Joseph (the Animal) Barboza was a murderer for hire from New Bedford, Massachusetts, who came by his nickname after an altercation with a minor mafioso which he elected to settle with his teeth. Barboza ultimately confessed to seven murders, and bragged to associates that he had committed many more, but he had the good fortune to be employed by the Mafia at a moment when authorities were trying desperately to better understand organized crime. In 1961, J. Edgar Hoover stressed, in a memo, the imperative to develop “live sources within the upper echelon of the organized hoodlum element.”
Barboza became a prized informant: he served as a government witness, helping to convict members of the Patriarca crime family. In fact, he was so valuable that when authorities began looking into a 1965 murder that Barboza had participated in, his contacts at the F.B.I. engineered a scheme to protect him. Barboza was never prosecuted for this crime; instead, he took the stand as the government’s star witness and implicated four innocent men in the murder. His F.B.I. handler, an agent named H. Paul Rico, boasted afterward about the ease with which the bureau had set up four “pigeons” for a crime they did not commit. All four men ended up with life sentences. (They were cleared of the murder in 2001, by which point two of them had died in prison.)
In 1969, the government placed Barboza in witness protection, relocating him to California. But in his new identity he killed a man, and when local prosecutors sought to try him for the murder, the F.B.I. concocted a second coverup, maintaining that the killing was an effort by the Mob to frame the Animal and dispatching federal agents to appear in court as witnesses for the defense. After prosecutors agreed to reduce the charge, Barboza served only four years. Upon his release, in 1975, he was promptly murdered. But the Boston F.B.I. continued to enjoy a relationship with one of his associates, Stephen Flemmi, a member of the Winter Hill Gang. Flemmi had recently become affiliated with another up-and-coming gangster, a cunning and disciplined South Boston hood named James Bulger, who was known, owing to his platinum hair, as Whitey. Bulger was an armed robber who had done a stretch in Alcatraz in the nineteen-fifties, which counted, in the underworld, as a badge of achievement. Kevin Cullen, the co-author, with Shelley Murphy, of the excellent 2013 biography “Whitey Bulger,” once pointed out that whereas in normal life we might be impressed to learn that somebody had gone to Harvard, “if you’re a wiseguy, you say, ‘Ooh, you went to Alcatraz.’ ”
Bulger exercised every day, lived with his elderly mother, and cultivated a mystique of righteous criminality. In 1975, he began coöperating with the government, joining Flemmi as what was known, in the taxonomy of the F.B.I., as a Top Echelon Informant. This defection amounted to a breach of street protocol, which was generally punishable by death. But Bulger had few worries about exposure. Even if the truth came out, he once explained to an F.B.I. official, his reputation as a ruthless but standup guy was such that nobody would believe it. “It would be too incredible,” he said.
In 2000, the Boston Globe journalists Dick Lehr and Gerard O’Neill published a book about Bulger’s years as an informant, “Black Mass: The Irish Mob, the F.B.I., and a Devil’s Deal.” Bulger was not wrong: it was incredible. A film adaptation, directed by Scott Cooper and also called “Black Mass,” has just been released; it dramatizes the story as a lethal minuet between the wily criminal Bulger (played by Johnny Depp) and the flashy, jocular F.B.I. agent named John Connolly (Joel Edgerton), who handles him. The film conveys the degree to which the relationship between informant and handler is indeed a relationship: bureaucrats can formalize the transaction in a mountain of paperwork, but in the end it hinges on two people binding their destinies together, navigating treacherous territory hand in hand.
Depp’s fine-boned beauty might seem ill-suited to the role, but he captures, with chilling precision, Bulger’s preening tough-guy narcissism. With his mortuary pallor, ice-water eyes, and swept-back yellow-white coiffure, Depp looks as if he’d climbed into the makeup chair each morning and allowed himself to be struck by lightning. He performs Whitey’s lip service to gentility as the elaborate pose that it was, assisting the old ladies of Southie with their groceries, while his squinty eyes and carnivorous smile flash hints of the monster underneath.
John Connolly once said that, for law enforcement, running criminal informants was a bit like the circus: “You need to have a guy in there with the lions and the tigers.” In a new book, “Where the Bodies Were Buried: Whitey Bulger and the World That Made Him” (Morrow), the journalist T. J. English makes clear that most F.B.I. agents do not excel in the role. It takes a certain personality type: the garrulous, glad-handing street guy. These agents are often indifferent to official protocol, English points out, and their paperwork can be atrocious. But on a barstool they’re Mozart. In “Black Mass,” Edgerton plays Connolly as a man who thrives on informality. His idiom consists exclusively of backslap and bluster. He’s the guy to see about Red Sox tickets.
