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Introduction

In the spring of 1988 we set out to write for the Boston Globe the story of two brothers, Jim “Whitey” Bulger and his younger brother Billy. In a city with a history as long and rich as Boston’s, brimming with historical figures of all kinds, the Bulgers were living legends. Each was at the top of his game. Whitey, fifty-eight, was the city’s most powerful gangster, a reputed killer. Billy Bulger, fifty-four, was the most powerful politician in Massachusetts, the longest-serving president in the State Senate’s 208-year history. Each possessed a reputation for cunning and ruthlessness, shared traits they exercised in their respective worlds.

It was a quintessential Boston saga, a tale of two brothers who’d grown up in a housing project in the most insular of Irish neighborhoods, South Boston—“Southie,” as it was often known. In their early years Whitey, the unruly firstborn, was frequently in court and never in high school. There were street fights and wild car chases, all of which had a kind of Hollywood flair. During the 1940s he’d driven a car onto the streetcar tracks and raced through the old Broadway station as shocked passengers stared from the crowded platform. With a scally cap on his head and a blonde seated next to him, he waved and honked to the crowd. Then he was gone. His brother Billy set off in the opposite direction. He studied—history, the classics, and, lastly, the law. He entered politics.

Both made news, but their life stories had never been assembled. So that spring we set out with two other Globe reporters to change all that. Christine Chinlund, whose interests lay in politics, focused on Billy Bulger. Kevin Cullen, the city’s best police reporter at that time, looked into Whitey. We swung between the two, with Lehr eventually working mostly with Cullen, and O’Neill overseeing the whole affair. Even though we usually did investigative work, this project was seen as an in-depth biographical study of two of the city’s most colorful and beguiling brothers.

We’d all decided that central to Whitey Bulger’s story was his so-called charmed life. To be sure, Whitey had once served nine years of hard time in federal prison, including a few years at Alcatraz, for a series of armed bank robberies back in the 1950s. But ever since his return to Boston in 1965 he’d never been arrested once, not even for a traffic infraction. Meanwhile, his climb through the ranks of the Boston underworld was relentless. From feared foot soldier in the Winter Hill gang, he’d risen to star status as the city’s most famous underworld boss. He had teamed up along the way with the killer Stevie “The Rifleman” Flemmi, and the conventional wisdom was that they were taking an uninterrupted underworld ride to fame and riches because of their ability to outfox investigators who tried to build cases against them.

But by the late 1980s the cops, state troopers, and federal drug agents had a new theory about Bulger’s unblemished record. Sure, they said, the man is wily and extremely careful, but his Houdini-like elusiveness went beyond nature. To them, the fix was in. Bulger, they argued, was connected to the FBI, and the FBI had secretly provided him cover all these years. How else to explain the complete and utter failure of all their attempts to target him? But there was a catch to this theory: not one of these theorists could show us proof beyond a doubt.

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To us, the idea seemed far-fetched, even self-serving.

For Cullen, who lived in South Boston, it cut against everything then known about a gangster with a reputation as the ultimate stand-up guy, a crime boss who demanded total loyalty from his associates. It defied the culture of Bulger’s world, South Boston, and his heritage, Ireland. The Irish have long had a special hatred for informants. We’d seen, some of us more than once, the famous John Ford 1934 movie The Informer, with its timeless and unmatched portrayal of the horror and hate the Irish have for a snitch. More local was a South Boston wiretap that became a classic in the city’s annals of wiseguy patter. The secret recording captured one of Bulger’s own underlings talking to his girlfriend.

“I hate fuckin’ rats,” John “Red” Shea complained. “They’re just as bad as rapists and fuckin’ child molesters.” And what would he do if he found an informant? “I’d tie him to a chair, okay? Then I’d take a baseball bat, and I’d take my best swing across his fuckin’ head. I’d watch his head come off his shoulders. Then I’d take a chainsaw and cut his fuckin’ toes off.

“I’ll talk to you later, sweetheart.”

This was Whitey’s world, where feelings about informants cut wide and deep, from the lowbrow to the high. Even brother Billy voiced a more refined version of Red Shea’s sentiments. In his 1996 memoir he recalled the time when he and some boyhood chums were playing baseball and broke a streetlight. The kids were told they’d get the ball back once they identified the offender. None broke rank. “We loathed informers,” wrote Billy Bulger. “Our folklore bled with the names of informers who had sold out their brethren to hangmen and worse in the lands of our ancestors.”

Because this was Whitey’s folklore too, the four of us back in 1988 were flat-out incredulous about the informant theory. We turned the idea over and inside out and decided: no way. The claim had to amount to nothing more than the wild and reckless flailings of embittered investigators who’d failed in their bid to bust Whitey Bulger. The idea of Bulger as informant seemed preposterous.

But the notion nagged, an irresistible itch that stayed close to the surface. What if it were really true?

