. After five days of feckless indecision, Gene Sawyer finally fired Cokely, but the damage to Chicago, never mind to Sawyer’s indelibly stained reputation, was already done. That evening, at a large West Side rally, Roseland’s Rev. Al Sampson introduced Cokely to a cheering crowd as “our warrior” and declared that “this is a case of Jewish organizations trying to stop one black man from having the right to speak.”

In the middle of this, Barack took Sheila to see the Eichmann exhibit. Both of them would long remember what ensued. In Obama’s later account, in the one single public reference he would ever make to his 1980s girlfriends, he created a character who was a conflation of Alex, Genevieve, and mostly Sheila who goes with him to “a new play by a black playwright.” Several weeks earlier Barack had taken Sheila to see a Chicago amateur production of August Wilson’s powerful 1985 play “Ma Rainey’s Black Bottom,” but Sheila would remember the aftermath of the Eichmann exhibit more vividly than Wilson’s play. As they left, she asked Barack not about Eichmann, but about Steve Cokely and why so many prominent black Chicagoans were defending him rather than denouncing his moronic anti-Semitism. In Obama’s version, his white girlfriend asked about black anger, and he replies: “I said it was a matter of remembering—nobody asks why Jews remember the Holocaust, I think I said—and she said that’s different, and I said it wasn’t, and she said that anger was just a dead end. We had a big fight, right in front of the theater,” and “When we got back to the car, she started crying. She couldn’t be black, she said. She would if she could, but she couldn’t. She could only be herself, and wasn’t that enough.”

Obama would admit that “whenever I think back” to that argument, “it somehow makes me ashamed.” Sheila and Barack did argue angrily that early May night on South Michigan Avenue, but it was because “I challenged him on … the question of black racism,” and his response was so disappointing that their argument became “pretty heated.” As Sheila recalled it, “I blamed him for not having the courage to confront the racial divide between us,” but in retrospect, she concluded that the chasm between them was not racial at all. Instead it lay in the profound tension between Barack’s insistence on “realism,” on pragmatism, and what she believed was simply a lack of courage on his part. “Courage was a big issue between us,” and their arguments over her belief that he lacked it were “very, very painful.”

In early May, Sheila and Barack’s mutual friend Asif Agha returned to Hyde Park after six months in Nepal. He remembers thinking at the time that “they had a good relationship. They were really tight, really solid,” but he also noted that the tensions between them were even greater than they had been during that tumultuous weekend in Madison nine months earlier. Asif thought Sheila had a deeper commitment to their lives together than did Barack, and now, listening to Barack talk about his goals, Asif understood that his friend “wanted to have a less complex public footprint” as a future candidate for public office, particularly in the black community. Asif recalls Barack saying, “The lines are very clearly drawn…. If I am going out with a white woman, I have no standing here.”

Asif realized just how profound the tension had become for Barack between the personal and the political. “If he was going to enter public life, either he was going to do it as an African American, or he wasn’t going to do it.” When asked if Barack had said he could not marry someone white, Asif assented. “He said that, exactly. That’s what he told me.”⁷⁹

Even as his time in Roseland was ending, Obama still had to keep up with DCP’s school reform alliance with UNO. Johnnie, Aletha Strong Gibson, and Ann West were more involved than he was, but DCP continued to follow UNO’s Danny Solis and Lourdes Monteagudo. By late April, what was left of Harold Washington’s official Education Summit had failed to endorse reform legislation that was muscular enough to satisfy top reformers like Don Moore, Fred Hess, and Pat Keleher of Chicago United. So UNO and DCP were now formally backing Chicago United’s proposal, which was introduced in the state legislature by Senate Education Committee chairman Arthur L. Berman as S.B. 1837.

