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CHAPTER TWO

South Boston

In order to wait for Whitey at Wollaston Beach, John Connolly had to first get himself home from New York. Flemmi’s boyhood pal “Cadillac Frank” Salemme would be his ticket.

Salemme’s arrest happened on a cold bright New York afternoon in December 1972, when the good guys and the bad guys floated past each other on Third Avenue. A face in the crowd suddenly clicked with Connolly, who told his FBI companions to unbutton their winter coats and draw their guns. A slow, almost comical footrace on snow ended with jewelry salesman Jules Sellick of Philadelphia protesting that he was not Frank Salemme of Boston, wanted for the attempted murder of a mobster’s lawyer. But indeed he was.

The young agent had no handcuffs with him and had to stuff Salemme into a taxi at gunpoint and bark at the bewildered cabbie to drive to the nearby FBI headquarters at East Sixty-ninth and Third. His boss chided him good naturedly about the handcuffs, but there were envious smiles and back slaps all around for bagging one of Boston’s most wanted mobsters. Some were amazed that Connolly had been able to recognize Salemme, but in fact it wasn’t quite as lucky as it first appeared. An old pro in the Boston FBI office had taken a shine to Connolly and earlier had sent him photographs and likely locations for spotting Salemme, gleaned from informant reports. It was a perfect example of how valuable informants could be. Connolly’s apprehension of Cadillac Frank resulted in a transfer back home, an unusually quick return for an agent with only four years of duty under his belt.

By 1974 Salemme was off to fifteen years in prison and Connolly was back to the streets of his boyhood. By this time Bulger was the preeminent Irish gangster in the flagrantly Irish neighborhood of South Boston. When Connolly returned, Bulger had just solidified his hold on Southie’s gambling and loan-sharking network, the culmination of a slow, steady climb that began in 1965 with his release from the country’s toughest prisons.

The two men spoke the same language and shared deep roots in the same tribal place. They came together as book ends on the narrow spectrum of careers available to Irish Catholics who lived in splendid isolation on the spit of land jutting into the Atlantic Ocean. Their cohesive neighborhood was separated from downtown Boston by the Fort Point Channel and a singular state of mind. For decades Southie had been immigrant Irish against the world, fighting first a losing battle against shameful discrimination from the Yankee merchants who had run Boston for centuries and then another one against mindless bureaucrats and an obdurate federal judge who imposed school busing on the “town” that hated outsiders to begin with. Both clashes were the kind of righteous fight that left residents the way they liked to be: bloodied but unbowed. The shared battles reaffirmed a view of life: never trust outsiders and never forget where you come from.

A retired cop once recalled the constricted choices a young man had coming of age in the South Boston of the 1940s and 1950s: armed services, city hall, utility companies, factory work, crime. “It was gas, electric, Gillette, city, cop, crook,” he said. The decades of travail made Southie residents quick to fight for limited opportunities.

Bulger and Connolly, crook and cop, grew up in the first public project in Boston, a spartan village of thirty-four tightly spaced brick tenement buildings. A contractor friend of the legendary Mayor James Michael Curley built it with money from the Public Works Administration of Franklin Delano Roosevelt. Both men were revered in the Bulger home on Logan Way—Curley for his roguish repartee and Roosevelt for saving the workingman from the ravages of capitalism.

Connolly’s parents—John J. Connolly, a Gillette employee for fifty years, and his stay-in-the-background mother, Bridget T. Kelly—lived in the project until John was twelve years old. In 1952 the family moved “up” to City Point, which was Southie’s best address because it looked out to sea from the far end of the promontory. Connolly’s father was known as “Galway John,” after the Irish county of his birth. He made the church, South Boston, and his family the center of his life. Somehow the father of three pulled the money together to send John to the Catholic school in the Italian North End, Columbus High. It was like traveling to a foreign country, and John Jr. joked about a commute that required “cars, buses, trains.” The Southie instinct for patriotic duty and a public payroll also led Connolly’s younger brother James into law enforcement. He became a respected agent with the US Drug Enforcement Administration, a subdued version of his swaggering older brother.

