James Joseph "Whitey" Bulger Jr. (/ˈbʌldʒər/; September 3, 1929 – October 30, 2018) was an Irish-American former organized crime boss of the Winter Hill Gang in Boston, Massachusetts. 

Federal prosecutors indicted Bulger for nineteen murders based on grand jury testimony from Kevin Weeks and other former associates. Bulger was the brother of William Bulger, former President of the Massachusetts Senate. 

He died in prison in 2018.

Contents

Overview

According to the FBI, Bulger served as a confidential informantfor the Bureau beginning in 1975, a claim Bulger denies. However, as a result, the FBI largely ignored his organization in exchange for information about the inner workings of the rival Italian-American Patriarca crime family. Beginning in 1997, the media exposed criminal actions by federal, state, and local law enforcement officials tied to Bulger. For the FBI especially, this caused great embarrassment.

On December 23, 1994, Bulger fled Boston and went into hiding after being tipped off by his former FBI handler, John Connolly, about a pending indictment under the Racketeer Influenced and Corrupt Organizations Act (RICO). For sixteen years, he remained at large. For twelve of those years, Bulger was second on the FBI Ten Most Wanted Fugitives list, behind Osama bin Laden.

On June 22, 2011, Bulger was arrested outside an apartment in Santa Monica, California along with his long-time girlfriend Catherine Greig. Bulger was 81 years old at the time. Soon after, Bulger and Greig were extradited to Massachusetts and taken under heavy guard to the United States Courthouse on Boston Harbor, which had to be partially closed for their arrival. Greig pleaded guilty to conspiracy to harbor a fugitive, identity fraud, and conspiracy to commit identity fraud and was sentenced to eight years in prison in June 2012. Bulger did not seek bail and remained in custody at the Plymouth County House of Correction in Plymouth, Massachusetts.

On June 12, 2013, Bulger went on trial for 32 counts of racketeering, money laundering, extortion, and weapons charges, including complicity in nineteen murders.

On August 12, 2013, Bulger was found guilty on 31 counts, including both racketeering charges, and was found to have been involved in eleven murders. 

On November 14, he was sentenced to two consecutive life sentences plus five years for his crimes by U.S. District Judge Denise Casper.[18] Bulger became inmate number 02182-748, incarcerated for life at the United States Penitentiary Coleman II in Sumterville, Florida.

On October 30, 2018, Bulger was found dead while in prison.

Early life

Bulger's father, James Joseph Bulger Sr., was from Harbour Grace, Newfoundland. After settling in Everett, Massachusetts, James Sr. married Jane Veronica "Jean" McCarthy, a first-generation Irish immigrant. Their first child, James Joseph Bulger, Jr., was born in 1929.

The elder Bulger worked as a union laborer and occasional longshoreman; he lost his arm in an industrial accident and the family was reduced to poverty. In May 1938, the Mary Ellen McCormack Housing Project was opened in the neighborhood of South Boston. The Bulger family moved in and the children grew up there. The other Bulger children, William Michael and John P. Bulger, excelled at school; James Bulger Jr. became drawn into street life.

Early in his criminal career, local police gave Bulger the nickname "Whitey" because of his blond hair. Bulger hated the name; he preferred to be called "Jim", "Jimmy", or even "Boots". The last nickname came from his habit of wearing cowboy boots—and his fondness for hiding a switchblade in those boots. However, the nickname "Whitey" stuck.

Early criminal career

Bulger developed a reputation as a thief and street fighter fiercely loyal to South Boston. This led to his meeting more experienced criminals and finding more lucrative opportunities. In 1943, fourteen-year-old Bulger was arrested and charged with larceny. By then he had joined a street gang known as the "Shamrocks" and would eventually be arrested for assault, forgery and armed robbery. He was sentenced to a juvenile reformatory for these crimes.

Shortly after his release in April 1948, Bulger joined the U.S. Air Force, where his character continued to show. He spent time in the military prison for several assaults and was later arrested by Air Force police in 1950 for going absent without leave. Nevertheless, he received an honorable discharge in 1952 and returned to Massachusetts.

Prison 

In 1956, Bulger served his first term in federal prison when he was sentenced to time in Atlanta Penitentiary for armed robbery and truck hijacking. He later told mobster Kevin Weeks that while there, he was involved in the MK-ULTRA program, the goal of which was to research mind control drugs for the CIA. For 18 months, Bulger and eighteen other inmates, all of whom had volunteered in return for reduced sentences, were given LSD and other drugs. Bulger later complained that they had been "recruited by deception" and were told they were helping to find "a cure for schizophrenia".  He described his experience as "nightmarish" and said it took him "to the depths of insanity."

Bulger was transferred from Atlanta to Alcatraz Federal Penitentiary. He became a close friend of fellow inmate Clarence Carnes, a.k.a. "The Choctaw Kid". In November 1962, he was transferred to Leavenworth Federal Penitentiary and, in 1963, to Lewisburg Federal Penitentiary. Bulger's third petition for parole, in 1965, was granted after he had served nine years in prison. He would not be arrested again for 46 years.

Killeen–Mullen War

After his release, Bulger worked as a janitor and construction worker before becoming a bookmaker and loan shark under Donald Killeen, the leader of the dominant mob, The Killeens, for over 20 years in South Boston. The Killeens were led by three brothers—Donnie, Kenny and Eddie—along with Billy O'Sullivan and Jack Curran. Their base was the Transit Cafe in South Boston, which later became Whitey's Triple O's. In 1971, Killeen's younger brother Kenny allegedly shot Michael (Mickey) Dwyer, a member of the rival Mullen Gang in the arm, and bit off part of his nose during a brawl at the Transit café. A gang war resulted, leading to a string of killings throughout Boston and the surrounding suburbs. The Killeens quickly found themselves outgunned and outmaneuvered by the younger Mullens. It was during the Killeen–Mullen war that Bulger set out to commit what Kevin Weeks describes as his first murder, of Paul McGonagle.

