“Whitey”: The Story of a Monster

Dick Lehr had long moved on from his fascination with legendary South Boston mob boss James Joseph “Whitey” Bulger, Jr., after the success of his book Black Mass: The Irish Mob, the FBI, and a Devil’s Deal, coauthored with former Boston Globe colleague Gerard O’Neill (COM’70) in 2000. But when Bulger was arrested in California in June 2011 after 16 years on the lam, Lehr, a College of Communication professor of journalism, and O’Neill, with whom he had also worked on the 1998 Globe Spotlight Team five-part series “The Search for ‘Whitey’ Bulger,” once again found themselves neck-deep in Bulger-land.

Their new book, Whitey: The Life of America’s Most Notorious Mob Boss (Crown Publishing), a far-reaching biography of the crime kingpin, hits shelves as Bulger, now 83, sits in prison awaiting trial in June for his role in 19 Boston murders. Bulger pleaded not guilty to a 32-count federal racketeering indictment that not only charged him with murder, but extortion, money laundering, and weapons charges.

At the end of their thorough examination of his ancestry, childhood, and life of crime, the authors characterize Bulger as shrewd, bent on self-preservation, but ultimately a “monster who could strangle young women, shoot people’s brains out, and tear apart a city without blinking.”

Whitey traces Bulger’s family history back to its Irish roots and is the first of the Bulger canon to probe the gangster’s blemished record in the Air Force, his incarceration in an Atlanta prison, where he was given experimental LSD, and his later role in an Alcatraz prison strike. In addition to unsparing descriptions of Bulger’s Boston reign of terror, the book draws on new information about his only child, a son who died at six from Reyes syndrome. Touched on also is his relationship to his brother, longtime Democratic politician William “Billy” Bulger (Hon.’96), a former president of the Massachusetts Senate and former president of the University of Massachusetts. The meticulously researched book pieces together Whitey’s life on the run with girlfriend Catherine Greig, including his racist rant against President Barack Obama, which played a critical role in his capture and arrest.

A former reporter at the Globe, where he won numerous awards and was a Pulitzer prize finalist, Lehr shared an Edgar Award with O’Neill for Black Mass. Judgment Ridge: The True Story Behind the Dartmouth Murders, cowritten with Mitchell Zuckoff, a COM professor of journalism, was an Edgar Award finalist, as was his most recent book, the Boston Globe best seller The Fence: A Police Cover-up Along Boston’s Racial Divide.

Lehr and O’Neill will speak and sign copies of their book tonight at 7 p.m. at Porter Square Books in Cambridge. The book’s publication was accompanied by the news that a Hollywood film version of Black Mass, to be directed by Barry Levinson, will feature Johnny Depp in the starring role.

BU Today sat down with Lehr recently to discuss his insights into Bulger the man and how he stands in the dark pantheon of famous gangsters, as  well as his reaction to Depp being cast in the upcoming film of Black Mass.

BU Today: You’ve spent so much time researching and writing about Whitey Bulger—is there anything likable about the man?

Lehr: It’s hard to get there. Women were drawn to his power, and my God, he was incredibly handsome. There’s that photo in the book of him at 26—that’s Hollywood good looks. There is an allure about him. In isolation he could do fine things for people. His loyalty to his brother, Bill, in isolation, might be admirable. But it can’t stay in isolation. His kindness to people, it’s all political, it’s all to make sure his immediate circle is a circle of protection. There’s always an ulterior motive. When you look at what he’s done and the lives he’s ruined, there’s just no way to see him as anything but a monster.

Who would you say Whitey has actually gotten close to in his life?

Not many people. His brother, Bill, and ultimately, Catherine Greig. Their 16 years on the run probably deepened their relationship. And then, to a degree I think, Kevin Weeks, Bulger confidant and former boss of the Winter Hill Gang, but that would be it. Bulger associate Stephen “The Rifleman” Flemmi wasn’t a coequal, he was a business partner, and the other guys in the gang were his pawns. He and former FBI agent John Connolly were certainly close, and they actually vacationed together, but I don’t know how revealing he was as to the true and inner Whitey Bulger. Theirs was a relationship of controller and controllee.

What were the earliest seeds of that now-infamous relationship?

John was so much younger. The teenage Whitey had charisma, so when they professionally linked up in the mid ’70s, Connolly would be perversely in awe of Whitey, that’s a given.

In what ways is Whitey like his brother, Bill?

Like Bill, he’s smart and controlling, for the most part, and contemplative, really thinking things through before acting. Really seeing the game board, the chessboard. For Bill it was politics, for Whitey it was the underworld.

What do you think Whitey’s life with Catherine Greig was like during their 16 years on the lam?

It was pretty ordinary, I think. At the time they left Boston, I’m not sure she knew where it was going to go, but they’d been together long enough that she’d already given up most of her life and become his possession. She started out as a career woman, a dental hygienist and a teacher. She wasn’t like girlfriend Teresa Stanley, a single mother with five mouths to feed and no skills. It took a few years, but Whitey took her out of Southie, put her in a house, got her to quit working. And all these lifelines got cut off, and she was in Whitey’s world. There’s a dose of real partnership, but she became his possession. I think she was happy to be there; it was a relationship that had evolved. This was the final act, but they’d been together, and it wouldn’t have worked if she wanted the big mansion in Nahant. Whatever her needs were, they matched his—good life, good travel, good food, but not being flamboyant about it.