The Connollys and Bulgers reached adolescence in a clean, well-lit place by the sea surrounded by acres of parks and football and baseball fields and basketball courts. Sports were king. Old Harbor had intact families, free ice cream on the Fourth of July, and stairwells that were clubhouses, about thirty kids to a building. The twenty-seven-acre project was the middle ground between City Point, with its ocean breezes and lace curtains, and the more ethnically diverse Lower End, with its small, box-shaped houses that sat on the edge of truck routes leading to the factories and garages and taverns along the Fort Point Channel. To this day the neighborhood consistently maintains the highest percentage of long-term residents in the city, reflecting a historic emphasis on staying put rather than getting ahead that engenders fierce pride. As South Boston bowed slightly to gentrification along its untapped waterfront in the late 1990s, its city councilor sought to reaffirm traditional values by outlawing French doors on cafés and roof decks on condos facing the sea.

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The us-versus-them mentality at the core of Southie life goes even deeper than its Irish roots. Before the first major wave of Irish immigrants washed over the peninsula after the Civil War, an angry petition to the “central” government had arrived at city hall in 1847 complaining about the lack of municipal services. It would be a couple decades before the famine immigrants, who stumbled ashore in Boston as the potato blight wracked Ireland from 1845 to 1850, made their way to the rolling grass knolls of what was then called Dorchester Heights. The famine had reduced Ireland’s population by one-third, with one million dying of starvation and two million fleeing for their lives. Many of them headed to Boston, as the shortest distance between two points, and spilled into the fetid waterfront tenements of the North End. By the 1870s they were grateful to leave a slum where three of every ten children died before their first birthday.

The newly arrived Irish Catholics took immediately to Southie’s grievance list with outside forces. Indeed, it became holy writ as the community coalesced around church and family, forming a solid phalanx against those who did not understand their ways. Over the decades since then, nothing has galvanized Southies more than a perceived slight by an outsider who would change The Way Things Are. In the Irish Catholic hegemony that came to be, a mixed marriage was not just Catholic and Protestant; it could also be an Italian man and an Irish woman.

Although Boston had been an established city for two centuries by the time the bedraggled famine immigrants arrived, South Boston did not become a tight-knit Irish community until after the Civil War, when newly created businesses brought steady employment to neighborhood residents. In the war’s aftermath the peninsula’s population increased by one-third to its present level of thirty thousand. Irish workers began to settle in the Lower End to take jobs in shipbuilding and the railroad that spoke to the era. Soon local banks and Catholic churches opened their doors, including St. Monica’s, the Sunday destination of Whitey Bulger’s younger brother Billy and his tag-along pal John Connolly.

In the latter part of the nineteenth century most men worked on Atlantic Avenue unloading freight ships. Women trekked across the Broadway Bridge after supper to the city’s financial district, where they scrubbed floors and emptied wastebaskets, returning home over the same bridge around midnight. By the end of the century the Irish Catholic foothold was such that residents congregated according to their Irish county of origin—Galway was A and B Streets, Cork people settled on D Street, and so on. The clannishness was part of the salt air. It was why John Connolly of the FBI could quickly resume an easy relationship with an archcriminal like Whitey Bulger: certain things mattered.

Beyond common ethnic roots, the magnet of daily life was the Catholic Church. Everything revolved around it—Baptism, First Communion, Confirmation, Marriage, Last rites, Wakes. On Sundays, a day apart, parents went to early mass, and sons and daughters attended the children’s mass at nine-thirty. There was a natural cross-fertilization with politics, with one of the first steps toward public office sometimes being the high-visibility job of passing the hat along the pews.

Like Ireland itself, Southie was a grand place—as long as you had a job. The Depression swung like a wrecking ball through South Boston’s latticed phalanx of family and church. The network that had worked so well collapsed when the father in the house was out of work. A relentless unemployment rate of 30 percent badly damaged the Southie worldview that the future could be ensured by working hard and keeping your nose clean. It changed the mood in a breezy place, and ebullience gave way to despair. And it wasn’t just Southie: Boston’s economy had calcified, and well into the 1940s, the formative years for the Bulger boys and John Connolly, the city was a hapless backwater down on its luck. Its office buildings were short and dreary, and its prospects were dim. Income was down, taxes were up, and business was lethargic. The legacy of a ruling oligarchy of Brahmins who lost their verve afflicted the city. The dynamic Yankees of the nineteenth century had given way to suburban bankers indifferent to downtown, a generation of cautious coupon clippers who nurtured trust funds instead of forging new businesses. In tandem, hopeful immigrants became doleful bureaucrats. Nothing much changed until the urban renewal of the 1960s.