Although [McGonagle] never did anything, he kept on stirring everything up with his mouth. So Jimmy decided to kill him. … Jimmy shot him right between the eyes. Only ... it wasn't Paulie. It was Donald. ... Jimmy drove straight to his mentor Billy O'Sullivan's house on Savin Hill Avenue and told O'Sullivan ... 'I shot the wrong one. I shot Donald.' Billy ... said, 'Don't worry about it. He wasn't healthy anyway. He smoked. He would have gotten lung cancer.'

According to former Mullen boss Patrick Nee, McGonagle, certain O'Sullivan was responsible, ambushed and murdered O'Sullivan. Bulger, realizing he was on the losing side, secretly approached Howie Winter, leader of the Winter Hill Gang, and claimed he could end the war by murdering the leaders of the Killeen gang. Shortly thereafter, on May 13, 1972, Donald Killeen was gunned down outside his home in the suburb of Framingham. Nee disputes this, claiming that Killeen was murdered by Mullen Gang enforcers James Mantville and Tommy King, not Bulger.

Bulger and the Killeens fled the city, fearing they would be next. Nee arranged for the dispute to be mediated by Winter and Patriarca crime family caporegime Joseph Russo. In a sit-down at Chandler's nightclub in the South End, the Mullens were represented by Nee and King, and the Killeens by Bulger. The two gangs joined forces, with Winter as overall boss. (Nee's recounting is contradicted by Winter. "I never knew [Bulger] before that. He knew I was friendly with the Mullens gang. He asked if I would intercede. I said, 'Are you serious about this? I don't want to intercede if you're not going to abide by it.' He said he would.") "Nobody talked fault.... Deep down, Whitey knew that he couldn't take over for the Killeens without cutting the Mullens in on their bookmaking and loansharking. ...The meeting lasted for six hours. ... It was business...." "The balance of the meeting was spent forming an alliance.... Everything was split down the middle. All the horses, dogs, bookmaking, and loansharking were now going to be under our mutual control. This was the beginning of our relationship. Whitey and I were now officially partners...."

Soon after, Donald Killeen's sole surviving brother, Kenneth Killeen, was jogging in the City Point neighborhood of Boston. Bulger's voice called him over to a car and said, "It's over. You're out of business. No more warnings." Kenneth would later testify at the trial of disgraced FBI agent John Connollythat Winter Hill enforcers Stephen Flemmi and John Martorano were in the car with Bulger.

Winter Hill Gang Further information: Winter Hill Gang

After the 1972 truce, Bulger and the Mullens were in control of South Boston's criminal underworld. FBI Special Agent Condon noted in his log in September 1973 that Bulger and Nee had been heavily shaking down the neighborhood's bookmakers and loan sharks. Over the years that followed, Bulger began to remove opposition by persuading Winter to sanction the killings of those who "stepped out of line". In a 2004 interview, Winter recalled that the highly intelligent Bulger "could teach the devil tricks". During this era, Bulger's victims included Mullen Gang veterans McGonagle, King, and Spike O'Toole.

According to Kevin Weeks:

"As a criminal, he made a point of only preying upon criminals…. And when things couldn't be worked out to his satisfaction with these people, after all the other options had been explored, he wouldn't hesitate to use violence. … Tommy King, in 1975, was one example. … Tommy's problems began when he and Jimmy had worked in Triple O's [a bar in south Boston]. Tommy, who was a Mullins, made a fist. And Jimmy saw it. … A week later, Tommy was dead. Tommy's second and last mistake had been getting into the car with Jimmy, Stevie, and Johnny Martorano. … Later that same night, Jimmy killed Buddy Leonard and left him in Tommy's car on Pilsudski Way in the Old Colony projects to confuse the authorities."

In 1979, Winter was arrested, along with many members of his inner circle, on charges of fixing horse races. Bulger and Flemmi were left out of the indictments. They stepped into the vacuum and took over the leadership of the gang. They transferred its headquarters to the Lancaster Street Garage in Boston near the Boston Garden in the West End.

FBI informant

In 1971, the FBI approached Bulger and attempted to recruit him as an informant as part of their effort against the Patriarca family. FBI Special Agent Dennis Condon was assigned to make the pitch. However, Condon failed to win Bulger's trust. Three years later, Bulger partnered with Flemmi, an Italian-American mobster who had been an FBI informant since 1965. Although it is a documented fact that Bulger soon followed Flemmi's example, exactly how and why continues to be debated. Special Agent John Connolly frequently boasted to his fellow agents about how he had recruited Bulger at a late-night meeting at Wollaston Beach inside an FBI-issue car. Connolly allegedly said that the Bureau could help in Bulger's feud with Patriarca underboss Gennaro Angiulo. After listening to the pitch, Bulger is said to have responded, "Alright, if they want to play checkers, we'll play chess. Fuck 'em."

Weeks considers it more likely that Flemmi had betrayed him to the FBI, given the choice to supply information to the FBI or return to prison. 

In 1997, shortly after The Boston Globe disclosed that Bulger and Flemmi had been informants, Weeks met with Connolly, who showed him a photocopy of Bulger's FBI informant file. In order to explain Bulger and Flemmi's status as informants, Connolly said, "The Mafia was going against Jimmy and Stevie, so Jimmy and Stevie went against them." In a 2011 interview, Flemmi recalled, "Me and Whitey gave [the Feds] shit, and they gave us gold."

…Connolly kept telling me that 90 percent of the information in the files came from Stevie. … But, Connolly told me, he had to put Jimmy's name on the files to keep his file active. As long as Jimmy was an active informant, Connolly said, he could justify meeting with Jimmy and giving him valuable information. Even after he retired, Connolly still had friends in the FBI, and he and Jimmy kept meeting to let each other know what was going on. …I could see that a lot of the reports were not just against the Italians. There were more and more names of Polish and Irish guys, of people we had done business with, of friends of mine. … I would see, over and over again, that some of these people had been arrested for crimes that were mentioned in these reports. …it had been bullshit when Connolly told me that the files hadn't been disseminated, that they had been for his own personal use. … If there was some investigation going on and his supervisor said, 'Let me take a look at that,' what was Connolly going to do? He had to give it up. And he obviously had.

