Paddy Whacked

by T. J. English

  In a late-night bull session at the downtown FBI office, Morris told Connolly, “John, we got a problem. Brian Halloran has implicated Jim Bulger and Flemmi on the Tulsa murder. We’ve got to head this off at the pass.”

  “Don’t worry,” said Connolly. “I’ll take care of it.”

  Connolly immediately set up an “interview” with his two informants, Bulger and Flemmi, supposedly to explore what they knew about the Tulsa matter. After talking to the two men, Connolly filed a report stating that Halloran’s claims “could not be substantiated by the facts,” after which Morris officially closed the investigation.

  Bulger and Flemmi were in the clear, and they celebrated with a wine and dinner party at Steve Flemmi’s mother’s house in Southie. The honored guests at the dinner party were agents Morris and Connolly. The two gangsters had reason to celebrate. Not only had they once again gotten away with murder, but they also now knew for sure—thanks to the FBI agents—that Brian Halloran was a rat.

  Halloran’s predicament just kept getting worse. No matter which way he turned, the shadow of Whitey Bulger was upon him. He had tried to come in from the cold and deliver the top mobster in Boston to the FBI on a silver platter, and now he was in even more danger than before.

  Robert Fitzpatrick, the agent with whom Halloran first established contact, was understandably concerned for his C.I.’s life. Although he did not yet know that his own agents had tipped off Bulger about Halloran, word on the street was that his informant was not long for this world. The agent approached Assistant U.S. Attorney Jeremiah O’Sullivan, whose approval Fitzpatrick needed to offer Halloran a plea-bargain deal for his cooperation and get him off the street and into protective custody.

  O’Sullivan, of course, knew all about Whitey Bulger’s role as an informant; he was the one who had severed Bulger from the 1978 race-fixing case, which had resulted in convictions for every high-ranking member of the Winter Hill Gang except Bulger and Flemmi. O’Sullivan also knew that, in accordance with government policy, the FBI was not allowed to keep Bulger on as a C.I. if he was under criminal investigation. In a sense, the prosecutor was being asked to choose between Brian Halloran and Whitey Bulger—a no brainer. Instead of listening to Fitzpatrick, who was telling him that Halloran’s life was in imminent danger, O’Sullivan went with Morris and Connolly, who were telling him that Halloran was a wannabe and a drunk who knew nothing about the activities of a man like Whitey Bulger. Halloran was denied protective custody.

  In May 1982, the low-level Irish hood’s official role as an informant was terminated, and he was cut loose. The FBI had chewed him up, set him up to be killed, and spit him back out on the street. He couldn’t live at home with his wife, who was pregnant with their second child, for fear that someone might bust through the door and shoot them all to death. Moving from safe house to safe house, he trusted no one and slept with a gun under his pillow.

  On the night of May 11, less than a week after being dumped by the FBI, Halloran got a call from his sister, who was living near the South Boston waterfront. She wanted to see him. A friend drove him into Southie, a place he’d been avoiding for months. Around six o’clock in the evening, he and his friend were sitting in a Datsun outside a restaurant on Northern Avenue. A blue Chevy pulled alongside them. Before Halloran had time to react, a fusillade of machine-gun fire rang out. Halloran was hit; he staggered out of his car and fell in the street. One of the assassins ran up to him and shot him several more times with a pistol. Halloran died with twelve bullets in him from two different guns. His friend—an innocent bystander—was also killed.

  A Boston detective at the murder scene claimed that the dying Halloran was able to identify his assailant. “Jimmy Flynn,” he supposedly said with his last breath. Jimmy Flynn was an established Charlestown gangster who was angry with Halloran for having allegedly ratted him out on a bank robbery. The Boston cops thought they had an iron-clad suspect, but it was all a carefully planned diversion. Bulger himself was the triggerman that night. He’d worn a disguise—a sandy-blond wig and prominent mustache—that made him look like Jimmy Flynn.

