Whitey Bulger

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Whitey Bulger
Whitey Bulger US Marshals Service Mug1.jpg
Full Name: James Joseph "Whitey" Bulger Jr.
Alias: Jimmy
Origin: Boston, Massachusettes, United States
Occupation: Mafia kingpin
Leader of the Winter Hill Gang
Goals: Continue with his criminal activities
Extrude power over South Boston
Crimes: Arms trafficking
Conspiracy to commit extortion
Conspiracy to commit money laundering
Conspiracy to commit murder
Narcotics distribution
Type of Villain: Gangster

There are lessons again and again throughout your whole life. You gotta learn from these things.
~ Whitey Bulger

James Joseph "Whitey" Bulger (September 3rd, 1929 - October 30th, 2018) was probably the most infamous Irish-American mob boss in American history and at one point, second on the FBI's Most Wanted List behind Osama bin Laden. He took over the Winter Hill gang in South Boston, Massachusetts after being released from Alcatraz prison in the 1960s. During his prison sentence in the 1950s and 60s, he was subject to LSD experiments by the CIA to test mind control, giving him night terrors for the rest of his life. He was convicted on 19 counts of murder. His criminal history was the subject of the 2015 film Black Mass in which he was portrayed by veteran actor Johnny Depp.


James Bulger's father, James Joseph Bulger Sr., was from Harbour Grace, Newfoundland, Canada. After settling in Everett, Massachusetts, James Sr. married Jane Veronica "Jean" McCarthy, a first-generation Irish immigrant. Their first child, James Joseph Bulger, Jr., was born in 1929.

Bulger's father worked as a union laborer and occasional longshoreman; he lost his arm in an industrial accident and the family was reduced to poverty. In May 1938, the Mary Ellen McCormack Housing Project was opened in the neighborhood of South Boston. The Bulger family moved in and the children grew up there. The other Bulger children, William Michael and John P. Bulger, excelled at school; James Bulger Jr. became drawn into street life.

Early in his criminal career, local police gave Bulger the nickname "Whitey" because of his blond hair. Bulger hated the name; he preferred to be called "Jim", "Jimmy", or even "Boots". The last nickname came from his habit of wearing cowboy boots, which he used to hide a switchblade. However, the nickname "Whitey" stuck.

Bulger developed a reputation as a thief and street fighter fiercely loyal to South Boston. This led to his meeting more experienced criminals and finding more lucrative opportunities. In 1943, 14-year-old Bulger was arrested and charged with larceny. By then he had joined a street gang known as the "Shamrocks" and would eventually be arrested for assault, forgery and armed robbery. Bulger was sentenced to a juvenile reformatory for these crimes.

Shortly after his release in April 1948, Bulger joined the United States Air Force, but he had not reformed. He spent time in the military prison for several assaults and was later arrested by Air Force police in 1950 for going absent without leave. Nevertheless, he received an honorable discharge in 1952 and returned to Massachusetts.

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.

Unlike most mobsters, Bulger was an informant to the FBI, an act despised by many mobsters. Corrupt agent John Connolly, also an Irish American, constantly tipped Bulger off about police and FBI bugs, wiretaps and other important information. His younger brother William "Billy" Bulger was also President of the Massachusetts State Senate until he was dismissed due to his connections. Throughout the 1970s and 1980s, Bulger and his associates operated rackets throughout eastern Massachusetts including extortion, loansharking, bookmaking, truck hijackings and arms trafficking. He killed anyone who ran afoul of him, including Louis Litif, a Lebanese-American bookmaker who didn’t seek Bulger’s approval and would also kill associates of fellow mobsters or their enemies (i.e their spouses). Bulger used a variety of methods to kill his victims, including running them over, stabbing them with an ice pick, strangling them, as well as shooting. Bulger and the gang would often lure victims into the basement, in which he would surprise the victim and tie them to a chair. He would often order his associates to bury their victims under the floorboards. Various associates would describe killing as Bulger's "stress relief". At one point, he called a victim's family claiming he was Santa Claus and that their father, whom he murdered, "wouldn't be coming home for Christmas". State and federal agencies were repeatedly stymied in their attempts to build cases against Bulger and his inner circle. This was caused by several factors. Among them was Bulger's fear of wiretaps and policy of never discussing business over the telephone or in the car. Other reasons were South Boston's code of silence, and corruption within the Boston Police Department, the Massachusetts State Police, and the FBI. Although Connolly was Bulger's most infamous source inside law enforcement, his associate Kevin Weeks has stated that Massachusetts State Police Lt. Richard J. Schneiderhan, the crew's only source inside that agency, was valued more highly.

Bulger sold weapons to the Irish Republican Army during the Troubles in Northern Ireland, as he was sympathetic to their cause.

Tipped one last time in 1995, Bulger went into hiding with his girlfriend Catherine Grieg. Ashamed and embarrassed for covering him in the past, the FBI added him to the Top Ten Most Wanted. He spent 16 years on the run until he was caught in Southern California in 2011. It was believed that an Icelandic beauty pageant queen who was once neighbors with the couple tipped them off. They used the aliases Charlie and Carol Gasko and were known as an elderly couple with many cats. He was convicted of 19 count so of murder in 2013 and sentenced to life in prison.

Just hours after he was transferred to FCI Hazleton in West Virginia, the wheelchair-bound Bulger was beaten to his death on October 30, 2018. He was 89 years old. He had been beaten to death by multiple inmates, including gangster Freddy Geas, armed with a sock-wrapped padlock and a shiv. His eyes had nearly been gouged out and his tongue almost cut off. They wheeled him to an area of the prison where cameras weren't present. Geas had reportedly been angry at Bulger for ordering the killings of women and children (which are seen as off-limits) as well as being an informant to the FBI (known as snitching or ratting out, considered one of the most hated things a mobster can do). 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. He was buried with his parents. His family later sued the Bureau of Prisons over his death, claiming that they deliberately transferred him to die.


  • One of the witnesses who testified against him has said that they regret convicting him had they known of his night terrors.