FBI Agent John Morris was put in charge of the Organized Crime Squad at the Bureau's Boston field office in December 1977. Morris not only proved himself unable to rein in Connolly's protection of Bulger, but even began assisting him. By 1982, Morris was "thoroughly compromised", having had Bulger buy plane tickets for his then-girlfriend Debbie Noseworthy to visit him in Georgia while he was being trained for drug investigations. Even after 1983, when he was transferred to head up the Boston FBI's drug task force, Morris remained an accomplice to Connolly and Bulger..

In 1995, Bulger and Flemmi were indicted on racketeering charges along with two Boston mafiosi, Frank Salemme and Bobby DeLuca. During the discovery phase, Salemme and DeLuca were listening to a tape from a roving bug, which is normally authorized when the FBI has no advance knowledge of where criminal activity will take place. They overheard two of the agents who were listening in on the bug mention that they should have told one of their informants to give "a list of questions" to the other wiseguys. When their lawyer, Tony Cardinale, learned about this, he realized that the FBI had lied about the basis for the bug in order to protect an informant. Suspecting that this was not the first time this had happened, Cardinale sought to force prosecutors to reveal the identities of any informants used in connection with the case.

Federal judge Mark L. Wolf granted Cardinale's motion on May 22, 1997. On June 3, Paul E. Coffey, the head of the Organized Crime and Racketeering Section of the Justice Department, gave a sworn statement admitting that Bulger had been an FBI informant. Coffey stated that since Bulger was accused of "leading a criminal enterprise" while working as an informant and was also now a fugitive, he had "forfeited any reasonable expectation" that his identity would be protected.

On September 5, 2006, federal judge Reginald C. Lindsay ruled that the mishandling of Bulger and Flemmi caused the 1984 murder of informant John McIntyre, awarding his family $3.1 million in damages. Lindsay stated the FBI failed to properly supervise Connolly (convicted and jailed in 2002) and "stuck its head in the sand" regarding numerous allegations that Bulger and Flemmi were involved in drug trafficking, murder and other crimes for decades.

Goodfellas in South Boston

Consolidating power 

In February 1979, federal prosecutors indicted numerous members of the Winter Hill Gang, including boss Howie Winter, for fixing horse races. Bulger and Flemmi were originally going to be part of this indictment, but Connolly and Morris were able to persuade prosecutor Jeremiah T. O'Sullivan to drop the charges against them at the last minute. Bulger and Flemmi were instead named as unindicted co-conspirators.

Bulger and Flemmi then took over the remnants of the Winter Hill Gang and used their status as informants to eliminate competition. The information they supplied to the FBI in subsequent years was responsible for the imprisonment of several of Bulger's associates whom Bulger viewed as threats; however, the main victim of their relationship with the federal government was the Patriarca family, which was based in Boston's North End, and in Federal Hill, Providence, Rhode Island. After the 1986 RICO indictment of Angiulo and his associates, the Patriarca family's Boston operations were in a shambles. Bulger and Flemmi stepped into the ensuing vacuum to take control of organized crime in the Boston area.

The murder of Louie Litif

In 1980, Bulger was approached in South Boston's Triple O's saloon by Louis Litif, a neighborhood bookmaker. Weeks, a bouncer at the establishment, said, "He wasn't a big guy, maybe five seven and 185 pounds. Of Arab descent, he had a mustache like Saddam Hussein. … That night, as always, he was talking in his obnoxious loud voice. Even when there were 400 people in the bar, you always knew Louie was there."

Litif had been stealing from his partners in the bookmaking operation and using the money to traffic cocaine, and had not only refused to pay Bulger a cut of his drug profits, but committed two murders without Bulger's permission. Litif told an outraged Bulger he was also going to kill his partner, "Joe the Barber", whom he accused of stealing money from the bookmaking operation. Bulger refused to sanction this, but Litif vowed to proceed. Bulger replied, "You've stepped over the line. You're no longer just a bookmaker." Litif responded that, as Bulger was his friend, he had nothing to worry about. Bulger coldly responded, "We're not friends anymore, Louie."

At the time, Weeks was about to get married and, shortly before the wedding, informed Bulger that he was having difficulty finding a seat for Litif at the reception. "Don't worry about it", Bulger responded. "He probably won't show." "[Louie] had always been a major moneymaker for Jimmy. … And now he wanted to kill a friend of Jimmy. There was no way that would be allowed. Shortly after that, a week or so before my wedding, Louie was found stuffed into a garbage bag in the trunk of his car, which had been dumped in the South End. He had been stabbed with an ice pick and shot. 'He was color coordinated,' Jimmy told me. 'He was wearing green underwear and was in a green garbage bag.'"

According to Kevin Weeks,

Strangley enough, Jimmy, told me, 'Louie's last words to me were a lie.' Apparently, Louie had insisted that he'd come by himself and that nobody had driven him over. It was hard to figure out why Louie lied to Jimmy that night. If he'd told Jimmy that someone had driven him, he might have gotten a pass. But it wouldn't have lasted long, since Jimmy had no intention of letting Louie run wild.

Halloran and Donahue murders

In 1982, a South Boston cocaine dealer named Edward Brian Halloran, known on the streets as "Balloonhead", approached the FBI and stated that he had witnessed Bulger and Flemmi murdering Litif. Meanwhile, Connolly kept Bulger and Flemmi closely briefed on what Halloran was saying to the FBI, specifically his knowledge of their participation, along with their youngest associate James "Gentleman Jim" Mulvey in the murder of Tulsa, Oklahoma businessman Roger Wheeler. Connolly reported that Halloran was shopping this information to the FBI for a chance for him and his family to be placed in the Witness Protection Program. Soon after, on May 11, 1982, Bulger, Flemmi, and Weeks were tipped off that Halloran had returned to South Boston. After arriving at the scene, Weeks staked out Anthony's Pier 4 Restaurant, where Halloran was dining. Michael Donahue, a friend of Halloran's from Dorchester, incidentally ran into him at the restaurant. In a decision that would prove costly to him, Donahue offered Halloran a ride home.

