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A window into Whitey’s brutal life and mind

The biography that traces Bulger’s rise, reign, and the reckoning ahead

A 1955 Miami Beach Police mug shot of Bulger (left), and his booking photo in 2011.

As he sits brooding in his drab cell awaiting trial, South Boston gangster James “Whitey” Bulger is telling friends that while he feels tortured by his cramped captivity, with its isolation, strip searches, and dismal food, he is ready and eager for “the big show” — the trial where he will defend his sense of honor if not exactly his innocence.

But however defiant he remains, Bulger was prepared to give prosecutors an easy way out, saying he offered himself up for execution if the government would let the woman he loves walk free.

“I never loved anyone like I do her and offered my life [execution] if they would free her — but no they want me to suffer — they know this is the worst punishment for me by hurting her!” Bulger wrote to a friend last year as his longtime girlfriend, Catherine Greig, faced the prospect of years in prison for her devotion to him.

Two other women are also much on Bulger’s mind these days — two whose murders he is charged with, but who he insists he did not kill. Despite the clear, contrary recollections of his criminal associates, Bulger is adamant on the point — murdering women, he claims, is against his personal code.


“I never killed any women,” Bulger wrote to a friend.

Bulger’s generous view of himself, not as a cunning killer and cynical informer but as a criminal with scruples and a kind of noble romantic, is detailed in a new and comprehensive biography of Boston’s most infamous criminal, to be published this week. Also detailed are all the reasons not to accept his self-serving self-portrait, from his long and murderous career as a gangster to his well-documented history of providing information to the FBI.

The book, “Whitey Bulger: America’s Most Wanted Gangster and the Manhunt That Brought Him to Justice,” written by the authors of this article (Kevin Cullen and Shelley Murphy), with editorial support from The Globe, reveals a host of new information about Bulger, from his pursuit of domestic tranquillity in a tangled romantic triangle, to his seeking out a psychiatrist a la Tony Soprano, to his heretofore little-known role as an agent of mayhem during the city’s school desegregation crisis. The book also provides a window into Bulger’s thinking and state of mind as he molders in jail, reflections recorded in letters he wrote to a close friend and which the authors reviewed. It is in one of those letters that the 83-year-old Bulger contends that he offered to plead guilty to 19 murders — including some he says he did not commit — and submit himself to the death penalty in Florida or Oklahoma in exchange for leniency for Greig.


A 1955 Miami Beach Police mug shot of Bulger (left), and his booking photo in 2011.

Prosecutors spurned his offer, he says, and Greig, 61, pleaded guilty and was sentenced last June to eight years in prison for harboring Bulger during the 16 years they spent on the run, most of them in a modest, two-bedroom rent-controlled apartment in Santa Monica, a few blocks from the Pacific Ocean.

Greig’s sentence infuriated Bulger, who confided in another letter to his longtime friend, Richard Sunday, that she had managed to do what the criminal justice system couldn’t: “Got me to live crime free 16 years – for this they should give her a medal.”


While he worries about Greig’s life in prison, Bulger says his attitude about his upcoming trial, scheduled to begin in June, is “bring it on.” He relishes the prospect of taking the stand and is especially determined to prove that he was not an FBI informant and did not kill two women whose murders are among the 19 he is charged with.

In the book, to be published Monday by W.W. Norton & Co.,Bulger comes off as part defiant, part delusional, cloaked in something of a persecution complex. His self-image is noteworthy for its self-regard. Much of it, especially his denial of being an informant, is completely at odds with the public record and appears to undermine his defense strategy of asserting that he had immunity from a federal prosecutor to commit his crimes.

The book also provides a fuller account than previously available of:

■  Bulger’s nine years in prison as a young man, where he vowed to reform, and how his politician brother William relied on influential politicians to get him parole.

■  His stealth campaign of violence to protest court-ordered busing of South Boston students, including the firebombing of President John F. Kennedy’s birthplace in Brookline.

■  His face-to-face meeting with the founder of the Provisional Irish Republican Army, which led to Boston’s Irish mob being enlisted as weapons procurers for the IRA.

■  His 2011 arrest in Santa Monica, where he refused his captors’ demand to drop to his knees, and risked being shot, because he didn’t want to get his pants dirty.


Bulger, as evidenced in his letters, now frames his legal predicament in grandiose, literary terms. While his enemies, including his former criminal confederates, might see him as the embodiment of Gypo Nolan, the treacherous protagonist in Liam O’Flaherty’s classic tale of betrayal “The Informer,” Bulger casts himself as Philip Nolan, the altruistic protagonist in “The Man Without a Country,” Edward Everett Hale’s short story. Nolan, a US Army officer, renounces his citizenship during his trial for treason and is sentenced to spend the rest of his life at sea, cut off from others. Bulger sees his isolation in high-security detention as he awaits trial in similarly epic terms, punishment for someone who knows too much about his government’s dark side.

The letters also suggest that Bulger is obsessed with refuting the charges that he strangled Debra Davis in 1981 and Deborah Hussey in 1985 before secretly burying their bodies. It is a point of honor for him; sorting out the truth will come down to his word against that of two former criminal associates.

