The Brother Bulger

WE ARRIVE AT CASTLE ISLAND, A BULGERITE REDOUBT if there ever was one, and stake out a bench overlooking the water. Bulger launches into a well-worn John Boyle O’Reilly poem, “In Bohemia,” a bit of doggerel about a land where “only there are the values true / And the laurels gathered in all men’s view.” “Curley used to wear all that stuff out,” Bulger says, referring to James Michael Curley, the legendarily orotund Boston mayor, Massachusetts governor, and occasional inmate. Recycling is something Bulger himself is routinely criticized for, and when I point that out, he rolls out another recycled line. “Oh, I do, I do, all the time. It’s terrible. I tell the same jokes. If they were looking for something new, I’d say, ‘Hey, does Frank Sinatra change the lyrics? No. So stop your squawkin’.’ Because Carr accuses me of that, doesn’t he?” Pause. “What does he have on me? Anything real?”

I tell him the gist of The Brothers Bulger: that he worked behind the scenes to help keep law enforcement off his brother’s back, and in return Whitey intimidated his political enemies, such as Bill Keating, the state senator who spearheaded the failed mid-’90s “insurrection” against Bulger for the Senate presidency, and Harold Brown, the developer who alleged he bribed Bulger’s law partner Thomas Finnerty—who then turned around and loaned $240,000 to Bulger—in the 75 State Street scandal in 1986 but later withdrew the charge.

“Oh, we’re a team, we’re a team,” Bulger says.

There are distinct takes on Bulger’s silence on Whitey. His supporters believe that they’re two totally separate people; their lives may have overlapped at points, but that was just Southie, a small town where everyone knew one another. His foes believe his silence is deliberate, that he’s hiding something. Somewhere in the middle are those who believe that Billy didn’t actively collude with his brother, but still benefited from people thinking he might have, as a way of preempting any potential challengers. “They’re free to speculate,” says Bulger. “Of all the things I should be feeling guilty about is that I had so little to do with—I could have tried to influence him. But you know, you couldn’t get a conversation going.” He adds, “All sorts of people did recognize that I was living my own life, and I could only be responsible for what I did, I can’t be responsible for someone else, an adult. I can’t.”

Even if all the allegations are false, as he maintains, Bulger’s reluctance to talk about his brother with the press has effectively forfeited control of the narrative, and by extension, his legacy: Anytime someone mentions Billy from now on, Whitey’s name is sure to follow. “There’s nothing I can do about it,” he says.

Bulger’s not the only one to suffer for what Whitey did, of course. So did his whole family, including his younger brother Jackie, a former clerk magistrate in the juvenile court who went to prison for protecting Whitey and later lost his state pension because of it. Entire swaths of Southie were ravaged by the crime Whitey brought into the neighborhood, as well. “Yeah,” Bulger says, “but you can’t look across the planet very far without seeing all sorts of people who are confronted by hardships and suffering that’s not of their own making. So what do you do? You bear with it. You bear up under it. That’s all you can do. And they always are trying to do something to condemn him. I’m not doing it. I’m just not doing it.”

So is Whitey not worthy of condemnation?

“Of course,” says Bulger. “But that’s not the question. That’s a different question. You have to be smarter than that, than to say that because I will not engage in condemnation that I don’t think it’s worthy of condemnation. I’m not going to satisfy the mob. I’m not saying anything about it, other than it’s another person.”

Bulger acknowledges that his reticence regarding his brother is “a source of anger and frustration” for people. I suggest that’s true not just for his critics and law enforcement officials, but also for his supporters. When people discuss the Bulgers, one question that often comes up is, What would it be like if I had a brother who was a mass murderer?

“But they don’t, do they?” Bulger says.

What if people just want to know how he feels about it?

“They can figure it out. I would be opening up a topic that I could never stop talking about.”

Bulger sighs. He looks completely spent. After a moment, he steers the conversation back to safer waters, recalling the time he upbraided Alan Dershowitz and lawyer Harvey Silverglate before the Governor’s Council back in 1990. Bulger’s longtime aide Paul Mahoney was up for a judgeship, and Dershowitz had attempted to block it on the grounds that the mild-mannered Mahoney was a “thug” and a Bulger “henchman.” At the council hearing, Bulger thrashed the pair, calling them “very manipulative and exceedingly crafty,” “true connivers,” and “murderers of reputations.” Dershowitz responded by denouncing Bulger for using anti-Semitic code words.

“I said, ‘This is a very crafty, crafty man,’” Bulger says. “I know the word, I’m deliberate about it. If we’re ‘thugs…’. But the fun of bracing him—you think that’s pretty mean of me?” As he says this, he winks a lightning-fast wink. It’s remarkable: The only part of his face that moves at all is his eyelid. It’s done for the same reason anyone winks, to convey wryness and warmth, but executed in such a way that, if pressed, he could easily deny it later.

Bulger’s enjoying himself now, but there’s still a hint of wistfulness about him. “I think of most of it as being pretty far behind, increasingly,” he says. “But I’m fortunate, because I’ve enjoyed it all. I think of someone like Carl Thayer [his mentor at BC]. He said, ‘Don’t ever get caught up in who approves or disapproves. It’s enough that you know.’ He used to have this expression—it’s so pious—but he wrote, ‘God knows the heart.’ I like that, even though I’m not sure God’s paying much attention.”

Later, Bulger stops to entertain a dozen older townie supporters hanging out on a couple of benches. “What is this, a work-release program?” They lap it up—“You betcha, Bill!”—and it clearly reinvigorates him. A woman with a black bouffant and a pink Sox T-shirt stops him to say how the St. Patrick’s Day Breakfast, a once riotous affair now descended well into its baroque period, just isn’t the same without him.

“They’re not doing a good job like you did a good job,” she says, patting his arm.

“That’s a very common complaint,” Bulger says.

He’s feeling good, “kiddish,” as we walk back to the car. “Sometimes I think about running again,” he says. “Just to get everybody’s ass. But I don’t know if that’s wise.”