As Donahue and Halloran drove out of the parking lot, Weeks signaled Bulger by stating, "The balloon is in the air," over a walkie talkie. Bulger drove up with a masked man armed with a silenced Mac 10; Bulger himself carried a .30-cal. carbine. A disguised Bulger and the other shooter opened fire and sprayed Halloran and Donahue's car with bullets. Donahue was shot in the head and killed instantly. Halloran lived long enough to identify his attacker as James Flynn, a Winter Hill associate, who was later tried and acquitted. Flynn remained the prime suspect until 1999, when Weeks agreed to cooperate with investigators and identified Bulger as one of the shooters. Flemmi has identified the second shooter as James Mulvey, who has denied the allegation and has yet to be charged.

Donahue was survived by his wife and three sons. His family, and Halloran's, eventually filed a civil lawsuit against the US government after learning that Connolly had informed Bulger of Halloran's informant status. Both families were awarded several million dollars in damages. However, the verdict was overturned on appeal, due to the late filing of the claims. Thomas Donahue, who was eight years old when his father was murdered, has become a spokesman for the families of those allegedly murdered by the Winter Hill Gang.

Peak years

Throughout the 1980s Bulger, Flemmi, and Weeks operated rackets throughout eastern Massachusetts including extortion, loansharking, bookmaking, truck hijackings and arms trafficking. State and federal agencies were repeatedly stymied in their attempts to build cases against Bulger and his inner circle. This was caused by several factors. Among them was the trio's paranoid fear of wiretaps and policy of never discussing their business over the telephone or in the car. Other reasons were South Boston's code of silence and corruption within the Boston Police Department, the Massachusetts State Police, and the Federal Bureau of Investigation. Although FBI agent John Connolly is Bulger's most infamous source inside law enforcement, Kevin Weeks has stated that Massachusetts State Police Lt. Richard J. Schneiderhan was valued far more highly. According to Weeks, this was because Schneiderhan was the crew's only source inside the Massachusetts State Police.

During the mid-1980s Bulger began to summon drug dealers from in and around Boston to his headquarters. Flanked by Kevin Weeks and Stephen Flemmi, Bulger would inform each dealer that he had been offered a substantial sum in return for that dealer's assassination. He would then demand a large cash payment as the price of not killing them. Eventually, however, the massive profits of drugs proved irresistible. 

Jimmy, Stevie and I weren't in the import business and weren't bringing in the marijuana or the cocaine. We were in the shakedown business. We didn't bring drugs in; we took money off the people who did. We never dealt with the street dealers, but rather with a dozen large-scale drug distributors all over the State who were bringing in the coke and marijuana and paying hundreds of thousands to Jimmy. The dealers on the street corner sold eight-balls, . . . grams, and half grams to customers for their personal use. They were supplied by the mid level drug dealer who was selling them multiple ounces. In other words, the big importers gave it to the major distributors, who sold it to the middlemen, who then sold it to the street dealers. In order to get to Jimmy, Stevie, and me, someone would have had to go through those four layers of insulation.

In South Boston most of the neighborhood's cocaine and marijuana trafficking was under the control of a crew led by mobster John Shea, known as "Red". According to Weeks, Bulger briefly considered whacking Shea, but eventually decided to just extort a weekly cut of his profits. Weeks also states that Bulger enforced strict rules over the dealers who operated on his home turf.

The only people we ever put out of business were heroin dealers. Jimmy didn't allow heroin in South Boston. It was a dirty drug that users stuck in their arms, making problems with needles, and later on, AIDS. While people can do cocaine socially and still function, once they do heroin, they're zombies.

Weeks also states that Bulger strictly forbade Angel Dust and selling drugs to children, and that those dealers who refused to play by his rules were violently driven from "The Town". In 1990 "Red" Shea and his associates were arrested at the end of an investigation by the Drug Enforcement Administration (DEA), the Boston Police Department and the Massachusetts State Police. Shea quietly served a very long prison sentence and refused to admit to having paid protection money to Bulger, Flemmi and Weeks. He repeatedly got in fights with other inmates who accused Bulger of being "a rat." This earned Shea a legendary reputation in South Boston.

Of course, Jimmy lost money once the drug dealers were removed from the streets in the summer raid, but he always had other business going on. Knowing I had to build something on the side, I had concentrated on my shylocking and gambling businesses. The drug business had been good while it lasted. But our major involvement in it was over.

It would not be until the 1999 cooperation of Weeks that Bulger, by then a fugitive, was conclusively linked to the drug trade by investigators. According to an interview conducted with Boston Globe reporters Kevin Cullen and Shelley Murphy, Kevin Weeks "estimated that Whitey made about thirty million dollars... most of it from shaking down drug dealers to let them do business on his turf."

During the most violent period of The Troubles, sympathy for the Provisional Irish Republican Army was very common in South Boston. So were efforts to raise money and smuggle weapons for the Provos' armed struggle against the British presence in Northern Ireland.

From the start of his involvement with the FBI, Whitey Bulger "insisted ... that he would never give up the IRA." Bulger had previously donated to NORAID, and shipped weapons—"guns and a block of C-4 plastic explosives"—in a van to the Provisional IRA in the early 1980s. After meeting with the IRA Chief of Staff Joe Cahill, Bulger and Patrick Nee raised $1 million "by shaking down drug dealers in South Boston and Charlestown." This money was used to buy weapons for the IRA, which would be shipped across the Atlantic in the trawler Valhalla. Bulger also personally donated some of his own weapons. Before the use of the Valhalla, Bulger shipped overseas a shipment of guns and C-4 in a van at least once. Bulger was annoyed when he learned that the IRA men he supplied had burned the van that contained the weapons.

