There was no indication that Billy Bulger had direct information about these killings or the fact that Whitey and Flemmi had used a shed behind the house—which abutted Billy’s own backyard—as an arsenal for other killings. Years later, under oath, Billy would hide behind a stream of lawyerly nondenials in the manner of “I do not remember” or “not to my recollection,” even claiming before a congressional hearing that he did not know Whitey and Connolly knew each other at all, much less had a working partnership.2
In some ways, Senator Billy Bulger was a man operating within the vortex of history. Maybe he knew Whitey was a killing machine and dispenser of cocaine (nearly everyone else in the neighborhood did), and maybe he didn’t. By advocating so brazenly on his brother’s behalf, he was taking part in an arrangement with deep roots in the Irish American underworld. In an earlier era, the intermingling of politicians, lawmen, and gangsters had been a way for the disenfranchised minority group to make some headway in the New World. But by the Age of Bulger, the overwhelming majority of Irish Americans no longer took part in or even made excuses for mobsterism, flagrant patronage, and political corruption. Put simply, Irish Americans no longer needed the extra edge that came at the end of a blackjack or a gun. They had arrived long ago.
And yet, in Boston, where the fear, anger and bitterness of the Irish immigrant experience had hardened into a kind of crucible—“Hell no, we won’t go!”—the Irish American underworld was hanging on. The entire 150-year run of the Irish Mob had come down to its essential distinguishing characteristic: the alliance between the gangster, the lawman, and the politician. In this light, it was not surprising that Connolly and the Bulger brothers forged their relationship as if it were well within their rights. They were like ancient legends walking among the ruins of the Irish American underworld.3
The Last Hurrah
John Connolly retired from the FBI in December 1990. Whitey Bulger did not attend his retirement party, but Senator Billy did. In fact, Billy Bulger was the Master of Ceremonies, as he had been at so many FBI retirement rackets in the 1980s and early 1990s that he was later unable to remember them all. Connolly’s fete was termed a “raucous occasion” by those in attendance. A few months later, the former FBI agent landed a high-paying position as head of corporate security at Boston Edison, a company closely aligned with Senate President Bulger. Five other former agents from the Boston office also landed jobs with the public utility company, thanks in part to references from Bulger.
Not long after his retirement, Connolly moved into a condominium in Southie that had an adjoining unit belonging to Whitey Bulger. They were now next-door neighbors and had every reason to believe they would grow old together sitting on the porch, telling stories about how they snookered the Mafia in Beantown and lived like kings during the Age of Bulger.
With Connolly gone from the Bureau’s Organized Crime Squad, Whitey was officially closed out as a confidential informant. He would now have to find other ways to establish an edge within the city’s criminal underworld. Apparently, he still had enough juice to pull off a classic gangster’s retirement scam: He “won” the Massachusetts State Lottery. Residents of the state were understandably suspicious when it was announced that one of numerous winning tickets was sold at Bulger’s Rotary Variety Store, next door to his Liquor Mart with the huge green shamrock painted on the exterior. Whitey’s portion of the $14.3 million jackpot—which came out to $89,000 a year for the next twenty years—was put on hold pending further investigation.
Also around this time, Bulger began a series of international forays, usually undertaken with one of his two girlfriends, which might have seemed suspicious if anyone in law enforcement were paying attention—they weren’t. Bulger opened bank accounts and safe deposit boxes in numerous locales, including the Caribbean, Ireland, and London. He acquired driver’s licenses under assumed names from multiple states, including New York.