  The day after the murder, FBI agent John Connolly met with Bulger and Flemmi, who told him that, as far as they knew, Charlestown gangsters acting on behalf of the Italians had taken out Brian Halloran. Connolly quickly filed an internal report to that effect, which was later used by local authorities to build a case against Flynn.1

  In Boston’s police squad rooms and prosecutorial chambers, few tears were shed for Brian Halloran. He was a gangster who trafficked on the dark side and apparently got what was coming to him. But in the city’s underworld of the 1980s, looks could be deceiving. In truth, Whitey Bulger had spun a web of treachery and deception unlike anything ever seen in the annals of the Irish Mob. FBI agents Connolly and Morris were literally on the payroll, supplying information to the Bulger organization that made it possible for them to engage in pre-emptive strikes. The hits just kept on coming.

  The next to go down was John Callahan, the accountant from World Jai Alai who first brought Halloran into the Tulsa murder plot. In July 1982, his body was found in the trunk of a car near Miami International Airport, having been murdered by the same Boston hit team who gunned down Roger Wheeler in Oklahoma.

  Then came Arthur “Bucky” Barrett, an expert Boston safecracker who had pulled off a daring bank heist, netting $1.5 million in cash. Whitey Bulger ratted out Barrett to Connolly and Morris. They, in turn, approached Barrett with a “friendly warning” that Bulger, as the mob boss of Boston, wanted his cut of the heist. The agents then offered Barrett a “safe haven” as an FBI informant, but Barrett rejected it. In 1983, he was kidnapped, tortured, and dragged to a South Boston home, where he was murdered and then buried in the basement.

  Less than a year later, John McIntyre met the same fate. He was a young boatman who ran afoul of Bulger after taking part in an IRA gun smuggling operation led by occasional Bulger associate, Pat Nee. When McIntyre started singing to federal authorities, Agent John Connolly tipped off Whitey. McIntyre disappeared, to be exhumed years later alongside Barrett and the corpse of Deborah Hussey, the ex-girlfriend of Bulger’s psychotic partner, Steve Flemmi.

  In the wake of all these murders, the Irish American underworld became even more oppressive than usual. In Southie, where many of the victims lived or operated, the worst thing you could be accused of was having an “Irish whisper,” talking too loudly about the neighborhood’s business. Residents mumbled about the latest disappearance, became defensive, or tried not to think about the reality: Bulger and Flemmi were not just mobsters, they were serial killers, racking up an ungodly body count with virtual impunity. No one was safe. Enemies, ex-girlfriends, fellow gangsters, and especially business associates who engaged in moneymaking criminal rackets with the Bulger organization all vanished, never to be seen again.

  Wrote Eddie MacKenzie (yet another small-time Southie hood who worked for Bulger) in his autobiography, Street Soldier: “Whitey Bulger was an institution unto himself…Lucifer personified. If the word on the street was to be believed—and what other word could I rely on?—Whitey Bulger could kill you and your dog, fuck your wife, burn down your house, and walk away clean.”

  Bulger’s power was mind-boggling and ubiquitous. It was based on a combination of his own innate skills and psychosis, his sinister relationship with the FBI, and his demonic partnership with Flemmi. And when all else failed, Whitey had another “ace in the hole” that seemed to hark back to the earliest days of the Irish Mob—when the underworld was a hushed intermingling of politics and gangsterism, and the American Dream a circumscribed commodity most obtainable to those with an edge. The days of Tammany Hall were a distant memory, but nobody ever told that to Whitey’s brother, the Senator from Southie, Mr. William Bulger.

  The Bulger Mystique

  In September 1988, the Boston Globe published a voluminous four-part series on the Brothers Bulger, who were by now a source of endless fascination in the city. Af
ter ten years in the state House of Representatives and nearly twice that time in the state Senate, where he rose steadily to be elected senate president in 1978, Billy Bulger was a force to be reckoned with in his own right. A proficient public speaker and skilled legislator, Billy, like his brother, had ridden the angry wave of resistance that swept over South Boston during the busing crisis. Bulger’s lacerating public critiques of the city’s WASP and Anglo-Irish elite, whom he characterized as “drowning in a sea of hypocrisy,” was a clear-eyed expression of working-class politics in the tradition of James Michael Curley, one of Bulger’s political heroes.

  Like Curley, Bulger had a talent for piercing rhetoric that skirted the edges of class and race-baiting, which turned out to be a much more volatile proclivity in the Boston of the 1970s than it had been in Curley’s time. It was de rigueur for Southie political leaders of the busing era to have a gangster at their side, either literally or metaphorically. Louise Day Hicks, the most vitriolic of the antibusing crusaders in Southie, had as her bodyguard Jimmy Kelly, a former member of the Mullin Gang, who would himself eventually became an elected state representative. Whitey Bulger’s reputation was such that he and brother Billy didn’t even need to be seen together; the relationship was simply understood.

