Paddy Whacked: The Untold Story of the Irish American Gangster (72 page)

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.

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.
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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.
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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 Connolly 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.”