The film plausibly depicts the bond that developed between Connolly and Bulger as predicated on neighborhood loyalty. Connolly grew up in Southie and was childhood friends with Whitey’s younger brother, Billy Bulger (Benedict Cumberbatch, in the film), who by the nineteen-eighties had become the president of the Massachusetts State Senate. Vocational options were circumscribed for men who came of age in Southie during the mid-twentieth century: if you couldn’t get a job at the Gillette plant or a utility, your career choices were neatly captured by Connolly (law enforcement), Billy (politics), and Whitey (crime). “Southie kids, we went straight from playing cops and robbers on the playground to doing it for real on the street,” one of Whitey’s underlings says in the movie, adding, “And, just like on the playground, it wasn’t always easy to tell who was who.” Tribalism is a recurring theme in the Bulger saga, but the film suggests that the tribe allegiance of scrappy neighborhood kids transcends any subsequent pledge they might make to a criminal gang, or to the feds. “I grew up with him in Southie,” Connolly says of Whitey. “That is a bond that doesn’t get broken.”
Few activities were more reviled in this Irish-American milieu than snitching. “We loathed informers,” Billy Bulger wrote in a 1996 memoir. “Our folklore bled with the names of informers who had sold out their brethren to hangmen and worse in the lands of our ancestors.” In deference to Whitey’s sensitivities on this point, Connolly never referred to him as an informant. Whitey preferred terms like “strategist” or “liaison.” He told Connolly that he would furnish information about his rivals in the Italian Mafia—but not his friends. And he had another condition: his brother Billy couldn’t know.
Imagine you work at the Central Intelligence Agency. Your objective right now is the fight against the so-called Islamic State, or ISIS. In the past, U.S. intelligence had a difficult time penetrating jihadist groups, because they were bound by ideology, which is stronger than a mutual interest in a shared criminal enterprise, and because they were careful about operational security. But ISIS is different: it actively recruits young Westerners to join its ranks. For the C.I.A., that is a critical opportunity.
In order to infiltrate ISIS, you handpick the perfect operator, then game out, in advance, how he should respond in a variety of situations. Suppose your infiltrator has crossed into Syria and been accepted by ISIS as a new recruit. He is taken to a house one day where somebody hands him a carving knife and instructs him to behead a hostage. Should he? If he refuses, his cover may be blown, and he could be taken hostage or killed himself. If he commits murder, he will solidify his bona fides as a member of the group, which could have real intelligence value. What if beheading the hostage might save a hundred lives? How about a thousand? How about just two?
This conjectural arithmetic of means and ends is what makes the handling of informants so fraught. An effective inside man in a criminal organization is also, necessarily, a criminal in good standing—and therefore a dangerous person with whom to be in business. After the attacks of September 11th, the Drug Enforcement Administration worked closely with a confidential informant named David Headley, a Pakistani-American who ran a video store in Manhattan. The agency sent him to Pakistan to gather intelligence on terrorism. But, when he arrived there, Headley became a terrorist himself, training with Lashkar-e-Taiba and eventually helping to plan the 2008 Mumbai bombing, in which a hundred and sixty-six people were killed.
In the reassuring argot of the bureaucracy, confidential informants like Headley or Bulger are often referred to as “assets”—a term that implies not just control of the source but outright ownership. Yet, if the asset is going to persist in the behavior that you are ostensibly combatting, how much control do you really exert? With Bulger, as with Barboza, the asset came to seem so valuable that the government did more than tolerate his bad behavior; it began to enable that behavior, even to engage in criminal activity itself. Suddenly, the government had lost control, and the asset had acquired it. Whitey Bulger knew that his friend Stephen Flemmi had coöperated with the F.B.I. and was still committing crimes with impunity. He also knew the story of Barboza. So his decision to coöperate makes a lot of sense. As T. J. English puts it, “If you were willing to sign on as a player in this ongoing conspiracy, you could not be touched.”