  The Globe series on the brothers was comprehensive and revealing, and it quoted Senator Bulger at length. He waxed eloquent about growing up in Southie and expressed distaste at the way he and his neighborhood had been wrongly characterized as narrow-minded, unduly tribal, and racist. When the subject turned to his brother, Bulger was tight-lipped, as he had been since the time he entered public life. “He was always a very good brother and cared very much for his mother…. I worry for him,” was all the Senator would say. Bulger’s loyalty to his brother was reiterated when the Globe series appeared in print and implied—for the first time ever in a public forum—that Whitey Bulger and the FBI had a “special relationship.” Billy Bulger felt that the Globe had accused his brother of being an informer, which was anathema to any card-carrying Irishman. In response, Bulger disowned the Globe and never again gave the paper an interview until his retirement from the Senate in 1996.

  Loyalty among brothers is an admirable trait and should not be construed to suggest, in Billy Bulger’s case, a direct criminal allegiance. In his long political career, Bulger was never overtly linked with his brother’s mobster activities in any way. In fact, Billy presented himself to the public as nearly puritanical. He was a devout churchgoer, scholar, teetotaler, devoted husband, and father of nine children. With his fastidiously groomed blond hair, cherubic face, quick wit, and alert, penetrating blue eyes (not unlike his older brother’s), the Senator from Southie was the kind of “good boy” who would make a mother proud. Some people even believed that Bill Bulger’s drive to achieve great things in legitimate society in spite of his brother’s dubious reputation was a gift to his aged mother, who lived as a veritable recluse in her own neighborhood.

  In personal presentation and public achievement, Whitey and Billy may have looked like the Cain and Abel of South Boston, but it wasn’t really that simple. Senator Bulger made no apologies for his brother and at times even seemed to bask in the dirty glory of Whitey’s untoward reputation. Their mutual careers had risen on a parallel track, with Bill ascending to the senate presidency at the same time that Whitey (with the help of FBI Agent John Connolly) was eliminating his former associates in the Winter Hill Gang and taking over as the city’s undisputed underworld boss. In the rough-and-tumble world of South Boston, where gangsterism was still perceived as a semilegitimate consequence of the city’s anti-Irish, anti-Catholic roots, Whitey Bulger’s mobster pedigree did not hurt Billy Bulger one bit. Some argued that it was the secret of his success.

  The Senator from Southie could be a dictator and a bully, and he was known to possess a well-honed Boston Irish taste for revenge. His political opponents often noted his tendency to personalize all battles, large or small. One junior member of the legislature, trying to enlist Bulger’s support for a bill on rules reform, said to the senate president, “You could be a hero, Mr. President.” Bulger shook his head and replied, “You guys from Cambridge can be heroes, but guys like me can’t. I’ll always be a redneck mick from South Boston.”

  Where Billy sometimes got even was on St. Patrick’s Day, at the annual breakfast that was a required stop for politicians and community leaders lucky enough to score an invitation. With Bulger presiding, the breakfast was like a Friar’s Roast. Political leaders such as Boston’s popular Mayor Ray Flynn (a rival of Bulger’s who was another up-from-the-bootstraps Southie success story), Senator Ted Kennedy (who was sure to be lampooned about his weight and for his liberal leanings) and campaigning national politicians like Ronald Reagan and George Bush stopped by to sing songs and prostrate themselves before the man commonly referred to as “the most powerful local politician in the state of Massachusetts.” The media was not allowed inside, except on rare occasions. Although never in attendance, Whitey Bulger was often referred to with jocularity at these Paddy’s Day breakfasts; on one occasion, Billy good-naturedly designated his brother “the Reverend”—a comment that would come back to haunt him years later, when the truth about Whitey came out and he was no longer viewed in the neighborhood as a subject of such ribald good humor.