On September 13, 1984, Bulger, Weeks and Nee supervised the loading of the Valhalla. The final cache included "91 rifles, 8 submachine guns, 13 shotguns, 51 handguns, 11 bullet-proof vests, 70,000 rounds of ammunition, plus an array of hand grenades and rocket heads." The Valhalla rendezvoused 120 miles off the Irish west coast with the Marita Ann, an IRA ship that had sailed from Tralee. During the return voyage, the Irish Navy stopped the Marita Ann and seized the hidden arsenal, arresting IRA members Martin Ferris, Mike Browne and John Crawley. The operation had been compromised by IRA member Sean O'Callaghan, who was an informant for the Irish National Police.

When Valhalla crew member John McIntyre was arrested "for trying to visit his estranged wife", he confessed his role in the weapons smuggling to Boston police. McIntyre implicated Bulger in the botched smuggling to FBI agent Roderick Kennedy, but Kennedy "insisted that [Bulger's handler] John Connolly overheard him ... talking about someone on the Valhalla cooperating." Connolly confirmed Bulger's suspicions of McIntyre, leading Bulger—and cohort Steve Flemmi—to murder McIntyre for his betrayal."

According to Kevin Weeks, when Bulger met with McIntyre in a South Boston house, he hoped to avoid murdering the informer and offered to send him to South America with money and the understanding that he was never to contact his family or friends again. After interrogating McIntyre over several hours, however, Bulger decided that he did not have the discipline to cut ties with everyone. He then killed McIntyre and went upstairs to take a nap while Weeks and Flemmi removed the corpse's teeth with a pliers and buried McIntyre in the basement.

Massachusetts state lottery

In the summer of 1991 Bulger and Kevin Weeks, along with associates Patrick and Michael Linskey, came into possession of the winning Massachusetts Lottery ticket, which had been bought at a store he owned. The four men shared a prize of around US$14 million. Bulger was widely thought to have obtained his share of the jackpot illegitimately.

Downfall

In April 1994 a joint task force of the Drug Enforcement Administration(DEA), the Massachusetts State Police and the Boston Police Department launched a probe of Bulger's gambling operations. The FBI, by this time considered compromised, was not informed. After a number of bookmakers agreed to testify to having paid protection money to Bulger, a Federal case was built against him under the RICO Act.

According to Kevin Weeks

In 1993, and 1994, before the pinches came down, Jimmy and Stevie were traveling on the French and Italian Riviera. The two of them traveled all over Europe, sometimes separating for a while. Sometimes they took girls, sometimes just the two of them went. They would rent cars and travel all through Europe. It was more preparation than anything, getting ready for another life. They didn't ask me to go, not that I would have wanted to. Jimmy had prepared for the run for years. He had established a whole other person, Thomas Baxter, with a complete ID and credit cards in that name. He had even joined associations in Baxter's name, building an entire portfolio for the guy. He had always said you had to be ready to take off on short notice. And he was.

He had also set up safe deposit boxes, containing cash, jewelry and passports, in locations across North America and Europe, including Florida, Oklahoma, Montreal, Dublin, London, Birmingham and Venice. In December 1994 he was informed by retired FBI Agent John Connolly that sealed indictments had come from the Department of Justice and that the FBI was set to make arrests during the Christmas season. In response, Bulger fled Boston on December 23, 1994, accompanied by his common-law wife Theresa Stanley.

Fugitive

After fleeing Boston, Bulger and Stanley spent four days over Christmas in Selden, New York, before spending New Year's Day in a hotel in New Orleans's French Quarter. On January 5, 1995, Bulger prepared to return to Boston, believing that it had been a false alarm. That night, however, Stephen Flemmi was arrested outside a Boston restaurant by the DEA. Boston police Detective Michael Flemmi, Stephen's brother, informed Weeks of the arrest. Weeks immediately passed the information on to Bulger, who altered his plans.

Bulger and Stanley spent the next three weeks traveling among New York, Los Angeles and San Francisco before Stanley decided that she wanted to return to her children. They traveled to Clearwater, Florida, where Bulger retrieved his "Tom Baxter" identification from a safe-deposit box. He then drove to Boston and dropped off Theresa in a parking lot. He met at Malibu Beach in Dorchester with Weeks, who had brought with him Bulger's girlfriend, Catherine Greig. Bulger and Greig then went on the run together.

In his memoirs, Weeks describes a clandestine meeting with Bulger and Greig in Chicago, Illinois. Bulger reminisced fondly about his time hiding out with a family in Louisiana. He told Weeks, who had replaced him as head of the Winter Hill Gang, "If anything comes down, put it on me." As they adjourned to a nearby Japanese restaurant, Bulger finally revealed how exhausted he was with life on the run. He told Weeks, "Every day out there is another day I beat them. Every good meal is a meal they can't take away from me."

In mid-November 1995 Weeks and Bulger met for the last time, at the lion statues at the front of the New York Public Library, and adjourned for dinner at a nearby restaurant. According to Weeks::236

At the end of our dinner, he seemed more aware of everything around him. His tone was a little more serious, and there wasn't as much joking as usual. He repeated the phrase he had used before that a rolling stone gathers no moss, which told me that he knew he was going to be on the move again. I got the feeling that he was resigning himself to the fact that he wasn't coming back. Up until then, I always believed he thought there was a chance he had beat the case. However, at that point, there was something different going on with him. I didn't fully understand all the aspects of his case. It would be another six months before it became clearer. Yet at that moment, in that restaurant in New York, I sensed that he had moved to a new place in his mind. It was over. He'd never return to South Boston.

On November 17, 1999, Weeks was arrested by a combined force of the DEA and the Massachusetts State Police. Although by this time he was aware of Bulger's FBI deal, he was determined to remain faithful to the neighborhood code of silence. However, while awaiting trial in Rhode Island's Wyatt Federal prison, Weeks was approached by a fellow inmate, a "made man" in the Patriarca crime family. The inmate told him, "Kid, what are you doing? Are you going to take it up the ass for these guys? Remember, you can't rat on a rat. Those guys have been giving up everyone for thirty years."