Sunday, 81, who served time with Bulger in both the Atlanta federal penitentiary and the infamous Alcatraz in the 1950s and 1960s, remains sympathetic to the gangster. He said Bulger admits to some crimes, but says former associates who cut deals with the government while he was on the run have blamed him for other crimes he didn’t commit.

“I think Jimmy figures, okay this is the end and I want the truth out there,” Sunday said during an interview at his home in a Pittsburgh suburb. “I don’t think he wants to leave this world or spend the rest of whatever time he has left in it being falsely accused. . . . He wants his day in court.”


Bulger insists that the FBI didn’t use him, he used the FBI, and that he never helped the agency send anyone to jail. Bulger’s attorney, J.W. Carney Jr., has said Bulger alleges that a former federal prosecutor, Jeremiah O’Sullivan, who is now deceased, promised him lifetime immunity for his crimes — including murder.

Bulger told Sunday he refused to become an informer, despite regular beatings from police officers in his youth. But Bulger’s old court records tell a different story, showing that his first known cooperation with law enforcement was in 1956, when he agreed to identify his bank robbery accomplices so that his then-girlfriend would not face criminal charges for accompanying him on a trip that culminated with a bank robbery in Indiana. That early turn as a snitch was first reported by WBUR, citing documents obtained by two former Globe reporters, Gerard O’Neill and Dick Lehr, who also have a biography of Bulger coming out soon: “Whitey: The Life of America’s Most Notorious Crime Boss.”

The season of Whitey’s courtroom reckoning is also a season of new accounts of his life and misdeeds.

Bulger’s defiant insistence that he wasn’t an informant – directly refuted by sworn testimony, countless judicial findings, and extensive records showing that from 1975 to 1990 he was an informant for the now imprisoned former FBI agent John J. Connolly Jr.— seems to rest on semantics: Bulger claims his information was never used to put anyone in prison, so he can’t be considered an informant.

In his letters, Bulger said he looks forward to clearing his name at his upcoming trial, though he is also coldly realistic about his future: “Chances are I’ll die in this cell,” he wrote.

The letters from jail paint a portrait of Bulger as being deeply in love with Greig and regretting that he had met her a decade after he got out of prison in 1965 after serving nine years for bank robbery. He felt he could have left behind the criminal life he returned to shortly after his release.

“By the time we met it was too late,” he wrote. “I was in too deep, had done too much to even consider an honest way of life.”

Bulger describes his time on the run with Greig, where they posed as a retired couple, as the happiest of his life and like a 16-year honeymoon. “Became a real citizen and became a different person,” he wrote, “experienced emotions, feelings that I’d shut down for years.”

He credited Greig with his transformation from scheming gangster to laid-back retiree. While he purposely remained a virtual recluse, venturing forth from their apartment mostly for early-morning or early-evening strolls, Greig did all the couple’s errands, shopping, and cooking.

Bulger has been prohibited from writing to Greig, who is serving her time at the federal penitentiary in Waseca, Minn. The last time the couple saw each other was in June 2011, when they sat handcuffed in a van, separated by deputy US marshals, as they were driven from the federal courthouse in Boston to separate jails. Greig watched Bulger step out of the van at the Plymouth jail, then continued on to a Rhode Island jail.

Sunday said Bulger felt the government was pressuring Greig to cooperate and insisting she share information that she did not have. He was especially aggrieved that the government moved to seize Greig’s family home in South Boston and the house in the Squantum section of Quincy that he bought for her. The government released its lien on the properties after Greig’s conviction so she could sell the Quincy house and pay a $150,000 fine.

In his letters from jail, Bulger complains about the tight security under which he has been held at the Plymouth County Correctional Facility since his arrest and his return to Massachusetts. He said he is kept in his 8-by-12-foot cell 23 hours a day, allowed out for an hour five days a week. Now 83, he keeps himself in shape by doing more than 100 pushups a day. He said he’s fed food, often cold, through a slot in the door, likening it to being in a zoo. During his hour of recreation, he’s watched by an officer with a canine. He is not allowed to watch TV or listen to a radio and spends much of his time reading, writing letters, and preparing for the trial he has dubbed “The Big Show.”

“Wish I was back on Alcatraz,” Bulger told Sunday in one letter.

Sunday said he’s worried about the toll that jail is taking on his friend’s health and believes the conditions are cruel, inhumane, and amount to pretrial punishment. “He’s pulling some hard time,’’ Sunday said.

Bulger and Sunday became friends at the US penitentiary in Atlanta, Bulger’s first stop in the federal prison system after his 1956 conviction for robbing three banks in Massachusetts, Rhode Island, and Indiana.

Sunday, a highly decorated US Army private, was court-martialed at age 19 on a charge of raping a woman while serving in Korea. He insisted it was a case of mistaken identity and he was innocent, but he was found guilty and sent to federal prison. He worked in the prison infirmary where Bulger volunteered to take part in a medical experiment testing LSD in exchange for shaving time off his sentence. Bulger suffered from severe hallucinations, and still complains that the effects of the LSD testing cause him constant nightmares and rob him of good sleep. Bulger says the nightmares faded as he and Greig settled into a comfortable life in Santa Monica, but they returned after his capture and incarceration.

