Whitey Bulger

Bulger's mugshot at Alcatraz (1959; age 30)

In 1956, Bulger served his first term in federal prison at Atlanta Penitentiary for armed robbery and truck hijacking. He later told mobster Kevin Weeks[35] that while there, he was used as a human subject in the CIA sponsored MK-ULTRA program. He was told the goal was to help find a cure for schizophrenia when in fact the goal was to research mind control drugs for the CIA.[36] For eighteen months, Bulger and eighteen other inmates, all of whom, under false information, had volunteered in return for reduced sentences, were given LSD and other drugs. None of the prisoners were informed of the truth about the experiment that was in fact part of the CIA MK-ULTRA program. Prisoners were used in these experiments without knowledge of the real facts involved.[35]

Bulger later complained that they had been "recruited by deception" and were told they were helping to find "a cure for schizophrenia."[35][37] The facts were later confirmed as the documents of the CIA experiments emerged.[38] He described his experience as "nightmarish" and said it took him "to the depths of insanity."[39] Notebooks Bulger wrote described the terror he felt at the thought of ingesting an additional dose of LSD.[40] He wrote that he heard voices, and feared that if he admitted this to anyone, he would be "committed for life".[41]

In 1959, Bulger was briefly transferred to maximum security at Alcatraz Federal Penitentiary in California. Later in his sentence, he was transferred to Leavenworth Federal Penitentiary and, in 1963, to Lewisburg Federal Penitentiary. Bulger's third petition for parole, in 1965, was granted after he had served nine years in prison. He would not be arrested again for 46 years.[42]

After his release, Bulger worked as a janitor and construction worker before becoming a bookmaker and loan shark under mobster Donald Killeen, whose gang, The Killeens, had dominated South Boston for over twenty years. The Killeens were led by three brothers—Donnie, Kenny and Eddie—along with Billy O'Sullivan and Jack Curran. Their base was the Transit Cafe in South Boston, which later became Whitey's Triple O's. In 1971, Killeen's younger brother Kenny allegedly shot and mauled Michael "Mickey" Dwyer, a member of the rival Mullen Gang, during a brawl at the Transit Cafe. A gang war resulted, leading to a string of killings throughout Boston and the surrounding suburbs. The Killeens quickly found themselves outgunned and outmaneuvered by the younger Mullens. It was during the war that Bulger set out to commit what Weeks describes as his first murder, of Mullen member Paul McGonagle. However, Bulger instead executed McGonagle's law-abiding brother Donald in a case of mistaken identity.

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

According to former Mullen boss Patrick "Pat" Nee, McGonagle ambushed and murdered O'Sullivan on the assumption he was the one responsible for his brother's killing. Bulger, realizing he was on the losing side, secretly approached Howie Winter, the leader of the Winter Hill Gang, and claimed he could end the war by murdering the Killeen leadership. Shortly thereafter, on May 13, 1972, Donald Killeen was gunned down outside his home in the suburb of Framingham.[31] Nee disputes this, claiming that Killeen was murdered by Mullen enforcers James Mantville and Tommy King, not Bulger.[43]^{: 123–125}

Bulger and the Killeens fled Boston, fearing they would be next. Nee arranged for the dispute to be mediated by Winter and Joseph Russo, caporegime of the Patriarca crime family in Rhode Island. In a sit-down at Chandler's nightclub in Boston's South End, the Mullens were represented by Nee and King, and the Killeens by Bulger. The two gangs joined forces, with Winter as overall boss.[43]^{: 127–134}[43] Soon after, Donald's sole surviving brother, Kenny, was jogging in Boston's City Point neighborhood when Bulger called him over to a car and said, "It's over. You're out of business. No more warnings."[44]^: 30 Kenny would later testify that Winter Hill enforcers Stephen Flemmi and John Martorano were in the car with Bulger.