It was to this hard time and place that James and Jean Bulger arrived in 1938, looking for a third bedroom for their growing family in the first public housing project in Boston. Whitey was nine, Billy four. The Bulgers would raise three boys in one bedroom and three girls in another. Although the Old Harbor project was a massive playground for the children, parents had to be nearly broke to get into it. The Bulgers easily met this criterion. As a young man James Joseph Bulger had lost much of his arm when it was caught between two railroad cars. Although he worked occasionally as a clerk at the Charlestown Navy Yard, doing the late shift on holidays as a fill-in, he never held a full-time job again.

A short man who wore glasses and combed his white hair straight back, James Bulger walked the beaches and parks of South Boston, smoking a cigar, a coat hanging over the shoulder of his amputated arm. His hard life had begun in the North End tenements just as the Irish neighborhood of the famine era was giving way to another immigrant wave, this one from southern Italy in the 1880s. He had a strong interest in the issues of the day; one of Billy’s boyhood friends remembered bumping into him on a walk and being waylaid by a long discussion of “politics, philosophy, all this stuff.” But the father was a loner who stayed inside the apartment most of the time, especially when the Red Sox were on the radio. In contrast, the loquacious Jean was usually found on the back stoop at Logan Way, chatting with neighbors, even after a hard day of work. Many of the neighbors recalled Jean Bulger as a sunny, savvy woman who was easy to like and hard to fool. They say Billy was like her—friendly and outgoing, running off to the library with a book bag or to the church for a wedding or funeral, his altar boy cassock flying over his shoulder.

But Billy also shared his father’s concerns for privacy and his solitary ways. In a rare interview about his family Bulger talked wistfully about his father, his stoic manner and hard-luck fate, wishing that they had talked more and that there had been more shared moments. He recalled the day he went off to the army toward the end of the Korean War, his parents tight-lipped with worry because their son-in-law had been killed in action two years earlier. James and Jean took Billy to South Station for the train to Fort Dix, New Jersey. His father, then nearly seventy years old, walked behind him down the aisle, following him to his seat. “I thought, ‘What’s this?’ You know how kids are. My father, and this was unusual for him, he took my hand and said, ‘Well, God bless you, Bill.’ I remember it because it was quite a bit more than my father was inclined to say.”

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Billy Bulger ran for public office in 1960 because he needed a job as he neared graduation from Boston College Law School and married his childhood sweetheart, Mary Foley. John Connolly was one of his campaign workers. Originally, Bulger was going to stay a few terms in the House of Representatives and then leave for private practice as a criminal defense lawyer. But he stayed on, juggling a small law practice, the legislature, and a booming family. The Bulgers would have nine children, about one a year during the 1960s. Billy moved up to the Senate in 1970 and went on to be president of the chamber longer than any man in Massachusetts history.

As he progressed through the legislature Billy came to epitomize South Boston, with his jutting jaw and conservative agenda. He became a provocative statewide figure who delighted in tweaking suburban liberals who thought busing was a good idea for his neighborhood but not for their own. He had a passion for refighting old lost battles, none more emblematic than the statewide referenda he forced on an indifferent electorate in the 1980s to right an ancient wrong he found in the state constitution. An anti-Catholic 1855 provision banned aid to parochial schools, and although Bulger readily admitted it had done no lasting harm, he wanted it smitten because of the original intent. That the correcting amendment was overwhelmingly rejected twice at the polls made no matter. The fight was the thing.

It was all part of what made him one of the dominating politicians of his time, a paradoxical figure who drew on a rare mixture of scholarship and mean streets. At once he was a petty despot and masterful conciliator, a reserved man who loved an audience, a puckish public performer who had a dark side and took all slights personally. His bad side remains a precarious place to be.

Though Billy Bulger was well known for his scholastic and high-minded style, he could show another side as well. In 1974, when antibusing protesters were arrested outside a neighborhood school, Bulger was on the scene and denounced the police for overreacting. He went nose to nose with the city’s police commissioner, Robert diGrazia, jabbing his finger at him about his “Gestapo” troopers and angrily walking away. DiGrazia yelled a retort about politicians lacking “the balls” to deal with desegregation earlier when things could have been different. Bulger spun around for more, working his way up to the much taller diGrazia. “Go fuck yourself,” the senator hissed into diGrazia’s face.

