Whitey Bulger Part II

 

Massachusetts Lottery

In the summer of 1991, Bulger and Weeks, along with associates Patrick and Michael Linskey, came into possession of a winning Massachusetts Lottery ticket that 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 DEA, the Boston Police, and the Massachusetts State Police launched a probe of Bulger's illegal 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 Racketeer Influenced and Corrupt Organizations Act (RICO).

According to 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.

Bulger 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 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, 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 to New York City, 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 safety deposit box. He then drove to Boston and dropped off Stanley in a parking lot. Bulger met with Weeks at Malibu Beach in Dorchester, where Weeks brought 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. 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 Main Branch, 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 Main Branch 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'd never return to South Boston.

On July 7, 1996, a federal grand jury in Boston returned a 29-count indictment against Bulger and four other leaders of the Winter Hill Gang and the Patriarca Family; Bulger was indicted on 13 counts of racketeering. On May 23, 2001, Bulger, along with Stephen and Michael Flemmi, were charged in a 48-count federal indictment with racketeering, murder, and other crimes.

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 family, who 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 was stashed and everybody 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 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. A businessman watching Hannibal recognized a photograph of Bulger in a scene featuring the website of the FBI's most wanted fugitives. However, there were unconfirmed sightings elsewhere. At one point, FBI agents were sent to Uruguay to investigate a lead. Other agents were sent to stake out the 60th anniversary celebrations of the Battle of Normandy, as Bulger was reportedly an enthusiastic fan of military history. Later reports of a sighting in Italy in April 2007 proved false. Two people on video footage shot in Taormina, Sicily, formerly thought to be Bulger and Greig walking in the streets of the city center, were later 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 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. He was 81 years old at the time of the arrest.

Bulger was captured as a result of the work of the Bulger Fugitive Task Force, which consisted of FBI agents and a Deputy U.S. 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 had been featured on the television show America's Most Wanted sixteen 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 fourteen television 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.

Some of the weapons found in Bulger's apartment

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". 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. 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), who was nearly 22 years his junior. 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, 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 death by drug overdose, McGonagle reportedly held Bulger responsible for the murders of his brothers, twins Donald and Paul McGonagle, who were killed in the fighting which occurred during the Mullen-Killeen gang war. The body of Paul McGonagle, of whom Greig's sister Margaret was a widow, lay hidden and buried for 25 years on Tenean Beach in Dorchester. Greig's younger brother David, a close associate of Bulger, was found shot dead on Cape Cod in an apparent 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 she was very subservient to and dominated by Bulger. She and Bulger lived together for a time at her home in Squantum, a section of Quincy.

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

Greig completed her sentence on July 23, 2020, and was later released from home confinement and electronic monitoring. She has been living quietly in South Boston with her twin sister Margaret McCusker.

Final detention

According to an excerpt of a book on Bulger published by Boston magazine, Bulger only made one friend during his post-sentencing detention, Clement "Chip" Janis, a young convict who was trusted to run art classes for other convicts.

When Bulger arrived at the United States Penitentiary in Tucson there were other famous inmates there, including Brian David Mitchell, Steven Dale Green and Montoya Sánchez.

According to Janis, Bulger was attacked by a fellow convict nicknamed "Retro", whose knife pierced Bulger's neck and skull and sent him to the prison infirmary for a month. Whether Bulger was targeted randomly or deliberately is not known. Apparently the inmate was not motivated by any personal issues with Bulger, but commmitted the near-fatal assault so that he would be sent to solitary confinement, allegedly to avoid paying for drugs he had acquired from other prisoners.

Bulger was able to begin taking part in counseling with a prison psychologist at the Tucson facility. However, rumors circulated that the psychologist was too sympathetic to Bulger, and may even have allowed him to use her cell phone. His counseling was soon terminated, and he was transferred to the Coleman Federal Correctional Complex in Florida.

At Coleman, Bulger started experiencing night terrors, which he attributed to the experiments he had taken part in while incarcerated in the 1950s, where he had been administered LSD. Bulger, who started his imprisonment with a rigorous exercise regime, was by this point using a wheelchair.

