Whitey Bulger

Sean Gullette
Originally Published in KGB
September, 1995

A sunny July morning in South Boston, 1989. Thomas Connolly, a Southie bar owner turned mortgage broker, has just done a favor for the Winter Hill Gang: approving a home equity loan for a cocaine customer who owes them $4000. Connolly, who had moved out of Southie to a cozy suburb, had been reluctant to get involved. "Ultimately," reads the FBI Organized Crime Unit affidavit, "albeit reluctantly and belatedly, Connolly was able to ensure that the loan was approved." From an impatient man's perspective, he had taken his sweet fucking time. And so Connolly finds himself in a small storeroom at the back of the Rotary Variety Store with James "Whitey" Bulger. Whitey and his partner Stephen "The Rifleman" Flemmi do not look happy, a condition which they are uniquely effective at projecting. Whitey has a big hunting knife and "punctuated his comments by stabbing nearby liquor cases repeatedly with the knife." Connolly's pants are drenched with vodka by the time Whitey holds the knife against his shirt and tells him to his relief that he can buy his life for $35,000. Two days later, Connolly is at the variety store holding a bag. Whitey steps out and Connolly hands him the bag. When Whitey comes back out, he is smiling the famously charismatic Bulger grin. He pats Connolly on the shoulder. "Now," he says, "we're friends." Another sunny day in South Boston.


Five years later, on January 10, 1995, Massachusetts State Police and Federal agents planned their biggest dragnet in years. Armed with a package of 37 indictments--for racketeering, loansharking, conspiracy and money laundering--they set out to collect the top leadership figures of the Winter Hill Gang and the Patriarca family, major wiseguys who had eluded prosecution for more than half a century. They intercepted Stephen Flemmi exiting The Schooner restaurant on High Street and read him his rights face down on a squad car. Unfortunately for their whole game plan, they had no warrant for Flemmi's female companion, who picked up a nearby pay phone as they carted their prize away. Within minutes, Winter Hill boss Whitey Bulger was on the road with his packed bags, his girlfriend Theresa Stanley and longtime confidant Kevin Weeks, starting out on the vacation of a lifetime. The other corner of the triangle, Francis Salemme, was gone, too. Years had been invested in building the evidence behind those indictments: the logistical F.U. was a major Bureau dummheit. The FBI picked up the remaining underlings on their list and sat down to talk it over.


There are those of us who feel a distinct nostalgia for the days of The Big Man. For the past century and more, America has been ruled and run by a nameless and self-perpetuating class: our "complicated, bad white men," as James Ellroy calls them. Whether politicians, businessmen, union bosses and mob bosses, generals or cops, they have been united by a fondness for tax-free income; large scotches, cigars, and hats; and a blunt approach to business which has defined our corporate culture--and succeeded at our expense. Bastards that they were, they had an undeniable style about them. Happy the society, one might muse amorally, that can support such lordly, autocratic sons-of-bitches.

Every St. Patrick's day in Boston, Billy Bulger, president of the State Senate for 17 years now, presides over a breakfast at the Bayside Club in Southie. Such heavies--literally as well as in political clout--as Ted Kennedy, Joe Moakley, Governor Bill Weld and Mayor Thomas Menino crowd up the Bayside's shaky fire escape to the sweaty packed tavern, where host Billy entertains the capacity crowd with a fat man's good humor. There are drinks, Irish songs, political anecdotes and Billy's uniquely well-informed brand of topical humor, which is said by one source to have turned at one point this past year to his brother, Whitey, two months a fugitive from justice. "Wherever he is," Billy reportedly said, "I hope he's wearing suntan lotion. Because you know light Irish skin burns easy."

Boston loves its gangsters as much and maybe more than any other big American city; and Irishness is its first defense against its provincial insecurities. In the days following Whitey's departure, the Globe (the quality daily) and Herald (the Murdoch tabloid) began a daily picnic of mob notes which brought forth lots of fun background gossip and showed that for many Bostonians, the end of an era which Whitey's departure spelled was indeed as nostalgic as it was welcome. The city launched itself down memory lane with a vengeance.

