Late Night Pulped Friction: Whitey Bulger (Probably) Died As He Had Lived

The parenthetical in the title is because the first breathless news reports out of Bulger’s home town said that the corpse was ‘so badly beaten as to be unrecognizable’ — exactly the suspiciously B-movie detail that *would* finish a novelization of Whitey’s career. But the sordid truth seems to be that the old man was killed by a professional thug from the Massachusetts sticks, apparently in the hope that one more murder would bump up his own status among the other lifers.

And just as Bulger survived to be a very old man by playing various law enforcement agencies for a bunch of grubby bureaucrats equally torn between envy of their targets and burning hatred for their interbureau rivals, the circumstances of his death have left many questions that will bedevil the FBI and the US Bureau of Prisons.

The Boston Globe, no suprise, is going all out on Bulger’s life and death. (If it weren’t for the Red Sox victory parade, Whitey would probably have had the entire front page to himself.) And who could blame them, given such material?

James “Whitey” Bulger’s life played out like any number of the violent Hollywood movies it spawned, reflecting a Boston that is no more, when bookmakers and gangsters peopled the taverns of the city’s working-class neighborhoods; when the locals wouldn’t dream of turning in the neighborhood hoodlum; when gangland murders were commonplace; and when the FBI was so hellbent on taking out the Mafia that it helped gangsters like Mr. Bulger kill rivals and rise to the top of the Boston underworld.

Mr. Bulger, one of America’s most manipulative criminals who eluded prosecution for decades because he was protected by corrupt FBI agents, was killed Tuesday in a federal prison in West Virginia. He was 89 and was serving two life sentences for 11 murders.

Mr. Bulger was charismatic and vicious, well-read and heartless. He persuaded a Jesuit priest to serve as his parole sponsor, torched the Brookline birthplace of John F. Kennedy during antibusing strife, kept house with two women in different locations at the same time, and routinely took naps immediately after shooting people in the head. He loved animals, crying over a puppy being put down, yet secretly buried at least six of his victims, denying their loved ones the bodies…

In his teens, James Bulger ran away with the circus, and when he returned home he took up with a much older woman who was a stripper in a traveling burlesque show. The stripper scandalized Mr. Bulger’s mother by sending him postcards from the road.

Mr. Bulger’s propensity for rule-breaking graduated to crime. He was a tailgater — stealing off the backs of trucks that took goods from the freighters on the South Boston waterfront.

In a neighborhood where hardly anyone had a car, he had one. When he wasn’t driving around town with his Jayne Mansfield-lookalike girlfriend Jacquie McAuliffe, Mr. Bulger often scouted for opportunities — not necessarily for crime, but to buff his credentials as a hoodlum with a heart of gold.

Such consideration was also a conscious act of mythmaking. From a young age, Mr. Bulger was determined to be a career criminal, but he knew that to survive he needed to be liked as much as feared…

… In 1955, he helped rob three banks, then was captured the following year and charged with those robberies. FBI reports show his first turn as an informer occurred in 1956, when he named two of his accomplices in the bank jobs. Ostensibly, he did it to save his girlfriend from potential accessory charges. She was credited with turning in his accomplices and never served any time.

Despite his cooperation and his guilty plea, Mr. Bulger received a 20-year sentence. He was sent to the federal penitentiary in Atlanta, where he volunteered to be part of an LSD experiment in exchange for a small reduction in his sentence. He was told it was part of a search for a cure for schizophrenia but later learned it was a secret CIA program to engage in mind control during the Cold War.

The experience left him bitter and suffering from night terrors. For the rest of his life, he complained of sleep disorders brought on by the LSD…

After struggling to adapt inside the Atlanta prison, Mr. Bulger was implicated in two escape plots and sent to Alcatraz, called The Rock, the island for incorrigibles.

It was at that point that his brother William emerged as his most vocal, steadfast advocate. First as a student at Boston College Law School, then as a freshly minted state legislator, Bill Bulger put together an influential array of supporters, including the Boston College Law School dean, the Rev. Robert Drinan, who would later go on to become the first congressman to call for the impeachment of President Richard Nixon…

Still, he viewed the three years he spent at Alcatraz with fondness. He honed his intellect, professing to read a book a day. He read about military history, war, philosophy, and politics and became a student of Machiavelli…

Any novelist tried to string that many tropes into a single paperback would be told to either dial it back, or turn it into a multi-season streaming series.

Whitey Bulger was in notoriously poor health, but in his last media appearance he walked under his own power from a black helicopter to a prison van, guarded by multiple armed men. He hadn’t reached the point of decline where ‘sympathetic’ media would portray him as a feeble, senile, babbling corpse-to-be confined more by his rotting flesh than the government’s authority. His death may not have been one that he’d have chosen, but I suspect he’d have appreciated the operatic brio of it all.