For John Connolly, Bulger and Flemmi represented a lesser evil: the chief priority for the F.B.I. was to eradicate the Italian Mafia, and, Connolly claimed, his informants were indispensable in that effort. Years later, he described the bargain in terms of return on investment. “We got forty-two stone criminals by giving up two stone criminals,” he says in the biography “Whitey Bulger.” “Show me a businessman who wouldn’t do that.” But, as Connolly and his colleagues were dismantling La Cosa Nostra, Bulger and Flemmi were quietly consolidating control of Boston’s criminal landscape. The F.B.I. never brought cases against them, and when other agencies, like the Massachusetts State Police, tried to target them, the gangsters always seemed to get tipped off. In one terrifying sequence of events that is depicted in the film “Black Mass,” Bulger and his gang were dismayed when World Jai Alai, a sports betting operation, appointed a new C.E.O., Roger Wheeler. Several Bulger cronies were employed by World Jai Alai, and they regularly skimmed money from its huge gambling revenues. But Wheeler wanted to audit the books. In the film, when Whitey is told that Wheeler cannot be persuaded to sell the company, he announces his intentions with a question: “Would his widow sell?”
To execute Wheeler, Bulger dispatched a schlubby assassin named John Martorano. As Wheeler finished a round of golf at his country club, in Tulsa, Martorano approached his car and shot him in the face. The hit was coördinated with the assistance of World Jai Alai’s head of security—H. Paul Rico, Barboza’s former handler, who had retired from the F.B.I. so that he could devote more time to criminality.
After the murder, a junior member of Bulger’s gang, Brian Halloran, approached the F.B.I. in Boston and said that he had information about the execution of Roger Wheeler: it had been ordered by Whitey Bulger. The bureau responded by questioning Halloran’s credibility. Fearing for his life, Halloran insisted that the authorities place him in witness protection. They refused. Instead, John Connolly informed Bulger that Halloran had betrayed him, and Bulger tracked Halloran down at a waterfront bar and shot him to death in the parking lot.
When I was growing up in Boston during the nineteen-nineties, the myth of Whitey Bulger as a standup criminal, a “good bad guy,” was still remarkably strong. It was an appealing idea, rooted in tribal solidarity, and you could see how it might have been a tempting archetype for Hollywood. But, to the credit of the film “Black Mass,” Johnny Depp plays Bulger as a bloodless psychotic, and does not stint on depicting his savagery. Deborah Hussey was the daughter of Stephen Flemmi’s common-law wife. A damaged young woman whom Flemmi had been molesting since she was a teen-ager, she fell into prostitution to support a heroin addiction, and Bulger worried that she might talk to the police. So they took her to a small house on East Third Street in South Boston. The property was just down the street from the home of Billy Bulger, but Whitey went there mainly to kill people. He called the house the Haunty. There were bodies buried in the basement. Inside, Bulger choked Deborah Hussey to death. She was twenty-six. Bulger derived much of his income by controlling bookies and vending machines, and it was part of his mythology that he kept drugs out of South Boston (though in fact he was bringing them in). It’s useful to remember that he was also, effectively, a serial killer.
For a 1999 study in the Fordham Law Review, Ellen Yaroshefsky interviewed former federal prosecutors about the tendency to grow close to a criminal informant and the perils of losing objectivity. It is possible, Yaroshefsky suggested, to “fall in love with your rat.” Something like this happened not just with Connolly but also with Connolly’s F.B.I. supervisor, John Morris. Flemmi and Bulger would go to Morris’s suburban house and indulge in long evenings of bonding. Morris was from the Midwest and lacked Connolly’s common touch. (His paperwork, T. J. English notes, “was impeccable.”) He liked wine, so Bulger gave him a case, and then another. On a separate occasion, the gangsters supplied a plane ticket so that Morris’s mistress could join him on a getaway to Georgia. For security reasons, relationships with informants are often carried out in secret, with little oversight; the usual temptations become hard to resist.
Much like the earlier F.B.I. agents who had handled Barboza, Connolly and Morris continued to cover for Bulger’s and Flemmi’s criminal activities. One reason is that Bulger compromised his handlers. A case of wine. A plane ticket. The gifts added up. Connolly reportedly took a quarter of a million dollars over a decade. But a subtler power shift was also in play: when Connolly and Morris broke the law to protect Bulger, they were furnishing him with grounds for blackmail. In 1994, despite the F.B.I.’s best efforts, a Massachusetts grand jury began to hear evidence about Bulger and Flemmi. A furious Whitey later telephoned Morris and said, “If I’m going to jail, you’re going to jail. I’m taking you with me.” Morris had a major heart attack. It was a vivid snapshot of Bulger’s leverage. As Lehr and O’Neill write, “Bulger had nearly killed him with a phone call.” The gangster was finally indicted, but before he could be arrested he fled. Connolly had tipped him off.
