On August 19 1999, Bulger became the 458th Ten Most Wanted fugitive listed by the Federal Bureau of Investigation (FBI). He is currently wanted for racketeering (under the Racketeer Influenced and Corrupt Organizations Act (RICO)) murder, conspiracy to commit murder, extortion, conspiracy to commit extortion, money laundering, conspiracy to commit money laundering and narcotics distribution. In October 2007, Interpol released a "red notice" for Bulger.
James Bulger was one of six children. When he was a small child, his parents moved the family to South Boston, Massachusetts. They moved into a new public-housing project called Old Harbor also known as Mary Ellen McCormick projects. James Bulger attended St. Mark's, a parochial school in Dorchester, for the first grade, before transferring to St. Margaret's School, where he allegedly suffered child abuse and sexual abuse. The memoirs of his brother, former state senator William Bulger, describe him as a mischievous child fond of pranks. By age 10, in 1939, he ran away from home, joined the circus, and kept a pet ocelot.
James Bulger was first arrested in 1943, at the age of 14, for larceny. He then went on to be arrested for assault and battery and armed robbery. At this time, he was associated with a juvenile street gang known as the Shamrocks. From 1943 to 1947, Whitey Bulger was arrested for larceny, forgery, assault and battery, and armed robbery. For all these crimes, he was sent to a juvenile reformatory from 1943 until 1948.
Shortly after release in April 1948, he joined the Air Force. After completing basic training, he was stationed at the Smoky Hill Air Force Base in Salina, Kansas, and later in Idaho. He spent time in the brig for a number of assaults. In 1950, he was arrested for going AWOL. On August 16 1952, he received an honorable discharge and returned to Massachusetts.
Bulger first served time at Atlanta Penitentiary (1956–59) for armed robbery and hijacking. There, according to Kevin Weeks, he underwent a torturous involvement in the MK-ULTRA program. The project goal 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 who had volunteered to lessen their sentences were given LSD and other drugs. Bulger is said to have suffered from frequent insomnia, nightmares, and occasional hallucinations.
He was then shipped from Atlanta Prison to Alcatraz Island (1959–62). Bulger arrived at Alcatraz 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 (1962–63), and in the following year to Lewisburg Penitentiary (1963–65). He was released after serving nine years in prison.
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 suburban Framingham, Massachusetts.
Former Mullen Gang boss Patrick Nee, however, 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 enforcer Jimmy Mantville.
Also according to Nee, Bulger and his fellow Killeens fled the city in the aftermath of their boss's murder, fearing that they would be next. Instead of murdering Bulger, however, Patrick Nee arranged for the dispute to be mediated by Howie Winter and Providence Mafia Patriarca crime family captain Joseph Russo. After a sitdown at Chandler's restaurant in the South End, Boston, the two gangs joined forces, with Winter as overall boss.
Beginning in 1973, he began to use his influence to remove opposition by persuading Howie Winter to sanction the killings of those whom he viewed as having "stepped out of line." These included former Mullen associate Spike O'Toole, who was killed by Johnny Martorano, and former Mullen Gang veteran Paulie McGonagle, who was shot in the head by Bulger and buried in a shallow grave in Boston's Tenean Beach. It is also alleged that he had direct involvement in the murder of Eddie Connors in January 1974, as well as those of Tommy King and Buddy Leonard in November 1975. After 1975, he began to also use his FBI deal to send his rivals to prison.
In 1979, Howie Winter was arrested along with many members of his inner circle on charges of fixing horse races. Bulger, who was left out of the indictments, stepped into the vacuum and took over the leadership of the gang. He transferred its headquarters to the Lancaster Street Garage in Boston near the Boston Garden in the city's North End. As of early 2008, this historic garage is up for sale.
While Howie Winter and most of his organization's leadership were sentenced for fixing horse races in 1979, 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 a threat. But the main victim of their relationship with the federal government was the Italian-American Patriarca crime family, which was based in the North End, Boston 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 illicit gambling and drug trafficking in and around Boston.
By 1988, Bulger headed an organization that ran all of the rackets (e.g. extortion, loansharking, bookmaking, truck hijackings and arms trafficking) not just in Boston but throughout New England. They were also the main narcotics distributor in the state, receiving their drugs from a Cuban-American gang based in South Florida. They were earning so much money that they set up "The X Fund," which was used for payoffs of individuals in politics and law enforcement. It has since been revealed that members of the Boston Police Department, the Massachusetts State Police and the Federal Bureau of Investigation accepted bribes from the X fund.
Bulger, Weeks, and Flemmi became heavily involved in narcotics trafficking in the early 1980s. Bulger began to summon drug dealers from in and around Boston to his headquarters. Flanked by Kevin Weeks and Stephen Flemmi, he 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. Bulger began to micromanage the New England drug scene. In South Boston, most of the gang's drug trafficking was managed by a handpicked crew of prize fighters led by John Shea. Edward MacKenzie Jr., a former member of Shea's crew, has stated that this was done because Bulger viewed athletes as less likely to abuse the drugs they were selling.