When Berman’s committee held a daylong hearing on four competing bills on Tuesday, April 26, Barack and a small group of DCP members including Loretta Augustine, Rosa Thomas, Aletha Strong Gibson, and Ann West traveled to Springfield to lobby legislators and to hear Lourdes Monteagudo testify on behalf of UNO and DCP in support of S.B. 1837. Writing in the Tribune, CPS superintendent Manford Byrd once again energized reform advocates by decrying their attacks on “some monolithic, intractable bureaucracy which in fact does not exist” and claiming that “the school system is broadly understaffed.” First the Sun-Times and then the Tribune began publishing multipart exposés on CPS’s failings. The Trib series debuted with a long feature on one elementary school, “a hollow educational warehouse” that is “rich in remedial programs that draw attention to a child’s failures.” An accompanying editorial warned that “Chicago’s public school system is failing its children and jeopardizing the city’s future.” The next day, in a culmination of negotiations that Don Moore’s Designs for Change colleague Renee Montoya had been conducting with UNO’s Danny Solis, DFC’s reform bill, H.B. 3707, sponsored by African American Chicago representative Carol Moseley Braun, was strengthened with the addition of provisions from Chicago United’s S.B. 1837. UNO and DCP joined in publicly shifting their support to the Braun bill, whose cosponsor was progressive Chicago Puerto Rican state senator Miguel del Valle, and reform energies increasingly coalesced behind the Braun–del Valle measure. In one Trib story, powerful 14th Ward alderman Edward Burke declared that “nobody in his right mind would send kids to public school.” In another, Manford Byrd called himself “probably the most gifted urban administrator in this country” while once again dismissing CPS’s obligations to its students: “When you’re all done, the learner must learn for himself.”⁸⁰

In the final ten days before Barack’s departure from Chicago for his two-month trip to Europe and then Kenya, things came completely apart at 5429 South Harper Avenue. Ever since Barack had transferred to Columbia almost seven years earlier, he had kept a journal, using it to record vignettes that might find their way into a future book and also sometimes for creating drafts of short stories and even letters to friends. Sheila knew of Barack’s practice, and sometime after their heated argument outside the Spertus museum, she decided to take a look at it. Lena Montes heard from Barack what ensued. “She reacted to this journal that he kept under his bed or mattress,” Lena recalled. “I remember when he says that she found some journal, and he talks about somebody in this journal and that she’s upset” after she read it. Barack did not tell Lena whether she was that someone. “Was it a straw that broke the camel’s back? I’m not sure. I just remember him saying that she … was leaving because of this journal.”

Just as Barack was about to leave Chicago, Sheila moved out of their apartment and moved in with her younger friend Simrit “Sima” Dhesi, who had just completed her undergraduate degree at the University of Chicago, and her sister in an apartment four blocks away at 5324 South Kimbark Avenue. Sheila later said that May 1988 “was kind of a blur for me.” Barack mentioned what was happening not only to Lena, but also to Loretta Augustine and even to his archdiocesan friend and Hyde Park neighbor Cynthia Norris. Cynthia understood that Sheila “was upset,” and that the tensions between her and Barack were “because of her race…. Yes, I do remember that.” Norris knew that Barack “had a lot of respect for” Sheila, and from what she knew, “I thought he handled things very, very well.” Loretta remembered it similarly. “He talked to me about her,” she recalled. “We had some really open and candid conversations” about the turmoil. “He obviously cared for her,” and was disturbed by what was happening. “I remember telling him, ‘If it’s really real, what you all have, you’ll come back’ ” after his trip and revive the relationship, “ ‘and if it’s not, you’ll go forward.’ ”

A number of small going-away parties occurred during Barack’s last week before he departed. Reformation Lutheran caretaker John Webster remembered one there, which was also where the small CEN program was now centered; Margaret Bagby recalled another one at St. Catherine’s with catered food. One evening everyone from DCP was invited to a quiet party at a small restaurant in suburban Blue Island. Greg Galluzzo, who had spent so many hours with Barack over the previous eighteen months, “bought him a briefcase and had it engraved” with just “Barack” as a useful going-away present for a law student.

On another night, Barack and Bruce Orenstein went out to drink beer, and Barack asked Bruce what he would be doing ten years from now. “I’m going to be making social change videos,” Bruce answered. Bruce in turn asked Barack the same question. He said he intended to write a book about his upcoming trip to Kenya, and then “I’m going to be mayor of Chicago.” Bruce was taken aback. “That was the first I heard of it,” and “I thought it was a lot of moxie to say that he was going to be mayor.”

