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. For 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 penitentiary 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 lam for 16 years, living incognito by the California seashore, was found dead today while completing the first of his two life sentences. He was 89.
The Bureau of Prisons confirmed that Bulger, 89, was found unresponsive at a penitentiary in Bruceton Mills, West Virgina. Responding staff attempted life-saving measures and he was pronounced dead by the county medical examiner. No other details were immediately available.
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 became a nationwide curiosity, sharing space with Osama bin Laden on the FBI's 10 Most Wanted list.
Captured in Santa Monica, Califorina, in 2011, Bulger was sentenced to two consecutive life terms plus five years after a Boston jury convicted him of 31 racketeering offenses. The indictment against him cataloged 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 lawmaker 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 by different means from a hardscrabble beginning in insular, working-class South Boston.
On Boston's Beacon Hill, William Bulger, 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 below, a tsar of bookmaking, loan-sharking, extortion and drug distribution.
"Where's Whitey?"
After Whitey Bulger skipped town in late 1994, a step ahead of an indictment, it came to light that throughout the 1980s, in his racketeering heyday, he had been listed in FBI records as a confidential "top echelon informant" for agents in Boston.
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.
The news that America's top crime-fighting agency had been in cahoots with Boston's most vicious gangster embroiled the FBI in scandal.
The revelation that Bulger had trampled on the underworld's cherished conceit about a code of silence ruined the ex-boss' good name among his peers.
Testifying at Bulger's 2013 trial, his former chief leg-breaker, Kevin Weeks, voiced the hoodlum community's dismay at Bulger's perfidy.
To Bulger's 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."
Hearing this, Bulger interrupted from the defendant's table, yelling vulgarities at the much younger Weeks.
Most of Bulger's murder victims were enemy thugs or duplicitous underlings, but some of the 19 killings he was accused of were collateral damage or cases of mistaken identity.
Bulger, a blue-collar Godfather, 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.
There were innocent "civilians" among the slain, as well, notably Roger Wheeler, a wealthy Oklahoma entrepreneur who refused to sell his East Coast jai alai frontons to cohorts of Bulger. After a round of golf one day in 1981, Wheeler, 55, was ambushed by a Bulger hit man in the parking lot of a Tulsa country club and shot between the eyes.
The FBI agents in league with Bulger back then effectively ignored the continuing bloodshed.
Bulger had stashed away a fortune in cash in case he had to retire from organised crime in a hurry. Starting in 1997, a few years after he vanished, he and a Boston girlfriend, Catherine Greig, lived comfortably in an apartment near the Santa Monica beach, posing as Midwest retirees Charlie and Carol Gasko.
Then, in 2011, a favourite South Boston guessing game - "Where's Whitey?" - abruptly ended with a phone call to authorities from 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.
Bjornsdottir collected a US$2 million federal reward. As for Greig, now 67, she got prison terms totalling nearly a decade for helping Bulger dodge justice and for dutifully keeping her mouth shut afterward - refusing to testify before a grand jury about others who might have aided Bulger as a fugitive.
James Joseph Bulger was born on September 3, 1929, in Everett, Massachusetts, across the Mystic River from Boston. When he was a child, his family moved to public housing in South Boston, or "Southie," as it's known. For most of his life, the neighbourhood was a hard-knocks Irish American stronghold steeped in an ethos of us-against-the-world.
His father, who had one arm, eked out a living in low-end jobs while young Whitey went around stealing with both hands. He graduated to bank robbery in the mid-1950s and landed behind bars, eventually in Alcatraz, with a 20-year sentence.
Not long afterward, his kid brother Billy began a career in the state legislature that would last 35 years and make him the most enduringly powerful figure of his era in Massachusetts government. "What Whitey does with a gun, Billy does with a gavel," a political foe once remarked.
William Bulger steadfastly looked out for his incarcerated brother's well-being, enlisting help from another son of Southie, John McCormack, the neighbourhood's 21-term Democratic congressman who was US House speaker for most of the 1960s.