Stephen Flemmi

After the 1972 truce, Bulger and the Mullens were in control of South Boston's criminal underworld. FBI Special Agent Dennis Condon noted in his log in September 1973 that Bulger and Nee had been heavily shaking down the neighborhood's bookmakers and loan sharks. Over the years that followed, Bulger began to remove opposition by persuading Winter to sanction the killings of those who "stepped out of line". In a 2004 interview, Winter recalled that the highly intelligent Bulger "could teach the devil tricks".[45] During this era, Bulger's victims included Mullen veterans McGonagle, King, and James "Spike" O'Toole.[46]

According to Weeks:

"As a criminal, he made a point of only preying upon criminals... And when things couldn't be worked out to his satisfaction with these people, after all the other options had been explored, he wouldn't hesitate to use violence. ... Tommy King, in 1975, was one example. ... Tommy's problems began when he and Jimmy had worked in Triple O's. Tommy, who was a Mullins, made a fist. And Jimmy saw it. ... A week later, Tommy was dead. Tommy's second and last mistake had been getting into the car with Jimmy, Stevie, and Johnny Martorano. ... Later that same night, Jimmy killed Buddy Leonard and left him in Tommy's car on Pilsudski Way in the Old Colony projects to confuse the authorities."[35]^: 90–91

In 1979, Winter was arrested, along with many members of his inner circle, on charges of fixing horse races. Bulger and Flemmi were left out of the indictments. They stepped into the power vacuum and took over the leadership of the gang, transferring its headquarters to the Lancaster Street Garage in Boston's West End, near the Boston Garden.[31]

In late August or early September 1974, Bulger and an accomplice reportedly set fire to an elementary school in Wellesley to intimidate U.S. District Court Judge Wendell Arthur Garrity Jr. over his mandated plan to desegregate schools in the city of Boston by means of busing. One year later, on September 8, 1975, Bulger and an unidentified person tossed a Molotov cocktail into the John F. Kennedy birthplace in Brookline in retaliation for Senator Ted Kennedy's vocal support for Boston school desegregation. Bulger then used black spray paint to scrawl "Bus Teddy" on the sidewalk just outside of the national historic site.[47][48]

In February 1979, federal prosecutors indicted numerous members of the Winter Hill Gang, including boss Howie Winter, for fixing horse races. Bulger and Flemmi were originally going to be part of this indictment, but Connolly and Morris were able to persuade prosecutor Jeremiah T. O'Sullivan to drop the charges against them at the last minute. Bulger and Flemmi were instead named as unindicted co-conspirators.[44]^: 64–68

Bulger and Flemmi then took over the remnants of the Winter Hill Gang and used their status as informants to eliminate competition. The information they supplied to the FBI in subsequent years was responsible for the imprisonment of several of Bulger's associates whom Bulger viewed as threats; however, the main victim of their relationship with the federal government was the Patriarca family, which was based in Boston's North End and in Federal Hill, Providence, Rhode Island. After the 1986 RICO indictment of Angiulo and his associates, the Patriarca family's Boston operations were in a shambles. Bulger and Flemmi stepped into the ensuing vacuum to take control of organized crime in the Boston area.[31]

In 1980, Bulger was approached in Triple O's by Louis Litif, a Lebanese-American neighborhood bookmaker. Weeks, a bouncer at the bar, said, "He wasn't a big guy, maybe five seven and 185 pounds. Of Arab descent, he had a mustache like Saddam Hussein. ... That night, as always, he was talking in his obnoxious loud voice. Even when there were 400 people in the bar, you always knew Louie was there."[35]^: 57

Litif had been stealing money from his partners in the bookmaking operation and using the money to traffic cocaine, and had not only refused to pay Bulger a cut of his drug profits but committed two murders without Bulger's permission.[35]^: 57–59 Litif told an outraged Bulger he was also going to kill his partner, "Joe the Barber", whom he accused of stealing from the bookmaking operation. Bulger refused to sanction this, but Litif vowed to proceed. Bulger replied, "You've stepped over the line. You're no longer just a bookmaker."[35]^: 58 Litif responded that, as Bulger was his friend, he had nothing to worry about. Bulger coldly responded, "We're not friends anymore, Louie."[35]^: 53

At the time, Weeks was about to get married and, shortly before the wedding, informed Bulger that he was having difficulty finding a seat for Litif at the reception. "Don't worry about it", Bulger responded. "He probably won't show."[35]^: 55 "[Louie] had always been a major moneymaker for Jimmy. ... And now he wanted to kill a friend of Jimmy. There was no way that would be allowed. Shortly after that, a week or so before my wedding, Louie was found stuffed into a garbage bag in the trunk of his car, which had been dumped in the South End. He had been stabbed with an ice pick and shot. 'He was color coordinated,' Jimmy told me. 'He was wearing green underwear and was in a green garbage bag.'"[35]^: 59

According to Weeks,

Strangely enough, Jimmy, told me, 'Louie's last words to me were a lie.' Apparently, Louie had insisted that he'd come by himself and that nobody had driven him over. It was hard to figure out why Louie lied to Jimmy that night. If he'd told Jimmy that someone had driven him, he might have gotten a pass. But it wouldn't have lasted long, since Jimmy had no intention of letting Louie run wild.[51]

