TOPICS > Politics

The ‘Long, Dark and Dirty’ Story of Whitey Bulger’s Career and Capture

June 23, 2011 at 12:00 AM EDT
James "Whitey" Bulger, the legendary Boston crime boss and one of the FBI's 10 Most Wanted, was arrested Wednesday in Santa Monica, Calif. Margaret Warner speaks with with Boston University's Dick Lehr about the notorious fugitive's career, influence on Hollywood and how he hid from authorities for 16 years.

JEFFREY BROWN: James “Whitey” Bulger, one of the FBI’s 10 most wanted and a legendary Boston crime boss, is a fugitive no more.

Margaret Warner has the story.

MARGARET WARNER: He’s been in hiding for 16 years, but James “Whitey” Bulger, wanted for 19 murders and countless crimes, was finally apprehended last night at this apartment complex in Santa Monica, Calif.

Today, in Boston, U.S. Attorney Carmen Ortiz celebrated the end of the long manhunt for the city’s mythic gang leader.

CARMEN ORTIZ, U.S. attorney: And this is a great day for Boston’s law enforcement community.

MARGARET WARNER: Over the years, tips placed Bulger around the country and the world. But, earlier this week, the FBI renewed efforts to find him and his longtime girlfriend, Catherine Greig.

A public service announcement running in 14 cities where the couple was thought to have ties focused attention on Greig.

NARRATOR: Have you seen this woman? The FBI is offering $100,000 for tips leading to Catherine Greig’s whereabouts.

MARGARET WARNER: It worked. On Wednesday, a tip pointed to the Santa Monica apartment.

RICHARD DESLAURIERS, FBI’s Boston Field Division: Although there are those who have doubted our resolve at times over the years, it has never wavered. We followed every lead. We explored every possibility. And when those leads ran out, we didn’t sit back and wait for the phone to ring.

MARGARET WARNER: For decades, Bulger had been the reputed leader of the Irish mob in South Boston and an FBI informant. His alleged brutality inspired Jack Nicholson’s character in the mob movie “The Departed.”

JACK NICHOLSON, Actor: Swear on your mother’s grave.

MARGARET WARNER: But Bulger disappeared suddenly in 1995, after being tipped off by his FBI handler of his pending indictment on racketeering charges. Now, at age 81, he will finally face murder charges in Boston and in Oklahoma City and Miami.

And for more on Whitey Bulger’s criminal career and larger-than-life aura in Boston, we turn to Dick Lehr, an attorney and former reporter for The Boston Globe. He is author of “Black Mass: The Irish Mob, the FBI and a Devil’s Deal.” He currently teaches journalism at Boston University.

And, Mr. Lehr, welcome.

Tell us a little bit more about Whitey Bulger. What put an Irish mobster on the 10 most wanted FBI list, along with the likes of Osama bin Laden?

DICK LEHR, Boston University: It is an epic story that has many chapters to it.

The first piece is that he was a crime boss of the Irish gang in Boston, overseeing the underworld for nearly two decades. But the big piece of it is that he is at the center of the FBI’s worst informant scandal in its history.

After — in the mid-1970s, when he agreed to provide information for the FBI, he quickly turned the tables and compromised a handful of agents in Boston. And they in effect became his private security team, keeping him posted on activities in law enforcement that was trying to catch him, tipping off the names of people who were trying to inform on him. Some of these people ended up dead.

So, it’s a long and dark and dirty story.

MARGARET WARNER: Now, how did he corrupt the bureau? Was it with money? Was it the value of his information? Because he was trying to help them roll up the Italian mafia in Boston, right, or New England?

DICK LEHR: Yes. In the mid — this really involves, you know, history here. We’re talking about the mid-1970s, when an agent by the name of John Connolly, his handler all these years — he grew up in South Boston. There was a personal relationship involved here that goes back to their boyhoods.

Whitey Bulger was a little bit older than John Connolly. And when John Connolly was an agent in Boston, there was a premium in the bureau of developing underworld informants. And John Connolly turned to Whitey Bulger and said, join us and we will take out — it will work for both of us. We can go after the LCN, the mafia in the north end of the city.

But, again, it quickly turned, where Bulger compromised Connolly, and through Connolly, other agents, so that they were in effect working for him.

MARGARET WARNER: Now, what about his — he had a brother who was leader of the Massachusetts Senate, very powerful, but on the law-abiding side. How did they choose different paths?

DICK LEHR: Yes. I mean, you’re referring to Bill Bulger, who, for many years, was the most powerful politician in Massachusetts, as president of the state Senate.

And this is one of those great Boston stories, a tale of two brothers. There is younger Bill, who went to Boston College and law school and became a politician, and then Whitey, that grew up in the same bedroom in a housing project in South Boston, who went in a different direction.

To be honest and candid, they shared a lot of the same personality trait, in terms of intimidation, but Bulger stayed inside — Bill Bulger stayed inside the lines at the statehouse and ran the show there in a different way than his brother did on the streets.

MARGARET WARNER: Now, then he disappears, Whitey Bulger does, in ’95. What did that do to his reputation in Boston, his aura?

DICK LEHR: Well, again, going back to the first chapter of his reputation, for the longest time, he was perceived as kind of a lovable gangster from South Boston, a Robin Hood who looked after his neighborhood.

And it was a public image that had been — that was promoted by his handler, his corrupt handler at the FBI, John Connolly, who maintained many relationships with reporters. By the time he takes off in 1995, all this has washed away.

The horrible truth has been tumbling out for — in court hearings and in other cases and in journalism in the city. And so, by this time, you know, the mythology was gone. And it just added to the cynicism in the city that yet again he was tipped off. He got ahead of everybody. And, for 16 years, he has been on the run.

MARGARET WARNER: So, what does his capture mean for both the FBI and for Boston?

DICK LEHR: Well, let’s start with the FBI. Ever since he ran in January of 1995, there has been a huge cloud over the Boston office of the FBI, on top of the corruption that had spilled out.

So, for the FBI, it was really important that they be part of his capture today, yesterday and today, and hopefully to move forward and to get past all the talk that has been the watercooler talk of this city and beyond in law enforcement circles: Where is Whitey? Does the FBI really want to get him? Are they still trying to protect him?

The FBI can now begin hopefully to move past that. As far as Boston, just a huge collective sigh of relief. I mean, anybody in the city, and particularly in his neighborhood, who had a family member who was killed by him, who was intimidated by him, shaken down, you know, finally, this guy who was at the center of it all, you know, is going to be coming back to Boston and go to court. It’s long overdue, but here it is.

MARGARET WARNER: Dick Lehr from Boston, thank you so much.

DICK LEHR: You’re welcome.