That is where the movie ends, and the Bulger story, too, might have ended there, with the man vanishing, forever untouchable. But in 2011, after a decade and a half on the lam, he was finally apprehended. For years, the F.B.I. had been unable to track him, and many people speculated that officials did not really want to find Whitey, for fear of the revelations about F.B.I. complicity that might emerge if he ever stood trial. John Connolly had eventually been prosecuted for his corruption, and for his involvement in yet another murder committed by John Martorano, on Bulger’s orders, in Florida. Connolly is serving forty years in prison; John Morris received immunity and testified against him. Bulger sightings were reported in Ireland, Italy, and all over the United States. But when Whitey was finally discovered, at the age of eighty-one, he was living a quiet life with his girlfriend, Catherine Greig, a few blocks from the boardwalk in Santa Monica. Their apartment was modest and unremarkable, except for the eight hundred and twenty-two thousand dollars in cash that investigators found hidden in the wall. Bulger had not shed his native hauteur. When the agents told him to kneel, he said, “I ain’t getting down on my fucking knees.” He didn’t want to dirty his trousers.
Bulger had been an avid reader as far back as his years in Alcatraz, and on his shelves in Santa Monica agents found a collection of true-crime books. Among them was “Paddy Whacked,” a 2006 book by T. J. English, about Irish-American gangsters. When Bulger was prosecuted in federal court in Boston, in 2013, English attended the trial, and his book offers a detailed account of the proceedings. Despite the underworld prohibition on snitching, everybody seems to snitch eventually. With Bulger in exile, his former associates negotiated bargains of one sort or another. Just as the F.B.I. gave a pass to Bulger in the interest of prosecuting the Mafia, the Justice Department gave a pass to the killers from Bulger’s gang in the interest of prosecuting Bulger. Stephen Flemmi, who avoided capital punishment by making a plea deal, testified about how Bulger murdered Deborah Hussey. A Bulger protégé named Kevin Weeks testified about burying Hussey’s body. “We killed people that were rats, and I had the two biggest rats right next to me,” Weeks said.
“You suck!” Bulger hissed.
Weeks, still on the witness stand, responded, “Fuck you, O.K.?”
“Fuck you, too,” Bulger shot back.
For all its drama, English argues, the trial was a sideshow. He begins his book not with Whitey but with Joseph Barboza, and he insists that any narrative that hews too closely to the relationship between Bulger and the “rogue agent” John Connolly overlooks a more systemic problem. It wasn’t just that Connolly introduced Bulger to his boss, Morris; he eventually introduced Bulger to Jeremiah O’Sullivan, a senior official in the U.S. Attorney’s office in Boston. (The two were, Connolly told English, “quite impressed with one another.”) When Brian Halloran walked into the F.B.I. and implicated Bulger in the Jai Alai hit, it was O’Sullivan who ultimately refused to put him in witness protection.
Federal law enforcement is no less a tribe than a Southie street gang is, and, English argues, it will always look after its own. This may simply be a lamentable feature of institutional culture: the Catholic Church covered for the predators in its midst. But one oddity of the Bulger case is that the prosecutors who brought the thirty-two-count indictment worked in the very office that Jeremiah O’Sullivan used to occupy. Their challenge, English argues, was how to “convict Bulger without collaterally tarnishing the reputation of the system they represented.”
The notion that Whitey Bulger’s pact with the F.B.I. represented not a gross aberration but something like business as usual is almost too bleak to contemplate. It suggests, as English writes, that “the entire criminal justice system was a grand illusion; a shell game presided over by petty bureaucrats more concerned with promoting their careers and protecting their asses than anything else.” Nobody knows how many confidential informants are working for the F.B.I. at any time, but in a 2008 budget request the bureau put the number at fifteen thousand. After the degree of official complicity in Bulger’s crimes was revealed, the Department of Justice ordered the F.B.I. to track any crimes committed by its informants. In a 2013 letter, the bureau disclosed that in the prior year it had authorized informants to break the law on 5,939 occasions. “Stone killers,” Connolly once remarked. “That’s who you’re trying to recruit. Then you’re supposed to tell them ‘You can’t do that anymore’? Are you shitting me?” To English, the cautionary tale of “one very crafty psychopath who had corrupted the system” obscures the “preexisting corrupt system” that created him.
