Whitey Bulger trial: A tip from Boston bookmakers—you better pay Whitey, or else.

A tip from Boston bookmakers—you better pay Whitey, or else.

J.W. Carney, left, and Hank Brennan, both attorneys for Bulger, spoke to reporters after the opening day of the trial.

J.W. Carney, left, and Hank Brennan, both attorneys for Bulger, spoke to reporters after the opening day of the trial.

Photo by Wendy Maeda/The Boston Globe via Getty Images

8:45 a.m.: Whitey is wearing a powder-blue Henley today. He clearly has a stack of these shirts in a rainbow of hues. I guess we can add a third item to the list of self-presentational Bulger themes: 1) He doesn’t rat. 2) He doesn’t kill women. 3) He hates collars.

9 a.m.: The prosecution calls James Katz. Katz is 72 years old, gray-haired and slight, and he clutches his liver-spotted hands as he sits on the witness stand. When the Whitey movie comes out (and there will be a movie—be it the Barry Levinson project, the Damon/Affleck project, or whatever it is Robert Duvall is cooking up), I expect Ben Stein will win the Katz role.

Katz explains that he was a bookie in Boston from the early ‘70s until the early ‘90s, when he got pinched by the feds. As his testimony begins, he’s asked to describe his bookmaking business in minute detail. He tells us the vigorish, or “juice,” was 10 percent on the bets he took, so gamblers paid $110 to bet $100. He says a “layoff” is when a bet is too big, or too many gamblers bet on the same outcome, so a bookie lays off some of the action on another bookie to share the risk. He defines a “makeup” as when a lower-rung bookie loses a bet, and an upper-rung bookie covers the loss until it can be made up.

At a certain point, Boston wiseguys realized they didn’t need to take bets themselves. They could just shake down all the local bookmakers for “rent.” Whitey’s gang charged Katz $1,000 a month during football season for the privilege of taking bets, and $500 a month in the offseason. Katz paid up. If he’d refused? “You would get in trouble one way or another,” he testifies. “You could wind up in the hospital, let’s put it that way.” Later, he adds, “There were a lot of beatings.”

(Katz often delivered his rent to one of Whitey’s crew at the B&D Deli on Beacon Street in Brookline, which was literally around the corner from the house I grew up in. I used to eat breakfast there with buddies every Friday morning before high school. The B&D is long gone now, and dearly missed—I’m going to pause here to pour out some egg cream for old times.)

Katz was indicted for money laundering in 1992 when the law began to close in on the Boston organized-crime rackets. There was a massive paper trail. Some of Katz’s customers couldn’t pay cash—especially those who lived out of state and didn’t want to mail currency—so he let them write checks made out to names like Babe Ruth and John Hancock. Katz would bring these to a friend with a check-cashing business and endorse them over. “I’d just sign Babe Root,” he explains now with a laugh. Millions of dollars in bank checks with fictitious names, sent by FedEx across state lines, means a passel of legal troubles.

At first, Katz refused to chirp to the feds. “If I were to testify,” he says now, “I doubted my safety. I was afraid. I knew that the people I would testify against”—meaning Whitey and his boys—“could even reach me in jail.” (I note that Katz still seems terrified of Whitey, who is right now sitting about six feet away from him in the courtroom. When asked to identify Whitey, Katz quickly waves his hand in Bulger’s direction and meets his steely eyes for a nanosecond before flinching and looking away.) But the prosecutor had threatened to take Katz’s house, putting his wife and three daughters out on the street. So he talked. And then he and his family went into the witness protection program.

10:01 a.m.: The defense cross-examines Katz. And like every witness in every trial who’s ever talked to the government in exchange for a reduced sentence, Katz is now accused of lying—of telling the prosecutors what they want to hear, implicating Whitey Bulger—to save his own keister and get out of the clink. Defense attorney Carney paints a picture for the jury of Katz in prison, facing a four-year sentence, $1 million in fines, and a life of emptiness and ennui.

“Were you lonely in prison?” asks Carney.

“I’m a grown man,” says Katz. “I wouldn’t use the word lonely.”

“Was your wife lonely?”


“Was there anyone in prison to gently touch your arm?” asks Carney. Katz’s eyes pop and several courtroom observers titter. “The kind of touch on your arm your wife might make, gentle and loving?”

At this point, I am thinking we are about to get some fascinating insights into either James Katz’s prison life, Jay Carney’s interior emotional landscape, or, ideally, both. But Katz disappoints.

“I don’t know where you’re going,” says Katz, “but there was nobody like my wife in prison.”

12:01 p.m.: Katz is excused, his testimony done. I look around the court and wonder if anyone here would be willing to touch my arm in a gentle, loving way.

12:02 p.m.: My arm remains untouched, yearning for a wifely caress. Meanwhile, the prosecution calls Richard O’Brien.

Dick O’Brien is another Boston bookmaker, even older and frailer than James Katz. At 84, he still seems tough as nails, but he’s moving a little slower. When the judge addresses him over her microphone, he looks around with a start and asks in bewilderment, “Who’s speaking to me?”

Like Katz, O’Brien paid tribute to Whitey and his gang for the right to take bets. He had no choice. Why not? “They were very capable,” he explains. What does that mean? “Well, there was a gang war in South Boston, people were shot, and Mr. Bulger ended up on top. You can draw your own conclusions.”

One bookie O’Brien knew tried to “go his own way” and not pay rent. O’Brien watched Whitey set him straight. “Mr. Bulger told him, ‘We have another business besides bookmaking,’ ” says O’Brien. “ ‘It’s killing assholes like you.’ ” I turn to Whitey to watch his reaction. He explodes into a guffaw. Either he’s attempting to express disbelief or he’s enjoying the memory.

Another time, O’Brien sat outside a room as Whitey talked sense into yet another bookmaker. When the bookie came out, “He asked me, ‘Will you drive me someplace so I can get a drink?’ ”

O’Brien paid his rent, up to $2,000 a month, for 14 years without fail. “I valued my own life,” he explains.

When O’Brien retired, he left the bookmaking business in the hands of his daughter. But Whitey’s associate Stevie Flemmi still came down to Florida, where O’Brien had settled, to make sure he wouldn’t rat like others had. “I should have taken care of him,” Flemmi said of another bookie who turned, “when I had the chance.”

“I knew what he meant,” says O’Brien. “He meant there wouldn’t be any witnesses.”

1 p.m.: Court ends for the day. O’Brien will be back on the stand Monday morning. If I were him—even though he’s not taking bets anymore—I might deliver a little rent to Whitey in his prison cell over the weekend. You know, just in case.