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The long, deadly career of James J. ‘Whitey’ Bulger

‘Whitey’ Bulger killed at federal prison in West Virginia

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.

The former South Boston crime boss was the city’s most infamous criminal. He became as widely known as some of Boston’s reputable citizens, and in his own milieu he insisted he was an honorable criminal who lived by a scrupulous code. He portrayed himself as the neighborhood’s protector, keeping drugs out of Southie and striking at the forces behind the imposition of school desegregation, which he and others saw as the beginning of the end of the insular, isolated South Boston, where they grew up.

But that self-serving narrative, which Mr. Bulger spent his entire career cultivating, was left in tatters after his 2013 racketeering trial in federal court in Boston. He was portrayed as a menacing figure who bribed FBI agents, flooded his own neighborhood with drugs, chained and interrogated men before shooting them, and strangled at least one woman.


A jury found him guilty of participating in 11 of 19 murders for which he faced charges, while running a sprawling criminal enterprise from the 1970s to the 1990s that rivaled the Mafia.

It was a trial that the families of many of Mr. Bulger’s victims thought they would never see. Mr. Bulger had been warned by a corrupt former FBI agent to flee just before his 1995 indictment and eluded an international manhunt for more than 16 years. He was one of the FBI’s 10 Most Wanted, with a $2 million reward on his head, when he was captured in June 2011, living with his longtime girlfriend, Catherine Greig, in a rent-controlled apartment just two blocks from the beach in Santa Monica, Calif.

He had transformed into the retired octogenarian he was pretending to be and looked unassuming and uninterested during most of his eight-week trial in 2013, taking copious notes as he worked on his memoirs. There were flashes of his old temper when he traded obscenities with former close associates who testified against him.

Mr. Bulger never took the stand at his trial, calling it “a sham,” and wrote letters from jail to friends and strangers alike, professing his love for Greig and casting himself as a victim of a deeply corrupt government.


Yet, nearly two years after that trial, Mr. Bulger, for the first time, offered a hint of repentance in a letter to students at Apponequet Regional High School in Lakeville who wrote to him for a history project on leadership and legacy.

“My life was wasted and spent foolishly, brought shame + suffering on my parents and siblings and will end soon,” Mr. Bulger wrote. “Advice is a cheap commodity some seek it from me about crime — I know only one thing for sure — If you want to make crime pay — ‘Go to Law School.’ ”

Rebel from a young age

James Joseph Bulger Jr. was born in Everett on Sept. 3, 1929, the second oldest of six siblings, and moved to Dorchester with his family. His father, James Sr., lost an arm as a teenager after falling under a train. His disability made it difficult for him to find work and left the family poor. In 1938, when Mr. Bulger was 8, his family moved into the Old Harbor public housing project in South Boston.

From a young age, James Jr. — Jimmy to his friends, Sonny to his mother, and Whitey to most everybody else because of his striking light blond hair — was a rebel. The nuns at St. Mark’s and St. Margaret’s schools in Dorchester had trouble controlling his wild streak. When he got to the public schools in Southie, it got worse.

“He’d just get up and walk out of class,” recalled the late Bobby Moakley, a classmate and neighbor of the Bulgers and brother to US Representative Joe Moakley.


It wasn’t any better at home, where his mother, the former Jean McCarthy, a genial woman and daughter of Irish immigrants, frequently wondered where her oldest son had wandered off to. He ignored his mother’s pleas that he spend time at their parish, St. Monica’s, where his younger brother William, the future politician, was an altar boy. James Bulger preferred the streets to the sports and games organized by the kindly pastor.

Even as a boy, Mr. Bulger was a rule breaker. He once brought home an ocelot, a small leopard, and his mother was appalled, fearing they would be kicked out of their apartment, his brother William wrote in his 1996 autobiography, “While the Music Lasts: My Life in Politics.” But James Bulger reassured his mother, saying he had read the lease and noted that it only specifically barred cats and dogs. “It doesn’t say anything about ocelots,” Mr. Bulger told his mother.

By the time he was 14, he had dropped out of school and had been arrested for the first of six times as a juvenile, none of which resulted in a conviction. He later told prison officials that his one-armed father beat him, so frustrated was the elder Bulger with his wayward namesake.

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.

Bobby Moakley said Mr. Bulger regularly gave Moakley’s mother a ride home from the shops and carried her groceries. “Jimmy did that for all the old ladies in the project,” Moakley said. “He was nothing but a gentleman.”