A few days later, with Sheila having moved from their apartment, Barack flew east. Almost that same day, a dinner announced several weeks earlier was taking place to honor Frank Lumpkin for the eight years he had devoted to winning recompense for the Wisconsin steelworkers who had been thrown out onto the streets of South Deering back in March 1980.

Frank’s loyalties had not changed. The banquet’s proceeds would “benefit the People’s Daily World,” the newspaper of the Communist Party USA, but that did not deter a trio of notable figures from signing on as public patrons. State Senator Miguel del Valle, sponsor of the pending school reform bill, was one, 22nd Ward reform alderman Jesus “Chuy” Garcia was a second, and Monsignor Leo T. Mahon was a third. “Best wishes to a man who fights for justice,” read Leo’s greeting in the banquet program. Maybe Foster Milhouse and the other right-wing zealots had been right all along, that social justice Catholicism and grassroots communism were indeed one and the same.

Roberta Lynch, CCRC’s first staff organizer, and Tribune business editor Dick Longworth both sent their apologies for being out of town, but a crowd of more than four hundred attended, including U.S. congressman Charles Hayes, a veteran of both labor struggles and the 1966 Chicago Freedom Movement. The Daily Calumet gave the event glowing coverage—“Lumpkin Honored at Dinner”—and three days later editorialized in his honor, simply and accurately calling him “a hero.” After eight years of organizing, Frank Lumpkin had prevailed, and even triumphed.

Just short of three, Barack Obama was headed toward Harvard Law School with the intent of becoming not just mayor of Chicago but eventually president of the United States.⁸¹

Barack had scheduled a full month to see the great cities of Europe all by himself: Paris, Madrid, Barcelona, and Rome, then to London and from there to Nairobi. He later wrote that he anticipated “a whimsical detour, an opportunity to visit places I had never seen before,” but his memory would be that “I’d made a mistake” in allocating so many days for his European grand tour, because “it just wasn’t mine.” After almost three years of interacting with a dozen or more people almost every single day, now he was entirely alone in countries where he knew virtually nothing of either the language or the culture.

Before the end of May he was busily dispatching postcards to Sheila, Lena, Cathy Askew, and Cynthia Norris from Paris, “some quite humorous,” Sheila remembered. To Cathy, he wrote about how beautiful the buildings were, to Cynthia he described the city’s astonishing appeal: “I wander around Paris, the most beautiful, alluring, maddening city I’ve ever seen; one is tempted to chuck the whole organizing/political business and be a painter on the banks of the Seine. You’ll be amused to know that since I don’t know a word of French, I’m left speechless most of the time. Wish you a fruitful summer. Love, Barack.”

Traveling largely by bus and train, Barack was also reading a journalistic account of modern Africa in preparation for his visit to Kenya. He later told about meeting and trying to converse with a Senegalese traveler on the way from Madrid to Barcelona, but in subsequent years, Barack never referred to any experiences or memories from his four weeks on the continent. By the last weekend in June, he was in London, where Hasan and Raazia Chandoo had moved six months earlier from Brooklyn. The three of them had lunch in a brasserie before seeing Wim Wenders’s new film, Wings of Desire, at a cinema in Notting Hill.

From London Heathrow, Barack flew to Nairobi. His sister Auma and his Aunt Zeituni, the family member who had been the closest to his late father, met him at the airport, but Barack’s suitcase did not arrive until several days later. In preparation for his visit, Barack also had read a brand-new book on Dedan Kimathi, a Kenyan anticolonial warrior of the 1950s whom the British had executed in 1957, but instead of discussing Kenyan history while he stayed at Auma’s apartment, sleeping on her couch, they talked mostly about their extended clan of relatives. “There was never a moment of silence or embarrassed awkwardness” between them, Auma recalled. But with Barack wanting to meet as many family members as possible, “It wasn’t all nice. Sometimes he wanted to see a relative I didn’t really get along with, and he’d be like ‘It’s my right, and I need to see them, and I’m not going alone, and you’re coming with me,’ ” she explained.