In 1982, a South Boston cocaine dealer named Edward Brian Halloran, known on the streets as "Balloonhead", approached the FBI and stated that he had witnessed Bulger and Flemmi murdering Litif. Connolly kept Bulger and Flemmi closely briefed on what Halloran was saying, specifically his claims, false according to Weeks, to having participated in the Tulsa, Oklahoma murder of businessman Roger Wheeler.[52]^: 216 Connolly reported that Halloran was shopping this information to the FBI for a chance for him and his family to be placed in the Witness Protection Program.[52]^{: 221–223} Soon after, on May 11, 1982, Bulger, Flemmi, and Weeks were tipped off that Halloran had returned to South Boston. After arriving at the scene, Weeks staked out the Anthony's Pier 4 restaurant, where Halloran was dining. Michael Donahue, a friend of Halloran's from Dorchester, incidentally ran into him at the restaurant. In a decision that would prove costly to him, Donahue offered Halloran a ride home.

As Donahue and Halloran drove out of the parking lot, Weeks signaled Bulger by stating, "The balloon is in the air" over a walkie-talkie. Bulger drove up with another man armed with a silenced MAC-10; Bulger himself carried a .30 Carbine. Bulger and the other gunman, both disguised, 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 Bulger associate James Flynn, who was later tried and acquitted. Flynn remained the prime suspect until 1999, when Weeks agreed to cooperate with investigators and identified Bulger as one of the shooters. Flemmi has identified the second shooter as Patrick Nee, who has denied the allegation and has yet to be charged.

Donahue was survived by his wife and three sons. His family, and Halloran's, eventually filed a civil lawsuit against the U.S. government after learning that Connolly had informed Bulger of Halloran's informant status. Both families were awarded several million dollars in damages. However, the verdict was overturned on appeal due to the late filing of the claims.[53] 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.[54]

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

Most of South Boston's cocaine and marijuana trafficking was under the control of a crew led by mobster John Shea. According to Weeks, Bulger briefly considered killing Shea, but eventually decided to extort a weekly cut of his profits. Weeks also said that Bulger enforced strict rules over the dealers who operated on his territory,[35]^: 156 strictly forbidding the use of PCP and selling drugs to children,[35]^: 179 adding that those dealers who refused to play by his rules were violently driven out of his turf. In 1990, Shea and his associates were arrested at the end of an investigation by the DEA, the Boston Police, and the Massachusetts State Police. He quietly served a long prison sentence and refused to admit to having paid protection money to Bulger, Flemmi and Weeks. He repeatedly got in fights with other inmates who accused Bulger of being "a rat." This earned Shea a legendary reputation in South Boston.[35]^: 167

It would not be until the 1999 cooperation of Weeks that Bulger, by then a fugitive, was conclusively linked to the drug trade by investigators. According to an interview conducted with Globe reporters Kevin Cullen and Shelley Murphy, Weeks "estimated that Whitey made about thirty million dollars... most of it from shaking down drug dealers to let them do business on his turf."[52]^: 194

During the most violent period of The Troubles, sympathy for Irish nationalism and the Provisional Irish Republican Army (IRA) was very common in South Boston, as were efforts to raise money and smuggle weapons for the IRA's campaign against the British presence in Northern Ireland. From the start of his involvement with the FBI, Bulger "insisted ... that he would never give up the IRA". Bulger had previously donated to NORAID and shipped weapons—"guns and a block of C-4 plastic explosives"—in a van to the IRA in the early 1980s. Bulger was annoyed when he learned that the IRA members he supplied had burned the van that contained the weapons. After meeting with IRA Chief of Staff Joe Cahill, Bulger and Nee raised $1 million (equivalent to $2.61 million in 2021) "by shaking down drug dealers in South Boston and Charlestown". This money was used to buy weapons for the IRA which would be shipped across the Atlantic Ocean in the trawler Valhalla. Bulger also personally donated some of his own weapons.

On September 13, 1984, Bulger, Weeks and Nee supervised the loading of Valhalla. The final cache included "91 rifles, 8 submachine guns, 13 shotguns, 51 handguns, 11 bullet-proof vests, 70,000 rounds of ammunition, plus an array of hand grenades and rocket heads".[57] Valhalla rendezvoused 120 nautical miles (220 km; 140 mi) off the west coast of Ireland with the Marita Ann, an IRA ship that had sailed from Tralee. During the return voyage, the Irish Navy stopped Marita Ann and seized the hidden arsenal, arresting IRA members Martin Ferris, Mike Browne, and John Crawley. The operation had been compromised by IRA member Sean O'Callaghan, who was an informant for the Irish National Police.

