From 'Black Mass' to 'The Departed': How Whitey Bulger Inspired Movie and TV Mob Bosses

Notorious Boston kingpin James “Whitey” Bulger’s reign over the city’s criminal underworld has proven one few gangsters could emulate in real life. But in Hollywood, the high-profile, Irish American mob boss has served as a blueprint for loathsome and complex characters in several blockbuster movies and television story lines. The late Bulger’s astonishing double life as an infamous, ruthless gang leader who simultaneously served as a top-level FBI informant is considered by some to be cinema gold.

“I have to imagine that there are many actors, writers and producers that look to him as a really archetypal way to look at mob bosses,” Claire White, historian and senior director of education at The Mob Museum in Las Vegas, tells A&E Crime + Investigation. “What sets him apart from some of the other guys is he displayed and acted upon a level of violence so late into his life and so far up the ranks that it definitely is an inspiration whenever we're looking at antisocial or even sociopathic criminal characters in movies and TV.”

Born in 1929, Bulger had a rough upbringing, growing up in the housing projects of South Boston with his five siblings. As a boy, he ran with the local Shamrocks gang and by age 14, he was arrested on a larceny charge. From then on, he regularly had run-ins with the law, and police officers soon became familiar with the young criminal.

Despite joining the U.S. Air Force in 1948, Bulger couldn’t stay out of trouble, and four years later, he was honorably discharged. As soon as he returned to his old Boston stomping grounds, Bulger fell back into a life of crime.

From 1956 to 1965, he served time in federal prison for armed robbery, only to land back in his Southie neighborhood upon release. He became grossly enmeshed in the Irish American Winter Hill Gang, where he operated as a bookmaker, loan shark and enforcer, until he eventually climbed the ranks to ringleader.

In 1974—in a shocking yet calculated move—Bulger agreed to become an FBI informant for childhood friend-turned-FBI agent John Connolly. The relationship quickly grew corrupt.

“Bulger saw this as an opportunity to consolidate power for himself,” White says. “This was really a double cross for him. He saw it as a way to continue his operations with a little extra information about what law enforcement was looking into in Boston. It gave him intel against his enemies, specifically the Italian American mafia group in Boston and the rest of New England. But ultimately, he had intel on all of his enemies.”

While the FBI was focused on bringing down Boston’s Italian mafia, Bulger took advantage of the dangerous yet unusual situation to expand his criminal enterprise.

“The FBI was really turning a blind eye to the activities that he was still participating in and in activities that he was growing—in a way that the FBI normally would expect an informant to kind of stay business as usual, rather than continue to become a larger and larger presence in a city's underworld,” White explains.

His unconventional alliance with Connolly, and the realm in which he was permitted to operate as a murderous, criminal overlord who seemingly knew no bounds, served as inspiration for the character of Frank Costello in the 2006 thriller The Departed starring Jack Nicholson. The veteran actor’s portrayal of a merciless, clever mob boss was crucial in the film securing its win for Best Picture at the 2007 Academy Awards, as well as a directing win for Martin Scorsese.

“While he had smarts, he also was ready to cut your throat,” University of Nevada, Las Vegas history professor Michael Greene tells A&E Crime + Investigation. “And those are not necessarily that far apart, but it does mean that you have a degree of intelligence to play with. He is not simply a thug, and that makes for a far more interesting character.”

In the 2015 biographical crime drama Black Mass, Johnny Depp showed audiences Bulger’s compassionate side for a moment as a grieving father dealing with the death of his 6-year-old son. The loss seemingly only amplified his criminalistic actions.

“There's a degree of humanity,” Greene admits. “Then, of course, there's the inhumanity that enables you to do the things Bulger did, and it makes him all the more fascinating because he’s tragic.”

Black Mass additionally highlights the complicated relationship between Bulger and his brother Billy, president of the Massachusetts Senate, played by Benedict Cumberbatch. The TV series Brotherhood starring Jason Clarke and Jason Issacs also pulled inspiration from how the Bulger brothers navigated their rapport while serving as a government official and top criminal.

Beginning in 1994, Bulger lived life on the run after Connolly tipped him off about an upcoming racketeering indictment against him. For 16 years, Bulger spent time at the top of the FBI’s Most Wanted List. But that all came crashing in 2011 when a tip from a neighbor led to his capture in Santa Monica, Calif., where he had settled down with his girlfriend.

His capture and time as an FBI informant inspired drama series The Blacklist, in which James Spader played a former U.S. Naval Intelligence officer who went on the run after landing on the FBI's 10 Most Wanted Fugitives list. James Woods’s Ray Donovan character, a Boston crime boss who goes into hiding after his partner rats him out, also boasts a likeness to Bulger.

The real-life ruthless and manipulative criminal mastermind would go on to be convicted of 31 felonies, including 11 counts of murder, following a two-month trial in 2013. A judge punished him with two life sentences.

In 2018, Bulger was bludgeoned to death by former Mafia hitman, Fotios Geas, at a federal penitentiary in West Virginia.

“His remains were wholly unrecognizable,” White says. “It was an absolutely horrific death. Regardless of the fact that he was a violent criminal who certainly deserved to be serving the amount of time that he was serving, he was also an 89-year-old man in a wheelchair.”

Still, Bulger’s notoriety lives on in the many on-screen portrayals he’s already inspired, and will no doubt continue to influence.