Whitey Bulger: How a notorious Boston gangster left his mark on popular culture

Whitey Bulger‘s life of crime has served as a constant source of inspiration in the world of entertainment, to the extent that the Irish-American gangster has become an archetype in his own right.

For years, writers have been telling the infamous Boston gang leader’s story, either directly, as was the case in a 2015 biopic starring Johnny Depp, or indirectly, by crafting TV series characters whose backgrounds borrow elements of Bulger’s biography.

James Joseph “Whitey” Bulger Jr died on Tuesday aged 89 in prison, where he was serving a life sentence following his 2013 conviction for a slew of crimes, including his participation in 11 murders. The gangster had just been moved to a new facility in West Virginia.

Bulger, who was arrested in 2011 in Santa Monica, California, was previously one of the FBI’s most-wanted fugitives over the course of 16 years. He became an FBI informant in 1975 and later embarrassed the agency by corrupting several of its agents – a story told in the biographical crime drama Black Mass, which stars Depp as the gangster.

The movie is based on the 2000 book Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal, written by journalists Dick Lehr and Gerard O’Neill. Both men also wrote a 2013 sequel titled Whitey: The Life of America’s Most Notorious Mob Boss.

In Black Mass, Depp is seen as the leader of Boston’s Winter Hill Gang back in 1975. After the death of his son Douglas due to Reye Syndrome, Depp’s Bulger goes on to work as an FBI informant. He quickly begins to use this new status to his advantage, manipulating the relationship to better assert his power of the Boston gang scene.

The movie also stars Benedict Cumberbatch as William Bulger, the gangster’s brother who served as the president of the Massachusetts senate for 18 years and that of the University of Massachusetts – a position he resigned from in 2003 over his ties and loyalty to his sibling.

Bulger was not impressed at the prospect of having Depp play him on the big screen according to his defence lawyer Hank Brennan. “Johnny Depp might as well have been playing the Mad Hatter all over again as far as James Bulger is concerned,” Brennan told People in 2015. “Hollywood greed is behind the rush to portray my client, and the movie missed the real scourge created in my client’s case, the real menace to Boston during that time and in other mob cases around the country - the federal government’s complicity in each and every one of those murders with the top echelon informant program.”

Nine years before Black Mass and while Bulger was still a fugitive, the gangster served as an inspiration for the character of Irish-American mobster Frank Costello in Martin Scorsese‘s The Departed, with Jack Nicholson starring as Costello. Scorsese has credited writer Bill Monahan with thinking of Bulger – also an Irish-American crime boss – when crafting the character of Costello. The Departed went on to win four Academy Awards in 2007, including Best Picture.

“Once we began to read the books on these people and the situation in Boston at that time, nothing we did in the film was, in a sense, exaggerated in any way,” Scorsese is quoted as saying in the interview anthology Directors Close Up 2: Interviews with Directors Nominated for Best Film by the Directors Guild of America: 2006 – 2012. “In fact, it was less.”

On the small screen as well, Bulger left his mark, serving as the inspiration behind several Irish-heritage criminals in various TV series.

Law & Order‘s 11th season includes an episode featuring an Irish criminal who is suspected of murder but is provided with an alibi by the FBI – a plot line that closely echoes Bulger’s own involvement with the agency. The episode aired in 2001, while Bulger was still a fugitive.

The gangster’s life and his relationship with his brother provided the premise for the Showtime TV series Brotherhood, which followed the lives of lifelong gangster Michael Caffee (Jason Isaacs) and his sibling Tommy Caffee (Jason Clarke), a local politician. Brotherhood aired between 2006 and 2008, during Bulger’s run from the law, and earned a Peabody Award in 2006.

Rizzoli & Isles features a character with a similar backstory to Bulger’s: Paddy Doyle, the biological father of Sasha Alexander’s Maura Isles, is an Irish-American mob boss from South Boston.

Bulger’s capture has also given grist to the pop culture mill. NBC’s The Blacklist, which premiered in 2013, tells the story of a Raymond “Red” Reddington, a former US Navy officer turned criminal. Reddington turns himself in to the FBI after spending decades on the run.

Producers explained in 2013 at Comic-Con International that they had been inspired to create the show around the time of Bulger’s capture, The Hollywood Reporter wrote at the time. The news of Bulger’s arrest prompted them to wonder what would happen if a longtime criminal started cooperating with the authorities. They have explored the idea for five seasons so far, with a sixth one currently in the making.