Bulger was transferred from the Atlanta prison to the island prison of Alcatraz in San Francisco Bay after being suspected of aiding an escape attempt, and Sunday soon joined him on The Rock, where they became part of a unique fraternity. The two men never saw each other after leaving Alcatraz, but had formed a bond that endured. Bulger called Sunday sporadically over the years, including several times while he was on the run, unsuccessfully trying to enlist his friend’s help in obtaining fake identification. After Bulger’s capture, Sunday reached out to him by letter and the two have been exchanging long letters since.

Sunday remains fond of Bulger and said he gave the authors access to the letters because he believed it showed a different side to the career criminal, who once bought a car for a former inmate so he could drive to his dialysis appointments.

The book also traces Bulger’s roots as a child of the Depression, whose family moved into South Boston and into the first public housing project in New England as part of the New Deal. Relying on previously undisclosed records from the National Archives, the authors describe how Bulger graduated to bank robbery in his 20s after a less than stellar few years in the Air Force.

According to letters Bulger wrote from prison, and the accounts of prison authorities, Bulger began his 20-year sentence for bank robbery intending to use this time in prison to make up for the education he spurned in his youth. Instead, an impetuous Bulger chafed at prison rules and constantly found himself accused of associating with troublemakers.

While Bulger’s transfer to Alcatraz was meant as punishment, he came to value his identity as a former inmate at the notorious prison as a badge of honor. He remained friendly with and generous to his Alcatraz friends, paying for the exhumation and reburial on sacred Choctaw land of Clarence Carnes, a Native American inmate who used to deliver library books to Bulger in his cell.

The book describes how a rebellious Bulger grew to realize the importance of political influence, as his brother William, elected as a state representative while Whitey was on Alcatraz, cobbled together an influential stable of supporters to lobby for Whitey’s parole, including US House Speaker John McCormack and future congressman Robert Drinan. At Bill Bulger’s request, Drinan began a prison correspondence with Whitey and eventually agreed to become his parole adviser. McCormack, meanwhile, kept the Bulger family informed on Whitey’s often rocky road through the federal prison system, intervening personally with the director of the US Bureau of Prisons.

While Bulger convinced many, including Sunday and prison authorities, that he was determined to go straight as soon as he got out, the authors describe his short-lived legitimate life in construction before he quickly drifted back into crime, signing on as an enforcer for the Killeen brothers, who ran the rackets in Southie during the 1960s and early 1970s.

The book contains an account of how the founder of the modern, or Provisional IRA, Joe Cahill, was smuggled into the United States and met with Bulger at his hangout, Triple O’s lounge on West Broadway. At that meeting, Cahill commissioned Bulger and a group of Irish-American gangsters that included Pat Nee of South Boston and the late Joe Murray of Charlestown to serve as arms procurers for the IRA. Cahill, who was barred from entering the country, was smuggled across the border from Canada on a bus chartered by Boston Bruins fans who journeyed to Montreal to see the Bruins play the Canadiens.

The authors also document the violence Whitey Bulger helped orchestrate to register his opposition to the court-ordered desegregation of Boston’s public schools that led to the busing of students to and from South Boston High. In one of the letters he sent to Sunday, Bulger boasted about riddling the offices of the Globe with gunfire in protest over what he called the Globe’s demonization of Southie and its residents during busing. The book also recounts his firebombing of the Brookline birthplace of President John F. Kennedy because of the Kennedy family’s support of US District Judge W. Arthur Garrity Jr., whose order imposed busing, and a separate attack on a Wellesley elementary school near Garrity’s home.

The authors have pieced together how Bulger and Greig arrived in Santa Monica and bought identification documents from mentally disabled and substance-abusing individuals to establish new identities. While the relationships were exploitive, Bulger took a shine to a lonely Army veteran whose identity he bought. He paid for the man’s rent until the man died in his bed of heart failure, and Bulger became emotional in describing his friendship with the man to the federal agents who brought him back to Boston after his arrest.

That arrest is spelled out in previously unreported detail, explaining how a deputy US marshal and an FBI agent working in a largely depleted fugitive task force were able to find Bulger in a matter of months after 16 years of a search that began as farce and descended into frustrating dead ends. A series of public service announcements focusing on Greig led to a news story on CNN that was seen in Iceland by a former beauty queen who rented an apartment for several months each year in the same Santa Monica neighborhood as Bulger and Greig. Murphy, one of the authors, tracked Anna Bjornsdottir down in Iceland, confirming that the woman had come to know the fugitive couple – known as Charlie and Carol Gasko — because they had shared a love of animals, in particular an abandoned cat in their neighborhood that Greig fed dutifully while Bulger stood at her side.

In one of his letters, Bulger seemed to appreciate the absurdity of how his life on the run, the climax to a criminal career that is the stuff of legends, came to an end. “A cat got me captured,” he lamented.

Bulger refused to cooperate with the authors of the book.

Kevin Cullen can be reached at Shelley Murphy can be reached at