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James Joseph “Whitey” Bulger, Jr. (born September 3, 1929) is a former organized crime figure from Boston, Massachusetts, United States. Local folklore depicted Bulger as a Robin Hood–style social bandit dedicated to protecting the neighborhood and its residents. Bulger allegedly masterminded a protection racket targeting drug kingpins and those running illegal gambling operations. Based upon the testimony of former associates, Federal prosecutors have indicted Bulger for 19 murders.
Beginning in 1975, Bulger served as an informant for the Federal Bureau of Investigation (FBI). As a result, the Bureau largely ignored his organization in exchange for information about the inner workings of the Italian American Patriarca crime family. Beginning in 1997, the New England media exposed criminal actions by federal, state, and local law enforcement officials tied to Bulger. For the FBI especially, this has caused great embarrassment. On December 23, 1994, after being tipped off by his former FBI handler about a pending indictment under the RICO Act, Bulger fled Boston and went into hiding. For sixteen years, he remained at large. For twelve of those years, Bulger was prominently listed on the FBI Ten Most Wanted Fugitives list.
On June 22, 2011, Bulger was arrested outside an apartment in Santa Monica, California. Arrested with him was his longtime girlfriend Catherine Greig. Bulger was 81 years old at the time of his arrest. Soon after, Bulger and Greig were extradited to Massachusetts and brought under heavy guard to the waterfront federal courthouse. This necessitated the closing of part of Boston Harbor. Greig pleaded guilty to conspiracy to harbor a fugitive, identity fraud and conspiracy to commit identity fraud, and was sentenced in June 2012 to eight years in prison. Bulger has not sought bail and remains in custody at the Plymouth County House of Correction in Plymouth, Massachusetts. On November 5, 2012, Bulger was taken to a hospital from his Plymouth prison cell after complaining of chest pains where he is awaiting trial on allegations he participated in 19 murders. On November 14, Greig filed an appeal aimed at cutting time off her prison sentence for helping him while he was a fugitive.
Bulger’s father, James Joseph Bulger, Senior, was the (something in/at/of) Harbour Grace, Newfoundland. His father married Jane Veronica “Jean” McCarthy, a first generation Irish-American, after settling in the North End, Boston. Their first child, James Joseph, Junior, was born in 1929.
The elder Bulger worked as a union laborer and occasional longshoreman; however, he lost his arm in an industrial accident and the family was reduced to poverty. In May 1938, the Mary Ellen McCormack Housing Project, now known as Old Harbor Village public housing project, was opened in South Boston. The Bulger family moved in and the children grew up there. His younger brothers (William Michael and John P.) excelled at school but young James Joseph, Junior preferred the streets.
Jimmy Bulger was arrested in 1943, at the age of 14 and charged with larceny. By then, Bulger had joined a street gang known as the “Shamrocks” and would eventually be arrested for assault, battery and armed robbery. He was sentenced to a juvenile reformatory. Shortly after his release in April 1948, he joined the United States Air Force. After his basic training, he was stationed first at the Smoky Hill Air Force Base in Salina, Kansas, then in Idaho. Bulger was sentenced to the stockade for several assaults. He was also arrested in 1950, for going absent without leave. Nevertheless, he received an honorable discharge in 1952, and returned to Massachusetts.
Early criminal career
Alcatraz mug shot of Bulger, 1959
Bulger was first in federal custody in 1956 at Atlanta Penitentiary for armed robbery and hijacking. There, according to mobster Kevin Weeks, he was involved in the MK-ULTRA program, the goal of which was to research mind-control drugs for the Central Intelligence Agency, headed by CIA chemist Sidney Gottlieb. For eighteen months, Bulger and eighteen other inmates, all who had volunteered to lessen their sentences, were given LSD and other drugs. Bulger later complained that he and the other inmates had been “recruited by deception,” and that they were told that they were helping to find “a cure for schizophrenia”.
He was then transferred from Atlanta to Alcatraz Federal Penitentiary, arriving on November 2, 1959, as prisoner #AZ1428. He became a close friend of fellow inmate Clarence Carnes, alias “The Choctaw Kid”. In November 1962, he was transferred to Leavenworth Federal Penitentiary and in the following year, 1963, to Lewisburg Federal Penitentiary. He was released in 1965, after serving nine years in prison.