According to Weeks, Bulger enforced very strict rules over his dealers. He allowed them to sell cocaine and marijuana, but forbidding heroin and PCP. By Bulger's reasoning, a cocaine addict can still function, while heroin junkies "become zombies." He also strictly forbade selling to children. Those dealers who refused to obey Bulger's rules were beaten, killed or otherwise driven out of the neighborhood. To those who obeyed, however, business was good. The Boston drug scene thrived as "Red" Shea and his crew arranged massive drug deals with Colombian and Cuban-American suppliers based in South Florida.
In 1990, however, "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. The entire crew refused to violate the neighborhood code of silence by informing on Bulger, to the fury of investigators who had hoped to build a case against him. It would not be until the cooperation of Kevin Weeks in 1999 that Bulger, by then a fugitive, was conclusively linked to the drug trade by investigators.
The following December, Bulger was allegedly informed by 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.
According to Kevin Weeks, this was something that Bulger had long prepared for. As early as 1977, he had acquired documents for himself under the name Thomas F. Baxter. He had also set up safe deposit boxes, containing cash, jewelry, and passports, in cities across North America and Europe including Florida, Oklahoma, Montreal, Dublin, London, Birmingham (UK) and Venice.
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 his restaurant by the DEA. Michael Flemmi, a Boston police officer and Stephen Flemmi's brother, informed Kevin 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 safety deposit box. Bulger then drove to Boston and dropped off Teresa Stanley in a parking lot. He then met Kevin Weeks, who had brought with him one of Bulger's favorite mistresses, Catherine Greig. Bulger and Greig then went on the run together.
In his memoirs, Weeks vividly describes his 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.
On November 17 1999, Weeks was arrested by a combined force of the DEA and the Massachusetts State Police. While awaiting trial in Federal prison, he learned that Bulger and Flemmi had been informing on their own underlings. Deciding that "you can rat on a rat," he cut a deal with federal prosecutors, and revealed where almost every penny and body was buried.
James J. Bulger is currently on the FBI Ten Most Wanted list. A reward of US $2 million is being offered for information leading to his capture. Bulger has been featured on the television show America's Most Wanted 14 times, first in 1995 and last in July 26, 2008.
The last confirmed sighting of Bulger was in London in 2002. Since then, however, there have been 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 an enthusiastic fan of military history.
Reports of a sighting in Italy in April 2007 have proven 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. Evidence was provided by viewers of the German television programme Aktenzeichen XY … ungelöst, which had aired an episode containing a film about Bulger.
In 1974, Bulger became partners with Stephen Flemmi, 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, beachfront meeting inside an FBI issue car. Author Howie Carr writes that Bulger had been an off-the-books informant since his teenage years and that, like Flemmi, he had been recruited by Special Agent H. Paul Rico. However, Kevin Weeks considers it more likely that Flemmi had helped build a federal case against him. He writes of his belief that Bulger was caught between a rock and a hard place: supply information to the FBI or return to prison.
In spite of his many violent acts, Bulger was capable of genuine acts of kindness toward South Boston's poor. Weeks' memoirs list a number of incidents, including handing out turkeys for Thanksgiving to poor families in the area and tenderly presenting the gift of a new puppy to a young boy whose dog had recently been killed.
Bulger watched very little television and was fond of reading books, especially true crime and military history. He led a very disciplined life, according to Weeks, and ninety-five percent of his time was devoted to making money through criminal activity. He did not drink, smoke, or use drugs. He also exercised religiously, reportedly having the body of a man 20-30 years his junior.
Bulger is the older brother of John "Jackie" Bulger, a retired Massachusetts court clerk magistrate who was convicted in April 2003 of perjury to two grand juries regarding sworn statements he gave concerning contacts with his fugitive brother.
Another brother is William Bulger, formerly an influential leader within the Democratic Party in Massachusetts. In a long political career, he rose from obscurity to become President of the Massachusetts State Senate. After his retirement he was appointed President of the University of Massachusetts. In his 2002 testimony before the United States Congress, Billy Bulger was grilled by legislators from both parties. When asked what he thought his older brother Jimmy did for a living, William 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".He also stated that he loves his brother and hopes that the most brutal rumors concerning him will be proved 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. As fall-out from these remarks, Billy was forced to resign as president of the University of Massachusetts in 2003.
According to the 2000 book Black Mass by Boston Globe writers Dick Lehr and Gerard O'Neill, Bulger once extorted a winning lottery ticket from the real winner, who had purchased the ticket at one of his stores.