In retrospect, Bulger’s activities made perfect sense. With his FBI benefactor in retirement, Whitey would have known or at least suspected that his long run as a protected mobster was over. There was a better-than-even chance that, without Connolly to hold down the lid, the dirty little details of their long alliance would one day bubble over. Bulger had already dodged one close call: In 1991, just a few months after Connolly’s retirement, a major narcotics investigation involving the DEA and Massachusetts State Police netted fifty-one Southie-based cocaine dealers, most of them associated with the Bulger organization. Bulger held no sway over the DEA, and the State Police hated him for what they felt had been years of political meddling and flagrant acts of payback on the part of his brother, the senate president. The indictments rocked the neighborhood of Southie, where Whitey’s upperworld supporters had always maintained the lie that he would never sell drugs in his own backyard. But even with all the indictments, not one high-ranking member of Bulger’s organization “flipped,” demonstrating the kind of esteem and fear that Whitey Bulger still inspired in his home neighborhood of Southie.
The DEA case against the Irish Mob may not have netted the Big Fish, but it left Whitey vulnerable, which he would have recognized. Bulger had always been, first and foremost, a survivor. After returning to Boston in 1965, following a nine-year stint in jail, he survived and even rose above the Boston Gang Wars through a Machiavellian ability to divide and conquer. He established his role as the neighborhood godfather with a keen understanding of the historical parameters of the Irish American underworld, doling out turkeys on the holidays and doing favors for his people as if he were a turn-of-the-century ward boss. Some in the community genuinely loved Whitey Bulger or at least loved the idea of Whitey Bulger. The man himself was somewhat taciturn and cold and rarely intermingled directly with neighborhood residents—the better to establish his standing as a near mythical figure, always talked about but rarely seen.
Whitey had also covered his bases through an unparalleled manipulation of upperworld forces. Whereas New York Mafia boss John Gotti, who was lionized by the national media as the “Teflon Don,” was constantly being brought to trial, Whitey Bulger never even stepped foot in a courtroom and was never even charged with a crime in the thirty years since he returned to his home neighborhood. His criminal life embodied the Irish mobster credo, borrowed from the Irish American ward boss, who was known to say: “All politics is local.” Bulger resisted overtures from other Irish American mob bosses like Jimmy Coonan of the Westies because he knew it would take him outside his sphere of influence. Bulger’s philosophy was the philosophy of the Irish Mob: Keep it small, local, even parochial, and you can make it last forever.
Granted, the forever part was a stretch, even for Whitey. As the long saga of the Irish American mobster has shown, few of them ever made it past their forties. Leaders like McLean, Killeen, and Spillane were all killed by younger, hungrier gangsters on the rise. By the 1990s, Whitey was in his early sixties, still pounding the pavement, still making money, still willing to whack people himself if the situation called for it. But as his operation grew with Whitey demanding a piece of everything that was going on in the Boston area (narcotics, gambling, loan-sharking, extortion), it was just a matter of time before Bulger got caught. Nobody knew that better than Whitey himself.
And so, in 1992, the chickens came home to roost. An aggressive federal prosecutor, working mostly with Massachusetts State Police, began rounding up a series of middle-aged bookies—Jewish, Italian, Portuguese, African American—who plied their trade in and around the city. Most of these bookies had been arrested numerous times before, pled guilty, and paid small fines. But this time, prosecutors were threatening to charge them as a group on multiple money laundering and RICO counts. One bookie in particular began to sing like a canary, and it soon became apparent that all of the bookies had one thing in common: In order to operate, they paid tribute to Whitey Bulger and the Irish Mob.
As the case grew, the FBI got involved. The local FBI office was now under a totally new regime. With John Co
nnolly retired, John Morris long since transferred elsewhere, and other individuals out of the picture, the Bureau was finally ready to move on Bulger. His years as a C.I. were, of course, well-known throughout the FBI command structure. There was some concern that by indicting the notorious South Boston Mob boss, the special relationship between Whitey and the feds would be revealed and maybe even become an issue. But there was nothing anyone could do. The Organized Crime Strike Force was going after Bulger anyway, and the FBI figured they might as well be on board.