Bulger mounted a surprising defense. His lawyers acknowledged that he had been a major organized-crime figure in Boston, and was guilty of racketeering, loan sharking, gambling, drug dealing. What he had never been, however, was a rat. “James Bulger was of Irish descent, and the worst thing an Irish person could consider doing was becoming an informant,” his lead lawyer, Jay Carney, explained. Whitey did not take the stand during the trial, but, in a documentary that later aired on CNN, he elaborated. “I asked the questions, I got the answers,” he said. “I was the guy that did the directing. They didn’t direct me.” In Bulger’s telling, he never gave any information to the feds; he only collected information from them. Connolly may have thought he was the handler, but in reality he was the informant.
On its face, this claim was laughable, belied by numerous witnesses and corroborating F.B.I. documents. Yet there is no disputing that the federal government gave Whitey a great deal more than it got in exchange. Indeed, one mystery of Bulger’s rapport with the F.B.I. had always been why the agents were so devoted to him. Connolly claimed that the bureau got “forty-two stone criminals” because of Bulger, but Bulger’s actual contributions to the work of the bureau were often exaggerated. Bulger’s defense pointed out that he was never deeply tied to the Mafia. In fact, in a bureaucratic sleight of hand that is dramatized in the film “Black Mass,” Connolly and Morris routinely padded Bulger’s official dossier by extracting tidbits from the files of other confidential informants and attributing them to Bulger.
So why did the agents stick with him? Once Connolly and Morris began to bend the rules for Bulger and Flemmi, they became bound to their sources. Part of the answer, too, is that the culture rewarded agents who landed top informants; throughout the years that Connolly was handling Bulger, he was promoted and given performance bonuses. But relationships can become pathological, and the more intimate the relationship the more it will assume a logic of its own.
Bureaucracies, like people, are also given to path dependency. The original rationale behind recruiting Whitey Bulger was that he would help take out the Italian Mob. But by the late nineteen-eighties the Boston Mafia had more or less disappeared, and the new locus of criminal power was Whitey Bulger and Steve Flemmi. A colleague of John Connolly, an F.B.I. supervisor named Bob Fitzpatrick, met with Bulger at one point and concluded that he enjoyed too much of a free hand. Besides, Fitzpatrick argued, the whole logic of informants is that you flip criminals on the lower rungs of an enterprise so that you can target the top of the hierarchy. “You can never have the top guy as an informant,” Fitzpatrick said. “If you have the top guy, he’s making policy, and then he owns you.” According to Fitzpatrick, he recommended that the bureau jettison Bulger as a source. He was overruled.
Whitey was convicted on thirty-one counts, including involvement in eleven murders, and received multiple life sentences. But T. J. English is not alone in feeling that the system got away without scrutiny. In a statement, David Wheeler, the son of Roger Wheeler, the murdered Jai Alai executive, cautioned that the verdict should not overshadow the “gross institutional misconduct” of the F.B.I. If the word “asset” implies ownership, then perhaps the government should bear some responsibility for the violent actions of criminals whom it shelters and protects. One of the men Barboza fingered for murder was released from prison after thirty years. He sued the F.B.I., and was awarded twenty-nine million dollars. Many relatives of Bulger’s victims (including David Wheeler) have launched similar suits, though a number of them have been thrown out on the ground that the statute of limitations has expired—a cruel technicality, given that it was through the contrivance of government officials that Bulger’s informant status remained secret for so long.
On the day that Whitey was arraigned, a diminutive, fastidiously groomed man appeared in the spectators’ gallery. It was Billy Bulger, the former senate president. The original tribal allegiance is blood, and Billy had never abandoned his older brother. “I could have tried to influence him,” Billy said, in a rare interview on the subject, in Boston in 2007. “But you know, you couldn’t get a conversation going.”
After two decades in the state senate, Bulger became president of the University of Massachusetts, but he was forced to step down seven years later when it was revealed that he had been less than forthcoming with the F.B.I. In January, 1995, Billy had spoken with his fugitive brother on the phone but had never informed the authorities.* “I told him I cared about him deeply and that I still do,” Billy later told a grand jury. He made no suggestion that Whitey should turn himself in.
When John Connolly left the F.B.I., he threw a retirement party in the North End. Billy Bulger had remained close to Connolly and helped him arrange a cushy new appointment as director of security at Boston Edison. There were speeches, and Bulger said a few words. He cited the philosopher Seneca, who held that loyalty is the “holiest good” in the human heart. “John Connolly is the personification of loyalty,” Bulger said. “Not only to his friends and not only to the job that he holds but also to the highest principles. He’s never forgotten them.” ♦
*An earlier version of this article said that Bulger lied to the F.B.I. He was never indicted for lying to federal agents.