The Killeen-Mullen War
After his release, Bulger worked as a janitor and construction worker before becoming a bookmaker and loanshark with ties to Donald Killeen, the leader of the dominant Irish mob in South Boston. In 1971, Killeen’s younger brother allegedly bit off the nose of Michael Dwyer, a member of the rival Mullen Gang. A gangland war soon 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 committed what Weeks describes as his first homicide.
According to Kevin Weeks:
“Killing Paulie McGonagle, however, took Jimmy longer than he originally expected. Paulie talked a big game, but he wasn’t a shooter. Although he never did anything, he kept on stirring everything up with his mouth. So Jimmy decided to kill him. One day while the gang war was still going on, Jimmy was driving down Seventh Street in South Boston when he saw Paulie driving toward him. Jimmy pulled up beside him, window to window, nose to nose, and called his name. As Paulie looked over, Jimmy shot him right between the eyes. Only at that moment, just as he pulled the trigger, Jimmy realized it wasn’t Paulie. It was Donald, the most likable of the McGonagle brothers, the only one who wasn’t involved in anything. Jimmy drove straight to his mentor Billy O’Sullivan’s house on Savin Hill Avenue and told O’Sullivan, who was at the stove cooking, ‘I shot the wrong one. I shot Donald.’ Billy looked up from the stove and said, ‘Don’t worry about it. He wasn’t healthy anyway. He smoked. He would have gotten lung cancer. How do you want your pork chops?'”
According to former Mullen boss Patrick Nee, Paul McGonagle was enraged by the murder of his twin brother. Certain that William O’Sullivan was responsible, McGonagle ambushed and murdered Bulger’s partner. The end of the war has usually been related as follows. Bulger, realizing that he was on the losing side, secretly approached Howie Winter, the leader of the Winter Hill Gang. He allegedly told Winter that he could end the fighting in South Boston by murdering the leaders of the Killeen gang. Shortly thereafter, Donald Killeen was gunned down outside his home in the suburb of Framingham. Former Mullen Gang boss Patrick Nee disputes this claim. According to Nee, the slaying of Donald Killeen on May 13, 1972, was carried out not by Bulger but by Mullen Gang enforcers James Mantville and Tommy King.
Also according to Nee, Bulger and the Killeens fled the city in the aftermath of their boss’s murder, fearing that they would be next. Instead of murdering them, however, Patrick Nee arranged for the dispute to be mediated by Howie Winter and Patriarca crime family captain Joseph Russo. In a sit-down at Chandler’s restaurant in the South End, Boston, the Mullens were represented by Patrick Nee and Tommy King and the Killeens by Bulger. Following the sit-down, the two gangs joined forces, with Winter as overall boss.
Nobody talked fault, although at first it was tense while we ran down the ‘who killed who’ list. Whitey was a defeated warrior looking to keep as much honor as possible. He knew the Mullens had courageous, fierce men willing to die for theirs, and he was perceptive. Deep down, Whitey knew that he couldn’t take over for the Killeens without cutting the Mullens in on their bookmaking and loansharking. Tommy and I felt victorious, but we didn’t want to gloat. The meeting lasted for six hours. We ate good steaks, chasing them down with nothing stronger than ginger ale. It was business, and contrary to media stereotype, we weren’t a bunch of lowlifes who sat around drinking beer all day and all night.
According to Nee,
The balance of the meeting was spent forming an alliance, and by far the hardest part was deciding whom to protect. After a war, each side usually gets to protect so many people from harm. Those who aren’t protected are fair game for retribution and ‘shake-downs.’ 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 and nobody at that table could ever have possibly imagined how this treacherous fuck would treat his 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 John Connolly that in the car with Bulger were Winter Hill Gang enforcers Stephen Flemmi and John Martorano.
The 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 loansharks. During the years that followed, Bulger began to remove opposition by persuading Howie 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 Spike O’Toole, Paulie McGonagle and Tommy King.