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 Debra Davis, though Bulger had already been found liable for her death in a civil suit.[99] 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 was indicted in Florida for the murder of Callahan and in Oklahoma for the murder of Roger Wheeler, and could have received the death penalty in those states.

In September 2014, Bulger entered the Coleman II United States Penitentiary in Sumterville, Florida. In October 2018, he was transferred to the Federal Transfer Center in Oklahoma City, and then a few days later to the Federal Penitentiary in West Virginia. According to prison documents obtained by The New York Times, Bulger gained a reputation for disconcerting behavior during his time in prison: "At the Coleman prison complex in Florida in September 2014, he was disciplined multiple times, including once for masturbating in front of a male staff member and once, in February, for threatening a female medical staff member". Bulger was also in poor health, as he was unable to walk and had a damaged hip, often falling out of bed. His health also declined due to a lack of exercise.

Death

Bulger was transferred from the Federal Transfer Center in Oklahoma City to United States Penitentiary, Hazelton, in West Virginia on October 29, 2018. At 8:20 a.m. on October 30, the 89-year-old Bulger was found dead. Bulger was in a wheelchair and had been beaten to death by multiple inmates armed with a sock-wrapped padlock and a shiv. His eyes had nearly been gouged out and his tongue almost cut off; a law enforcement official described Bulger as "unrecognizable". This was the third homicide at the prison in a 40-day span. Correctional officers had warned Congress just days before the most recent Hazelton death that facilities were being dangerously understaffed. Massachusetts-based mafia hitman Fotios "Freddy" Geas was the primary suspect in orchestrating the killing of Bulger. Geas, 51, and his brother were sentenced to life in prison in 2011 for their roles in several violent crimes, including the 2003 killing of Adolfo "Big Al" Bruno, a Genovese crime family capo who was shot in a Springfield, Massachusetts parking lot. According to ABC News, Bulger's medical status had been lowered on October 8, 2018, shortly before he was transferred.

On November 8, 2018, a funeral Mass was held for Bulger at Saint Monica – Saint Augustine Church in South Boston. Family members, including his brother, former Massachusetts state Senate president William M. Bulger, and the twin sister of Catherine Greig attended. Bulger's death came as a relief to many Bostonians, especially for family members of his victims; Steven Davis, whose sister Debra was reportedly killed by Bulger in 1981, stated that "[h]e died the way I hoped he always was going to die."

Bulger is buried at St. Joseph's Cemetery in the Boston neighborhood of West Roxbury under the Bulger family headstone inscribed with the names of his parents. In September 2019, the Bulger family filed a wrongful death lawsuit against the Justice Department, alleging that, by lowering Bulger's medical status and transferring him to Hazelton, he "was deliberately placed in harm's way. There is simply no other explanation for the transfer of someone in his condition and inmate status to be placed in the general population of one of the country's most violent federal penitentiaries." The Bulger family sought US$200,000 in damages. In January 2022, U.S. District Judge John Preston Bailey dismissed the lawsuit, ruling federal law did not allow his family the right to sue Bureau of Prisons (BOP) officials because Congress expressly puts custody of inmates in the hands of the BOP, and "has repeatedly limited judicial authority to review BOP housing decisions and to entertain claims brought by prisoners."

On August 18, 2022, three men were indicted in connection with the beating death of Bulger: Fotios Geas, Paul J. DeCologero, and Sean McKinnon.

Family

Bulger had two younger brothers, William Michael "Billy" Bulger (born 1934) and John "Jackie" P. Bulger (born 1938). William 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, William 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 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." He 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." William 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 governor Mitt Romney waged an extended and ultimately successful effort to get William to resign from the presidency of the University of Massachusetts, which he finally did 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 relationship 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. Lindsey Cyr later recalled it as:

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."

After Bulger's arrest, Cyr 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

According to Weeks:

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's 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 stated 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.  In his 2006 memoir Weeks said that, although he was aware of the public outcry that would have followed, he regretted 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."

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

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 1 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 initially inspired by Bulger's arrest and trial.

In season 2 of Power Book II: Ghost, the character of Dante "Mecca" Spears, played by Daniel Sunjata, is loosely based on Bulger.