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.

He was on the verge of being sent to prison in 1949 for his latest arrest when he suddenly enlisted in the Air Force. His three years in the military were hardly distinguished: He never went overseas during the Korean War, he earned his high school diploma, and he continued to demonstrate a reckless streak. He was arrested for going AWOL and for rape. But like all the other criminal charges in his life up to that point, he beat the charge.

The criminal allure

He wasn’t as lucky when he came home and got involved with a bank robbery crew. 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.

“It’s 3 a.m. and years later I’m still effected [sic] by LSD in that I fear sleep,” Mr. Bulger wrote in personal papers later seized by the FBI. “The horrible nightmares that I fight to escape by waking. The taste of adrenaline, gasping for breath often I’m woken by a scream and find it’s me screaming.”

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.

William Bulger also prevailed upon old family friend John McCormack, at that time the speaker of the US House, to take an interest in his brother’s incarceration. McCormack prevailed upon the director of the US Bureau of Prisons to fly to San Francisco to visit James Bulger, a two-bit bank robber, at the infamous island prison on Alcatraz.

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.

His father died while he was in prison and James Bulger was not allowed to attend the funeral. He had, meanwhile, convinced his family and parole officials that he was tired of being the black sheep and was determined to make a legitimate life on the outside. Drinan corresponded with Mr. Bulger during his incarceration and vouched for him with parole officials.

He was released from prison in 1965 after nine years but quickly tired of the legitimate work his brother had lined up, including a job as a court custodian and backbreaking work as a construction laborer. He dove back into crime.

“After prison, I may have worked for one year legit and then packed it in,” Mr. Bulger later wrote to a friend. “Back to banks and deep into rackets + violence.”

Mr. Bulger worked as an enforcer for the Killeen brothers, who ran the rackets in Southie at the time. He also quickly found himself in the middle of a small, vicious gang war against a rival Irish-American gang, the Mullens, a group of upstart Vietnam vets who were in no mood to be told what to do by what it viewed as a bunch of corpulent, entitled hoodlums like the Killeens.

Mr. Bulger was anything but fat and beer swilling. He was a physical fitness buff and frowned on those who drank to excess, viewing them as weak.

Stalking his prey

Under the tutelage of Billy O’Sullivan, a former Marine and the Killeens’ top enforcer, he learned how to stalk his prey. As he told it to his criminal associates, however, his first hit was a disaster. He pulled up alongside a man who he thought was Paul McGonagle, titular leader of the Mullens, and shot him dead through the car window. As soon as he fired, he realized his mistake: it was Donald McGonagle, Paul’s innocent brother.

In retaliation, the Mullens managed to kill O’Sullivan, then murdered gang leader Donald Killeen by luring him away from his 4-year-old son’s birthday party. The Mullens had the upper hand in the gang war when Mr. Bulger did something rash and brash. He orchestrated a truce, not with the Mullens, but with Howie Winter, leader of the Somerville-based Winter Hill Gang, Greater Boston’s preeminent Irish gang.

Winter said he was impressed by Mr. Bulger’s intelligence, and especially by his time at Alcatraz. Winter anointed him leader of the Southie rackets and made him a partner in the Winter Hill Gang.

The Mullens stewed when Winter ordered them to make peace and join forces with Mr. Bulger.

“We shoulda killed Whitey when we had the chance,” Tommy King, one of the wilder Mullens, grumbled to fellow gang member Patrick Nee.

King was prescient. In 1975, Mr. Bulger accepted the invitation of FBI agent John Connolly Jr., who had grown up in the same housing project and was a protégé of Mr. Bulger’s brother William, to become an FBI informant. It empowered and emboldened James Bulger: He began killing off the Mullens, including King and Paul McGonagle, and using Connolly to file reports that steered law enforcement attention away from him.

Mr. Bulger never married, but he had many relationships with women. In May 1967, Lindsey Cyr, a waitress and legal secretary who lived in Weymouth, gave birth to Mr. Bulger’s only known child, Douglas. Cyr said Mr. Bulger wanted her to have an abortion, but when she refused, he supported her and became a doting father. Mr. Bulger was devastated when 6-year-old Douglas died of Reye’s syndrome, a severe reaction to aspirin.

“When he died, Jimmy was out of his mind,” Cyr said. The boy’s death changed Mr. Bulger, according to Cyr. “He was colder.” Their relationship ended.