According to Kevin Weeks,
“As a criminal, he made a point of only preying upon criminals, as opposed to legitimate people. 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. Certainly, if he thought there was a chance of this person coming back to cause him some harm, there was no sense in bothering to give him a beating. He might as well fucking kill him. And he did. Tommy King, in 1975, was one example. Although I was nineteen at the time and not yet working for Jimmy, he told me the whole story. Tommy’s problems began when he and Jimmy had worked in Triple O’s. Tommy, who was a Mullins, made a fist. And Jimmy saw it. The next day, Tommy went to the Old Colony projects were Jimmy was living with his mother and tried to make amends. He said he had been drunk and hadn’t meant what he had said the night before. Jimmy told him, ‘Don’t worry about it. Forget 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. That night, Jimmy put Tommy in the passenger seat with Stevie and Johnny in the back seat, and told him they were looking for someone to kill. That someone of course was Tommy. As they were driving around, Tommy banged on his supposedly bulletproof flak jacket and joked, ‘If we don’t find him we can try this out.’ The minute he finished the joke, Johnny shot him in the head from the back seat. The bullet went right through his head, splattering blood and brains all over the place, but Jimmy just reached over, propped Tommy up, and put a baseball cap on his bloodied head. A minute later, Johnny said he had to make a phone call and asked Jimmy to pull over by the Dunkin Donuts in Quincy. He was gone a few minutes, supposedly to make a bet, then got back in the car and the four of them drove off. Jimmy drove around for a few minutes and then found a spot on the Neponset River where they buried Tommy. 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.”
Also according to Kevin Weeks,
“Before he was killed, Tommy King had threatened a Boston police detective that he was going to kill him. Knowing Tommy’s violent reputation and that he was a capable guy, the detective was afraid of him. Jimmy met with the detective, who was a tenacious investigator, and promised to talk to Tommy and make him listen to reason. If Tommy wouldn’t listen to him, Jimmy said, he would put himself between Tommy and the detective to defuse the situation and make sure no harm came to the detective. About a week later, Jimmy informed the detective that he no longer had a problem. He told him Tommy hadn’t listened to him, but he didn’t have to worry about anything, that Tommy would no longer bother him. The truth was that even though Tommy King had made the threats, when Jimmy met with the detective, Tommy had already been dead for two weeks. Jimmy had ended up using Tommy’s death as leverage with this detective. He had become friends with him by letting him think Tommy was gone on his behalf. It was another case of Jimmy’s Machiavellian side, turning a potentially bad situation to his advantage.”
In 1979, Howie Winter was arrested, along with many members of his inner circle, on charges of fixing horse races. Bulger and his then partner Stephen 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 North End.
In 1971, the FBI, searching for reliable information in their battle against the Patriarca crime family, approached Bulger and attempted to recruit him as an informant. FBI Special Agent Dennis Condon was assigned to make the pitch. However, Condon reported that Bulger was too concerned about his own safety to start working with the FBI.
In 1974, Bulger became partners with Stephen Flemmi, an Italian American mobster and 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 Mafia 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.”
Author Howie Carr alleges that Bulger had been an off-the-books informant since the 1940s. Carr dubiously claims that a teenaged Bulger worked as a male prostitute in Boston’s gay bars. Carr also claims that Bulger was blackmailed into informing after Special Agent H. Paul Rico tailed him into a gay bar. This has never been confirmed, however.
Kevin Weeks dismisses all of these allegations. According to Weeks, the charismatic Bulger, “had more women than Hugh Hefner.” As for Bulger’s informant status, Weeks considers it more likely that Bulger’s partner Stephen Flemmi had betrayed him to the FBI. He writes of his belief that Bulger was caught between a rock and a hard place: supply information to the FBI or return to Federal prison.
In 1997, shortly after The Boston Globe disclosed that Bulger and Flemmi had been informants, Weeks met with retired FBI Agent John 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.”