Bulger is alleged to have been a predatory bisexual by persistent rumor. Conservative author Howie Carr in his 2006 book The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century writes that while a teenager, Bulger worked as a male prostitute in Boston's gay bars. He further claims that Bulger's acquaintance with mobbed-up FBI agent H. Paul Rico dates from this time. Rico allegedly recruited Bulger as an informant after following him into a gay bar. Some critics have suggested most of Carr’s real motivations stem from his dislike of William Bulger’s politics and thus, he may be a less than unbiased source of information.
Edward MacKenzie Jr., a former member of the "Red" Shea crew of the Winter Hill Gang, has gone even further in his 2003 memoir Street Soldier: My Life as an Enforcer for Whitey Bulger and the Irish Mob, accusing Bulger of being a cross dresser and a pedophile who preyed on the young boys and girls of South Boston. These allegations are repeated almost verbatim in Carr's book.
However, longtime friend and confidant Kevin Weeks, insists that there is no truth to any of these claims.
"All the stuff and rumors that questioned Jimmy's sexuality were lies spread by the media. He had more women than Hugh Hefner. Guys like Donald Trump weren't even in his league. Whenever we went out to bars and clubs, women of all ages were after him. 'Variety is the spice of life,' he'd say as he enjoyed all of them.
In 2007, a New Hampshire newspaper published a story in an April Fool's Day edition claiming that Bulger had been captured. The Berlin, New Hampshire Daily Sun published an account of FBI agents taking Bulger into custody after a stand-off at the trailer park where he had been hiding. The article jokingly claimed that the FBI was able to force Bulger into surrender by blasting Barry Manilow tunes at the trailer where he was hunkered down.
In the Law & Order episode "Brother's Keeper", Detectives Lennie Briscoe and Ed Green investigate a string of murders linked to "Cally Lonegan", a devious, but charming Irish mob boss dubbed, "The Last of the Westies." Sharing Bulger's FBI deal, but lacking his exceptionally high intelligence, Lonegan is described as having worn a wire on a Mafia sitdown. The Lonegan character is eventually stabbed to death in the Riker's Island jail in New York City prior to his arraignment. It is implied that Lonegan's murder was ordered by the Italian mobsters whom he had previously handed over to the FBI.
People have speculated that Bulger is also the inspiration for the ruthless crime kingpin Francis "Frank" Costello, played by Jack Nicholson in Martin Scorsese's Academy Award-winning film The Departed. In fact, the Costello character is a combination of Bulger, and the Chinese Triad boss Hon Sam from the 2002 Hong Kong action movie Infernal Affairs. Matt Damon's character is loosely based on Triad member Ming from the original film. Undercover policeman Costigan (Leonardo DiCaprio), is a combination of Richard Marinick, an ex-State trooper turned Bulger associate, and Officer Yan from Infernal Affairs. The character of Costigan also lives in Somerville, Massachusetts, where the Winter Hill Gang was founded during the 1960s. Thomas Duffy, the film's technical advisor, is a former Major in the Massachusetts State Police who was assigned to investigate the Winter Hill Gang upon making detective. Kevin Weeks also worked as an advisor on the film. Reports have surfaced that Bulger was seen coming out of a theater showing the film in San Diego in November 2006.
Another popular portrayal appears on the TV series Brotherhood, which is inspired by Bulger's rumored alliance with his politician brother William. The series, takes place in "The Hill", a Irish-American neighborhood in Providence, Rhode Island. Actor Jason Isaacs, who plays a character based on Bulger, describes his character as follows:
"Well actually, "Michael Caffee" is not a bad guy. I wouldn't have done this if he was a bad guy. He's a really interesting man. He has a really strict ethical code that he adheres to and he thinks he is better for the neighborhood and the future of the city than his brother is. He thinks his brother is corrupt, he's part of the system.
In the 2007 mystery novel Along Comes A Stranger, author Dorie McCullough Lawson offers a suspenseful tale about a stranger who shows up in a small town in Wyoming, who may or may not be Whitey Bulger.
In The Kickass Press's Boston based religious satire "Sex with THE Virgin Mary" author Charles Webb's character Tinker Greene (along with his politician brother) is alleged to be influenced by Whitey Bulger.
Also according to Carr, many journalists, especially those working for the Boston Globe, were friendly towards Democratic Senator William Bulger and downplayed his brother's criminal activities, portraying the mob boss as a latter-day 'Robin Hood,' who kept drugs out of South Boston.
According to former associate Kevin Weeks, Bulger always enjoyed reading the newspapers and laughing hysterically at all they got wrong in their coverage of him and his associates. He was fond of saying,
"The Boston press is not known for its accuracy and they never let the truth get in the way of a good story.
INFORMATION ISSUED BY U.S. ATTORNEY'S OFFICE FOR MASSACHUSETTS ON SEPT. 14: LAW ENFORCEMENT ASKING FOR PUBLIC ASSISTANCE - POSSIBLE SIGHTING OF JAMES J. BULGER IN ITALY
Sep 14, 2007; The U.S. Department of Justice's U.S. Attorney's office for Massachusetts issued the following press release: On April 10, 2007,...