What were Whitey’s passions?

He wasn’t extravagant. His needs did not extend to having a mansion or boats. He had nice cars, he liked to eat out, he liked a glass of wine, but not in any extravagant big-spending way like Mafia dons. He didn’t take all his ill-gotten gains and wear them on his sleeve the way a lot of gangsters do. His appetite and ambition for that weren’t that large. But that isn’t to say he didn’t like nice things. He was into cowboy boots in the ’80s, and he’d pay $1,100 for a pair. But he was also really smart, and he knew that if he were to live high in a showboaty way, he’d be drawing attention to himself, and he didn’t need that for his ego. He was never flamboyant. For him it wasn’t about showing off, it was about power—the power of being a crime boss, of being Whitey Bulger, of being feared, of being in control.

He loved to travel, is that right?

Yes, he was self-educated, but he considered himself really smart, and travel fed his sense of worldliness. His brother was classically educated at Boston College, and Whitey’s the street version of that. In prison, he read like crazy and really educated himself. His attitude was, I’m smart, smarter than you, and he always talked down to people. He knew everything about everything. Weeks and Flemmi talk about how Whitey used to drive them nuts with his know-it-all monologues, boring them to death.

You write about what you describe as his Robin Hood years. Tell us about the Whitey myth, how he was a hero in Southie before the whole grisly truth came out.

I think everyone was shocked that he was an FBI informant. In his Robin Hood days, my assessment would be that he was their good bad guy. He’s a gangster. Gangsters are violent. He may kill people, but he’s our bad guy, our Robin Hood—he protects us. That’s the myth. And he’s loyal, the whole Southie pride thing, so in that sense he’s an asset. It’s the same as when they say that when the Mafia was in the North End, street crime went down. And there’s the big myth that he kept drugs out of Southie. When you’re in the projects, you know that Whitey was behind the drugs, but you didn’t challenge the public myth.

Did the media play a role in fueling that myth?

The way it worked, the fundamental dynamic that was so clever and so powerful, is that the media perpetrated the myth that was spread by Jack Connolly. No one had access to Whitey himself. But most reporters who covered law enforcement had access to Connolly, a popular source during the 1970s and 1980s. The big myth they got out of him, in addition to many real stories, was the Whitey as Robin Hood story. It was the same thing Connolly was doing inside the FBI, cooking the books. It came easy to him. He was so social and outgoing and extroverted. He enjoyed talking to reporters, and it just flowed. It’s only afterward you look back and say, wow, that was damaging. But everyone was getting what they wanted. And the media was getting this from the organized crime guy in the FBI. We were all unwitting fools looking back, but at the time we were scribbling madly to write whatever he said.

How does Whitey’s Boston mob activity compare with organized crime in other cities?

The body count is huge, the criminal profits and enterprise, scope and power are huge. The most distinguishing thing we talk about in the book is Whitey’s harnessing of FBI power in the name of the gang. It’s unprecedented. I think that’s why history will show him as the most notorious mob boss in the history of organized crime. If you get into the accolades of being an underworld figure and crime boss, that’s what he could say—I did this and no one else has done it. And he’s distinguished by his longevity as a result of harnessing that power. Check out how long John Dillinger was around. I don’t think anybody had the ride that Whitey had. At some point he’ll be a household name in the crime world. And his gang was a cult of personality. There’s no Whitey Bulger successor. The Mafia has been hurt, but it is an organization that has continued for generations. Whitey’s reign was a one-off.

Bulger has argued that he should be granted immunity because he was an FBI informant at the time of the crimes. How do you think the judge will rule on his bid for immunity?

It would completely flabbergast me if he is found to have legal immunity. I would say he believes he has immunity because Flemmi believed the same thing, based on the reality of their lives. I’m talking immunity in quotes. They were protected by corrupt FBI all through the ’70s and ’80s, and if you put yourself in their shoes, that equals immunity as far as how you’re living your life and what you expect and what you’re entitled to. I have a license to kill and I have immunity, that’s where his head is at. So I get where he’s coming from, but it’s just outrageous. In the American judicial system and government, no one’s ever been given a license to kill that’s legal.

How does your collaboration with Gerard O’Neill work?

We each write alternating chapters, then look at each other’s, and go back and forth to achieve a consistent voice. We’re used to collaborating from the years we worked together on the Globe Spotlight Team, when I was a reporter and Gerry was the editor.

How do you feel about Johnny Depp’s playing the role of Whitey in the film version of Black Mass?

Great choice. He has great range as an actor. Anyone who can become Edward Scissorhands can put on the mask of Whitey Bulger. Whitey has some real tics and eccentricities. I think Johnny Depp can get inside, and do Whitey better than a lot of other people who might be violent and fierce and glaring.

Are you consulting on the film?

Yes. Since it’s been in development and all along the way Gerry and I have consulted in the sense that the screenwriter or producer will call with questions about Whitey, or about the story. They’ll ask us to explain what happened in this or that murder. But it’s just about the history, not anything creative. We’re just a resource.

Dick Lehr and Gerard O’Neill will speak and sign copies of Whitey: The Life of America’s Most Notorious Mob Boss at 7 p.m. tonight, Thursday, February 21, at Porter Square Books, in the Porter Square Shopping Center, Massachusetts Ave., Cambridge, directly across from the Porter Square Red Line T stop. More information is available here.