Yet, even when Cyr was pregnant, Mr. Bulger had already begun a relationship with another woman, Teresa Stanley, that would last 30 years. She was a divorced South Boston mother with four young children when they met, and he raised the children as his own. He had firm, deeply traditional views about what constituted a family and how a family should behave. He insisted on sit-down family dinners every night, with no interruptions. He lectured the children on the importance of studying hard, staying physically fit, and steering clear of unsavory characters.

Then he would disappear late into the night to preside over his growing criminal empire.

A double life

When he was 45, Mr. Bulger began another serious relationship, with Greig, a divorced dental hygienist who was 22 years his junior and whose two former brothers-in-law – Paul and Donald McGonagle — had been killed by Mr. Bulger. For nearly 19 years, he split his time between Stanley in South Boston and Greig in Quincy. While Stanley remained ignorant of his other affair, Greig, who quit her teaching job at Forsyth Dental School to tend to Mr. Bulger, constantly objected to playing “second fiddle” and tried to force him to choose between them, according to one of Mr. Bulger’s associates.

Mr. Bulger became adept at leading a double life, not only with his two primary girlfriends, but with his underworld cohorts and his protectors in the FBI. In the mid-’70s, Mr. Bulger teamed up with Stephen “The Rifleman” Flemmi, an Italian-American gangster, bringing together the two main strands of organized crime in Boston. More importantly, Flemmi was an FBI informant, too, going back to the 1960s. Together, they provided information that helped the FBI take out the local Mafia, which greatly enhanced Connolly’s reputation within the FBI. It also cleared the playing field for Mr. Bulger and Flemmi to become the most powerful criminals in Boston.

It was a Faustian deal for the FBI. Mr. Bulger and Flemmi murdered and extorted money from bookmakers, drug dealers, and legitimate business people alike.

In 1979, the FBI and US Justice Department removed Mr. Bulger and Flemmi from a federal race-fixing indictment that decimated the rest of the Winter Hill Gang. Mr. Bulger established his base of operations to South Boston and later operated out of a liquor store he extorted from a local couple.

Kevin Weeks, Mr. Bulger’s protégé, estimated that Mr. Bulger made about $30 million over the nearly 20 years he was with him, most of it from shaking down drug dealers.

Mr. Bulger and Flemmi paid Connolly about $235,000 over two decades and in exchange, according to Flemmi, the agent gave them information about ongoing criminal investigations and other informants who were cooperating against them and their gang. The leaks prompted Mr. Bulger and Flemmi to orchestrate the murders of three informants and a potential witness, according to Flemmi.

Mr. Bulger used to joke that “Christmas is for cops and kids” as he stuffed envelopes with cash for corrupt FBI agents and police officers, according to Weeks. The gangster also swapped gifts with some agents. By the mid-1980s, Mr. Bulger had corrupted Connolly’s FBI supervisor, John Morris, who frequently wined and dined with Mr. Bulger and Flemmi and, by his own admission, pocketed bribes totaling $7,000 from the pair.

In 1982, Connolly warned Mr. Bulger and Flemmi that Brian Halloran, a Winter Hill Gang associate, was cooperating with the FBI and had implicated the two gangsters in the 1981 slaying of Tulsa businessman Roger Wheeler. Halloran said the murder was commissioned by John Callahan, a Boston businessman who had organized crime ties and who was trying to force Wheeler to sell him his company, World Jai Alai.

The leak prompted Mr. Bulger to ambush Halloran after he left a bar on South Boston’s waterfront. He opened fire, killing Halloran and Michael Donahue, an innocent truck driver from Dorchester who was giving Halloran a ride home.

A few months later, after Connolly warned Mr. Bulger that Callahan was being sought for questioning by the FBI and wouldn’t hold up, Mr. Bulger and Flemmi persuaded hit man John Martorano to lure Callahan to Florida and kill him.

The investigation into the slayings of Wheeler, Halloran, Donahue, and Callahan highlighted the depth of Mr. Bulger’s corrupt relationship with the FBI. Government documents made public years later revealed that Mr. Bulger was protected from prosecution. Efforts by honest agents and police officers to target Mr. Bulger were thwarted by the FBI.

Further emboldened, he continued his reign of terror. In 1983, he lured a Quincy safe cracker, Arthur “Bucky” Barrett, to a house in South Boston, chained him to a chair, and interrogated him about where his money was stashed. After collecting money from Barrett’s house and business, Bulger shot Barrett in the head and buried his body in the basement.

