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.

Mr. 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, died Oct. 30 while completing the first of his two life sentences. He was 89.

The Bureau of Prisons confirmed Tuesday that Mr. Bulger was found unresponsive at a penitentiary in Bruceton Mills, W.Va. After responding staffers tried to save his life, he was pronounced dead by the county medical examiner. The U.S. attorney’s office for the Northern District of West Virginia and the FBI are investigating.


This 1953 booking-photo combo shows James "Whitey" Bulger after an arrest. (Boston police/AP)

Two prison employees familiar with the investigation said the death is being investigated as a homicide. The employees, who spoke on the condition of anonymity because they were not authorized to talk about the ongoing probe, said Mr. Bulger was found with severe head trauma. They said two inmates have been identified as possible suspects, partly based on surveillance cameras.

Although notorious in Boston, Mr. 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, Calif., in 2011, Mr. 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 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.

Mr. Bulger, dubbed Whitey in his fair-haired youth, was a brother of William M. “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 czar of bookmaking, loan-sharking, extortion and drug distribution.

'Where's Whitey?'

After Whitey 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 “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 the country’s top crime-fighting agency had been in cahoots with Boston’s most vicious gangster embroiled the FBI in scandal. Meanwhile, the revelation that Whitey had trampled on the underworld’s cherished conceit about a code of silence ruined the ex-boss’s good name among his peers.

Testifying at Whitey’s 2013 trial, his former chief leg-breaker, Kevin Weeks, voiced the hoodlum community’s dismay at the gangster’s perfidy.

To Whitey’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, unbeknown to him in the 1980s, one of “the biggest rats” had been “right next to me.”

Hearing this, Whitey interrupted from the defendant’s table, yelling at the much younger Weeks, “You suck!”

“F--- you!” retorted the erstwhile henchman, who had once been like a sociopathic son to him.

“F--- you, too!” Whitey shouted, before the judge barked, “Hey!”

Most of Mr. 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. Whitey, 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 Mr. 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 Whitey back then effectively ignored the continuing bloodshed.

Mr. Bulger had stashed away a fortune in cash in case he had to retire from organized 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 favorite 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 Mr. Bulger and his moll on TV and recognized the couple as neighbors of hers in Santa Monica.

Bjornsdottir collected a $2 million federal reward. As for Greig, now 67, she got prison terms totaling nearly a decade for helping Whitey dodge justice and for dutifully keeping her mouth shut afterward — refusing to testify before a grand jury about others who might have aided Mr. Bulger as a fugitive.

A bank robber in his youth

James Joseph Bulger Jr. was born Sept. 3, 1929, in Everett, Mass., 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 neighborhood 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 W. McCormack, the neighborhood’s 21-term Democratic congressman, who was U.S. 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, Whitey 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.

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 Mr. Bulger’s fearsome outfit, known as the Winter Hill Gang.

In those days, the FBI was fixated on crushing the Italian American mob nationwide. Whitey was recruited to inform on the Angiulos by a Southie-bred agent, John J. Connolly Jr., who was a protege and longtime friend of soon-to-be state 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 Mr. 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 Whitey wound up dead in a Cadillac trunk at Miami International Airport.

Mr. 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.

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-Gov. Mitt Romney (R), 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 did not 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, 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, Mr. Bulger opted not to testify, telling the judge, “Do what youse want with me.”

Amy Brittain and Mark Berman contributed to this report.