In the aftermath, Weeks decided to cut a deal with federal prosecutors and revealed where almost every penny and body was buried. Writing in 2006, Weeks recalled::235

I had known all along, however, that it would not be easy for anyone to capture Jimmy. If he saw them coming, he would take them with him. He wouldn't hesitate. Even before he went on the run, he would always say, "Let's all go to hell together." And he meant it. I also knew that Jimmy wouldn't go to trial. He would rather plead out to a life sentence than put his family through the embarrassment of a trial. If he had a gun on him, he would go out in a blaze of glory rather than spend the rest of his life in jail. But I don't think they'll ever catch him.

Manhunt

The first confirmed sighting of Bulger before his capture was in London in 2002. However, there were unconfirmed sightings elsewhere. FBI agents were sent to Uruguay to investigate a lead. Other agents were sent to stake out the 60th memorial of the Battle of Normandy celebrations, as Bulger is reportedly an enthusiastic fan of military history. Later reports of a sighting in Italy in April 2007 proved false. Two persons on video footage shot in Taormina, Sicily, formerly thought to be Bulger and his lover Catherine Greig walking in the streets of the city center, were finally identified as a tourist couple from Germany.

In 2010 the FBI turned its focus to Victoria, British Columbia, on Vancouver Island. In pursuit of Bulger, a known book lover, the FBI visited bookstores in the area, questioned employees and distributed wanted posters. Following his arrest, Bulger revealed that instead of being reclusive, he had in fact traveled frequently, with witnesses coming forward to say they had seen him on the Santa Monica Pier and elsewhere in Southern California.  A confirmed report by an off-duty Boston police officer after a San Diego screening of The Departed also led to a search in Southern California that lasted "a few weeks".

Capture 

After 16 years at large and 12 years on the FBI Ten Most Wanted Fugitives list, Bulger was arrested in Santa Monica, California, on June 22, 2011. He was 81 years old at the time of the arrest.

He was captured as a result of the work of the Bulger Fugitive Task Force, which consisted of FBI agents and a Deputy US Marshal. According to retired FBI agent Scott Bakken, "Here you have somebody who is far more sophisticated than some 18-year-old who killed someone in a drive-by. To be a successful fugitive you have to cut all contacts from your previous life. He had the means and kept a low profile."

A reward of US$2 million had been offered for information leading to his capture. This amount was second only to Osama Bin Laden's capture reward on the FBI's Ten Most Wanted Fugitives list. Bulger has been featured on the television show America's Most Wanted 16 times, first in 1995, and finally on October 2, 2010. According to authorities, the arrests were a "direct result" of the media campaign launched by the FBI in 14 markets across the country where Bulger and Greig reportedly had ties. The campaign focused on Greig, describing her as an animal lover who frequently went to beauty salons.

Authorities received a tip from a woman in Iceland that Bulger was living in an apartment near a beach in Santa Monica. The Boston Globe identified the tipster as Anna Björnsdóttir, a former model, actress, and Miss Iceland 1974, who lived in Bulger's neighborhood. A day later, "using a ruse, agents and other task force members lured Mr. Bulger out of his apartment", "arrested him 'without incident', then went in the house and arrested Greig". Bulger was charged with murder, "conspiracy to commit murder, extortion, narcotics distribution and money-laundering". Agents found "more than $800,000 in cash, 30 firearms, and fake IDs" at the apartment. Carmen Ortiz, U.S. attorney for the District of Massachusetts, said "she believes the death penalty is not an option in the federal charges Bulger faces in her district, but that he could face the death penalty for two cases outside the district". In Oklahoma, where Bulger is alleged to have ordered the killing of businessman Roger Wheeler Sr., in 1981, Tulsa County District Attorney Tim Harris said, "It is our intention to bring Bulger to justice and to be held accountable for the murder of Mr. Wheeler".[citation needed] In Florida, Miami-Dade State Attorney Katherine Fernandez Rundle said, "After a 16-year delay, I will be working to ensure that a Miami jury has the opportunity to look [Bulger] in the eyes and determine his fate".

Immediately after being brought back to Boston, Bulger began talking to authorities. He said that during his days as a fugitive he often went back and forth across the border to Mexico to buy medicine for his heart disease. He also visited Alcatraz prison and had a souvenir photograph taken, wearing a striped suit and standing behind mock prison bars. Many anticipated, and some feared, that Bulger, in exchange for favorable treatment in sentencing, would have much to tell authorities about corruption at the local, state and federal levels, which allowed him to operate his criminal enterprise for so long.

Bulger was arraigned in federal court on July 6, 2011. He pleaded not guilty to 48 charges, including 19 counts of murder, extortion, money laundering, obstruction of justice, perjury, narcotics distribution and weapons violations.

In a 2011 interview Kevin Weeks expressed surprise at Bulger's decision to cooperate after his arrest. Weeks said, "I don't understand because he's not the same as I remember him. I can't believe he's so chatty right now. So I don't know what he's doing". Weeks added that he is not afraid of Bulger, and that the residents of Boston should not be either: "I don't think he's Pablo Escobar where he can just walk out of his prison cell and come to South Boston or anywhere. No, no one's worried about him."

Catherine Greig 

Bulger's companion during his years as a fugitive was his longtime girlfriend Catherine Greig [born April 3, 1951 (age 67)], who is almost 22 years younger than Bulger.[66] Greig grew up in Boston and had an identical twin sister, Margaret, and a younger brother, David. Their father was a machinist from Glasgow, Scotland, and their mother was from Canada, as was Bulger's father.

At about age 20, Greig married Robert "Bobby" McGonagle of South Boston, a Boston firefighter. He was from a family that led the Mullen Gang and was injured during a mob gunfight in 1969. Before his 1987 drug overdose death, Bobby McGonagle reportedly held Bulger responsible for the murders of his brothers. Twins Donald McGonagle and Paul McGonagle were killed during fighting between the Mullen and Killeen Gangs. The body of Paul McGonagle lay hidden and buried for 25 years on Tenean Beach in Dorchester. Greig's twin sister Margaret is the widow of Paul McGonagle. Greig's younger brother David Greig was a close associate of Bulger. David was found shot dead on Cape Cod, a death characterized as a suicide.