The following year, Mr. Bulger was involved in an ill-fated plot to ship guns to the outlawed Irish Republican Army aboard the Gloucester-based trawler Valhalla. The shipment was seized off the coast of Ireland and Connolly warned Mr. Bulger that there was an informant among Valhalla’s crew.

After concluding the informer was John McIntyre, a Quincy boat mechanic and carpenter, Mr. Bulger lured him to the same house in South Boston, chained him to a chair, interrogated him, then shot him in the head and buried him in the cellar alongside Barrett, according to Flemmi and Weeks.

A year later, Mr. Bulger and Flemmi conspired to murder Deborah Hussey, the daughter of Flemmi’s longtime live-in girlfriend, after she had talked openly about their relationship with the FBI. She, too, was buried in that cellar.

When that house, owned by a relative of a Bulger associate, was going to be sold, Mr. Bulger insisted on moving the bodies to another location. But he wouldn’t take part in the exhumation. Instead, Mr. Bulger relaxed upstairs while his associates did the work.

On the run

In 1988, the Boston Globe Spotlight Team exposed Mr. Bulger as an FBI informant. The FBI denied it and Mr. Bulger dismissed it as an attempt to embarrass his brother William, by that time the powerful and longest-serving president of the Massachusetts Senate. Mr. Bulger reassured his FBI handlers that other criminals wouldn’t believe the story and he remained an FBI informant until 1990, when Connolly, his handler, retired.

Mr. Bulger continued to rob and kill with impunity until 1994, when Connolly tipped him off that investigators from the Massachusetts State Police and US Drug Enforcement Administration were poised to arrest him. Mr. Bulger fled with his longtime girlfriend, Stanley, shortly before his January 1995 racketeering indictment. She, however, quickly grew tired of a life on the run and asked him to bring her home. He dropped Stanley off in a parking lot in Hingham, and then drove to Malibu Beach in Dorchester, where Greig was waiting for him. The two fled and would remain on the run for more than 16 years.

The search for Mr. Bulger was initially assigned to the same FBI squad that had been corrupted by him. But, after US District Judge Mark L. Wolf forced the FBI to publicly acknowledge in 1997 that Mr. Bulger and Flemmi were longtime informants, the search was assigned to an FBI-led multi-agency task force. Mr. Bulger became the target of an international manhunt and one of the FBI’s 10 Most Wanted – alongside Osama bin Laden – with a $2 million reward on his head.

Wolf held year-long hearings that delved into Mr. Bulger’s corrupt relationship with the FBI, triggering a nationwide scandal, an overhaul of the FBI’s informant guidelines, and congressional hearings.

The government cut controversial deals with some of Mr. Bulger’s former underworld associates, who turned against him, leading to the discovery of the graves of some of Mr. Bulger’s victims and a sweeping new federal racketeering indictment in 2000 charging him with participating in 19 murders. He also faced the death penalty in Oklahoma and Florida, where he was charged with the slayings of Wheeler and Callahan.

William Bulger, who admitted before a federal grand jury that he had received a telephone call from his fugitive brother shortly after he fled, was pressured to resign from his job as president of the University of Massachusetts in 2003 after he appeared evasive while testifying before Congress about his gangster brother.

Mr. Bulger’s youngest brother, John, a former Boston Juvenile Court clerk magistrate, was sentenced to six months in prison for lying to federal grand juries that were targeting his brother, and he lost his pension as a result.

But for years Mr. Bulger remained elusive and the common refrain in Boston became, “Where’s Whitey?”

After briefly living in Louisiana, where he and Greig befriended a Cajun family, Mr. Bulger and Greig in late 1996 moved into a rent-controlled apartment in Santa Monica. Neighbors knew them as unassuming retirees Charlie and Carol Gasko, who paid their rent in cash and lived frugally. Mr. Bulger bought fake identities from homeless people who resembled him. He limited his time out in the open, remaining the nocturnal character he had been in Boston, staying up most nights, sleeping late most days.

Mr. Bulger later compared his years on the run to a 16-year honeymoon with Greig, whom he credited in a letter to a friend with doing something no one in law enforcement could do: “Got me to live crime free 16 years – for this they should give her a medal.”

He was captured in 2011 after the FBI launched a new publicity campaign targeting Greig. A woman living in Iceland watched a CNN report about the fugitives and recognized Mr. Bulger and Greig as her former neighbors in Santa Monica. She remembered them because they took care of a stray cat.

