He was a major inspiration for the lead character in a dark, violent, Oscar-winning movie, but he was brought down by ads on daytime television.
For Boston mobster James "Whitey" Bulger, who was arrested on Wednesday in Santa Monica at the age of 81, the Hollywood connection was a strange one.
Details of his reign as the head of the Winter Hill Gang made it into Martin Scorsese's Best Picture winner "The Departed," which was based on a Hong Kong film but also drew liberally from Bulger's story.
And Bulger, who became a fugitive in 1994 when he learned that an arrest was imminent, probably saw the film in which he helped inspire Jack Nicholson's character: according to November 2006 reports in the Boston Herald and KFMB.com, he was spotted leaving a San Diego theater that was showing the movie shortly after its release.
(A spokesperson for Scorsese did not respond to a request for comment.)
The final step in the decades-long manhunt, during which Bulger rose to number two on the FBI's 10 most wanted fugitives list behind Osama bin Laden, came with a barrage of ads on daytime television shows. The ads, which ran on shows that appeal to women, asked for tips as to the whereabouts of Bulger's longtime companion, 60-year-old Catherine Greig.
According to the FBI, the ads began airing on Monday, a tip came in on Tuesday, and agents moved in and arrested the couple on Wednesday.
Although Scorsese's "The Departed" was based on the 2002 Hong Kong thriller "Infernal Affairs," writer William Monahan used details of Bulger's story in fashioning the world around Boston mob boss Frank Costello, played by Jack Nicholson.
In the film, Costello is a vicious crime lord sought after by the authorities; he plants an informant (Matt Damon) inside the Massachusetts State Police at the same time that the police assign their own undercover operative (Leonardo DiCaprio) to infiltrate Costello's organization.
In real life, Bulger, who faces numerous counts of racketeering, murder, extortion and money laundering, had his own mole within the FBI, while at the same time he and one of his top aides in the Winter Hill Gang were being used as informants for the bureau.
An FBI agent who tipped off Bulger that an indictment was coming, John Connolly Jr., later served time for his role in helping Bulger, while a Boston Globe investigation into the FBI's arrangement with the mobster caused major embarrassment to the bureau.
Kevin Weeks, a former confidant of Bulger's and a member of his gang, published his own memoir in 2006, "Brutal: My Life in Whitey Bulger's Irish Mob."
It is just one of several books about Bulger, including "Rat Bastards: The Life and Times of South Boston's Most Honorable Irish Mobster," by John "Red" Shea and "The Brothers Bulger: How they Terrorized and Corrupted Boston for a Quarter Century," by Howie Carr.
In 2010, Carr told the Boston Herald that he would welcome news of Bulger's arrest because it was "just what I need to get a sixth printing for the paperback."
And now that there's a dramatic ending, can a movie deal be far behind?