Whitey Bulger Trial: Author T.J. English Talks About Boston's Biggest Mobster

In the world of organized crime, gangster James “Whitey” Bulger is among the most notorious. We caught up with journalist T.J. English, author of 'Whitey’s Payback and Other True Stories,' to get his take on Bulger’s life of crime and how he thinks this wise guy’s final chapter will play out.
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In the world of mobsters, gangster James “Whitey” Bulger is among the most notorious. For more than 20 years, Bulger controlled Boston as a violent mob boss turned FBI informant who had virtually free rein over the city because of his corrupt relationship with law enforcement. He infamously went on the lam in 1995 and remained in hiding for 16 years until he was finally captured living quietly in Santa Monica, California, at the age of 81.

Bulger’s stranger-than-fiction story loosely inspired the 2006 movie The Departed, starring Jack Nicholson as a Bulger-like crime boss, and there’s buzz about upcoming Hollywood biopics including one that would reunite Boston’s own Ben Affleck and Matt Damon. But it’s more than just Hollywood that’s riveted to Bulger's story, especially as his explosive trial (complete with Bulger and his former right-hand crony Kevin Weeks hurling f-bombs at each other) unfolds in a Boston courtroom.

We caught up with journalist T.J. English, author of Whitey’s Payback and Other True Stories, to get his take on Bulger’s life of crime and how he thinks this infamous wise guy’s final chapter will play out.

What makes Whitey Bulger different than any other mobster?

For one thing, the longevity of his criminal reign, from the early 1970s to 1995, with a criminal career that was extended by his 16 years on the lam. But even more important was the reach of Bulger’s criminal influence, through his brother William Bulger, president of the Massachusetts State Senate for close to 20 years, and through his role as a top echelon informant for the FBI. Bulger had the entire Organized Crime squad of the Boston FBI in his pocket for 15 years. All of these factors contributed to a career as a racketeer and killer that was unique in its power and scope.

How did Bulger’s role as a secret FBI informant fuel his power as a crime boss?

For one thing, he had his handler, Special Agent John Connolly, and Connolly’s supervisor, John Morris, head of the Organized Crime squad, routinely feeding him information about his rivals in the mafia. Not only that, they were also feeding him information about potential informants within his own organization (information that Bulger used to then kill these potential informants). And finally, they tipped him off whenever he was being investigated by other law enforcement agencies, such as the Massachusetts State Police and the DEA. All of this made Bulger virtually untouchable in the Boston underworld.

Bulger's mug shot in 1953.

Bulger's mug shot in 1953.

What did you learn about Bulger’s life story in your reporting that surprised you the most?

Basically, that he is just a failed human being. Yes, he is likely a sociopath, and he was Machiavellian and engaged in a high level of deceit with both his enemies and associates; he was cunning and scheming and capable of horrific acts of murder. But he was not a Hannibal Lecter-type, larger-than-life monster. In many ways, he was a typical working-class, knock-around guy with criminal tendencies, not unlike a lot of criminal types of his generation. He was simply smarter than most (or so it seemed for a long time), with certain skills and characteristics that might have made him equally successful in the legitimate world, had he gone in that direction.

What shocked you the most about Bulger’s life of crime?

What shocks me most about the Bulger story is the degree to which his criminal career was enabled and protected by people and institutions within the criminal justice system. Not just the FBI but Justice Department officials going all the way up the chain of command to Washington, DC. The standard story is that the FBI and other cops and agents enabled Bulger out of a desire to make cases against the mafia. That is true. But it’s also true that the Feds covered for Bulger and his partner Steve Flemmi, also an informant, as a way of safeguarding a history of corruption in New England law enforcement going back to the days of Joseph Barboza, a murderous gangster-informant who predated the Bulger era. When it comes to the Department of Justice in New England, corruption runs deep and goes back at least half a century.

In 1995, Bulger was tipped off that he was going to be indicted. How had he planned his escape?

There is no credible evidence that Bulger was tipped off. I myself have reported that in the past, but I’ve come to believe it isn’t true. Bulger heard about his indictment and the arrest of his partner, Flemmi, over the car radio when he was driving back to Boston from a vacation with his longtime female companion, Teresa Stanley. Stanley herself told me this, before her death from cancer last year, and she had no reason to lie...Bulger had, however, planned for his life on the run, because he knew that day would eventually come. According to Kevin Weeks, his right-hand man, Whitey planted money in various accounts around the globe under different names.

Watch a video of T.J. English discussing Whitey Bulger's reign of terror

He was #2 after Osama bin Laden on the FBI’s Most Wanted list. How did he steer clear of the law for 16 years?

For one thing, the FBI wasn’t searching for him very hard. In those years after he first disappeared, the FBI [that was] assigned to hunt him down was the same unit that had served as his corrupt partners when he was active in Boston. They had a motive to NOT find Bulger. Whitey was able to “hide in plain sight” in Santa Monica, living a nice life for a long time.

How would you describe Catherine Greig’s relationship with Bulger? How was she the key to his getting caught?

Catherine was apparently sincerely in love with Bulger over the course of decades. She chose not to know much about the details of his criminal life. She was a key factor in his getting caught. In fact, it was only when the U.S. Marshals Service became involved in the hunt for Bulger and devised a strategy of disseminating information about Greig through various media outlets (with the offer of a sizeable reward) that Bulger was caught. FBI agent John Connolly, whom I interviewed in prison, says he thinks if it had just been Whitey on the run alone, they never would have caught him.

How do you think Bulger’s trial will play out? What will we learn that we don’t know about him?

In the years since Bulger disappeared in 1995, there have been hearings, numerous trials, documentaries, many books and even a feature film (The Departed) supposedly based on Bulger’s story. There’s not much left about his criminal life that we don’t know. What has not been fully explored, however, is the full extent to which Bulger is, in many ways, the creation of a corrupt criminal justice system. Many cops and agents over the years covered for Bulger and used their various institutions as part of that cover-up. Many of these people have long-since retired or passed away, but what I’m hoping is that the trial will be a final and full accounting of the Bulger era, that names will be named and documents unearthed that show who knew what and when they knew it. Only then will this dark cloud that has hovered over the criminal justice system in Boston be lifted and the city have a chance to finally escape a long and ugly legacy of corruption.