The big news in Boston in 1988 was the presidential candidacy of Massachusetts Governor Michael Dukakis, but all during these months of presidential politics we grew more intrigued and committed to the Whitey story. So Cullen went back out. Lehr joined in. There were more interviews with the investigators who’d stalked Bulger and tried to build cases against him. The investigators painstakingly reviewed their casework, all of which ended the same way: Bulger walked away, uncharged and unscathed, laughing over his shoulder. They talked about a certain FBI agent, John Connolly, who, like the Bulgers, had grown up in Southie. Connolly had been seen with Whitey.

We wrote to the FBI in Boston and requested, under the Freedom of Information Act, intelligence files and material on Bulger. It was a formality; that the request was stonewalled came as no surprise. But we certainly could not write a story reporting that Bulger was an FBI informant. We had only the strong suspicions—but with no proof—of others in law enforcement. No confirmation was forthcoming from inside the FBI. The best we had, we decided, was a story about how Bulger had divided local law enforcement. It would be a piece about cop culture, with troopers and drug agents always coming up short and then hinting at their dark suspicions of the FBI. In a way, Bulger had divided and conquered; he’d won.

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The Boston underworld and the interplay between investigators involved ghost stories, smoke and mirrors; the idea of Bulger as an informant still seemed unlikely to us. Nonetheless, we launched a final round of reporting to test what we’d learned on our FBI sources. The gist of that reporting is described in Chapter 16 of this book. In the end we were indeed able to confirm, from within the FBI, that the unthinkable was true: Bulger was an informant for the FBI and had been so for years.

The story in September 1988 was published to heated denials from local FBI officials. In Boston, FBI agents were used to playing the press, feeding information to reporters thankful for a scoop that, of course, made the FBI look good. In this context, it came as no surprise that the Boston FBI acted offended, betrayed. And many people accepted their denials; after all, who was more believable? The FBI—the stand-tall G-men who’d been getting good ink for taking down the Italian mob? Or a group of reporters whom the FBI portrayed as having an ax to grind? With the utter unlikeliness of Bulger being an informant and the sheer vehemence of the FBI denials, the story was seen as speculation, not the dark truth.

Nearly a decade would pass before a court order required the FBI to confirm what it had steadfastly denied for so long: that Bulger and Flemmi had in fact been informants, Bulger since 1975 and Flemmi since before that. The disclosures were made in 1997 at the outset of an unprecedented federal court examination of the corrupt ties between the FBI and Bulger and Flemmi. In 1998 ten months of sworn testimony and stacks of previously secret FBI files revealed a breathtaking pattern of wrongdoing: money passing hands between informants and agents; obstruction of justice and multiple leaks by the FBI to protect Bulger and Flemmi from investigations by other agencies; gift exchanges and extravagant dinners between agents and informants. Many of the agents’ remarks featured an unmistakable arrogance—as if they owned the city. It was easy to imagine the FBI and Bulger and Flemmi celebrating their secret, holding their wineglasses high and toasting their success in outwitting the state troopers, cops, and federal drug agents who’d tried to build a case against them, never realizing the fix was in.

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Of course, the Bulger case does not mark the first time trouble involving agents and their informants has exploded publicly for the FBI. In the mid-1980s a veteran agent in Miami admitted to taking $850,000 in bribes from his informant during a drug trafficking case. Better known is the affair involving Jackie Presser, the former Teamsters Union president, who served as an FBI informant for a decade before his death in July 1988. Presser’s handlers at the FBI were accused of lying to protect him from a 1986 indictment, and one FBI supervisor was eventually fired.

But the Bulger scandal is worse than any other, a cautionary tale that is, most fundamentally, about the abuse of power that goes unchecked. The arrangement might have made sense in the beginning, as part of the FBI’s war cry against La Cosa Nostra (LCN). Partly with help from Bulger and, especially, from Flemmi, the top Mafia bosses were long gone by the 1990s, replaced by a lineup of forgettable benchwarmers with memorable nicknames. In sharp contrast, Bulger was the crime boss who, throughout the years, was the constant fixture in the underworld. Whitey was the household name, and he and Flemmi the varsity players.

“Top echelon informant” means an informant who provides the FBI with firsthand secrets about high-level organized-crime figures. FBI guidelines require that FBI handlers closely monitor informants. But what if the informant begins to “handle” the FBI agents? What if, instead of the FBI, the informant is mainly in charge, and the FBI calls him their “bad good guy”?

What if the FBI takes down the informant’s enemies and the informant then rises to the top of the underworld? What if the FBI protects the informant by tipping him off to investigations other police agencies are conducting?

What if murders pile up, unsolved? If working folks are threatened and extorted, with no recourse? If a large-scale cocaine ring, time and again, eludes investigators? If elaborate government bugging operations, costing taxpayers millions, are leaked and ruined?

This could never happen, right? A deal between the FBI and a top echelon informant going this bad?

But it did.

Today we know that the deal between Bulger and the FBI was deeper, dirtier, and more personal than anyone had imagined, and it was a deal that was sealed one moonlit night in 1975 between two sons of Southie, Bulger and a young FBI agent named John Connolly.

DICK LEHR AND GERARD O’NEILL

Boston, April 2000