As busing turned Southie on its ear, even Whitey Bulger got into the act, but in the incongruous role of peacemaker. He worked behind the scenes to try to bring some calm to the streets among his followers. His exhortations were hardly the stuff of civic altruism. By raising the prospect of a protracted police presence in South Boston, busing was simply bad for business. So Whitey spread the word to his associates not to exacerbate the tensions boiling over in the schools.

Despite the fractious 1970s, Billy rose quickly in the Senate and ruled it with an iron hand by decade’s end. But he would struggle with an image steeped in Southie lore, the good and the bad. It made him a hero in the town and anathema in a liberal Democratic state. His dilemma was captured in the late 1980s when he was fighting off the latest reform movement to bring debate and democracy to the Senate. A colleague tried to convince him he could be a hero if he loosened his grip on the chamber ever so slightly. But Bulger just shook his head. “No, not guys like me,” he said. “I’ll always be a redneck mick from South Boston.”

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As a project kid Connolly got to know both Bulger brothers. He became good friends with Billy, drawn to the maturity and humor that made Billy as distinctive as Whitey was notorious. Billy was the one who Connolly tagged along after on the way home from mass at St. Monica’s and who got him into books, though Connolly and his friends generally thought that was a crazy notion in such a sports-mad environment.

Connolly also came to know the infamous Whitey as the hellion of Old Harbor who kept the project in an uproar with his street fights and audacious antics. Indeed, everyone knew Whitey, even eight-year-old kids like Connolly. Once Connolly was in a ball game that turned ugly. An older boy decided Connolly was taking too much time retrieving a ball and fired another one into the middle of his back. His back stinging, Connolly instinctively picked up the ball and fired a high hard one into the kid’s nose. The older boy was all over the smaller Connolly, pounding away, beating him up pretty good. Then, from the margins of the playground, Whitey swooped in to break up the one-sided fight. Bloodied, Connolly staggered to his feet, forever grateful. At some level Connolly would always stay a poor city kid looking for acceptance in a hardscrabble world, permanently susceptible to the macho mystique of Whitey Bulger.

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When John Connolly was a toddler on O’Callahan Way, Whitey Bulger was already tailgating merchandise off the back of delivery trucks in Boston’s minority neighborhoods. He was thirteen years old when first charged with larceny and moved on quickly to assault and battery as well as robbery, somehow avoiding reform school. But he was nevertheless targeted by the Boston Police, who frequently sent him and his fresh mouth home more battered than they’d found him. His parents worried that the bruising encounters would only make him worse, and indeed, the stubborn teenager exulted in his confrontations at the police station, swaggering around the tenement and daring younger kids to punch his washboard stomach so he could laugh at them. In a few short years he became a dangerous delinquent with a Jimmy Cagney flair, known for vicious fights and wild car chases. His probation files reveal him to have been an indifferent student who was lazy in school, the polar opposite of his brother Bill. He never graduated from high school, but he always had a car when everyone else took the bus.

One Bulger contemporary, who grew up in Southie before going into the Marines and law enforcement, played in the ferocious no-pads football games on Sundays and recalled Bulger as an average athlete but a fierce competitor. “He wasn’t a bully, but he was looking for trouble. You could sense him hoping someone would start something. There was some admiration for the way he handled himself. At least back then, there was a sense he would be loyal to his friends. That was the culture of the time. It was incredibly tribal, and the gang affiliation meant so much to poor city kids.”

Bulger did most of his tailgating with the Shamrocks, one of the successor gangs to the mighty Gustins. The Gustins had had a chance to be Boston’s dominant crime organization during Prohibition, but its leaders reached too far in 1931 when they sought citywide control over bootlegging along Boston’s wide-open waterfront. Two South Boston men were murdered when they went to the Italian North End to dictate terms to the Mafia and guns roared out at them from behind the door of C&F Importing. Law enforcement still views the Gustin gang’s fate as a demarcation point in Boston’s crime history. Boston’s stunted Mafia would survive in Italian sections of the city, and the more entrenched Irish gangs would retreat to South Boston, ensuring a balkanized underworld in which factions stayed in ethnic enclaves. Sometimes, for the sake of high profits, the two groups collaborated. But Boston, along with Philadelphia and New York, would be one of the few cities where persistent Irish gangs would coexist by putting the Mafia loan-shark money out on the streets of their neighborhoods.