Greig met Bulger in her late 20s, after she divorced Bobby McGonagle. She worked as a dental hygienist. Greig has been described as intelligent, hardworking and educated, although very subservient to, and dominated by, Bulger. She and Bulger lived together for a time at her home in Squantum, a section of Quincy, Massachusetts. While on the run, Greig confided to a neighbor that she feared that Bulger was suffering from senile dementia.

Greig had been wanted by the FBI since 1999. The criminal complaint against her alleges that she harbored a fugitive, Whitey Bulger. She was represented in the criminal proceedings by the prominent criminal attorney Kevin Reddington of Brockton, Massachusetts. After being captured alongside Bulger, Greig sought release on bail and home confinement, a request that was denied.

Greig initially indicated that she would go to trial rather than accept a plea bargain. In March 2012, however, Greig pleaded guilty to conspiracy to harbor a fugitive, identity fraud and conspiracy to commit identity fraud. On June 12, 2012, she was sentenced to eight years in federal prison. She declined to speak during her sentencing.

In September 2015, Greig was indicted on a charge of criminal contempt stemming from her refusal to testify before a grand jury about whether other people aided Bulger while he was a fugitive. In February 2016, Greig pleaded guilty to this charge. Greig's attorney recommended 12 months in prison, while prosecutors—citing Greig's "unrepentant ... obstruction"—asked for 37 months. In April 2016, U.S. District Judge F. Dennis Saylor IV sentenced Greig, then midway through her sentence for harboring Bulger, to 21 months on the contempt charge, pushing her release date to late 2020.

Greig has served much of her eight-year sentence at the Federal Correctional Institution, Waseca in Minnesota, but has also been detained at various points in Rhode Island ahead of proceedings in the criminal contempt case.

Racketeering trial and conviction

On June 12, 2013, Bulger went on trial in South Boston's John Joseph Moakley United States Courthouse before Judge Denise J. Casper on 32 counts of racketeering and firearms possession. The racketeering counts included allegations that Bulger was complicit in 19 murders. The trial lasted two months and included the testimony of 72 witnesses; the jury began deliberations August 6. On August 12, the jury convicted Bulger of 31 out of 32 counts in the indictment.  As part of the racketeering charges, the jury convicted Bulger of the murders of 11 victims—Paul McGonagle, Edward Connors, Thomas King, Richard Castucci, Roger Wheeler, Brian Halloran, Michael Donahue, John Callahan, Arthur "Bucky" Barrett, John McIntyre, and Deborah Hussey. The jury acquitted Bulger of killing Michael Milano, Al Plummer, William O'Brien, James O'Toole, Al Notorangeli, James Sousa and Francis Leonard. They also reported themselves unable to agree about the murder of Deborah Davis, though Bulger had already been found liable for her death in a civil suit. Following the verdict, Bulger's attorneys J. W. Carney Jr. and Hank Brennan vowed to appeal, citing Casper's ruling which prevented Bulger from claiming he had been given immunity.

On November 14, 2013, Bulger was sentenced to two terms of life imprisonment, plus five years. Casper told Bulger that such a sentence was necessary given his "unfathomable" crimes, some of which inflicted "agonizing" suffering on his victims. He was also ordered to forfeit $25.2 million and pay $19.5 million in restitution. Prosecutors in Florida and Oklahoma announced after Bulger's conviction that they would wait until after sentencing concluded before deciding whether or not to prosecute Bulger in their states. Bulger has already been indicted in Florida for the murder of Callahan and in Oklahoma for the murder of Roger Wheeler, and could face the death penalty in those states.

In September 2014, Bulger entered the Coleman II United States Penitentiary in Sumterville, Florida. In October 2018, it was reported that he was transferred to the Federal Transfer Center in Oklahoma, and then again a few days later to the Federal Penitentiary in West Virginia.

Death

Bulger was transferred from Oklahoma to United States Penitentiary, Hazelton in West Virginia on October 30, 2018. Later that day, he was found dead in the prison. Details about his death have not yet been released. Sources told WCVB that Bulger was killed; the Hazelton prison confirmed that a homicide had taken place there the morning of Bulger's death (the third homicide in a 40-day span) but did not confirm Bulger was the victim.

Family

Bulger has two younger brothers, William Michael "Billy" Bulger (born 1934) and John P. Bulger (born 1938). Billy Bulger served in the military during the Korean War but was never posted to Korea. He was formerly an influential leader of the Democratic Party in Massachusetts. In a long political career, Sen. Bulger rose to become President of the Massachusetts Senate. After his retirement he was appointed President of the University of Massachusetts system.

In December 2002, William Bulger appeared before the House Committee on Oversight and Government Reform and refused to testify, citing his Fifth Amendment right against self-incrimination. In April 2003, the committee voted "to grant William Bulger immunity to obtain information concerning Whitey's whereabouts and the FBI's misuse of informants." In June 2003, William Bulger appeared before the committee, where he was grilled by legislators from both parties. He testified: "I do not know where my brother is. I do not know where he has been over the past eight years. I have not aided James Bulger in any way while he has been a fugitive." Bulger added: "while I worried about my brother, I now recognize that I didn't fully grasp the dimensions of his life. Few people probably did. By definition, his was a secretive life. His actions were covert, hidden even from—or perhaps hidden especially from those who loved and cared about him. The subject that interests so many, the life and the activities of my brother James is painful and difficult for me." Bulger said that the only contact with his brother during the fugitive years was a short telephone call in January 1995, shortly after his brother was indicted. Following this testimony, Massachusetts governorMitt Romney waged an extended and ultimately successful effort to get Senator Bulger to resign from the presidency of the University of Massachusetts; Bulger resigned in August 2003.

John "Jackie" Bulger, a retired Massachusetts court clerk magistrate, was convicted in April 2003 of committing perjury in front of two grand juries regarding sworn statements he gave concerning contacts with his fugitive brother.

Personal life

Bulger fathered one child, Douglas Glenn Cyr (1967–1973), during a 12-year common-law marriage with Lindsey Cyr, a waitress and former fashion model living in North Weymouth, Massachusetts. Bulger and Cyr began living together in 1966, when Cyr was 21 and a waitress at a North Quincy café. According to Cyr, "He used to say that there were four people he would turn up on a street corner for: Douglas, me, Billy, or his mother. And we all made him vulnerable." At six years of age, Douglas died from Reye syndrome after having a severe allergic reaction to an aspirin injection.

