Talking to the Journalist Who Literally Wrote the Book on Whitey Bulger

For nearly two decades, James "Whitey" Bulger ruled Boston's Irish mob, racking up bodies, controlling the flow of drugs throughout the city, and earning millions of dollars in dirty money along the way. By the time he fled Boston at the end of 1994—hopping from state to state to escape charges of murder, extortion, and drug trafficking—even the FBI had blood from Bulger on their hands.

The nation's top law enforcement agency had secretly protected Bulger since the late 70s, tipping him off to investigations that threatened to put the mobster in jail. Each time someone came forward to testify against Bulger, the FBI let him know, and the informants disappeared. Their bodies were found days, weeks, and sometimes months later.

In exchange for what amounted to total immunity, Bulger gave the FBI dirt on other gangsters while he tightened his grip on Boston's criminal underworld. When federal prosecutors finally got a chance to lock Bulger up, the FBI dropped him one last tip: They're coming for you, Whitey. It's time to get out.

Bulger remained in hiding for 16 years, until he was finally arrested in 2011. He's now serving time at a prison in Florida, where—at age 86—he'll sit in a cell for the rest of his life.

In 1988, a team of journalists at the Boston Globe revealed that Bulger was an informant for the FBI, and had been one for years. The journalists—Dick Lehr, Gerard O'Neill, Christine Chinlund, and Kevin Cullen—knew they were breaking big news. But it wasn't until the late 90s, when Bulger's closest associates in the mob and the FBI testified in open court, that they learned how dark Bulger's deal with the Bureau really was.

After reporting on Bulger sporadically for about ten years, Lehr and O'Neill decided to put together a comprehensive look at his corrupt ties to the FBI. Their book, Black Mass: Whitey Bulger, the FBI, and a Devil's Deal, came out in 2000. Now, 15 years later, it's been adapted into a film starring Johnny Depp and Benedict Cumberbatch, along with a few other big names in Hollywood.

Lehr wrote for the Globe for almost 20 years, where he worked on the paper's investigative team and, ultimately, landed a spot as a Pulitzer Prize finalist. I sat down with him in his office at Boston University—where he's taught journalism classes since the mid-2000s—to talk about what it was like to break open one of the most damaging scandals in FBI history, and how Black Mass wound up on the big screen.

VICE: You write in Black Mass that when you first started reporting about Whitey Bugler with the Globe's investigative team, you were "incredulous" about the idea that he could've been an informant. What was it like to find out, for sure, that he was a rat?
Dick Lehr: It just blew our socks off. I remember going back and saying, "OK. We've confirmed it from within the FBI, two credible sources." Our jaws were dropping. We kind of wandered around in a fog, because it did go against everything that was then understood about the persona and career of Whitey Bulger.

We got into the project not so much as hard-hitting, investigative reporters—we got into it to do an in-depth narrative about the two Bulger brothers, because it hadn't been done before. Which was sort of surprising, given that this was the late 80s, and Whitey was the major crime boss, and meanwhile, his younger brother Bill was the most powerful politician [in Boston]. It was a great story that hadn't been told. And in the course of that, we stumbled into what became an exposé: that Whitey had a special relationship with the FBI. At that time, it was still only the tip of the iceberg. We didn't realize—no one knew, at that point—how deep and dark it was, how long it had gone on for, that the FBI had blood on its hands, all the horror.

I imagine that nearly everybody in Boston, at the time your exposé came out, thought the theory of Bulger-as-informant was unbelievable. When that information was published, did people buy it?
Well, certainly those close to the situation—and by that I mean cops, law enforcement, prosecutors who had been after this guy—it was confirmation for what they'd been suspecting. So they bought it. But generally, in the public? In Southie, they didn't buy it. They didn't want the myth shattered, that Whitey was a Robin Hood, that Whitey was a protector. And the FBI continued to lie to the public.

In the underworld, where it was a very big deal with the Mafia, and Whitey, and even his gang members, it was a crisis of sorts. But Whitey—and we didn't learn about this until years later—he went into red-alert mode, in the sense that he had to do some damage control. He's almost like a politician. He masterfully spun it to satisfy both his immediate underlings and his gang, but also even the Mafia. Whitey had been seen with John Connolly, the FBI agent, his handler. And Whitey had already pre-sold the whole thing to the gang as, "Connolly's my guy. He's corrupt, he's giving us information." He would never share that what he was doing was tit-for-tat.

When the Globe story came out, he was able to say, "They got it wrong. It's an agenda, they're out to get me, they're out to get my brother. You guys know Connolly's in my pocket." That worked in the underworld. People didn't want to believe it. Certainly, if you did believe it, if you were the Mafia, that means you'd have to take action. And not very many people wanted to take on Whitey Bulger.

Did you receive any backlash from the FBI or the Bulger gang after you published the piece?
Not directly from the Bulger gang, but from the FBI, yeah. They called us lousy liars. They said the Globe was publishing untruths. It only made it worse for the FBI, that they continued to lie in the face of internal confirmation.

Right before publication, an FBI agent called. I answered the phone and he asked for Kevin Cullen, who was working on the project with us. And he kind of scared us all by saying, "Whitey doesn't like what he reads. He'll shoot your brains out." So that was a little spooky. The Globe took that seriously, because Kevin happened to live in Southie. So they put him up in a hotel for a couple weeks after the story ran.