The Gustin gang’s standoff with the Mafia also gave Whitey Bulger the freedom to move around South Boston’s freewheeling crime circuit, graduating from tailgating trucks in Boston to robbing banks and, at age twenty-seven, doing hard time in the country’s toughest federal prisons. His prison file portrays a hard case who was fighting all the time and doing long stretches in solitary. He was viewed as a security risk and once did three months in the hole in Atlanta before being moved to the ultimate maximum-security prison, Alcatraz, because he was suspected of planning an escape. He wound up in solitary there too, over a work stoppage, but finally settled down to do his time, moving east to Leavenworth in Kansas and then to his last stop—Lewisburg, Pennsylvania—before returning to Boston. Bulger went to prison when Eisenhower was still in his first term in 1956 and returned home in 1965 when Lyndon Johnson was firing up the Vietnam War. His father, who had lived long enough to see Billy elected, had died before Whitey’s release.

Bulger came home as a hard-nosed ex-con who nevertheless moved back in with his mother in the projects. For a while he took a custodian’s job, arranged by Billy, at Boston’s Suffolk County Courthouse. The job reflected the politics of South Boston—a magnified version of Boston’s old-style ward system in which bosses built fiefdoms by controlling public jobs. In the old days this system had been a lifeline for unskilled immigrants with large families, but in the 1960s it could result in a janitor’s job for an ex-con. After a few years of keeping his nose clean on parole, Whitey took a deep breath and jumped back into the underworld, quickly becoming a widely feared enforcer. The Southie barroom patrons from whom he collected gaming and shylock debts were seldom late again.

The disciplined, taciturn Bulger was clearly a cut above in the brutal world he so readily reentered. For one thing, he was well read, having used his decade in prison to focus on World War II military history, searching for the flaws that had brought down generals. It was part of an instinctive plan to do it smart the second time around. This time he would be a cagey survivor, mixing patience with selective brutality. He would no longer provoke police with flip remarks but rather present himself as someone who had learned the ropes in prison, someone who would assure detectives during routine pat-downs that they were all good guys in their small gathering and he was just a “good bad guy.”

A couple years after being released from prison in 1965, Whitey Bulger did much of his work with Donald Killeen, then the dominant bookmaker in South Boston. But after a few years Bulger developed misgivings about Killeen’s faltering leadership and incessant gangland entanglements. More important, Bulger began to fear that he and Killeen would be killed by their main rivals in South Boston—the Mullen gang of Paul McGonagle and Patrick Nee. One of Bulger’s closest associates had been gunned down in a desperate run for his front door in the Savin Hill section of Boston. It seemed a matter of time before Killeen or Bulger himself met the same fate.

In May 1972 Whitey’s dilemma about standing with the beleaguered Killeen was resolved when he ruthlessly chose survival over loyalty; even though he was Killeen’s bodyguard, Bulger entered into a secret alliance with his enemies. In order to survive, Bulger had to make a hard choice about business partners in Boston’s bifurcated underworld: subordinate himself to the Italian Mafia, which he detested, or forge a deal with the Winter Hill gang, which he distrusted.

But Bulger was in a bind that could never be resolved, with stubborn Donald Killeen calling the shots and the Mullen gang bent on revenge. There would be no truce with the Killeen brothers, what with Paulie McGonagle’s brother being murdered, Buddy Roache paralyzed for life by gunfire, and the nose that got bitten off Mickey Dwyer’s face.

Desperate for mediation, Bulger chose the lesser of two evils and went, hat in hand, to Winter Hill. In the spring of 1972 he sought a secret truce with the Mullens through the aegis Winter Hill boss, Howie Winter. The terms: Bulger would help arrange the end of Donald Killeen, and Winter would guarantee the end of the Southie gang war and sanction Bulger as the town’s new boss. Bulger’s wedge was that he controlled the lucrative gambling and loan-sharking business and the Mullens were hand-to-mouth thieves.

The clandestine meeting, held at Chandler’s Restaurant in the South End, ran several hours into the early morning. Bulger faced off with four Mullens, with Winter sitting in the middle of the table and ultimately ruling that the conflict was long past the point of diminishing returns and, not incidentally, there was plenty of money to go around. Whitey agreed to cut truck hijackers into the steady income to be had from hard-luck Southie gamblers.