According to Weeks,
As I read over the files at the Top of the Hub [restaurant] that night, Connolly kept telling me that 90 percent of the information in the files came from Stevie. Certainly Jimmy hadn’t been around the Mafia the way Stevie had. 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 listened to all that, but now I understood that even though he was retired, Connolly was still getting information, as well as money, from Jimmy. As I continued to read, 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. Whenever I came across the name of someone I knew, I would read exactly what it said about that person. I would see, over and over again, that some of these people had been arrested for crimes that were mentioned in these reports. It didn’t take long for me to realize that it had been bullshit when Connolly told me that the files hadn’t been disseminated, that they had been for his own personal use. He had been an employee of the FBI. He hadn’t worked for himself. 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. I thought about what Jimmy had always said, ‘You can lie to your wife and to your girlfriends, but not to your friends. Not to anyone we’re in business with.’ Maybe Jimmy and Stevie hadn’t lied to me. But they sure hadn’t been telling me everything.
A federal judge ruled on September 5, 2006, that the mishandling of Bulger and Flemmi caused the 1984 murder of informant John McIntyre. As a result, the McIntyre family was ordered to receive more than $3 million from the U.S. Federal Government. The judge stated the FBI failed to properly supervise their own agent John Connolly (convicted and jailed in 2002) and also failed to investigate numerous allegations that Bulger and Flemmi were involved in drug trafficking, murder, and other crimes over decades.
In a 2011 interview, Stephen Flemmi recalled, “Me and Whitey gave [the Feds] shit, and they gave us gold.”
Federal Bureau of Investigation surveillance photograph of Bulger (right) with enforcer Stephen Flemmi (left) c. 1980.
Winter and most of his organization’s leadership were sentenced for fixing horse races in 1979, but the FBI persuaded federal prosecutors to drop all charges against Bulger and Flemmi. 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 Bulger associates whom Bulger viewed as threats; however, the main victim of their relationship with the federal government was the Italian-American Patriarca crime family, which was based in Boston’s North End, and in Federal Hill, Providence. After the 1986 RICO indictment of underboss Gennaro Angiulo and his associates, the Patriarca family’s Boston operations were in shambles. Bulger and Flemmi stepped into the ensuing vacuum to take control of organized crime in the Boston area.
In 1980, Bulger was approached in South Boston’s Triple O’s saloon by Louis Litif, a neighborhood bookmaker. Kevin Weeks, who was then a bouncer at Triple O’s, witnessed the discussion that followed. He has recalled,
“He wasn’t a big guy, maybe five seven and 185 pounds. Of Arab descent, he had a mustache like Saddam Hussein. He had a wife and a couple of kids, and a three decker townhouse on East Broadway and G. I was friendly with his daughter Louanne, who was a few years younger than me. 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.
According to Weeks, Litif had been stealing from his partners in the bookmaking operation and using the money to traffic cocaine. What is more, Litif had not only refused to pay a cut of his drug profits, but had also committed two murders without Bulger’s permission.
As Weeks listened, Litif told an outraged Bulger that he was also going to kill his partner, “Joe the Barber,” whom he falsely accused of stealing money from the bookmaking operation. Bulger refused to sanction this, but Litif vowed to kill him anyway. Seething with anger, Bulger informed Litif, “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 icily responded, “We’re not friends anymore, Louie.”
At the time Kevin Weeks was about to get married to his high school sweetheart, Pamela Caveleri. A short time before the wedding, Weeks informed Bulger that he was having difficulty seating Louis Litif. “Don’t worry about it,” Bulger responded. “He probably won’t show.”
According to Weeks,
“Personally, I liked Louie. Every Sunday night, he had come down to Triple O’s and we’d play cards or pinball, twenty bucks a game. He was loud but funny, and he had always been a major moneymaker for Jimmy. He should have just stayed a bookie and not tried to jump from the minor leagues to the majors. 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 under wear and was in a green garbage bag.’ At the wedding, when I went around to greet his table, Jimmy pointed to the empty chair beside him and said, ‘Say hi to Louie.’ Stevie picked up a napkin and made a show of wiping his face. ‘He keeps on drinking and it keeps on leaking out of him,’ he said, reminding us that Louie had been shot in the head and any drink he might have put in his mouth would pour right out of his face. And they all broke out laughing.”
