Whitey Bulger

Prison

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

In 1956, Bulger served his first term in federal prison when he was sentenced to time in Atlanta Penitentiary for armed robbery and truck hijacking. He later told mobster Kevin Weeks^[28] that while there, he was involved in the MK-ULTRA program, the goal of which was to research mind control drugs for the CIA. For 18 months, Bulger and eighteen other inmates, all of whom had volunteered in return for reduced sentences, were given LSD and other drugs.^[28] Bulger later complained that they had been "recruited by deception" and were told they were helping to find "a cure for schizophrenia".^[29] He described his experience as "nightmarish" and said it took him "to the depths of insanity."^[30]

Bulger was transferred from Atlanta to Alcatraz Federal Penitentiary. He became a close friend of fellow inmate Clarence Carnes, a.k.a. "The Choctaw Kid". In November 1962, he was transferred to Leavenworth Federal Penitentiary and, in 1963, to Lewisburg Federal Penitentiary. Bulger's third petition for parole, in 1965, was granted after he had served nine years in prison. He would not be arrested again for 46 years.^[31]

Killeen–Mullen War

After his release, Bulger worked as a janitor and construction worker before becoming a bookmaker and loan shark under Donald Killeen, the leader of the dominant mob, The Killeens, for over 20 years in South Boston. The Killeens were led by three brothers—Donnie, Kenny and Eddie—along with Billy O'Sullivan and Jack Curran. Their base was the Transit Cafe in South Boston, which later became Whitey's Triple O's. In 1971, Killeen's younger brother Kenny allegedly shot Michael (Mickey) Dwyer, a member of the rival Mullen Gang in the arm, and bit off part of his nose during a brawl at the Transit café. A gang war resulted, leading to a string of killings throughout Boston and the surrounding suburbs. The Killeens quickly found themselves outgunned and outmaneuvered by the younger Mullens. It was during the Killeen–Mullen war that Bulger set out to commit what Kevin Weeks describes as his first murder, of Paul McGonagle.^[28]:171

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

According to former Mullen boss Patrick Nee, McGonagle, certain O'Sullivan was responsible, ambushed and murdered O'Sullivan. Bulger, realizing he was on the losing side, secretly approached Howie Winter, leader of the Winter Hill Gang, and claimed he could end the war by murdering the leaders of the Killeen gang. Shortly thereafter, on May 13, 1972, Donald Killeen was gunned down outside his home in the suburb of Framingham.^[24] Nee disputes this, claiming that Killeen was murdered by Mullen Gang enforcers James Mantville and Tommy King, not Bulger.^{[32]:123–125}

Bulger and the Killeens fled the city, fearing they would be next. Nee arranged for the dispute to be mediated by Winter and Patriarca crime family caporegime Joseph Russo. In a sit-down at Chandler's nightclub in the South End, the Mullens were represented by Nee and King, and the Killeens by Bulger. The two gangs joined forces, with Winter as overall boss.^{[32]:127–134} (Nee's recounting is contradicted by Winter. "I never knew [Bulger] before that. He knew I was friendly with the Mullens gang. He asked if I would intercede. I said, 'Are you serious about this? I don't want to intercede if you're not going to abide by it.' He said he would."^[33]:90) "Nobody talked fault.... Deep down, Whitey knew that he couldn't take over for the Killeens without cutting the Mullens in on their bookmaking and loansharking. ...The meeting lasted for six hours. ... It was business...."^{[32]:131–132} "The balance of the meeting was spent forming an alliance.... Everything was split down the middle. All the horses, dogs, bookmaking, and loansharking were now going to be under our mutual control. This was the beginning of our relationship. Whitey and I were now officially partners...."^[32]:132

Soon after, Donald Killeen's sole surviving brother, Kenneth Killeen, was jogging in the City Point neighborhood of Boston.^[34]:30 Bulger's voice called him over to a car and said, "It's over. You're out of business. No more warnings." Kenneth would later testify at the trial of disgraced FBI agent John Connolly that Winter Hill enforcers Stephen Flemmi and John Martorano were in the car with Bulger.

Winter Hill Gang

Stephen Flemmi.