Auma always assented, although her thoroughly unreliable Volkswagen Beetle was their primary mode of transport around sprawling Nairobi. One drive took them to see Auma’s mother Kezia and her sister Silpa Jane, who six years earlier had been the telephone caller who told Barack of his father’s death. On another, Zeituni took Barack to meet her older sister Sarah, who was living in a scruffy slum. But the most difficult visit was to Ruth Baker Ndesandjo, whose son Mark—Barack’s younger brother—was home for the summer and about to begin graduate school at Stanford after having just graduated from Brown. Barack later imagined that Ruth had invited him and Auma to come for lunch, but both Ruth and Mark convincingly remember Barack and Auma turning up with no forewarning. As Mark recounts, a “very awkward, cold” encounter ensued, as Ruth found the unexpected arrival of her ex-husband’s namesake “pretty traumatic.” Years later she recalled, “I closed up. I had nothing to say,” for “I didn’t have the capacity to talk with him or exchange with him because he was a reflection of a man I hated. So I didn’t want anything to do with him.”

Barack wanted to see more of Mark, and they arranged to have lunch a few days later. Mark remembered thinking that Barack had a “cold” demeanor, “absolutely no sense of humor,” and “wanted to shut out any emotional involvement” with his likewise half-Luo, half-white American brother, especially when Mark bluntly stated that “our father was a drunk and he beat women.” Barack later admitted that meeting Ruth and Mark, and grasping at least in part how abusively his father had treated them, affected him deeply. “The recognition of how wrong it had all turned out, the harsh evidence of life as it had really been lived, made me so sad,” far more so than he had been three years earlier when he had learned during Auma’s visit to Chicago just how deeply tragic a life Barack Obama Sr. had led.

During Barack’s second week in Kenya, Auma took him on a wild-game safari, and then the two of them plus Zeituni and Kezia took a train northwest to Kisumu and then a jitney bus to the family homestead at Nyang’oma Kogelo. There Barack met Sarah, the stepmother who had raised his father. Barack asked her if anything of his father’s still survived. “She opened a trunk and took out a stack of letters, which she handed to me. There were more than thirty of them, all of them written by my father,” carbon copies “all addressed to colleges and universities all across America” from when Obama Sr. was seeking admission to the University of Hawaii and other colleges. Holding them reminded Barack of the letters he had written a few years earlier, “trying to find a job that would give purpose to my life.”

That moment, even more than standing at his father’s unmarked grave in the side yard of Sarah’s small, tin-roofed brick home, marked the most powerful and direct paternal link Barack had ever experienced. The connection was underscored when relatives remarked that Barack’s voice sounded “exactly how his father spoke.” Barack’s visit to Nyang’oma Kogelo, like his earlier one to Aunt Sarah in that Nairobi slum, made Barack realize that his Kenyan relatives’ lives sometimes paralleled those of people whom he knew in Altgeld Gardens. Pondering John McKnight’s analysis, in Kogelo Barack wondered whether “the idea of poverty had been imported to this place, a new standard of need and want.”

Barack later wrote that while in Kenya, “for the first time in my life, I found myself thinking deeply about money,” perhaps foreshadowing the debt load he was about to take on to follow his father’s footsteps to Harvard rather than attend Northwestern cost free. He told Auma that his decision to attend law school was a response to his experiences in Chicago, because as a community organizer he could not “ultimately bring about significant change.” Back in Nairobi, everyone went to a photography studio so that a family portrait could be taken, and Barack and Auma made a brief visit to an elementary school so that he could meet his youngest sibling, George, the son of Jael Atieno.

One night Auma took Barack to meet one of her former teachers, a woman who had also known their father. Barack recounted her presciently telling him that being a historian “requires a temperament for mischief” and instructing him that when confronted with roseate fictions, “truth is usually the best corrective.” For his final weekend in Kenya, Auma and Barack took a train eastward to the country’s second largest city, coastal Mombasa. Overall, “it was a magical trip,” Barack remembered, an immersion into the life of the father who had abandoned him, an immersion that “made me I think much more forgiving of him” than he had been before experiencing Luo life and culture for the very first time.⁸²

Before the end of July, Barack returned to Chicago, where he was all alone in the 5429 South Harper apartment until the lease expired in early August. When Asif’s friend Doug Glick stopped by, he was struck by how different the place looked without Sheila. But Barack and Sheila’s two months apart had not ended the relationship between them. Johnnie Owens had run into Sheila in Hyde Park during the summer and remembers how “upset,” even “brokenhearted” she seemed about what had happened just before Barack’s trip. But Barack’s more-than-weekly letters from Europe and Kenya had rebuilt much of their bond. Even so, in little more than two weeks he had to head to Massachusetts before the start of Harvard’s fall semester. He needed to purchase a better car than the blue Honda Civic that he had driven from Manhattan just over three years earlier, and he replaced it with an off-yellow 1984 Toyota Tercel hatchback he bought for $500 from a suburban police officer.

