The Real Story: Whitey Bulger

“Black Mass” stars Johnny Depp as Whitey Bulger, now serving two consecutive life terms plus five years in prison for racketeering, drug dealing, and multiple murders, just a small part of the crime, terror, and mayhem he was responsible for as a Boston crime boss of a mob crew known as the Winter Hill gang. For 16 years he was hiding out until he was arrested in 2011. For 12 of those years, Bulger was listed second on the FBI Ten Most Wanted Fugitives list, behind only Osama bin Laden.

James Joseph “Whitey” Bulger, Jr. was born in 1929, the son of a longshoreman. The family was poor and he got involved with crime very early. His first arrest was at age 14, served time in juvenile detention, and then served his first prison sentence in his 20’s for armed robbery. After he got out, he became involved in organized crime. Meanwhile, his brother Billy became involved in politics and served as President of the University of Massachusetts and also as President of the Massachusetts Senate for a record-breaking 18 years. He is played in the film by Benedict Cumberbatch.

In 1971, according to reports, he first became an informant for the FBI, which overlooked his crimes to obtain his help in going after his biggest rival, the Patriarca crime family. This association is the primary focus of an excellent documentary about Bulger from director Joe Berlinger, who told me:

The three star witnesses for the government are murderous thugs. I mean could you imagine somebody going up for trial for 20 murders and getting 12 years? He’s a serial killer and yet the government treats him as a star witness, now how is that guy incentivised? It’s what I love about the movies, it is a true Rashomon experience and yet the truth rises to the top and something stinks. The real story has been swept under the rug because it’s just implausible on so many levels that all that murder and mayhem and bad behavior is solely the responsibility of one relatively low level agent and his corrupt supervisor, it’s just not plausible.

I really want to know how truthful is the claim that he had a deal of protection and frankly it’s an important question that is the major disappointment that I had in observing the trial because that was a question that was not allowed to be aired. Even before the trial began, the judge ruled that the immunity claim was not allowed to be brought up in trial so that was disallowed as a line of inquiry. It’s a complicated question but he should have been allowed to bring that up at trial because it’s a central question to the saga and I was disappointed that the judge would not allow because I think it was pretty clear that no matter what happened at trial Whitey Bulger was not going to walk out of that preceding a free man. Right from the start he admitted to being a drug dealer and loan shark.

This week’s film is based on the book Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal. There is also a 60 Minutes story about Bulger’s capture.