Ruthless killer or Robin Hood? Mob boss James ‘Whitey’ Bulger to stand trial

The case of James ‘Whitey’ Bulger will bring Boston gangland into the courtroom, reports Rupert Cornwell

His exploits make Tony Soprano look like a novice. Long before he was captured in 2011 after a decade and a half on the run, books had been written about him, and a Hollywood movie had featured Jack Nicholson playing the character inspired by him. Now, finally, the real James “Whitey” Bulger is about to appear in court to answer for his alleged crimes that include racketeering, trafficking and extortion, not to mention 19 murders.

He’s far older now, a slow-moving man of 83. Long gone is the rich crop of silver hair that earned Bulger his nickname. But once the jury selection that starts today is complete, America will be treated to a history of organised crime in Boston for much of the second half of the 20th century.

The Mafia, be it old-style Italian or Irish, or more modern Chinese, may have lost some of its clout in recent times, but none of its hold on America’s imagination. And the scheduled witness list at the trial of a man who used to rule the old Irish neighbourhoods of South Boston will not disappoint.

It was unclear whether the court will hear testimony from John Connolly, the former FBI agent who tipped off Bulger to his impending arrest in 1994 and whose dealings with the mob boss formed the basis for the 2006 film The Departed. But three of Bulger’s former lieutenants will give evidence.

One is Stevie “The Rifleman” Flemmi, a hitman and former FBI informant who is serving a life sentence for 10 murders, among them the garotting of his step-daughter. He’ll be followed on the witness stand by John Martorano, another enforcer for Bulger’s gang, who has admitted killing 20 people; and by Kevin Weeks, a close Bulger associate who shortly after his 1999 arrest led the authorities to the graves of half a dozen Bulger victims.

Bulger’s lawyers, JW Carney Jr. and Hank Brennan, look likely to use the trial to attack the credibility of the former associates testifying against him. “The government now offers these men as witnesses against James Bulger with no apparent regard for their complete lack of credibility,” they wrote in a recent court filing.

But the star of the show will be Bulger himself. In another lifetime he might have achieved conventional eminence – his younger brother William was for 18 years leader of the state Senate. James, however, made a living on the streets of South Boston. He started out as a teenager in the 1940s with a street gang named The Shamrocks. He was intelligent, scheming and tough. But arrests followed, and nine years in a string of federal prisons. After his release in 1965 he returned to Massachusetts and by the early 1970s was dominating the criminal universe in South Boston. His alleged activities covered the usual mob specialities: extortion and protection, racketeering, loan-sharking, arms trafficking and, indirectly, drugs.

At times, Bulger acquired something of a Robin Hood aura as he kept streets relatively free of petty crime, and imposed an order of sorts on drug dealers and illegal gambling operations.

The truth, however, was rather different. The FBI and Massachusetts prosecutors believe he personally killed at least 19 people, among them the innocent brother of a rival, and two girlfriends who Bulger feared had come to learn too much about his operations. His resourcefulness and ruthlessness were legendary. “He could teach the Devil tricks,” a gangland associate once said.

Ultimately, he could not escape the grasp of the law. Sealed indictments for racketeering were drawn up by the Drug Enforcement Agency and the Massachusetts state police. Some time in December 1994, Bulger was tipped off by Connolly, and two days before Christmas he fled Boston, accompanied by his common-law wife, Theresa Stanley.

His movements thereafter are a blur: a series of stops inside the US, a last confirmed sighting in London in 2002, and various reported other ones in America, Europe and beyond, some of them spurred by a $2m FBI reward on his head, and a record 16 citations on the TV show America’s Most Wanted. At some point too his companion changed, from Ms Stanley to girlfriend Catherine Greig.

Police finally arrested Bulger and Greig on 22 June 2011. In the apartment they found $800,000 in cash, two dozen firearms, and a selection of false IDs. After 16-and-a-half years on the run, the game for James “Whitey” Bulger was finally up.

Winter Hill Gang: Key witnesses

Stephen ‘The Rifleman’ Flemmi

Bulger’s former partner in the Winter Hill Gang, who pleaded guilty to 10 murders and is serving a life sentence. A former soldier, Flemmi earned his nickname for his marksmanship skills.

John ‘The Cook’ Martorano

A former hit man for the Winter Hill Gang, Martorano has admitted to killing 20 people. After going on the run for 16 years, he took a plea bargain in 1999 and served 12 years. He was released in 2007.

Kevin ‘Two’ Weeks

A former Bulger lieutenant, Weeks served five years for racketeering. He earned the nickname Kevin Two Weeks for the time it took him to agree to become an informant after being arrested in 1999.