The decline and fall of James "Whitey" Bulger

Whether you know about him from the movie The Departed or from the many documentaries made on his life, James “Whitey” Bulger certainly made a name for himself. Coming from the ranks of abject poverty in post-depression era Boston, Bulger went on to become one of the most notorious of the Irish mobsters in the nation’s history, eventually winding up on the FBI’s most wanted list. And now he’s in custody. (Again)

Legendary Boston crime boss James “Whitey” Bulger, who has been on the run for more than a decade, was arrested Wednesday in Santa Monica, multiple law enforcement sources told The Times…

He was arrested by the FBI inside a building without incident, according to the sources, who asked not to be named because they were not authorized to speak on the matter. The details surrounding his arrest were unclear Wednesday night.

The FBI in Los Angeles declined to comment.

The arrest came as the FBI launched a media campaign in 14 cities to help determine Bulger’s whereabouts.

What made Whitey such a standout figure in the world of crime wasn’t simply the fact that he was from the Irish mobs, rather than the early Jewish and Italian organizations. The Irish mobs were a lot more common than some might think in the early part of the 20th century. It also wasn’t his raw viciousness or the trail of death and wreckage he left in his wake. What really made him fascinating to me was the way he played the FBI for so many years and, in the long run, probably hurt them more than they damaged his crime syndicate.

By the time he was rising through the ranks of gangsters at a young age, Whitey was already in frequent contact with federal agents. His handlers saw in Bulger a terrific opportunity to get first hand information on gang bosses and other criminals, making their lives much easier. Sadly, rather than demonstrating some early streak of remorse or a sense of civic duty, Whitey saw the FBI as a terrific opportunity to get rid of a lot of his competitors and bosses without the risk of him or his boys coming down with a sudden and terminal case of lead poisoning.

Apparently the FBI mishandled their informant badly. According to some reports, they were fully aware that he was continuing a career of killing and racketeering even while he was supposed to be working on the side of the good guys. The more they let this go on, the dirtier the agents in question looked and the less able they became to do anything about him. In some documentaries, Bulger is credited with being the original author of a line later co-opted in many movies: “A guy with a mouth like mine could make a lot of trouble around here.”

It certainly looks like that may have been a factor. He didn’t exactly make himself hard to find in many cases, and yet he wasn’t brought to justice for the later, bigger portion of his criminal career until now. And even today, at the age of 81 and in failing health, I have to think that he probably feels like he got away with murder.