An absolute nightmare, and it was very difficult for Jimmy because, no matter what, there was nothing that could save this. Money didn't matter, his power didn't matter. ... I remember that we were walking out of the hospital the night that he died, and he was holding my hand. And Jimmy said, "I'm never going to hurt like this again."

Since Bulger's arrest, Cyr has publicly announced her support of him, stating:

If he wanted to see me, I'd be happy to. If he needs help getting attorneys and what have you, I'd be happy to help him. Part of me does [still love him]. I still care for him. I would always help him. I certainly always stand by him. He is the father of my child. He is 12 years of my life. I want to see him well protected. ... And I'm not particularly sympathetic to some of the people involved, some of the victims' families.

After his split from Cyr, Bulger began a relationship with Theresa Stanley, a South Boston divorcée with several children. Bulger bought her an expensive house in suburban Quincy, Massachusetts, and acted as father to her children while commuting to "work" in South Boston. However, he was repeatedly unfaithful to her with a host of other women, and was often absent while overseeing the running of his organization. In a 2004 interview Stanley stated that she was planning to publish her memoirs; however, she died of lung cancer in 2012 at the age of 71.

Press relations

Most of the time, The Boston Globe wasn't as inaccurate as the Herald. They just knocked the people from Southie during busing. They also liked to describe me as, 'Whitey's surrogate son', another example of the media putting labels on people they wrote about. Jimmy and I were friends, not like father and son. Even though he was the boss, he always treated me equally, like an associate, not a son. The reporter who seemed to do the most research and put real effort into getting the true story without having been there was Shelley Murphy, who had been at the Herald for ten years when she went to work for the Globe in 1993. But Jimmy and I usually ended up laughing at most of the news stories, as time and time again the media had it wrong, over and over again holding to their pledge to never let the truth get in the way of a good story.

Paul Corsetti

According to Weeks' memoirs, in 1980 Boston Herald reporter Paul Corsetti began researching an article about Louis Litif's murder and Bulger's suspected involvement. After reporting the story for several days, Corsetti was approached by a man who said, "I'm Jim Bulger and if you continue to write shit about me, I'm going to blow your fucking head off." Corsetti sought help from the Patriarca crime family, but they said that Bulger was outside their control. "The next day, Corsetti reported the meeting to the Boston police. He was issued a pistol permit within 24 hours. The cop who gave him the permit told him, 'I'm glad my last name is not Corsetti.' A couple days later Jimmy told me about the scene with the cop and was glad to hear how uncomfortable he had made Corsetti."

Howie Carr

In his memoirs, Kevin Weeks related his participation in an attempt to assassinate reporter Howie Carr at his house in suburban Acton. Weeks states that Carr was targeted because he was "writing nasty stories about people, he was an oxygen thief who didn't deserve to breathe." Carr has been among the most aggressive critics of the Bulger brothers, Whitey and Billy, for their careers in the Boston area; among his works is the book The Brothers Bulger, detailing the Bulger brothers' 25-year period of controlling Boston politics and the Boston underworld.

Weeks stated that, although several plans were considered, all were abandoned because there was too much risk of injuring Carr's wife and children. The plans climaxed with Weeks' own attempt to shoot Carr with a sniper rifle as he came out of his house. However, when Carr came out the front door holding the hand of his young daughter, Weeks could not bring himself to shoot. He wanted another opportunity to "finish the job," but Bulger advised him to forget about Howie Carr.:205–206 In his 2006 memoirs Weeks has stated that, although he is fully aware of the public outcry that would have followed, he regrets not murdering Carr. "His murder would have been an attack on the system, like attacking freedom of the press, the fabric of the American way of life, and they would have spared no expense to solve the crime. But in the long run, Jimmy and I got sidetracked and the maggot lived. Still, I wish I'd killed him. No question about it.":206

Depictions in fiction and non-fiction

The 2014 documentary film Whitey: United States of America v. James J. Bulger, made by Joe Berlinger, is based on Bulger's trials

The film Black Mass—released September 18, 2015 in the US—stars Johnny Depp as Bulger and was directed by Scott Cooper. The film's screenplay, by Mark Mallouk and Jez Butterworth, is based on the 2001 non-fiction book Black Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob, by Dick Lehr and Gerard O'Neill. The film chronicles Bulger's years as an FBI informant, and his manipulation of his FBI handler as a means to eradicate his rivals for control of the Boston underworld, the Italian Mafia.

Bulger is mentioned considerably in the book All Souls: A Family Story From Southie by Michael Patrick MacDonald – a memoir about the author's life growing up in Boston during the 1970s and 1980s.

Characters based on Whitey Bulger

In Season 11 Episode 21 of the television series Law & Order entitled "Brother's Keeper," certain plot details are inspired by Bulger's criminal career. Specifically, an Irish-heritage criminal having a secret working relationship with the FBI via a childhood friend in the agency.

The character of Frank Costello (played by Jack Nicholson) in the 2006 Martin Scorsese film The Departed is loosely based on Bulger, though the plot of the movie is adapted from the 2002 Hong Kong film Infernal Affairs.

The 2006–2008 Showtime TV series Brotherhood, about two Irish-American brothers on opposite sides of the law, was inspired by the relationship between Whitey and Billy Bulger, although the show takes place not in Boston but in nearby Providence, Rhode Island.

In the TV series Rizzoli & Isles, which premiered in 2010, the character of Paddy Doyle, an Irish-American mobster who is the biological father of lead character Maura Isles, is based on a romanticized vision of Bulger.

In season one of the Showtime series Ray Donovan, the character of Patrick "Sully" Sullivan, played by James Woods, is loosely based on Bulger.

The 2013 television drama The Blacklist starring James Spader about a career criminal who turns himself in to work with the FBI on his own terms was inspired by Bulger's story.