How Whitey Bulger became the most notorious member of the Boston Irish mafia

On October 30, 2018, the notorious and much-feared mob boss James "Whitey" Bulger was killed in prison in West Virginia. As the FBI continues to investigate his death, we look back at the violent life of the infamous murderer. 

Don’t be taken in by the blue-eyed evil of Whitey Bulger’s sociopathic gaze. There was much more to his rise and fall than just his ability to do whatever it took to become Boston’s gangland capo. Back in 2015, Cahir O’Doherty talked to T.J. English, the bestselling author who understands Bulger’s case and the lingering questions that have not been answered better than any other writer.

If you watch "Black Mass," the 2015 Whitey Bulger biopic, you’ll be terrified by the blue-eyed sociopath that actor Johnny Depp has turned himself into.

The trailer suggests the flick has the look and feel of a horror film, which of course it probably should. But it would be a mistake to imagine that Bulger’s murderous rampage was the only relevant part of his decades-long criminal reign. It turns out there was a lot more to his rise and fall than all the blood and mayhem.

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By now almost everyone has their own fixed impression of the notorious South Boston mobster, but few have had the stomach to learn the lessons that his epic rise and fall could teach us.

One man who knows those lesson better than most is author T.J. English. In his riveting book "Where the Bodies Were Buried" (HarperCollins), he contends that although Bulger was charged and imprisoned with two life sentences, that does not imply that justice has been completely served.

“This book is an attempt to move the discussion beyond Whitey Bulger,” English tells the Irish Voice.

“We all got caught up in his cult, and I include myself in that as a journalist and as someone who has written about it over the years. Bulger is such a fascinating character, and as a case study, it’s such an appealing story. I’m not saying it was illegitimate to focus on him, I’m just saying now after all that has been written, it’s time to ask the broader question of how did this guy ever get into this position of power that he was in?”

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Prison union official says the death of Boston gangster James 'Whitey' Bulger is being investigated as a homicide. https://t.co/ESjhzr37KO

— The Associated Press (@AP) October 30, 2018

It’s a good question. But a surprising number of government agencies don’t really have the stomach to ask it, English discovered.

“I think that in the asking of that question there’s a lot of things about the Bulger story that have been untouched. This book is an attempt to get at that,” English says.

A long-time criminal investigative author who Bulger himself would read religiously, English attended every day of Bulger’s trial in 2013 and assumed that the multiple allegations of collusion between the criminals and the Feds would be addressed.

“It turned out that the trial was illuminating in the ways that it intentionally didn’t address those claims. It actually sought to reconfigure the narrative so that those larger issues would be buried forever,” English maintains.

It was frustrating for English because he realized the trial was going to be the last opportunity to burrow deep into the Bulger story and find out what elements within the system made it possible for this ruthless man to get his hands on so much unprecedented power.

“There were things we know, like his relationship to his brother (the former Democratic power broker Billy). There was also the history of the Irish mob. But I just wanted to know how the system itself had enabled this guy.”

Obituary: The long and deadly career of James J. "Whitey" Bulger. https://t.co/d4dxY8xKaB pic.twitter.com/aZynbrxnxR

— The Boston Globe (@BostonGlobe) October 30, 2018

The answer to that, English discovered, lied with the generation of criminals that came just before Bulger. The dirty dealings of the Joseph Barboza era, which came to a head while Bulger spent his first stint in prison, had led to the conviction of four innocent men for a murder they didn’t commit.

“The dirty practices of the Barboza era were passed on to the next generation of people within the criminal justice system. Some of the handlers of Barboza were the same people who later recruited and initially handled Bulger,” says English.

“There was a passing of the baton – which is fascinating to me – so 'Where the Bodies Were Buried' is a story of criminal justice over the last half-century and how Bulger fit into that.”

English knows he’s made explosive claims, but he says Bulger’s ascension to crime kingpin was almost an inevitable extension of what had preceded it. In other words, the corrupt play was cast and all it needed was a new principal actor. And what did the federal prosecutors learn from Bulger’s trial? “The answer is they learned how you bury history. I can understand why the level of corruption is mind-boggling,” says English.

“The system is rotten. The use of informants and then the need to cover up the things that go wrong with those informants has been a full-time job up there.”

English says he received a general lack of cooperation from people within the system, like the U.S. Attorney’s office in New England.

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“People don’t want to talk or take responsibility for this. The position they all took within the trial was that this was all a case of a few bad apples like John Connolly, the FBI agent who allowed himself to be manipulated and played by Bulger,” English offers.

“They narrowed the criminal conspiracy down to four or five people (Bulger, his associate Stephen Flemmi, and former FBI agents John Connolly and John Morris) when in fact it’s way more vast than that.”

The line everyone kept using at trial was that Bulger had corrupted the system in New England. But that’s bogus, English says. Bulger simply plugged into a preexisting corrupt system and played it for all it was worth.

Mobster Whitey Bulger has been found dead in prison, @PeteWilliamsNBC reports on @MSNBC. https://t.co/H50tSSvnl4 pic.twitter.com/IocPFxDe2e

— MSNBC (@MSNBC) October 30, 2018

“The problem with the agent/informant relationship is that you often have criminals who are sociopathic getting the advantage over the agents recruiting them. As someone who follows the broader world of crime (English has written about the drug gangs in New Mexico and Cuba), I see this agent/informant relationship in many permutations. It’s a real problem.”

Bulger and Flemmi have been repeatedly described as pawns to help take down the mafia in Boston. But that misleading line is used to obscure a multitude of sins.

“I’m glad you brought that up, it’s an essential part of the book. Prosecutors and the local media in Boston have put that official narrative forth. They say the FBI locally was corrupted in their overwhelming desire to make cases against the Italians. So they made a deal with Bulger and Flemmi. But I don’t see it that way.”

What English sees is that the FBI, the former federal prosecutor Jeremiah O’Sullivan and others in the Department of Justice were interested in protecting Bulger because he and Flemmi had become what he calls purveyors of the secret (dirty) history of their organizations.

“Their role, the job of everyone who formed that partnership up there, was to keep that partnership buried. By that, I mean the history of Joe Salvati and the others being framed for the murder of Teddy Deegan they didn’t do. And a host of other crimes that were overseen by agents H. Paul Rico and Dennis Condon.”

Their concern was not to get the mafia, English says. It was to preserve the dirty secrets of the criminal justice system. And in that sense, the agents and the criminals had become partners.

Did English expect controversy when the book published?

“We’ll see how the media in Boston react. But the system protects itself, and in a way, that’s what this book is all about. The system has protected itself from the dirtier implications of the Bulger story.”

The agents and prosecutors involved in maintaining this conspiracy are not bad people, English adds. These are people we know.

“They’re supposed to be the good guys. They come from God-fearing families and they don’t see themselves as bad guys. And yet they’ll utilize their power to crush you if you go against the system.”

Asked if he thinks "Where the Bodies Were Buried" will open a hornet’s nest, English is candid.

“I hope so. I haven’t seen Black Mass. The most agonizing thing about the Bulger story is that this all been narrated in such a tidy way.

“It ends being all about Whitey and what a sociopath he was. But all the troubling questions about the criminal justice system and the way good men and women within it behaved gets buried. If my book plays a role in making that a little more difficult for people then that’s a good thing.”

* Originally published in September 2015.