As anyone who's seen "The Departed" and spent much time in Boston knows, the film parallels the saga of James "Whitey" Bulger and the tangled relationship of the Irish Mob in Boston with the local FBI office. Bulger, of course, sits on the FBI's 10 most wanted (just below Osama bin Laden). In the film, the character Frank Costello (played by Jack Nicholson), is loosely based on Bulger.
Bulger, along with cohort Stephen "The Rifleman" Flemmi, were both key members of the Somerville, Ma.-based Winter Hill Gang. In the mid-1970s, both became informants for the FBI, helping the bureau drive the Italian Mafia out of Boston. But as part of the deal, Bulger's FBI handlers also tipped him off to sting operations targeting him and Flemmi. Special Agent John Connolly, who grew up down the street from Bulger in South Boston, would later be charged with leaking information to Bulger that led to three killings.
But the biggest tip to Bulger may have come in 1995, after he and Flemmi were secretly indicted on racketeering and extortion charges. Bulger disappeared, and the FBI has apparently lost his trail. For more information on the history and search for Bulger, check out the Boston Globe's extensive coverage of the scandal here.
A few other tidbits worth noting: Bulger's younger brother William served as president of the Massachusetts State Senate and later president of the University of Massachusetts.
Howie Winter, Bulger's old boss in the Winter Hill Gang, was first convicted by a young assistant district attorney named John Kerry.
This past weekend, Bulger's other brother John, 68, made news for filing suit against the state of Massachusetts, seeking to reclaim a $65,000 annual pension that was revoked after he admitted he'd lied to grand juries in the investigation of his brother's whereabouts. The move has infuriated relatives of Whitey's alleged victims (hat tip: the Associated Press, via the Boston Herald).
Alleged Bulger sitings abound, but perhaps the most tantalizing rumor came in November when the Boston Herald reported that Bulger was supposedly spotted leaving a screening of "The Departed" in San Diego.