After the 1972 truce, Bulger and the Mullens were in control of South Boston's criminal underworld. FBI Special Agent Condon noted in his log in September 1973 that Bulger and Nee had been heavily shaking down the neighborhood's bookmakers and loan sharks. Over the years that followed, Bulger began to remove opposition by persuading Winter to sanction the killings of those who "stepped out of line". In a 2004 interview, Winter recalled that the highly intelligent Bulger "could teach the devil tricks".^[35] During this era, Bulger's victims included Mullen Gang veterans McGonagle, King, and Spike O'Toole.^[36]

According to Kevin Weeks:

"As a criminal, he made a point of only preying upon criminals…. And when things couldn't be worked out to his satisfaction with these people, after all the other options had been explored, he wouldn't hesitate to use violence. … Tommy King, in 1975, was one example. … Tommy's problems began when he and Jimmy had worked in Triple O's [a bar in south Boston]. Tommy, who was a Mullins, made a fist. And Jimmy saw it. … A week later, Tommy was dead. Tommy's second and last mistake had been getting into the car with Jimmy, Stevie, and Johnny Martorano. … Later that same night, Jimmy killed Buddy Leonard and left him in Tommy's car on Pilsudski Way in the Old Colony projects to confuse the authorities."^[28]: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 vacuum and took over the leadership of the gang. They transferred its headquarters to the Lancaster Street Garage in Boston near the Boston Garden in the West End.^[24]

Consolidating power

Federal Bureau of Investigation surveillance photograph of Bulger (right; age 51) with enforcer Stephen Flemmi (left) c. 1980.

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.^[34]: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.^[24]

The murder of Louie Litif

In 1980, Bulger was approached in South Boston's Triple O's saloon by Louis Litif, a neighborhood bookmaker. Weeks, a bouncer at the establishment, said, "He wasn't a big guy, maybe five seven and 185 pounds. Of Arab descent, he had a mustache like Saddam Hussein. … That night, as always, he was talking in his obnoxious loud voice. Even when there were 400 people in the bar, you always knew Louie was there."^[28]:57

Litif had been stealing from his partners in the bookmaking operation and using the money to traffic cocaine, and had not only refused to pay Bulger a cut of his drug profits, but committed two murders without Bulger's permission.^[28]:57–59 Litif told an outraged Bulger he was also going to kill his partner, "Joe the Barber", whom he accused of stealing money from the bookmaking operation. Bulger refused to sanction this, but Litif vowed to proceed. Bulger replied, "You've stepped over the line. You're no longer just a bookmaker."^[28]:58 Litif responded that, as Bulger was his friend, he had nothing to worry about. Bulger coldly responded, "We're not friends anymore, Louie."^[28]: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."^[28]: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.'"^[28]:59

According to Kevin Weeks,

Strangley enough, Jimmy, told me, 'Louie's last words to me were a lie.' Apparently, Louie had insisted that he'd come by himself and that nobody had driven him over. It was hard to figure out why Louie lied to Jimmy that night. If he'd told Jimmy that someone had driven him, he might have gotten a pass. But it wouldn't have lasted long, since Jimmy had no intention of letting Louie run wild.^[38]

Halloran and Donahue murders

In 1982, a South Boston cocaine dealer named Edward Brian Halloran, known on the streets as "Balloonhead", approached the FBI and stated that he had witnessed Bulger and Flemmi murdering Litif. Meanwhile, Connolly kept Bulger and Flemmi closely briefed on what Halloran was saying to the FBI, specifically his knowledge of their participation, along with their youngest associate James "Gentleman Jim" Mulvey in the murder of Tulsa, Oklahoma businessman Roger Wheeler.^[33]: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.^{[33]: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 Anthony's Pier 4 Restaurant, where Halloran was dining. Michael Donahue, a friend of Halloran's from Dorchester, incidentally ran into him at the restaurant. In a decision that would prove costly to him, Donahue offered Halloran a ride home.

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

Donahue was survived by his wife and three sons. His family, and Halloran's, eventually filed a civil lawsuit against the US government after learning that Connolly had informed Bulger of Halloran's informant status. Both families were awarded several million dollars in damages. However, the verdict was overturned on appeal, due to the late filing of the claims.^[39] 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.^[40]

Extortion of drug dealers

During the mid-1980s Bulger began to summon drug dealers from in and around Boston to his headquarters. Flanked by Kevin Weeks and Stephen Flemmi, Bulger would inform each dealer that he had been offered a substantial sum in return for that dealer's assassination. He would then demand a large cash payment as the price of not killing them. Eventually, however, the massive profits of drugs proved irresistible. According to Weeks:^[28]:152

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

In South Boston most of the neighborhood's cocaine and marijuana trafficking was under the control of a crew led by mobster John Shea, known as "Red". According to Weeks, Bulger briefly considered whacking Shea, but eventually decided to just extort a weekly cut of his profits. Weeks also states that Bulger enforced strict rules over the dealers who operated on his home turf:^[28]:156

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

Weeks also states that Bulger strictly forbade Angel Dust and selling drugs to children,^[28]:179 and that those dealers who refused to play by his rules were violently driven from "The Town."

