How Whitey Bulger Became a Crime Boss and a Snitch

My wife loves Johnny Depp and I'm a big fan of gangster movies, so it's a safe bet that we'll see Black Mass, the new movie about former Boston Irish Mob boss Whitey Bulger, which opens this weekend. From what I've gathered checking out reviews and watching the trailer, the film—based on the book of the same name by local investigative journalists—glamorizes Bulger's criminal escapades in Boston's underworld, details his bone-chilling psychopathic tendencies, and probes his secret-squirrel dalliances with FBI handlers.

The only thing that will trouble me as I watch the movie is a voice whispering in my head: "He's a rat. He's a rat. He's a rat!" Due to years of prison conditioning, I still have an adverse reaction to snitches. Not that I hate them or want to kill them or anything—it's just hard for me to celebrate or idolize these people. Of course, I consider myself a gangster aficionado and can't lie: Bulger's criminal career intrigues me. But his infamy leaves a sour taste in my mouth. I've been out now for a little over a year, enjoying all the world has to offer, but old habits die hard, and in prison if you were a snitch, you didn't get any play. You got checked in to protective custody—or worse.

Bulger has maintained that he's not a rat, but on the compounds that I was on in the federal Bureau of Prisons, no one was buying that story—especially his homeboys from Boston. To them a snitch was a snitch was a snitch. During my incarceration I read a lot of books on Bulger and numerous other gangsters with names like Gotti, Escobar, Gaspipe, Sammy the Bull, Supreme, Big Meech, and Fat Cat. As I sat inside the belly of the beast cavorting with gangsters and reading about them, I discovered the true crime books of TJ English, who became one of my favorite writers— Born to Kill and The Westies were two of my favorites. Amid the hoopla surrounding Whitey Bulger's legacy, the Johnny Depp movie and the intricacies of Bulger's relationship with the FBI, I reached out to English, who has just published his own tome on Bulger, Where the Bodies Were Buried , to get his take.

VICE: When did you decide to write a book on Whitey Bulger?
TJ English: When I saw that the trial of Whitey was shaping up to be a whitewash of the full dimensions of the Whitey fiasco, how the criminal justice system was complicit in Bulger's criminal career, how they enabled him, protected him, helped to create him. Little of that was touched upon at the trial. Any time it came up, the prosecutors objected on the grounds of relevance, and the judge ruled in their favor. The trial was a carefully orchestrated deception. Not that it wasn't interesting. It was an extraordinary casting call of Boston hoodlums—bookies, loansharks, hitmen, etc.—from a previous generation telling tales about organized crime in the city. The book uses the trial as a jumping-off point to explore aspects of the story that were deliberately being kept out of the trial.

What did you learn about Whitey that you didn't know before?
That Bulger was the inheritor of his domain and not the creator. There existed a network of corrupt relationships between gangsters and lawmen in Boston at least since the creation of the Top Echelon Informant program by J. Edgar Hoover in the mid 1960s. I focus much attention on this in Where the Bodies Were Buried, because I think it is key to understanding the full dimensions of the Bulger years. The relationship Bulger had with Special Agent John Connolly, his FBI handler, was not new. In fact, it was the type of relationship that the FBI and US Attorney's office in Massachusetts had used to make major cases against the mafia for decades. In that sense, Bulger was not special. His partner Stephen Flemmi was a Top Echelon Informant before Whitey.

Explain the whole dynamic between Whitey and the FBI. Who was working who?
In 1967, the FBI and prosecutors in New England had a murderous informant named Joe "the Animal" Barboza take the witness stand and finger innocent men for a murder they didn't commit. These men were convicted and sentenced to life in prison. FBI agents not only encouraged Barboza to tell his lies, they helped orchestrate his testimony. And this travesty of justice was authorized all the way up the chain of command to Director J. Edgar Hoover. Many people knew it had happened. It was a dirty secret that, were it ever revealed, would have destroyed the credibility of the FBI and entire criminal justice system. Barboza was a precursor to Whitey Bulger. When Bulger was recruited by the FBI, part of the understanding was that he and his partner Steve Flemmi were now custodians of this dirty history. The FBI and these gangsters formed a pact that involved making sure this history would stay buried. It helped give Bulger and Flemmi their power. They were now in a partnership with the US government.

To this day, it's often said that Whitey does not consider himself a rat. What's your take on that?
He was a rat. He may not believe he was, but I've seen his entire informant file. He was providing information not only on the Mafia but on criminals within his neighborhood of South Boston. He was using his informant relationship to plant in some cases false information designed to take down his rivals int he underworld.

Who did you interview and talk to while researching and writing the book?
The book was a culmination of people I've been talking to for years about the Bulger story. I spoke with Teresa Stanley, Bulger's common-law wife for 30 years. I spoke with FBI agent John Connolly, by phone in prison, where he resides on murder charges stemming from his relationship with Whitey. Spoke with Kevin Weeks, Bulger's right-hand man. Spoke with a retired gangster named Pat Nee, who was a rival and then a key associate of Bulger's. Spoke with retired FBI agents, various criminals defense lawyers, and many others,

Explain the Southie mentality and why rats are so despised.
It has to do with Ireland and the history of rebellion stemming from the Troubles. The Informer was a masterful Irish novel by Liam O'Flaherty (published in 1928), later made into a movie by director John Ford, that captures it beautifully. An informer is viewed as a betrayer of community, family, all that matters in this world.

What do you think Whitey's legacy ought to be?
Whitey the person will be forgotten, but what will be remembered is this legacy of corruption that spawned Whitey. The Bulger fiasco is arguably the worst law enforcement scandal of the last half century. People will forever look at this scandal and say, "How the hell did this ever happen?"

Do you think the movie Black Mass will cement his place in popular culture next to gangster legends like Pablo Escobar and John Gotti?
Perhaps. That is how things work in this country. The mythology of Bulger is now having its pop culture moment. But when the razzle dazzle dissipates, what remains are the books, the historical record. The Bulger story is mind-blowing; it's multilayered and complex. You'll have to see the movie and then read at least one book, maybe more, to bend your mind around it. But, yes, I do believe its a gangster saga that will have a lasting legacy.

Follow Seth Ferranti on Twitter and check out TJ English's book here.