John Connolly was retired, but he was not disconnected. “Once a lawman, always a lawman,” is a phrase commonly used throughout law enforcement. Connolly, more than most, maintained ties with friends and former colleagues throughout the law enforcement community. He monitored the grand jury investigation of Bulger and his partner Flemmi. Shortly after New Year’s Day, 1995, Connolly was tipped off that the indictment would be handed down on January 9 or 10. The retired agent’s next move was not surprising. He had once told his former boss, John Morris, that he had secured Bulger’s cooperation as an informant partly by agreeing to the condition that Bulger be given a “head start” in the event of an indictment. And so, keeping his word, Connolly called Bulger immediately and told him everything he knew.
Whitey was already out of town when he got the call. He and his longtime girlfriend, Theresa Stanley, had been on the road since August. They visited Graceland, Elvis Presley’s home in Memphis. They traveled to Dublin, London, Rome, and around the United States to New Orleans, California, and the Grand Canyon. Whitey squirreled away money in all of these locations, and he was ready for the call when it came from Connolly. The only problem was that Theresa Stanley, the girlfriend, did not want to go on the lam. She did not want to leave her family forever.
“I want to go home,” she told Whitey.
He was driving her back toward Boston when it was announced over the car radio that Steve “the Rifleman” Flemmi had been arrested. Apparently, the feds, fearing that Bulger and Flemmi would be tipped off, did not wait around for the racketeering indictment. They quickly arrested Flemmi on a criminal complaint charging him with conspiracy to extort a bookmaker, knowing they could hold him until the superseding indictment was announced.
Whitey turned his car around and headed toward a safehouse in New York state, where he dropped off his girlfriend. He then disappeared into the great unknown and has been on the run ever since.
The inability of the Organized Crime Strike Force to catch Bulger was big news, but even bigger news came months later. It had slowly dawned on Steve Flemmi that he was quite possibly going to take the fall for the entire Irish Mob—and he wasn’t even Irish. The federal prosecutors had put together a big case against the South Boston Mob, and it included a number of rats, most notably Timothy Connolly (no relation to John), who was the proprietor of a South Boston tavern that had been the hub of Bulger’s cocaine operation. Connolly also had information that linked Bulger and Flemmi to at least two murders, which was enough to put the two mobsters away for their natural born lives.
The myth of the stand up guy has always been one of the central precepts of the American underworld, dating back to the earliest immigrant gangs. In New York’s Five Points, where the American underworld got its start, ballads were written about gangsters who refused to talk to the authorities and were willing, if necessary, to do time in prison. Being a stand up guy was akin to being a prince of the underworld, and it was a revered attribute that crossed all ethnic lines—Italian, Jewish, Latino, Irish, or whatever.
The stand up guy, however, was borne of a time before RICO, government-sponsored C.I.s, and the Witness Protection Program, which offered the illusion of a fresh start under an assumed name far from the old neighborhood. Back in the day, a gang member or racketeer with a strong constitution was willing to take the fall because it rarely involved more than a three-, five-, or seven-year bit in the joint. For many hard-core criminals, this was seen as a right of passage, one that taught them toughness and did wonders for their reputation once they returned to the underworld.
Steve Flemmi had a reputation as a stand up guy. In Street Soldier, Eddie MacKenzie, who was part of the South Boston coke ring, writes about the time he wound up at Danbury Federal Prison and was confronted by a big-time mafiosi who told him, “You’re here because you got ratted out by your boy Whitey. We’ve known for years he was a canary…. Not Stevie, though. Stevie’s good.”
The Mafia clung to the myth that Flemmi was a stand up guy when, in fact, he’d been an informant even longer than Whitey Bulger. You might rightfully ask how a government informant—a rat—can be a stand up guy at the same time. Only in the underworld would such an ethical perambulation be accepted because in the underworld the myth of the stand up guy is more powerful than Santa Claus, the Easter Bunny, and the Tooth Fairy combined.