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 Louis Litif. Meanwhile, FBI agent John Connolly kept Bulger and Flemmi closely briefed on what Halloran was saying to the Bureau. According to Kevin Weeks, Bulger and Flemmi were most enraged that Halloran was falsely claiming involvement in their assassination of Tulsa, Oklahoma businessman Roger Wheeler. Ultimately, the FBI discovered Halloran’s falsehoods and refused him and his family a place 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, Kevin Weeks staked out Anthony’s Pier 4 Restaurant, where Halloran was dining. Michael Donahue of Dorchester, a construction worker, neighbor, and friend of Halloran, incidentally ran into him at the restaurant. In a decision that would prove costly, 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 hand held radio. Bulger drove up with a masked man armed with a silenced Mac 10; Bulger himself carried a .30 caliber carbine. Bulger, wearing a floppy hat and a long haired wig, 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. Stephen Flemmi has identified the second shooter as Mullen Gang leader Patrick Nee. Nee denies the allegation and no charges have yet been filed.
Michael Donahue was survived by his wife and three sons. The Donahue and Halloran families eventually filed a civil lawsuit against the United States Federal Government after learning that FBI Agent John 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.
Throughout the 1980s, Bulger, Flemmi and Weeks ran shakedowns throughout eastern Massachusetts, e.g., 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, South Boston’s code of silence, and also corruption within the Boston Police Department, the Massachusetts State Police, and the Federal Bureau of Investigation. Although disgraced FBI agent John Connolly has long been Bulger’s most infamous friend in law enforcement, Kevin Weeks has insisted that Lieutenant Richard J. Schneiderhan was valued far more highly. According to Weeks, this was because Schneiderhan was the Winter Hill Gang’s only source inside the Massachusetts State Police.
During the middle 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 to assassinate them. He would then demand a large cash payment not to do so. Eventually, however, the massive profits of drugs proved irresistible. According to Weeks,
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 trade was managed by John Shea. According to Weeks, Bulger briefly considered murdering Shea, but eventually decided to just shake him down.
According to Weeks, Bulger enforced strict rules over the dealers who were paying him protection.
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 alleges that Bulger strictly forbade PCP and selling to children, and that those dealers who refused to play by his rules were violently driven out of the neighborhood. In 1990, “Red” Shea and his associates were arrested as part of a joint investigation involving the Drug Enforcement Administration (DEA), the Boston Police Department and the Massachusetts State Police. All refused to testify against Bulger, Flemmi, and Weeks. According to Weeks,
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.
Won Massachusetts state lottery
One week in the summer of 1991, Bulger and three friends 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 $14 million.
Photographed in 1994
In April 1994, a joint task force of the 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 (UK) and Venice. In December 1994, Bulger was informed by retired FBI Agent John Connolly that sealed indictments had come from the Department of Justice and that the FBI were due to make arrests during the Christmas season. In response, Bulger fled Boston on December 23, 1994, accompanied by his common law wife, Theresa Stanley.
After fleeing Boston, Bulger and Stanley initially spent four days over Christmas in Selden, New York, before spending New Year’s Day in a hotel in New Orleans’ 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 then spent the next three weeks traveling between New York, Los Angeles and San Francisco before Stanley decided that she wanted to return to her children. They then traveled to Clearwater, Florida, where Bulger retrieved his “Tom Baxter” identification from a safe deposit box. Bulger then drove to Boston and dropped off Theresa Stanley in a parking lot. He then met with Weeks at Malibu Beach in Dorchester, 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.”
New York Public Library, 42nd Street and 5th Avenue
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,
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 had 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, Weeks 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 wiseguy 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.”
Retouched photo done in 2004.
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,
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 had 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 had 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.
The last 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. FBI agents were also 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 he had in fact traveled frequently. Also following his arrest, it was clear that he had not been reclusive, 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”.
The apartment building in Santa Monica, California where Bulger lived as a fugitive for at least fifteen years.
After sixteen years at large and twelve years on the FBI Ten Most Wanted Fugitives list, Bulger was arrested in Santa Monica, California, on June 22, 2011.
Bulger 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 Ten Most Wanted Fugitives list. Bulger has been featured on the television show America’s Most Wanted 16 times, first in 1995, and last on October 2, 2010. According to the 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 goes to beauty salons.