In Washington, McCormack, who died in 1980, made it clear to federal prison officials that he was keenly interested in the welfare of his constituent James Bulger, according to a stack of books about Whitey. The authors include current and former Boston Globe journalists Kevin Cullen, Shelley Murphy, Dick Lehr and Gerald O'Neill, all prolific chroniclers of the Bulger clan.
With the two politicians, one a titan, advocating for him, Bulger was transferred out of Alcatraz in 1962 and paroled three years later. Back home, he found a niche as an entry-level enforcer in the Southie rackets and rose fast. Through treachery, intimidation and murder, he muscled his way to criminal dominion over a large share of the region.
Obituary: The long and deadly career of James J. "Whitey" Bulger. https://t.co/d4dxY8xKaB pic.twitter.com/aZynbrxnxR
— The Boston Globe (@BostonGlobe) October 30, 2018
When his secret alliance with the FBI began, in 1975, two rival groups stood supreme in the Boston underworld: the local Mafia franchise, ruled by brothers named Angiulo in the city's North End, and Bulger's fearsome outfit, known as the Winter Hill Gang.
In those days, FBI Director J Edgar Hoover was intent on crushing the Italian American mob nationwide. Whitey was recruited to inform on the Angiulos by a Southie-bred agent, John Connolly, who was a protege and longtime friend of soon-to-be Senate President William Bulger. Over the years, while the crime boss was on the FBI's books as a snitch, the relationship devolved into one of payoffs and protection.
Prosecutors said Connolly, who pocketed about a quarter-million dollars in bribes, schemed to thwart investigations of the Winter Hill crew and alerted the boss to turncoats in his midst, occasionally with lethal results. Finally, in December 1994, as a grand jury was about to indict Whitey Bulger, Connolly gave him a heads-up, and the gangster beat feet, eventually to his West Coast hideaway.
The disgraced former agent, now 78 , got a 10-year prison term for racketeering and other crimes and was sentenced to an additional 40 years for complicity in a 1982 mob hit. In that one, a potential witness against Bulger wound up dead in a Cadillac trunk at Miami International Airport.
Bulger's survivors include three siblings, one of them William Bulger, who retired from the legislature in 1996 and became president of the state's University of Massachusetts system. He has always been publicly reticent about Whitey, saying little more than that "Jim" was his brother and he loved him.
Bulger was more than a gangster. He orchestrated the biggest shipment of weapons from America to the IRA, in 1984. https://t.co/wBBnGugXj0
— Kevin Baron (@DefenseBaron) October 30, 2018
After invoking his Fifth Amendment right against self-incrimination at a 2002 congressional hearing on the FBI scandal, William Bulger was granted immunity by a House committee and forced to answer questions. His grudging testimony, ridiculed in Massachusetts, sparked months of political warfare between him and then-Governor Mitt Romney, a Republican, who pressured the ex-lawmaker into resigning his university post.
William Bulger told the House panel that he had spoken by phone with his fugitive brother but didn't know where he was. And in the tight-lipped manner of an old-school Southie stalwart, he professed to know little about Whitey's former livelihood.
"It was vague to me," he said at the hearing.
As for Whitey Bulger, in a documentary produced after his arrest, he acknowledged bribing federal agents but indignantly denied being "a rat."
Despite a 700-page FBI informant file bearing his name, he insisted that the underworld ethic against snitching was sacred to him and that the file was a pack of lies, a big smear by the feds.
At his trial, though, when he could have taken the witness stand to defend his integrity as a gangster, Bulger opted not to testify, telling the judge, "Do what youse want with me."
Whitey is dead.
— Bryan Suits. KFI Los Angeles (@darksecretplace) October 30, 2018
The Departed is not based on Whitey Bulger's story. But Jack Nicholson's character is loosely based on Bulger.
The film is actually a remake of a 2002 Hong Kong film, Infernal Affairs.
Disregard anyone who claims the original is better. It ain't. Stupid ending.
Nice @joshrottenberg piece on how Whitey Bulger film 'Black Mass' re-creates the lost Boston of 1975 http://t.co/DbG967so1g
— Saba Hamedy (@saba_h) September 19, 2015
Trump was praised as deserving 'six Nobel Peace Prizes' and a spot on Mount Rushmore.