As with most gangsters, however, Steve Flemmi’s instinct for survival outweighed all other criminal codes of behavior. In early 1997, after sitting in prison for two years waiting for Whitey to make things better, as he had always done in the past, Flemmi dropped a bomb that would reverberate throughout the underworld and the Halls of Justice for at least the next five years. Through his attorney, Flemmi put forth the defense that he could not be prosecuted for the crimes he and Whitey had committed together because they had been authorized by the FBI to commit those crimes in a trade for underworld intelligence. To support his claim, he began filing sworn affidavits describing his life with the Bureau and the promises he said FBI agents had made never to prosecute him and Whitey Bulger. These claims included details about a multitude of criminal acts, including many murders, that implicated just about every underworld figure in Massachusetts going back to the waning days of the Boston Gang Wars.
Even to those who had always suspected Whitey’s special relationship with the FBI, Flemmi’s revelations were astounding. Had the government actually underwritten one of the most murderous duos in gangland history, making it possible for the Irish Mob to survive in Boston long after it had disappeared elsewhere, so that the government could build cases against the Mafia? It was an extraordinary proposition, the truth of which was about to be dragged into the public domain. U.S. District Court Judge Mark L. Wolf, after months of closed door hearings and legal briefs filed by Flemmi’s attorney, granted a defense request for an open evidentiary hearing to determine if Bulger and Flemmi had indeed been “secretly providing information to the government in exchange for criminal immunity.”
What became known as “the Wolf Hearings” were held throughout 1998. In many ways, the hearings were similar to the Westies trial in New York a decade earlier—a final denouement for the Irish Mob in which numerous faces from the past were called forth to bear witness against aspects of the underworld that had been in place for over a hundred years. In this case, most of the people who were subpoenaed to testify were from the government—FBI agents, federal prosecutors, city officials, and various other representatives of the U.S. Justice Department who were compelled for the first time to come clean about what they knew of the FBI’s pact with Bulger and Flemmi. For many who had observed Whitey Bulger’s miraculous criminal career from afar, it was like the Nuremberg Trials; the unearthing of many long-hidden details verified everyone’s worst suspicions about how Whitey had managed to get away with multiple murders and escape prosecution all these years.
Outside the room where the hearings were held, John Connolly held court. The retired FBI agent knew that his reputation, and perhaps his liberty, was at stake. In keeping with his temperament and personality, he waged an energetic counteroffensive, regaling reporters with comments like, “Handling informants is kind of like a circus…if the circus is going to work, you need to have a guy in there with the lions and tigers. My job was to get in there with the lions and tigers.” And later: “All of them, top echelon informants, are murderers. The government put me in business with murderers.”
As to whether or not the deal with Bul
ger and Flemmi had been worth it, Connolly said, “We destroyed the Angiulos in exchange for a gang of two, Whitey Bulger and Stevie Flemmi. Who wouldn’t make that deal?” And later: “The proof is in the pudding. Look at the decimated New England Mafia.”
Connolly’s defense to aiding and abetting the murderous reign of Bulger’s Irish Mob in exchange for taking out Cosa Nostra was a fitting parting shot in the long-running rivalry between the dagos and the micks. Engineered by the last Irish Mob boss in America, the manipulation of Connolly had been a delirious act of counterespionage, based on the knowledge that the FBI would do almost anything to nail the Mafia. The Mafia had become a victim of its own success, which included a public relations bonanza fueled by Hollywood and embraced by the mafiosi themselves, who no doubt thrilled at the sight of being portrayed by the most dynamic actors in the business. The Mafia had become so big, such a ubiquitous part of American pop culture, that the prosecution of even a small localized Mafia crew was sure to garner national headlines. Some prosecutors, like New York’s Thomas Dewey and Rudolph Giuliani, had even launched political careers through their perceived prowess as mob busters. The FBI was determined to make up for all those years lost to J. Edgar Hoover’s steadfast denial of the Mafia’s existence. The game now was to rehabilitate the reputation of the Bureau on the backs of LCN. If that meant making a backdoor deal with the Irish Mob, who were mostly below the radar and whose prosecution was less likely to bring about major kudos, then so be it.
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