  Senator Bulger’s talent for political payback went well beyond a few pointed jibes on March 17. A political operative who identified himself in the Globe as “a friend” of Bulger’s, put it this way: “[He] at times personifies the iron hand in the velvet glove…. And the stiletto in that hand is so slim, slender and sharp that it’s only after it’s been withdrawn that you feel that you know what happened.” Some of Bulger’s more notorious acts of legislative revenge could be chalked up to political hardball, an example of the kind of politics that had been practiced in the state of Massachusetts since the days of the Boston Tea Party. But other acts were more pointed in their defense of brother Whitey, giving the impression—intended or not—that the Bulgers were “in it together.”

  For example, when a court clerk finally eliminated James “Whitey” Bulger from the state payroll, years after he’d stopped showing up for his post-prison job as a courthouse janitor, Senator Billy—in an act of brotherly payback—froze the clerk’s pay.

  When Massachusetts State Police officers undertook an investigation of Whitey Bulger’s criminal operation in 1981 (going so far as to plant a bug in his garage headquarters on Lancaster Street, to which Whitey was tipped off by FBI Agent Connolly), they found a strange addendum tagged onto the following year’s state budget that would require state police officers age fifty or older to take a reduction in pay and rank, or retire. The amendment affected only five officers in the Boston office, three of whom had worked the Whitey Bulger case. Senator Billy’s response to this mysterious budget amendment was “no comment,” but many in local law enforcement saw it for what it was: another instance of one Bulger running interference for the other.

  An even more ominous incident occurred in September 1987, when Whitey Bulger and his girlfriend were passing through Logan Airport and were stopped with a bag filled with $50,000 in cash. According to an incident report filed by a state trooper, Whitey lost his cool and became verbally abusive to a number of airport security workers and to the trooper. Bulger was detained but eventually let go. In the weeks that followed, the state trooper came under intense scrutiny from his supervisors, who claimed that State Senator Bulger was demanding a copy of the incident report. The trooper was an exemplary employee—a Green Beret in Vietnam who was twice awarded a Medal of Merit and the Trooper of the Year Award—but he became the target of a campaign of political harassment and payback, which turned out to be the beginning of the end of his distinguished career. The trooper’s relationship with his superiors soured, and he retired early, a broken man. A few years later, in the woods of southern New Hampshire, penniless and despondent, he blew out his own brains.

  According t
o the legend, Billy Bulger punished those who went after his brother and rewarded those who didn’t. The senator, by his own admission, was good friends with FBI Agent John Connolly. Like Whitey, he’d known Connolly since they were kids growing up on the same block in Southie. Connolly had worked on many of Billy’s early political campaigns, and when Southie protégé Ray Flynn got himself elected mayor, Bulger lobbied hard for Connolly to be appointed the city’s new chief of police. Connolly didn’t get the job, but he was still grateful and maintained a close, affectionate relationship with the senator.

  Years later, Bulger claimed—none too convincingly—that he had no idea about Connolly and Whitey’s “special relationship,” but he did admit to telling the agent, “I expect you to take care of my brother.” The implied understanding was that Connolly would be Whitey’s protector inside law enforcement. In return, Bulger would write reference letters and exert his considerable influence for a steady stream of FBI agents whom Connolly brought by his senate office (many wound up with cushy retirement jobs on the state payroll). It was the classic patronage arrangement; Connolly looked out for Whitey and his friends, and Billy took care of Connolly and his people. It all seemed benign until you stopped to consider the fact that Whitey Bulger had whacked at least nineteen people—eight of them while he was a registered informant with the FBI.

  There was nothing subterranean about the alliance. On at least one occasion, Whitey, his partner Flemmi, and their FBI handlers were having a celebratory dinner at the Southie home of Flemmi’s mother when Billy Bulger walked in. Bulger lived next door, merely twenty feet away. A junior FBI agent who was there that night (having been invited for the first time) would later testify that he was shocked; here were the two most notorious mobsters in the city together with two leaders of the FBI’s organized crime squad, later joined by the president of the state senate, all interacting as if they were longtime friends and members of the same club—which, in fact, they were. It was later revealed that at least two murders had taken place at this same home, just next door to Senator Bulger’s place. One of those murders involved a twenty-six-year-old woman whose sole crime was that she wanted to break up with Flemmi, and therefore posed a threat to the Bulger-Flemmi partnership. Whitey Bulger strangled her to death with his bare hands.