Jimmy Bulger got his nickname as a towheaded blond lad growing up in tough, windy South Boston, the Irish ghetto-stronghold on a hill bordered on one side by the Fort Point channel and Mass. Turnpike, and on the other by the Atlantic ocean. Little Jimmy and Billy went to Catholic school, learned the names of the saints and said their prayers going to bed. Like generations of Boston Irish, they also heard the stories of the era of Anglo power, when downtown businesses would hang out help-wanted signs with the addendum: No Irish Need Apply. The Bulgers were part of the new generation dreaming a way in. In Whitey's case, however, aiming high started out low. He was a black sheep like he was born to it: fucking up in school, hanging out with the wrong kids, giving the finger to the police and the nuns. At 26, while he was being tried for robbing banks in Massachusetts, Rhode Island and Indiana, his brother Billy was graduating from Boston College with honors and heading to law school, on the trajectory which would make him President of the State Senate, second only to a string of Governors in statewide political clout for two decades running. Whitey served 9 years in various Federal prisons, three of them at Alcatraz. He got out early on the "good time" earned by participation in an FBI -sponsored LSD testing program--tripping his brains out on high octane government acid in the federal penitentiary in Atlanta. 35-year old Whitey returned to Boston with a menacing glint in his eye. Brother Billy got a him a job as a janitor at a Boston courthouse, but he didn't need it for long. Like many professional criminals' first terms, his undergraduate stint in jail had built character and ambition. Whitey was ready to graduate to the big leagues. The first messy chore on his return was breaking open the Italians' near-monopoly on the Boston rackets. There were plenty of freelance Irish players who were more than happy to sign on with a leader who could help them break out of second class-criminal status. The process was bloody, prolonged and ultimately successful. Although both sides would continue boasting--privately--for years about how many micks and wops they had respectively clipped, the concord which Whitey ultimately built with Flemmi and Salemme was a well-kept pact of racial equality. ("They're all the same," a State Trooper told The Globe of the city's multicultural racketeers in 1994, "except some of them have o's at the beginning of their name and some have o's at the end.") In the next 4 decades, as Whitey built a crime organization rivaling any in the country for discipline and profitability, the most serious charges brought against him were for traffic violations. He paid the fines, and his power over the rackets grew as Boston became the Northeast's second city for crime, especially drugs. When New York Harbor was effectively sealed in the early '80s, Boston began to see a huge volume of cocaine and tons of marijuana, and Whitey saw a cut of almost everything moving in or out, although the Chinese tongs controlled most of the heroin.

Like all good gangsters, Whitey shared the wealth with the community which housed his efforts, in the form of jobs, handouts, private policing and the enforcement of community standards. Often described as "a city of neighborhoods," Boston has kept American-style apartheid alive for years, with the black population largely isolated in Dorchester, Mattapan, and Roxbury, the area of projects and brownstones separated from the downtown financial and tourist center by the eight-lane Mass. Turnpike. On the east, "Mandela, Mass." is bounded by Broadway, the western wall of Southie--where little old ladies still refer to Whitey as "a gentleman." Although it isn't mentioned among the "great things" which some Southie Irish stolidly insist to reporters that he did for the neighborhood, part of Whitey's role as godfather was to help enforce the line which keeps Southie all-white. In a city of neighborhoods, it is people like Bulger who enforce the boundaries--securing their own power bases in the process. If you've ever lived in a mob-run neighborhood, you know that feling of security, solidarity and silence. So when "busing"--transporting black kids from the Boston ghettos to better public schools elsewhere in the city and suburbs--became the hotbutton issue of the '70s, it ripped the city nearly in half. Whitey's opinion fell with his constituency, on the throwing-rocks-at-schoolbuses side of the issue. Tempers ran so high on the topic that Mayor Kevin White, running for re-election on a pro-busing ticket in 1975, was genuinely afraid that Whitey was going to murder him. On a tape which was recently released from WGBH vaults, White ranted at PBS "10 O'Clock News" host Christopher Lydon: "No, no, no, you don't wanna ask the tough one...in the '75 fight, in the end the Mob was in the fight. A blind man knew that. And if they shot me they win all the marbles. So why not shoot the son of a bitch? Do you know it was, for me, I'm not exaggerating...I was never more scared in my life. I figured if they pump me out--which, why not, Whitey would be...they were crazy enough even then to do it to me--then they drew Gerry O'Leary as council president." Instead, White was elected, and the buses rolled, but the change it brought in city dynamics was minimal. The Boston Police--and some of its citizenry--were vigilant enough in their own ways, and Whitey & Co. continued doing their bit to keep the Irish-African line drawn. There were nasty beatdowns of black kids in South Boston and South End parking lots, seldom reported and never taken to law, since witnesses were tight-lipped out of sympathy or fear.