When Valhalla crew member John McIntyre was arrested "for trying to visit his estranged wife", he confessed his role in the weapons smuggling to the Boston Police. McIntyre implicated Bulger in the botched smuggling to FBI agent Roderick Kennedy, but Kennedy "insisted that [Bulger's handler] Connolly overheard him ... talking about someone on the Valhalla cooperating". Connolly confirmed Bulger's suspicions of McIntyre, leading Bulger and Flemmi to consider murdering McIntyre for his betrayal.[52]^{: 206–268}

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

In the summer of 1991, Bulger and Weeks, along with associates Patrick and Michael Linskey, came into possession of a winning Massachusetts Lottery ticket which had been bought at a store he owned. The four men shared a prize of around US$14 million. Bulger was widely thought to have obtained his share of the jackpot illegitimately.[58]

Photograph taken in 1994 (age 65)

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:[35]^: 215

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.[59]

The first confirmed sighting of Bulger before his capture was in London in 2002.[60] A businessman watching Hannibal recognized a photograph of Bulger in a scene featuring the website of the FBI's most wanted fugitives.[61] 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.[62] In pursuit of Bulger, a known book lover, the FBI visited bookstores in the area, questioned employees and distributed wanted posters.[62][63] 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.[64] 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".[65]

The apartment building in Santa Monica, California, where Bulger lived as a fugitive for at least 15 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. He was 81 years old at the time of the arrest.[66][67][68]

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."[69]

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.[70][71] 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.[72]

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.[73][74] The Boston Globe identified the tipster as Anna Björnsdóttir, a former model, actress, and Miss Iceland 1974, who lived in Bulger's neighborhood.[74][75] 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".[72][76] 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.[72] 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".[72] 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".[77] 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".[77]

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.[78] 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.[8][9][10]

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.[79]

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".[80] 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."[80]

Catherine E. Greig (age 60), Bulger's girlfriend (2011).

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.[81] 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.[81]

At about age 20, Greig married Robert "Bobby" McGonagle, a Boston firefighter.[81] He was from a family that led the Mullen Gang and was injured during a mob gunfight in 1969.[82] 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.[83] 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.[84] 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.[81] Greig has been described as intelligent, hardworking and educated, although was very subservient to, and dominated by, Bulger.[82] She and Bulger lived together for a time at her home in Squantum, a section of Quincy.[85]

Greig had been wanted by the FBI since 1999.[86] The criminal complaint against her alleges that she harbored a fugitive, Whitey Bulger.[87] She was represented in the criminal proceedings by the prominent criminal attorney Kevin Reddington of Brockton, Massachusetts.[88] After being captured alongside Bulger, Greig sought release on bail and home confinement,[89] a request that was denied.

Greig initially indicated that she would go to trial rather than accept a plea bargain.[90] 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.[91]

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.[92] In February 2016, Greig pleaded guilty to this charge.[92] Greig's attorney recommended 12 months in prison, while prosecutors—citing Greig's "unrepentant ... obstruction"—asked for 37 months.[92] 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.[93]

Greig served much of her eight-year sentence at the Federal Correctional Institution, Waseca in Minnesota,[94] but was also detained at various points in Rhode Island ahead of proceedings in the criminal contempt case.[92][94]

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.

According to an excerpt of a book on Bulger published by Boston magazine, Bulger only made one friend during his post-sentencing detention,[95] 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.[95]

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.[95] 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.[95] 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.[95] Bulger, who started his imprisonment with a rigorous exercise regime, was by this point using a wheelchair.

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."[35]^: 207 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."[35]^: 207

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.[31]

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.[35]^{: 205–206} 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."[35]^: 206

• The character of Frank Costello (played by Jack Nicholson) in the 2006 Martin Scorsese film The Departed is loosely based on Bulger,[135] 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.[136]
• 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.[136]
• In season one of the Showtime series Ray Donovan, the character of Patrick "Sully" Sullivan, played by James Woods, is loosely based on Bulger.[136]
• 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.[137][138]
• In season 2 of Starz Original show Ghost, the character of Dante "Mecca" Spears, played by Daniel Sunjata, is loosely based on Bulger.