Whitey Bulger’s brutal murder at the hands of fellow prisoners proved a very important point that applies to most gangsters sooner or later: no matter how hard or fast you run, sooner or later fate catches up with you. As an enforcer and later head of Boston’s Winter Hill organized crime syndicate, Bulger career was characterized by cold, calculated brutality; he was also one of the canniest gangsters in organized crime history, avoiding major prosecutions due to relationships he cultivated with corrupt law enforcement agents, then laying low as a fugitive for over sixteen years.
Despite Bulger’s gruesome end, for years it seemed like Bulger might never be punished for any of his crimes and that his luck would never run out.
Early Years: A Bad Seed from the Start
James “Whitey” Bulger was born in a poor South Boston neighborhood in 1929, the second
of six children. Bulger’s father lost his arm in an industrial accident, and had trouble making ends meet after that. The young Bulger, nicknamed Whitey due to his light blond hair, was often in trouble with the law. He was arrested for the first tie when he was only thirteen, for delinquency. Many of his siblings, however, excelled in school and public life; his brother, William, became the President of the Massachusetts State Senate and later the President of the University of Massachusetts.
Bulger quickly developed a reputation for himself in the streets. He was an accomplished thief, forger and hired muscle for people that needed it. For a time, he also ran with a local Boston street gang, the Shamrocks. Small time gangsters and other criminals took note of the younger Bulger, noting his toughness as well as his competence. After a brief and unremarkable stint in the Air Force. Whitey soon returned to his criminal ways in the streets of Boston. Arrested after a series of armed robberies, Bulger convicted and spent nine years in prison.
Rising to the Top
After his release from prison, Whitey Bulger again returned to his criminal ways. He became involved with the Killeen brothers, south Boston gangsters who ran loansharking and other rackets. Shortly after joining their ranks, the Killeens became involved in a brutal gang war with Boston rivals the Mullens. Bulger killed one of the Mullen gang’s leaders in cold blood, intensifying the feud. Later, sensing that the Killeens were losing the war, the ambitious Bulger saw an opening. He approached another mob leader, Howie Winter, and offered to end the costly fighting between the Killeens and Mullens. Then, with Winter’s blessing, he allegedly killed Donald Killeen, and the Mullen-Killeen feud ended shortly afterwards. Howie Winter’s gang emerged as the most powerful criminal network in Boston, and Bulger became a key player within it.
Whitey was the Winter Hill gang’s brutal enforcer. He forced subordinates – the loan sharks, grifters and other criminals in the gang – to toe the line, or else. Gangsters that got greedy, or otherwise started to show disrespect were dealt with harshly. One or more Winter Hill gangsters and associates disappeared, or were killed outright, after Whitey Bulger lost confidence in their abilities. Bulger’s willingness to take an icepick to a rival or shoot another gangster right between the eyes became the stuff of Boston legend.
Law enforcement organizations also took a strong interest in the Winter Hill Gang’s criminal activities. In the early 1970s, the Federal Bureau of Investigation allegedly made Bulger an informant. However, Bulger was able to leverage his relationship with the FBI to his advantage. Two of the FBI agents involved in his case ultimately became corrupted after years of working with Bulger, at times protecting his criminal interests and fending off criminal prosecutions. After Howie Winter’s arrest and conviction in 1979, Bulger stepped up to become the leader of the Winter Hill gang.
The Kingpin of South Boston
Bulger did not temper his brutal methods after he took charge of the Winter Hill Gang. He continued to personally murder or sanction the deaths of criminals who disobeyed or disrespected him. He took control of the burgeoning Boston drug trade, shaking down drug dealers and forcing them to pay him a cut to operate on his streets. He also expanded the Winter Hill Gang’s loansharking and arms dealing operations, even dealing weapons to the IRA.
Despite a wide range of criminal activity, Bulger avoided criminal prosecution for over a decade. Corrupt FBI and police officials often alerted him to danger; in one case, information one FBI agent provided Bulger led to the murder of a potential witness against him. Bulger’s reputation in Boston, where many revered him as a sort of Robin Hood, no doubt helped keep him one step ahead of the law as well.
In the the mid-1990s, a series of indictments were prepared against Bulger based on several lower ranking mobsters whom the Drug Enforcement Agency had turned. Tipped off by corrupt law enforcement officials that he was about to be arrested, Bulger fled Boston. He would spend the next sixteen years of his life as a fugitive from the law, much of it as number two on the FBI’s most wanted list.
Fugitive, Capture, and Death
Bulger spent much of his nearly two decades on the run hiding in plain sight. He would
travel overseas at times, allegedly visiting Europe and Canada, and take forays into Mexico to buy prescription medication for his heart condition. However, after an anonymous tip, Bulger’s good luck finally ran out. Authorities arrested Bulger and his longtime girlfriend, Catherine Greig, at an apartment they shared in Santa Monica California. The FBI’s number two most wanted fugitive was now in custody.
While awaiting trial, there was much speculation about what Bulger would tell authorities about corrupt law enforcement officials and politicians. However, after a lengthy trial, Bulger was found guilty of multiple counts of racketeering charges and sentenced to two life terms plus five years. He was indicted for other crimes in Florida and Oklahoma and could have faced the death penalty if convicted of those crimes. However, he never made it to trial.
On October 30th, 2018, Whitey Bulger was murdered shortly after his transfer to a prison in West Virginia. While the murder remains under investigation, inmates with mafia ties are alleged to have carried out the crime, and many suspect it was a revenge hit for Bulger’s alleged role as an FBI informant. The wheelchair-bound Bulger was 89 at the time of his death.
Parting Thoughts: Nothing Lasts Forever
Whitey Bulger terrorized the streets of South Boston for decades; he was also a source of perverse pride for down-on-their-luck Southies throughout his career as well, who romanticized his role as the head of the Boston mob. He was a brutal criminal with enough smarts to stay out of reach of the law until he was well into his mid-seventies. However, Whitey’s luck eventually ran out, and his life was snuffed out with the same brutal violence that so many of his victims has suffered in the back alleys of South Boston.