In 1990 "Red" Shea and his associates were arrested at the end of an investigation by the Drug Enforcement Administration (DEA), the Boston Police Department and the Massachusetts State Police. Shea quietly served a very long prison sentence and refused to admit to having paid protection money to Bulger, Flemmi and Weeks. He repeatedly got in fights with other inmates who accused Bulger of being "a rat." This earned Shea a legendary reputation in South Boston.

According to Weeks:^[28]:167

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

It would not be until the 1999 cooperation of Weeks that Bulger, by then a fugitive, was conclusively linked to the drug trade by investigators. According to an interview conducted with Boston Globe reporters Kevin Cullen and Shelley Murphy, Kevin Weeks "estimated that Whitey made about thirty million dollars... most of it from shaking down drug dealers to let them do business on his turf."^[33]:194

Arms trafficking

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

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

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

When Valhalla crew member John McIntyre was arrested "for trying to visit his estranged wife", he confessed his role in the weapons smuggling to Boston police. McIntyre implicated Bulger in the botched smuggling to FBI agent Roderick Kennedy, but Kennedy "insisted that [Bulger's handler] John Connolly overheard him ... talking about someone on the Valhalla cooperating." Connolly confirmed Bulger's suspicions of McIntyre, leading Bulger—and cohort Steve Flemmi—to murder McIntyre for his betrayal."^{[33]:206–268}

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

Massachusetts state lottery

In the summer of 1991 Bulger and Kevin Weeks, along with associates Patrick and Michael Linskey, came into possession of the winning Massachusetts Lottery ticket, which had been bought at a store he owned. The four men shared a prize of around US$14 million. Bulger was widely thought to have obtained his share of the jackpot illegitimately.^[43]

Downfall

Photographed in 1994 (age 65).

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

According to Kevin Weeks:^[28]: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.

He had also set up safe deposit boxes, containing cash, jewelry and passports, in locations across North America and Europe, including Florida, Oklahoma, Montreal, Dublin, London, Birmingham and Venice. In December 1994 he was informed by retired FBI Agent John Connolly that sealed indictments had come from the Department of Justice and that the FBI was set to make arrests during the Christmas season. In response, Bulger fled Boston on December 23, 1994, accompanied by his common-law wife Theresa Stanley.^[44]

Manhunt

The first confirmed sighting of Bulger before his capture was in London in 2002.^[45] However, there were unconfirmed sightings elsewhere. FBI agents were sent to Uruguay to investigate a lead. Other agents were sent to stake out the 60th memorial of the Battle of Normandy celebrations, as Bulger is reportedly an enthusiastic fan of military history. Later reports of a sighting in Italy in April 2007 proved false. Two persons on video footage shot in Taormina, Sicily, formerly thought to be Bulger and his lover Catherine Greig walking in the streets of the city center, were finally identified as a tourist couple from Germany.

In 2010 the FBI turned its focus to Victoria, British Columbia, on Vancouver Island.^[46] In pursuit of Bulger, a known book lover, the FBI visited bookstores in the area, questioned employees and distributed wanted posters.^[46][47] 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.^[48] 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".^[49]

Capture

The apartment building in Santa Monica, California, where Bulger lived as a fugitive for at least 15 years

After 16 years at large and 12 years on the FBI Ten Most Wanted Fugitives list, Bulger was arrested in Santa Monica, California, on June 22, 2011. He was 81 years old at the time of the arrest.^[50][51][52]

He was captured as a result of the work of the Bulger Fugitive Task Force, which consisted of FBI agents and a Deputy US Marshal. According to retired FBI agent Scott Bakken, "Here you have somebody who is far more sophisticated than some 18-year-old who killed someone in a drive-by. To be a successful fugitive you have to cut all contacts from your previous life. He had the means and kept a low profile."^[53]

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.^[54][55] Bulger has been featured on the television show America's Most Wanted 16 times, first in 1995, and finally on October 2, 2010. According to authorities, the arrests were a "direct result" of the media campaign launched by the FBI in 14 markets across the country where Bulger and Greig reportedly had ties. The campaign focused on Greig, describing her as an animal lover who frequently went to beauty salons.^[56]

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.^[57][58] The Boston Globe identified the tipster as Anna Björnsdóttir, a former model, actress, and Miss Iceland 1974, who lived in Bulger's neighborhood.^[58][59] 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".^{[56] [60]} 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.^[56] 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".^[56] 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".^[61]