Southie sentiment on the race question went hand-in-hand with passionate feelings about the ancient war of Northern Ireland, for which Boston has always been a Republican staging area, R & R facility and cheering gallery. Since the IRA rigorously prohibits its members from drug dealing to raise funds, friends of The Cause sometimes lend a hand. So in September of '84, the ship Valhalla left Boston harbor loaded with a million dollars worth of guns and ammo--91 rifles, 8 submachineguns, 13 shotguns, 51 handguns, 11 bulletproof vests and so on--bound for Belfast. Off the coast of Ireland, the Valhalla's cargo was transferred to the Irish vessel Marita Ann, which was then intercepted by tipped-off Irish authorities, two miles off shore. Back in Boston, Federal agents monitoring a wiretap heard Whitey Bulger, watching the news, say "that's our stuff." Bulger lieutenants Joe Murray and Pat Nee had organized the mission, which they had financed with help from Whitey and by smuggling 36 tons of marijuana into Boston Harbor. Both plead guilty; Murray was shot to death shortly after his release. A member of the Valhalla's crew, an idealistic young man named John McIntyre was also killed under suspicion of being the informer. (The Globe's Kevin Cullen, perhaps the leading scholar of Boston's criminal institutions, later learned that another man, Sean O'Callaghan, was the real informer.) But for every mission that failed, many more were successful. Being part of the struggle gave a meaning beyond dollars to the work that the Boston hard men did, and the bond of loyalty and nationalism it provided was good for morale, too.

5:30 in the morning and a bookmaker in Southie answers the front door in his underwear. Standing there are Whitey and Stephen Flemmi, along with bookmaker Joseph Yerardi, who would later recount the episode to the FBI. The bookie owes 'rent.' "Where's the money?" Whitey asks him, holding a machete. "We're telling you to come up with it. This is the end of it." They take him down into the basement and start to beat the shit out of him. Whitey picks up the machete. "And (Whitey) says 'Okay, it's all over buddy,"' Yerardi said in his deposition. "And then he goes 'Ahhh, I'm, I'll pay! I'm gonna pay!"'

At its heart the Business is relatively simple. From Hong Kong to Little Italy, the mob is the IRS and the FBI of an alternative economy, extorting money from bookies, loan sharks and drug dealers, who in return have a succinct and effective verbal formula to use in collecting unpaid debts--and also enjoy the use of their legs and the daily sight of their wives, children, cars and homes. But resourceful outfits have more on their plates than that. Whitey's Winter Hill Gang was a diversified operation. In their heyday, the Winter Hill Gang and their Italian colleagues saw a piece of everything that moved in or out of Boston. Gennaro (Jerry) Angiulo, talking to an audience of hoods in Vegas (and Feds out in the van) said of his Boston operation with Whitey, "We got some very tough boys. We're a shylock. We're a goddamn bookmaker. We're selling marijuana. We're illegal here, illegal there. Arsonists! We're every-fucking-thing." Their hegemony extended from Providence to Cape Cod to the Canadian border, and geared in smoothly to the activities of its acknowledged superiors in New York and New Jersey. It bought Whitey, Flemmi, and company a man-sized chunk of the American dream: dozens of cars, 3rd and 4th houses, big, well-funded families on the move in Boston business.

Since Whitey's departure, the Boston rackets have pretty much gone to hell. With the exception of a few "made" guys still wandering around--Angiulo's son the current favorite--the leadership is all in prison, dead, dying in prison, dying in the hospital or wearing ankle bracelets on house arrest. A half-dozen shootings in the past year have pointed to failed efforts to assert control. But after years of laissez-faire, the State Police Special Services unit and the FBI have made the role of new boss look relatively undesirable. You'd have to be pretty stupid to try it--and pretty smart to succeed. Besides, as far as we know Whitey hasn't given his OK, and some people think he will be back. Kevin Weeks, his closest confidant and traveling companion, who was not named in the indictment, returned to the city in February and is presumed to be acting chief of the Winter Hill Gang. Theory goes that Whitey is sitting in the sun, talking to expensive lawyers and close friends about the charges and evidence against him, and his prospects for a day in court. Others say he's got no reason to return, and that new charges and wiretap evidence will be brought forward if he does. Brother Billy--whose blunt media blackout on the Whitey question is respectfully mimicked by everyone else in State politics--has said only, "He's my brother. I care about him. I've always encouraged him to come by often."

There will be no real successor for Whitey Bulger. Mobsters are businessmen now. The world is better off without him, one less Top Hoodlum to bust everyone else's balls. History moves on, and the criminals who ultimately replace him will be invisible, "buffered" and mediated from the mechanics of crime and the pain they inflict. Such is progress.