At the peak of his nefarious career, James ‘Whitey’ Bulger, the long-ago murderous Boston mob boss, wasn’t one to dwell on his mistakes, even when he killed the wrong guy a few times. Back then, as whispers had it, Whitey was untouchable.
However, in 2015, after three schoolgirls wrote to him in prison as part of a history project, seeking his views on “leadership” and “legacy,” the octogenarian ex-gangster, a ninth-grade dropout, responded with a rueful letter.
In the Coleman II federal prison in Florida, he filled a sheet of college-ruled notebook paper with tidy cursive, lamenting: “My life was wasted and spent foolishly, brought shame + suffering on my parents and siblings and will end soon.”
Now it has.
Bulger, whose bloody reign in the Boston underworld was aided by crooked FBI agents in the 1980s and who later went on the run for 16 years, living incognito by the California seashore, was found murdered yesterday while completing the first of his two life sentences. He was 89.
The Bureau of Prisons confirmed that Bulger was found unresponsive at a jail in Bruceton Mills, West Virgina. Staff attempted life-saving measures and he was pronounced dead by the county medical examiner. An inmate with Mafia ties is now under investigation for the killing.
Although notorious in Boston, Bulger was largely unknown to the wider world until after he disappeared in 1994. In his absence, his darkest secrets, including his corrupt ties with FBI agents, were gradually laid bare in court hearings, media exposés and a congressional inquiry. He shared space with Osama bin Laden on the FBI’s 10 Most Wanted list.
Captured in Santa Monica, California, in 2011, Bulger was sentenced to two consecutive life terms plus five years after a Boston jury convicted him of 31 racketeering offences. The charges catalogued 19 alleged murders and he was found guilty of ordering or carrying out 11 of them.
The verdicts, in 2013, climaxed a gangland opera of fealty and betrayal that spanned half a century and combined two of Boston’s abiding fixations: ethnic crime and politics.
Bulger, dubbed “Whitey” in his fair-haired youth, was a brother of William “Billy” Bulger, a longtime Democratic state politician and iron-fisted boss of Massachusetts government. Theirs was a family epic – a tale of two siblings, each ruthless in his own way, and each ever loyal to the other, who climbed to power from insular, working-class South Boston.
Billy, an erudite lawyer schooled in classic literature, dominated the statehouse as Senate president for 18 years, while the shadowy, menacing Whitey, once a bank robber and Alcatraz inmate, loomed over the streets as a czar of bookmaking, loan-sharking, extortion and drugs.
After Whitey skipped town in late 1994, a step ahead of an indictment, it came to light that throughout the 1980s he had been listed in FBI records as a confidential “top echelon informant”.
The so-called ‘Irish Godfather’, recruited to snitch on his competitors in the Mafia, had also regularly lavished his FBI handlers with illicit cash and gifts. And the agents, for their part, had connived to shield him from law enforcement interference, allowing a homicidal mob kingpin to operate with virtual impunity for years. Testifying at Bulger’s 2013 trial, his former chief leg-breaker, Kevin Weeks, voiced the hoodlum community’s dismay at Bulger’s perfidy.
To his old cronies, it made no difference that he had supposedly dished dirt only on their Italian American rivals. As a matter of principle, “we used to kill people that were rats,” Weeks told the jury, evincing disgust that, unbeknownst to him in the 1980s, one of “the biggest rats” had been “right next to me.”
He had been finally caught in 2011 when an ex-beauty queen – Anna Bjornsdottir, Miss Iceland 1974 – had seen age-enhanced images of Bulger and his moll on TV and recognised the couple as neighbours of hers in Santa Monica.
Bulger had often rolled up his sleeves and did the dirty work himself. “He stabbed people; he beat people with bats; he shot people, strangled people, run them over with cars,” Weeks said on CBS’s ’60 Minutes’ in 2006.
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