Shortly afterward Killeen was called away from his son’s fourth birthday party. As he was starting his car he saw a lone gunman racing at him from the nearby woods. As Killeen went for his gun under the seat the gunman pulled open the driver’s door and jammed the machine gun near his face. He then fired off a fifteen-bullet burst. The gunman fled down the driveway to a revving getaway car. No one was ever charged with the shooting, but it became part of Southie lore that Bulger was behind it. The finishing flourish occurred a few weeks later when Kenneth, the youngest brother in the Killeen family, jogged past a car parked near City Point with four men in it. A voice called out “Kenny.” He turned to see Bulger’s face filling the open window, a gun tucked under his chin. “It’s over,” the last Killeen bookmaker standing was told. “You’re out of business. No other warnings.”

The fast, bloody “Godfather” takeover was the stuff of legends. It was the kind of dramatic, decisive move that by nightfall would be known throughout Southie, a formal notice to the underworld that Bulger was soon to manipulate and control.

It was a new era awash in blood, as Bulger eliminated the Killeens and then showed up for work at the Marshall Motors garage in Somerville that served as Howie Winter’s base of operations. Bulger spoke for all the South Boston rackets and was looking for bigger opportunities. Whitey had Southie, and, for a short time, Howie had Whitey.

Though his wealth grew exponentially, Bulger’s lifestyle would never change. He was the antithesis of the gaudy mafiosi of the North End—no Cadillacs, no yachts, no oceanfront homes. Bulger seldom drank, never smoked, and worked out daily. His one weakness was for a Jaguar that he kept garaged in City Point most of the time. Overall, he lived a quiet life with his mother in the Old Harbor project, staying with her until her death in 1980.

His new agenda was to stay disciplined and not give in to the anger of his youth, when he had been charged with rapes in Boston and in Montana while in the air force. He would indulge neither the restlessness that had led him as a fourteen-year-old to bound impulsively out the door in Old Harbor and join Barnum & Bailey’s circus as a roustabout, nor the recklessness of the young gangster who walked into an Indiana bank with a silver gun and his accomplices to take away $42,112 in deposits from an Indiana bank. Gone were his days as a crook on the run who dyed his hair black to go into hiding from the FBI, only to be arrested at a nightclub surrounded by agents. No, the second time around he would stay in control and behind the scenes. Those years of reading in prison libraries had sharpened his instincts, and his mind had become an encyclopedia of law-enforcement tactics and past mobster mistakes. Like a chessmaster, Bulger was confident that he knew the moves, that he could watch your opening and lead you straight to checkmate. He vowed to friends that he would never, ever go back to jail.

Like all mobsters, Bulger worked the underworld’s night shift, starting out in the early afternoon and ending in the wee hours. He presented a studied, icy detachment for those in his world but a small smile for his mother’s aging friends at the project, where he would hold doors for them and tip his hat. For a time he delivered holiday turkeys to families in need at Old Harbor. In his own way he remained devoted to his family and was fiercely protective of Billy. When their mother died in 1980, Whitey kept a low profile for his brother’s sake, fearing that a news photographer would put him and the new president of the Massachusetts state senate in the same frame on page 1. His furtive and alienated life was such that he sat up in the balcony behind the organist during the services and then watched as his five siblings slowly walked the casket out of the church below. As a parish priest summed it up, blood is blood.

But Bulger had a fearsome mystique about him that terrified Southie’s rank and file. When a resident accidentally bumped into him coming around a corner in Bulger’s liquor store, the cold, hard glare he got was enough to make him soil his pants. As John Connolly conceded, “You cannot have a problem with him.”

Ellen Brogna, wife of the usually incarcerated Howie Winter, had been around gangsters most of her life, but Whitey Bulger chilled her. Not long after Bulger began working out of the garage in Somerville, they were all having dinner one night. For some reason Bulger had to move Brogna’s Mustang. She flipped him the keys, but he came raging back in when he was unable to turn the car over, not realizing there was a button to press before the key would turn. She tried joking with him that he should be an expert now that he was hanging around Marshall Motors. Bulger just stared daggers at her and then stormed off. Later that night she told Howie that dealing with Bulger was like looking at Dracula. Howie just thought it was funny.