That's insane.
It is insane. It's insane that the messenger is the FBI. I mean, it'd be one thing to get a call from a gangster warning you. That'd be scary. But when it's the FBI, that sort of adds another dimension to it that's like: "Whoa. The world's upside-down."

Wow. Why did you and Gerard O'Neill decide to write Black Mass, and how much more comprehensive was it of a look at Whitey Bulger's relationship with the FBI than your original reporting?
Well, it was hugely more comprehensive, which is why we wanted to write a book. We really felt we had enough here to tell the story—an important story, because this is the worst informant scandal in FBI history—and through the telling, try to analyze and explain why this happened, how it happened, how it got started, and then how it got incredibly off-track, and everything went so horribly wrong.

How did Black Mass wind up being adapted into a film?
The short version is that even before it was a book we had published, our publisher had sold the move rights to Harvey Weinstein and his Miramax company. So it has always been in what they call "development," since day one, but it's 15 years later before the movie is finally made. Miramax dropped it and it got picked up by another producer/director named Robert Greenwald, who has a fairly prominent name, and he was going to do a six-hour cable thing on it.

That ended up fizzling, but waiting in the wings was a young producer named Brian Oliver who was just at the front-end of his career. When the rights became available in '06, he optioned it. And then he hired a screenwriter and he got a script going, but he struggled, and it never got off the ground. Then [Oliver's] career changed, and I think this was the big turning point. He produced Black Swan, and that was a monster hit. He suddenly had a lot of juice.

Once Whitey was captured in 2011, [Black Mass] took on a new life: polishing the script, getting a director. First it was Jim Sheridan who might direct it, or Barry Levinson; Johnny Depp wanted to play Whitey—all this stuff started to happen. I think Brian Oliver deserves the most credit in terms of seeing it early, staying on it, determined to make it, and he did. He partnered up with Warner Brothers, and they made it a major-studio picture.

What role did you play in the production of Black Mass?
Whether it was on-set or answering the phone, whenever anyone had a question about the story, we consulted. We always made it clear that we sure hoped they didn't turn Whitey into the myth of Whitey, try to sanitize him, and buff him up into somebody he's not. He's a horrible killer, a monster. That was our worry, and that's the one thing we ask, is to be true to that, to the story, the black mass.

How closely does the on-screen adaptation resemble what actually went down in those 20 or so years?
I don't keep track of it. Because I understand that for dramatic, film purposes, you're going to rearrange the time a little bit, you're going to compress characters, things like that. They have to invent dialogue. There's no way we ever had access to Whitey talking about his son, for example.

This story spans at least 20 years. The movie's two hours. Things have to change for the movie. I get that—I can put my arms around it intellectually. But still, as a journalist, part of me wishes everything could be as accurate as we know the story to be.

I really think the standard to judge it is: Is it true to the spirit of the story? And in that, I think Johnny Depp nails Whitey Bulger, really captures his character, and all that we know about him.

Did you ever interact with Johnny Depp? What was that like?
That was interesting. There was a first meeting that just seemed like, "Whoa, this is strange." When he was on set, he was in some strange place between himself and Whitey. But yeah, a whole bunch of times. We had story meetings, and we were talking about how to play this scene, me and the director and all the producers and Johnny. It just became part of the creative, consulting work, and that was kind of neat.

He never played the prima donna thing. I don't know how often they do this, but I happened to be on set his last day, and when they were done for the day, he ended up giving a speech to everybody, saying, "There are a few movies that you never want to stop making. This is one of them." Everyone gave this big applause, and all these hugs. It felt pretty special to him, and that was interesting to observe.

I'm sure that some things in the movie are exaggerated, but the tale itself, the truth, is pretty disturbing. And it seems to only get worse as the story goes on. I imagine as you're learning more and more about this, the journalist in you is ecstatic—you're getting all this great information, it's getting more complex, dirtier—but then the person in you, that just had to be pretty horrifying to be learning all that.
The dark truth about this is horrifying. You get really worked up realizing that this wasn't a single instance in time, a single case that went sour in terms of investigation, but that this was a way of life that went on for several decades, this culture of corruption. And it caused harm that could be calculated, that could be quantified. Murders. But there's also incalculable harm to the city, to justice, law enforcement, to the public, to the FBI as an institution. It's just so big, because it went on for so long. That's pretty scary, and that's the thing that always has given me pause: How did something like this go on for so long, and bleed in so many directions?

What kind of effect did that have on you during the reporting of it all?
Journalists are trained to be skeptical, but there's a level of disbelief that an agency like the FBI—which is supposed to be the nation's top law enforcement agency—could be so corrupt, institutionally, for so long. This is an informant scandal, but the FBI's had other scandals as well. I mean the Bureau's done a lot of good things in terms of public safety, but it is kind of scary that throughout its history, with disturbing regularity, there are these major, major scandals.

How did reporting this story and writing this book change your life? I imagine that at the very least, in terms of your career, it was a pretty big shift?
I don't know if I can assess it. All I can say is, this was one of the biggest stories that I was in and out of my career, and one of the most important ones I've worked on. But there are others I feel almost as strong about. It is in that category of, "OK, this is what journalism is all about. Making a difference." And I was part of a reporting team that, I think, has made a difference in terms of the public understanding, and the exposing of something that was really, deeply wrong. In that way, it's been really important.

Follow Drew on Twitter.

Black Mass opens Friday, September 18 in theaters nationwide.