Anybody who knows me knows of my affection for the movie The Departed – surprise surprise, the Boston kid likes The Departed, I know. But while Jack Nicholson’s character is based on Whitey Bulger (in surprisingly accurate detail), my interest in all things Whitey Bulger doesn’t end there. I live in Somerville, just up Broadway from Winter Hill – the initial home to Bulger and the notorious Winter Hill gang. I even semi-seriously considered buying a condo that was for sale directly across the street from the garage that served as home base for the Winter Hill gang. As of late, I’ve been reading up on all things Bulger – and yes, I can’t wait for Ben Affleck’s upcoming movie based on Bulger’s life.
For anyone truly interested in learning the ins and outs of how Bulger was able to elude the FBI for basically his entire life, this is the book you should read first. Dick Lehr and Gerard O’Neill, the authors, are Boston Globe columnists who have covered Bulger and his activities throughout their respective careers. In Black Mass they go to painstaking lengths to stick only to the facts as they explore the “Unholy alliance between the FBI and the Irish Mob.”
In short, FBI agent John Connolly threw out the rulebook for cultivating informants when it came to Bulger. He didn’t file required reports about their meetings, tipped Bulger off to potential stings against him, and generally protected him from prosecution claiming Bulger’s importance to the FBI in taking down the Italian mob and their activities in Boston’s North End. While Connolly was Bulger’s primary contact in the FBI, he in no way acted alone – and the book includes all the juicy details about friendships, dinner parties, and lavish gifts exchanged between the FBI and Bulger’s Irish mob.
The strength of this book isn’t its glorification of Bulger or its prose – it’s the fact that it may represent the most historically accurate account of Bulger’s activities and his methods of avoiding prosecution despite being wanted on 19 accounts of murder, extortion, money laundering, and drug trafficking.
The relationship between John Connolly and Whitey Bulger made the FBI completely rethink their strategy and requirements for handling underworld informants – and this book will certainly make you contemplate whether or not law enforcement should be turning a blind eye to obvious crimes in exchange for information on other wrong-doings. Check it out.