Barack also wanted to be sure that Johnnie’s transition was going as smoothly as possible, not just at DCP, where everyone already knew Johnnie, but also with DCP’s downtown supporters. “He made sure that the leaders were comfortable,” Johnnie remembered, but “the main thing he did was transfer those financial funder relations” with Jean Rudd at Woods, Anne Hallett at Wieboldt, and Aurie Pennick at MacArthur. Just a few weeks later, MacArthur would award DCP its second annual $20,000 grant. Barack “left the organization in a very good position,” Johnnie explained, and the effort Barack put into the transition further showed that he intended to return to Chicago after law school.

Barack’s greatest disappointment was the lack of state funds to expand DCP’s after-school tutoring program, but with state government consumed by the struggle over Chicago school reform, the legislature had remained in session beyond its normal end-of-June adjournment to pass a compromise bill. At the end of May, reform forces had reunified themselves into a new coalition called the Alliance for Better Chicago Schools, or ABCs, with UNO playing a lead role and DCP a minor one. A massive June 6 rally had called upon reform supporters to make their case in person to state legislators in Springfield, and the slogan “Don’t come home without it!” became reformers’ new rallying cry.

The Chicago City Council approved a vote of no confidence in Manford Byrd by 39 to 4, soon followed by the resignation of a board of education member who now felt similarly. “I assumed education was the first priority of the whole system, and it is not,” retired business executive William Farrow announced. Down in Springfield, House speaker Michael J. Madigan brought the interested parties together for marathon negotiation and drafting sessions in his office. Danny Solis and Al Raby both took part, but the most influential participant was one of Madigan’s deputies, Chicago state representative John Cullerton. By the end of June Al Raby was proclaiming that “real reform of Chicago schools is within our grasp,” and on Saturday, July 2, both houses of the state legislature passed a compromise bill. Failure to adopt the measure by the end of June would delay its effective date for a year, but Chicago United’s Patrick Keleher said the bill represented “as much if not more than any of us had hoped for.”

Barack heard far less encouraging news about his other top concern, the Southeast Side landfill tussle. Mayor Sawyer’s new UNO-and-DCP-dominated task force had held additional public hearings during June, and in late July met privately with both city and Waste Management representatives. By the end of the summer, its report to Sawyer was complete, though several weeks would pass before cochairs Loretta Augustine and Mary Ellen Montes joined the mayor at a City Hall press conference. “The city of Chicago is facing a crisis,” Sawyer announced. “We’re going to have to bite the bullet and do some things that we would prefer not to do,” namely allow the O’Brien Locks site to become a landfill. That outcome had always looked inevitable, but Bruce, Barack, and Mary Ellen’s strategic success in blowing up the Fitch negotiations meant that any landfill now would be controlled not by Waste Management but by the Metropolitan Sanitary District.

Alinsky-style warfare had not only destroyed a likely Southeast Side consensus to accept a quid-pro-quo deal with Waste Management, it had deprived those neighborhoods of the multimillion-dollar bounty WMI had been willing to pay. It was a debacle all around. A decade later, Jim Fitch would be sent to federal prison for eighteen months and fined $1 million for looting bank funds throughout the 1980s in order to contribute to Southeast Side politicians. Another decade further on, with UNO having abandoned South Chicago and transformed itself into something that bore no resemblance to the organization that Mary Gonzales, Greg Galluzzo, and Mary Ellen Montes had originally built, UNO would endorse a Waste Management effort to expand Southeast Side landfills.

