In 2011, when James “Whitey” Bulger was arrested, tried, and sentenced, I was in law school. As a result, I didn’t pay very close attention to the story. I remember Tony Kornheiser talking about it a few times but mostly just saying, “Wow–this is incredible! And now he’s so old! He looks like me!” and the like. But all I remember is that he had been on the run for a long time after having been a mobster and government informant. It’s possible that I heard more, but I find it strange to believe that I forgot what a bizarre story his was. He spent two decades growing his criminal empire in Boston while the FBI blocked all investigation of his activities because he was supposedly an informant of theirs, even though he apparently was essentially providing no information. His handler was falsifying information to make Bulger appear more important than he was in order to advance his own career while allowing Bulger to take over the city.
According to the film, the handler, John Connolly, doesn’t appear to have been on Bulger’s payroll or to have been placed in the FBI in order to execute this plan. So, the fundamental question that occurs to me is, “Why the hell did he protect Bulger like this?” This film, while it is supposedly about Bulger’s career, essentially attempts to answer that question. The answer that it gives is that Connolly, Bulger, and all of the other main players in this enterprise were children playing at a game of advancement and “success.” They never grew into men, remaining at heart kids on a playground even as they beat and murdered rivals and broke every law on the books. Continue reading