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.^[62] He also visited Alcatraz prison and had a souvenir photograph taken, wearing a striped suit and standing behind mock prison bars.^[63] 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.^[9][10][11]

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.^[64]

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".^[65] 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."^[65]

Catherine Greig

Catherine E. Greig, Bulger's girlfriend

Bulger's companion during his years as a fugitive was his longtime girlfriend Catherine Greig [born (1951-04-03) April 3, 1951], who is almost 22 years younger than Bulger.^[66] Greig grew up in Boston and had an identical twin sister, Margaret,^[66] and a younger brother, David. Their father was a machinist from Glasgow, Scotland, and their mother was from Canada.^[66]

At about age 20, Greig married Robert "Bobby" McGonagle of South Boston, a Boston firefighter.^[66] He was from a family that led the Mullen Gang and was injured during a mob gunfight in 1969.^[67] 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.^[68] The body of Paul McGonagle lay hidden and buried for 25 years on Tenean Beach in Dorchester.^[69] Greig's twin sister Margaret is the widow of Paul McGonagle. Greig's younger brother David Greig was a close associate of Bulger. David was found shot dead on Cape Cod, a death characterized as a suicide.

Greig met Bulger in her late 20s, after she divorced Bobby McGonagle. She worked as a dental hygienist.^[66] Greig has been described as intelligent, hardworking and educated, although very subservient to, and dominated by, Bulger.^[67] She and Bulger lived together for a time at her home in Squantum, a section of Quincy, Massachusetts.^[70] While on the run, Greig confided to a neighbor that she feared that Bulger was suffering from senile dementia.^[71]

Greig had been wanted by the FBI since 1999.^[72] The criminal complaint against her alleges that she harbored a fugitive, Whitey Bulger.^[73] She was represented in the criminal proceedings by the prominent criminal attorney Kevin Reddington of Brockton, Massachusetts.^[74] After being captured alongside Bulger, Greig sought release on bail and home confinement, a request that was denied.^[75]

Greig initially indicated that she would go to trial rather than accept a plea bargain.^[76] 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.^[77]

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.^[78] In February 2016, Greig pleaded guilty to this charge.^[78] Greig's attorney recommended 12 months in prison, while prosecutors—citing Greig's "unrepentant ... obstruction"—asked for 37 months.^[78] 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.^[79]

Greig has served much of her eight-year sentence at the Federal Correctional Institution, Waseca in Minnesota,^[80] but has also been detained at various points in Rhode Island ahead of proceedings in the criminal contempt case.^[78][80]

Paul Corsetti

According to Weeks' memoirs, in 1980 Boston Herald reporter Paul Corsetti began researching an article about Louis Litif's murder and Bulger's suspected involvement. After reporting the story for several days, Corsetti was approached by a man who said, "I'm Jim Bulger and if you continue to write shit about me, I'm going to blow your fucking head off."^[28]: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."^[28]:207

Howie Carr

In his memoirs, Kevin Weeks related his participation in an attempt to assassinate reporter Howie Carr at his house in suburban Acton. Weeks states that Carr was targeted because he was "writing nasty stories about people, he was an oxygen thief who didn't deserve to breathe." Carr has been among the most aggressive critics of the Bulger brothers, Whitey and Billy, for their careers in the Boston area; among his works is the book The Brothers Bulger, detailing the Bulger brothers' 25-year period of controlling Boston politics and the Boston underworld.^[24]

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.^{[28]:205–206} In his 2006 memoirs Weeks has stated that, although he is fully aware of the public outcry that would have followed, he regrets not murdering Carr. "His murder would have been an attack on the system, like attacking freedom of the press, the fabric of the American way of life, and they would have spared no expense to solve the crime. But in the long run, Jimmy and I got sidetracked and the maggot lived. Still, I wish I'd killed him. No question about it."^[28]:206

Characters based on Whitey Bulger

In Season 11 Episode 21 of the television series Law & Order entitled "Brother's Keeper," certain plot details are inspired by Bulger's criminal career. Specifically, an Irish-heritage criminal having a secret working relationship with the FBI via a childhood friend in the agency.^[101]

The character of Frank Costello (played by Jack Nicholson) in the 2006 Martin Scorsese film The Departed is loosely based on Bulger,^[102] 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.^[103]

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.^[103]

In season one of the Showtime series Ray Donovan, the character of Patrick "Sully" Sullivan, played by James Woods, is loosely based on Bulger.^[103]

The 2013 television drama The Blacklist starring James Spader about a career criminal who turns himself in to work with the FBI on his own terms was inspired by Bulger's story.^[104][105]