Some of the weapons found in Bulger’s apartment
Authorities received a tip from a woman in Iceland that he was living in a Santa Monica, California, apartment near a beach. 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, stated that “she believes the death penalty is not an option in the federal charges Bulger faces in her district, but that she believes 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 stated: “It is our intention to bring Bulger to justice and to be held accountable for the murder of Mr. Wheeler.” 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 informed them that during his days as a fugitive he was able to go back and forth frequently across the border to Mexico to buy medicine that he needed for his cardiac problems. It is anticipated by many, and feared by some, that Bulger will have a lot to say to authorities about the corruption on the local, state, and federal levels, which enabled him to operate his criminal enterprise for so long, and that such disclosures may earn Bulger some special treatment in sentencing.
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.
The tipster was identified by The Boston Globe as Anna Bjornsdottir, a former model, actress, and Miss Iceland 1974, who lived in Bulger’s neighborhood.
In a 2011 interview, Kevin Weeks expressed surprise at Bulger’s decision to cooperate after his arrest. He 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.”
However, Weeks also declared that he is not afraid of Bulger and that the residents of Boston should not be either. Weeks declared, “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.”
Bulger’s companion during his years as a fugitive was his longtime girlfriend Catherine Greig. 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.
Catherine E. Greig, long-time girlfriend of James Joseph “Whitey” Bulger, Jr., August 2, 2011 mugshot, United States Marshals Service
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 twenty five years on Tenean Beach in Dorchester. Greig’s twin sister Margaret is the widow of Paul McGonagle. She remarried and is now Margaret McCusker. McCusker is a licensed practical nurse. Greig’s younger brother David Greig was a close associate of Bulger. David was found shot dead on Cape Cod, a death which was 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. Reddington stated that Greig would be going to trial and would not be accepting a plea bargain, explaining: “I question that the government can prove the case.”  According to Reddington, Greig’s actions did not constitute “harboring” of a fugitive. Greig sought release on bail and home confinement, a request that was denied.
After their arrest, Kevin Weeks expressed hope that Bulger would try to do something to clear Greig. “Catherine is a nice person,” he said, “a loyal person, compassionate, intelligent. I can’t say enough about her. She’s a good person.”
In March 2012, Greig pled guilty to conspiracy to harbor a fugitive, identity fraud, and conspiracy to commit identity fraud. On June 12, 2012, she was sentenced to 8 years confinement in a Federal penitentiary. She refused to speak during her sentencing.
Bulger has two younger brothers, William Michael Bulger (born 1934) and John P. Bulger (born 1938).
Senator William “Billy” Bulger is a Korean War veteran and formerly an influential leader of the Democratic Party in Massachusetts. In a long political career, Senator Bulger rose to become President of the Massachusetts State Senate. After his retirement he was appointed President of the University of Massachusetts system.
In 2002, testimony before the United States Congress, Senator Bulger was grilled by legislators from both parties. When asked what he thought his brother did for a living, Senator Bulger responded:
“I had the feeling that he was in the business of gaming and . . . or whatever. It was vague to me, illegal but I didn’t . . . not all that violent . . . For a long while, he had some regular jobs, but ultimately it was clear that he was not, he wasn’t doing what I’d like him to do. Let’s just say I was naive in retrospect.”
Senator Bulger added that he loves his brother and hoped the most brutal allegations concerning him will be proven false. In addition, he grudgingly admitted to visiting an isolated pay phone in order to speak to his older brother, who was by then a fugitive. In 2003, as a direct result of these comments, Senator Bulger was forced by then-Governor of Massachusetts Mitt Romney to resign from the presidency of the University of Massachusetts.
Judge John “Jackie” Bulger, a retired Massachusetts court clerk magistrate, was convicted in April 2003, of perjury to two grand juries regarding sworn statements he gave concerning contacts with his fugitive brother.
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. Bulger and Cyr began living together in 1966, when Cyr was 21 and a waitress at a North Quincy cafe. According to Cyr,
“He used to say that there were four people he had 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’s syndrome after having a severe allergic reaction to an aspirin injection.
According to Cyr,
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 is planning to publish her memoirs.