Black Mass: Whitey Bulger comes to your neighborhood

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I read the book, and I can’t wait for the movie. Johnny Depp looks eerily like Whitey Bulger, the main subject and notorious Boston gangster.

I’m hoping the actors have mastered the Boston accent. It’s very distinct. An imposter is easily recognized.

James “Whitey” Bulger’s Alcatraz mug shots
James “Whitey” Bulger’s Alcatraz mug shots

James “Whitey” Bulger. Local gangster. Prisoner at Alcatraz. FBI’s Top Ten Most Wanted. Apprehended in California in 2011.

I arrived on Alcatraz in March of 1959 (Bulger would have been 29years old), and stepped behind the mythical steel curtain which was to become my new home. You may be surprised to find that I look back at Alcatraz with a sense of nostalgia. James J. Bulger #1428 (Alcatraz History)

Nostalgia is a sentimentality for the past, typically for a period or place with happy personal associations

This is beyond my comprehension.Alcatraz is now a great place to visit as a tourist. I’m not sure it was where you’d foster fond memories if you were an inmate. It’s interesting that he felt that way about Alcatraz.

Why are we so fascinated with local gangsters? Maybe growing up during the time these thugs were actually running the streets, gives us a weird sense of curiosity. We knew of these gangsters.We walked the same streets, but we didn’t know them, or did we? What was going on right under our young noses?

Growing up in Somerville, MA, we had Howie Winter of the Winter Hill gang. The Angiulo’s, (Italian mafia) were in the North End (Boston). Whitey Bulger was in South Boston. The Charlestown Mob, in Charlestown.

A surveillance photo from the Drug Enforcement Agency (DEA)
A surveillance photo from the Drug Enforcement Agency (DEA)

That’s a lot of gangster activity for a small state, don’t you think? Massachusetts is 7,840 square miles, in comparison; New York is 47,214 square miles. (World Atlas)

And then there’s this weird dichotomy. The State Senate President was William “Billy” Bulger, Whitey’s brother.

Bulger was elected President of the Massachusetts State Senate in 1978 and was re-elected every two years to 1996, making his time as State Senate president the longest tenure in Massachusetts history. (

Let this fact sink in. The most powerful man in Massachusetts politics, William Bulger, was in power the same time his gangster brother, Whitey Bulger, also powerful in his own world, is running amuck? Was the Senate President able to separate himself from his brother Whitey? It would seem so as far as the citizens could tell; they continued to re-elect him for years!

Then enter FBI Agent John Connolly, assisting Whitey as his “informant,” and the story just takes off. You can’t make this stuff up.

As the FBI handler for Bulger and Flemmi, Connolly (who had grown up in the Old Harbor Housing Project with Bulger) had been protecting them from prosecution by feeding Bulger information about possible attempts to catch them. (Wikipedia)

Bulger and his girlfriend Catherine Greig in a photo used as evidence by federal prosecutors.
Bulger and his girlfriend Catherine Greig in a photo used as evidence by federal prosecutors.

Connolly was prosecuted and convicted for racketeering, obstruction of justice and second-degree murder. He received ten years in Federal prison, and forty years in State prison, and is currently incarcerated. (Wikipedia)

As far as Whitey goes, he was captured in 2011, in Santa Monica, California.

On June 12, 2013, Bulger went on trial for 32 counts of racketeering, money laundering, extortion, and weapons charges, including his complicity in 19 murders. On August 12, 2013, he was found guilty on 31 counts, including both racketeering charges, and was found to have been involved in 11 murders. On November 14, 2012, Bulger was sentenced to two consecutive life terms plus five years for his crimes, he is currently incarcerated. (Wikipedia)

William “Billy” Bulger was appointed President of the University of Massachusetts by the Board of Trustees on November 28, 1995. (Whitey went on the lam in 1994). On August 6, 2003, Bulger announced that he would resign as president of the system effective September 1, 2003. His resignation came due to pressure from Governor Mitt Romney after Bulger had refused to cooperate with authorities who were searching for Bulger’s brother, the notorious mobster. Senate President William Bulger is now retired, living in South Boston with his wife, collecting a state pension for his years of service to the Commonwealth of Massachusetts. (Wikipedia)

It is a fascinating story, with big players that are still alive today, and plenty of twists and turns. It makes for a great book, and undoubtedly a great movie. Unfortunately it’s a true story, with many, many victims.

Bulger’s Santa Monica mug shots
Bulger’s Santa Monica mug shots

I asked my friends who grew up in Southie if they had anything to say about growing up there while Whitey was in charge, for this article … Nobody is quoted here.

Whitey turned 86 years old on September 3rd, still powerful …. Still able to silence Southie?

We are fascinated with anything local; whether it’s a great brewery, a great rock band, great sports teams, gangster/mob history, or the start of the revolution. It’s all a part of our local history. The good, the bad and the ugly …

The movie, the real life story, opens September 18th.