In Barack’s final days before he left for Harvard, the DCP members to whom he had become closest held a small barbecue for him at Loretta Augustine’s home. He assured them, “If you have problems, you can contact me and I’ll do what I can.” He also had a trio or more of presents for them, wooden figurines he said he had brought back from Kenya. Dan Lee remembered that Barack gave him “a statue of a warrior with a chipped beard.” Cathy Askew recalled admiring a giraffe, but “I think he gave me the zebra because of the mixed black and white stripes,” an acknowledgment of their disagreement about biracial identity.

Mary Ellen Montes did not attend that party, but one evening Barack took her out to dinner at a downtown restaurant. “We had our own kind of little going-away party, Barack and I, and it was just Barack and I,” she remembered. Barack promised to write to her, and he would, but that night, or the next morning, was the last time Lena and Barack would see each other in person.

With the lease on the South Harper apartment expiring several days before Barack planned to leave, he joined Sheila in her apartment on South Kimbark. She was preparing to leave Chicago soon too to begin her dissertation fieldwork in South Korea thanks to a Fulbright fellowship, and when she joined Barack for a farewell visit to Jerry Kellman’s home, they had a question for Jerry and his wife. “They come to dinner at our house,” Jerry remembered, “and they say ‘Could you please keep this cat?’ ” The Kellmans willingly agreed to give Max a new home. “Barack was not sad to give Max away,” Sheila explained, but for Max the transition was all to the good, and he would enjoy eight years of love with the Kellmans.

Jerry knew that Barack and Sheila were not breaking up, just headed in different geographical directions. He thought “they had a great, healthy relationship,” although one that was now constrained by Barack’s career plans. “By the time Barack left to go to law school, he had made the decision that he would go into public life,” Jerry realized. Indeed, “my sense is that Barack’s dream was to come back and possibly become mayor of Chicago.”

But Barack was still trapped between his belief in his own destiny and his deep emotional tie to Sheila. One day that final week “he said that he’d come to a decision and asked me to go to Harvard with him and get married, mostly, I think, out of a sense of desperation over our eventual parting and not in any real faith in our future,” Sheila recalled. Her memory was reminiscent of Genevieve’s from three summers earlier, when Barack had asked her to come to Chicago with him, and Genevieve had thought Barack was asking her only because he was certain her answer would be no.

Now, once again, the answer was no, and Sheila was upset by Barack’s presumption that she should postpone, if not abandon, her dissertation research in order to accompany him to Harvard. A “very angry exchange” followed, with Sheila feeling that Barack believed that his career interests should trump hers.

Barack started eastward within a day or two, knowing he could stay temporarily with his uncle Omar, who had remained in greater Boston ever since first arriving there thanks to his older brother a quarter century earlier and whose phone number and address Aunt Zeituni had given Barack while he was in Nairobi. But before heading back down Stony Island Avenue to the Skyway and then the Indiana Toll Road, Barack needed to have one other conversation.

“I was a little troubled about the notion of going off to Harvard. I thought that maybe I was betraying my ideals and not living up to my values. I was feeling guilty,” he told a college audience just six years later. Barack called Donita at Trinity and made an appointment to see Jeremiah Wright to seek his counsel about those doubts. In a way, it was just like the conversation he had had nine Augusts earlier, in Honolulu, when eighteen-year-old Barry had gone to visit Frank Marshall Davis before leaving for Occidental and life on the mainland.

Years later, before their relationship was torn apart, Wright would say that Barack was “like a son to me.” One of the most knowledgeable and savvy women in black Chicago would make the same point: “Jeremiah Wright was the black male father figure for Barack,” she emphasized. “Don’t underestimate the influence that Jeremiah had on Barack.” Wright would not specifically remember their conversation that August day, but Barack always would. In a way, it was a three years’ bookend to the admonishing monologue about being a do-gooder that Bob Elia have given him that night in the motel lobby on South Hermitage Road.

That exchange would stay with Barack always, as would this one, but the substance of Wright’s message was identical to the warning that old Frank had voiced: “You’re not going to college to get educated. You’re going there to get trained,” trained “to manipulate words so they don’t mean anything anymore,” trained “to forget what you already know.” Wright’s message was just five words, ones that would ring in Barack’s ears for the entire two-day drive eastward: “Don’t let Harvard change you!”⁸³