Whitey Bulger: Air Force Service Member Turned Organized Crime Boss

Photo Credit: 1. U.S. Federal Bureau of Investigation / Wikimedia Commons / Public Domain 2. Federal Bureau of Prisons / Wikimedia Commons / Public Domain

The 1900s was the century of mobsters in America, and few are more well-known than James “Whitey” Bulger. The leader of the notorious Winter Hill Gang spent much of his career on the streets. Prior to his days as a mob leader, however, Bulger spent time in the US Air Force.

Whitey Bulger had a troubled youth

James “Whitey” Bulger was born in Massachusetts in 1929. His father, a union worker and longshoreman, lost his arm in an accident, leading the family into a life of poverty. When the Mary Ellen McCormack Housing Project opened, the Bulgers moved to the hardscrabble area of South Boston.

James 'Whitey' Bulger and mob enforcer Kevin Weeks walking around Castle Island
James “Whitey” Bulger and mob enforcer Kevin Weeks. (Photo Credit: John Tlumacki / The Boston Globe / Getty Images)

Despite their circumstances, Bulger’s brothers, John and William, excelled in school. Unlike them, however, he had a distaste for education. He preferred to spend his time on the streets, running with gangs. Bulger also didn’t like to be referred to as “Jim” or “Jimmy,” but didn’t mind being called “Whitey.” The nickname came about due to his blond hair.

The teenage criminal is given a choice

Whitey Bulger quickly developed a reputation as one of the toughest kids in the area, and was particularly adept at street fighting. He was seen as someone with a bright future in the world of organized crime. Bulger’s first arrest came at the age of 14 for larceny, and soon after he joined the Shamrocks gang.

More arrests followed for forgery, assault and armed robbery.

Street view of Winter Hill, Massachusetts
Winter Hill, where Bulger plied his trade, has become gentrified over the years. (Photo Credit: Keith Bedford / The Boston Globe / Getty Images)

Due to his young age at the time, Whitey was sentenced to a juvenile reformatory. When he turned 18, he was given the option to leave the streets and join the US Air Force. He entered the service in 1948.

Whitey Bulger’s time in the US Air Force did not go well

Some troubled youths who end up in the US military take to the discipline and end up bettering themselves. That is not what happened with Whitey Bulger. Stationed at Smoky Hill Air Force Base, Kansas, he constantly found himself in trouble. Frequent fights led to him being arrested and spending time in the stockade.

In 1950, the Boston youth was arrested for going AWOL. He lasted two more years in the service, before the Air Force gave up on him in 1952 and sent him home to Massachusetts.

Mugshots of Whitey Bulger
Whitey Bulger’s mugshots from his time imprisoned in Alcatraz Federal Penitentiary. (Photo Credit: Donaldson Collection / Michael Ochs Archives / Getty Images)

Back in Boston, Bulger went back to his life of crime. Four years after serving in the military, he was off to federal prison in Atlanta for hijacking a truck, where he claimed to have been a test subject for the CIA’s MK-ULTRA program. Bulger was later transferred to Alcatraz Federal Penitentiary, in California. He was transferred, again, later in his sentence, and released in 1963.

Bulger committed a lot of crimes before returning to prison

Once Whitey Bulger was released from Alcatraz, he made a commitment to never go back. For a number of years, his power continued to grow in the Boston area, and by the mid-1980s, the Winter Hill Gang hit their peak.

The group was involved in loansharking, bookmaking, hijacking and extortion. Bulger was reticent to deal drugs himself, but had no problem shaking down drug dealers. This may have been his most lucrative practice.

Whitey Bulger's mugshot
Whitey Bulger’s mugshot, taken in 2011 after 17 years on the run. (Photo Credit: US Marshals Service / Wikimedia Commons / Public Domain)

Nearly the entire time Bulger was running a gang in Boston, he was cooperating with the FBI. Agent John Connolly flipped the gangster in the 1970s, and the relationship was certainly symbiotic for both men. Connolly became a rising star in the bureau, although he was tried and convicted of corruption in 2002.

In 1994, Connolly tipped Bulger off about an upcoming raid by a joint task force containing members of the Boston Police, the Drug Enforcement Administration (DEA) and the Massachusetts State Police. For nearly two decades, he lived on the run, eventually being arrested in June 2011. The mobster was convicted on 31 counts, and was later murdered in prison in 2018.

Portrayals and legacy

The story of Whitey Bulger is definitely one Hollywood wanted to tell. Martin Scorcese’s The Departed (2006) was adapted from a 2002 Hong Kong film, titled Internal Affairs. Scorcese, however, heavily based his characters on the Winter Hill Gang and Bulger’s relationship with the FBI. The main character, renamed Frank Costello, was played by Jack Nicholson.

Jack Nicholson played Frank Costello, a character based on Whitey Bulger, in the departed
Jack Nicholson as Frank Costello in The Departed, 2006. (Image Credit: Warner Bros. Pictures / MovieStillsDB)

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Another film, 2015’s Black Mass, was directly about Bulger and the Winter Hill Gang. He was portrayed by Johnny Depp, and later spoke out against its release, saying he wouldn’t be watching it.