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The post-Alcatraz Bulger was still a volatile man, but one who had learned the value of controlling himself. He was a poster boy for the stoic, stand-up Southie, with a chiseled, macho look that gave him an instant presence. His ice-cold manner cut like a cleaver to the heart of the matter. This trait, of course, made him the perfect informant, which is why Dennis Condon, the wily FBI agent who worked organized crime for decades, had kept after Bulger in the early 1970s. But though he came from a similar background across the harbor in Charlestown, Condon didn’t come from the unique place at issue—South Boston. Condon closed out the Whitey Bulger informant file with great reluctance, sensing it might work for the bureau if he could just put Bulger with a “handler” from “the town.” The young agent John Connolly was from central casting—streetwise, fast talking, and, best of all, born and raised in the Old Harbor project.

Condon had first met Connolly through a Boston detective who knew them both. Connolly, finishing up a stint as a high school teacher, was attending law school at night but eager to join the bureau.

After Connolly signed on with the FBI in 1968, Condon kept in touch with him during his tours of duty through Baltimore, San Francisco, and New York. They talked when Connolly came home to marry a local woman, Marianne Lockary, in 1970. While Bulger bobbed and weaved for survival, Condon took steps that would help Connolly get transferred back to Boston. It was believed that the precise details on Frank Salemme’s whereabouts, given to Connolly by Condon, came from Stevie Flemmi, who had had a falling out with his boyhood buddy.

Connolly returned to the smaller, more intimate scale of Boston, readily swapping Brooklyn for Southie, Yankee Stadium for Fenway Park. He left an office with 950 agents focusing on New York’s five crime families for one with 250 agents who were barely up to speed on Gennaro Angiulo. He could see that playing field better, and he knew the people by their nicknames. He was a Boston boy and he was back home, raring to fill out the G-man’s suit with style. But Connolly was also an empty vessel who got filled up by those around him. As a teenager he was seen as a “shaper,” a wanna-be who looked good in a baseball hat but was never much of a player. As an agent he was more about playing the role than doing the work. He was always more glib salesman than hard-eyed cop. When he returned home from New York, he was an impressionable young agent suddenly plunged into a movie-script life. His dream assignment became getting close to a bad guy he had long admired. John Connolly fell in love.

It was a fatal attraction to the seductive personality of Whitey Bulger. Bulger was magnetic in the reverse glamour way of elite gangsters who break all the rules and revel in it. For Connolly it was an enthralling prospect, a future assured. Working with Whitey—what could be better? What could be easier? It sure beat being one of 250 selfless agents riding around in a government car. Whitey would be the head on Connolly’s glass of beer.

In the first few years of his renewed relationship with Whitey Bulger, Connolly’s “209” informant reports were split between accounts of disenchantment within the ranks of Gennaro Angiulo’s chronically unhappy Mafia family and more concrete tips about Bulger’s rivals within South Boston. Connolly did not remind Bulger that he had originally pledged to inform only about the Italians. And though the Mafia information was mostly generic gossip about problems in the House of Angiulo, the rat file on South Boston came with addresses, license plates, and phone numbers. For instance, Tommy Nee, one of a handful of homicidal maniacs who were regularly committing mayhem out of South Boston barrooms in the 1970s, was arrested for murder by Boston Police, with an assist from the FBI, in New Hampshire—just where Whitey said he would be.

But the FBI priority was the Mafia, not sociopaths like Tommy Nee. Through Flemmi, Bulger found out that Angiulo had removed his office phone for fear of wiretaps. Angiulo and his brothers, Bulger told Connolly, were talking only on walkie-talkies. Gennaro was “Silver Fox” and Donato Angiulo was “Smiling Fox.” Bulger even recommended a Bearcat 210 automatic scanner to monitor conversations.

In the button-down FBI office in Boston, such reports were impressing the top bosses even as Connolly’s increasingly brash ways were irritating his colleagues, who began jokingly to call him “Canolli” because he dressed and acted like a slick mob dude, with jewelry, chains, pointed shoes, and black suits. But for his part, Connolly was unconcerned. He knew what he had in Bulger and what it was worth to his career. Bulger’s 209 files were a coup for him and the bureau, a synergy possible only because of who he was and where he came from: South Boston Irish. “Whitey only talked to me,” Connolly bragged, “because he knew me from when I was a kid. He knew I’d never hurt him. He knew I’d never help him, but he knew I’d never hurt him.”

But sometimes in Whitey’s world, not hurting could be very helpful.