The FBI found 30 guns that Mr. Bulger had bought while a fugitive and $822,000 in cash hidden in the walls of his apartment.

From his jail cell in Plymouth, Mr. Bulger wrote letters to an old prison friend that were wistful, defiant, and prideful. He complained bitterly about Greig being prosecuted.

“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!” Mr. Bulger wrote to Richard Sunday in April 2012. He was furious when she was sentenced to eight years in prison for helping him evade capture.

‘Last Man Standing’

He called his upcoming trial “the Big Show” and fumed about the lenient deals prosecutors gave some of his underworld cohorts in exchange for cooperating against him.

“I’m the Last Man Standing and all these guys made deals that Donald Trump couldn’t at my expense,” Mr. Bulger wrote to Sunday, who shared the letters with the Globe. “I’m innocent of these charges but they have guys who will testify for Gov. and if they get me – to hell with them – I’ll go out smiling.”

According to the letters, Mr. Bulger was obsessed with refuting the notion that he was an informer and had murdered two women. His defense focused on those themes during the two-month trial in 2013. Mr. Bulger’s lawyers argued that he paid corrupt FBI agents for information and that his voluminous informant file had been fabricated by agent Connolly to cover up their corrupt relationship.

In a shocking admission, one of his lawyers, J.W. Carney Jr., conceded in his opening statement that Mr. Bulger was a drug trafficker. Mr. Bulger and his apologists had always claimed he kept drugs out of Southie, when even the most cursory examination showed that drug abuse in the neighborhood was disproportionately high.

His trial showed that he made millions from shaking down drug dealers who had to pay him for the right to peddle drugs on his turf. He even had his own drug distribution ring that at one point was paying him $10,000 a week.

Carney elicited guffaws when he claimed Mr. Bulger couldn’t be an informer because he was Irish and being an informer is the worst thing in the Irish consciousness.

Mr. Bulger exploded in rage when Weeks described him from the witness stand as a rat. The two men, once the closest of friends, exchanged shouted profanities, making the Southie courtroom sound more like a Southie locker room.

Mr. Bulger had vowed to take the stand and expose what he said was the government’s duplicity in his handling. But he ultimately declined to testify, insisting that his decision was based on the presiding judge’s refusal to let him mount a defense based on his assertion that a prosecutor had given him immunity to commit crimes, including murder.

Mr. Bulger insisted Jeremiah T. O’Sullivan, the former head of the New England Organized Crime Strike Force, promised him immunity decades earlier. O’Sullivan died in 2009.

“As far as I’m concerned, I didn’t get a fair trial, and this is a sham,” Mr. Bulger told US District Judge Denise Casper just before his defense rested. “Do what youse want with me. That’s my final word.”

His decision not to testify left the relatives of many of his victims bitterly disappointed. They had been waiting to hear his version of the depth of government corruption.

Many court observers thought Mr. Bulger’s decision was based more on his fear of being confronted with evidence that he was an informer as far back as 1956 and with conversations he had with his brother William and other relatives during his pretrial detention. Had he taken the stand, prosecutors could have asked him questions about crimes and situations that went beyond the previous testimony, including whether anyone helped him while he was a fugitive.

Jurors found that Mr. Bulger participated in the slayings of Hussey, Wheeler, Halloran, Donahue, Callahan, Barrett, McIntyre, Paul McGonagle, King, Edward Connors, and Richard Castucci. They found prosecutors failed to prove he participated in the slayings of Michael Milano, Al Plummer, William O’Brien, James O’Toole, Al Notarangeli, James Sousa, and Francis Leonard.

Jurors were unable to reach a verdict on whether Mr. Bulger participated in the 1981 slaying of 26-year-old Debra Davis, who was Flemmi’s girlfriend.

In addition to his longtime companion Greig, who remains incarcerated, and his brothers, William and John, both of South Boston, Mr. Bulger leaves three sisters, Jean Holland of Quincy, Sheila McKeon of Hull, and Carol McCarthy of South Boston.

In a letter after his capture to Sunday, his former prison friend, Mr. Bulger wrote: “I had a good life and I Lived! . . . [expletive] Society + its Court System! I’ll laugh when I exit this world.’’

Shelley Murphy can be reached at shelley.murphy@globe.com. Follow her on Twitter @shelleymurph. Kevin Cullen can be reached at cullen@globe.com.