Ex-bookie recalls ‘Whitey’ Bulger’s veiled threat

Richard O’Brien (right), left the US courthouse Friday after testifying in the racketeering trial against Bulger.
Wendy Maeda/Globe Staff
Richard O’Brien (right), left the US courthouse Friday after testifying in the racketeering trial against Bulger.

A retired bookmaker held jurors spellbound Friday as he recounted how an intimidating James “Whitey” Bulger mediated a dispute decades ago between the bookie and a worker who had the audacity to default on gambling debts.

The bookmaker, Richard O’Brien, now 84, said he was paying monthly “rent” to Bulger, who called a meeting at a bar in the mid-1970s after learning that one of his agents, George LaBate, had walked away from his job without paying thousands of dollars in gambling debts.

“It was a no-no in the business,” said O’Brien, and Bulger was not pleased that LaBate had gone to work for another bookmaker, presumably one who wasn’t under the South Boston gangster’s protection.


As they sat drinking coffee at the bar, Bulger politely pressed LaBate about whether O’Brien had treated him all right. When LaBate conceded that he had, Bulger asked, “What are you doing? You owe him a big amount of money. That isn’t right.”

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LaBate promised to pay up, saying, “I’ll take care of it and go my own way.”

“Oh, you’re going to go your own way?” said Bulger, asking LaBate if he was aware that his gang had another business besides bookmaking.

“What’s that?” LaBate asked.

“Killing [expletives] like you,” Bulger said.


The anecdote, told enthusiastically and in rich detail by one of his old contemporaries, prompted Bulger to erupt in spontaneous, soft laughter. It was the first display of emotion by the 83-year-old since testimony began Wednesday in his racketeering and murder trial in US District Court. Seated at a table between his two lawyers several feet from the witness box, Bulger has appeared solemn, staring straight ahead most of the time, avoiding eye contact with anyone in the courtroom.

But during the Friday session, Bulger’s eyes kept drifting toward O’Brien, now a Florida resident with a shock of white hair, who looked as if he could have just stepped off a yacht with his navy-blue blazer, brass buttons, and red-striped tie. His reminiscence brought Bulger, and the courtroom, where relatives of some of his 19 alleged victims sat, back to an era when the gangster’s reputation instilled fear.

O’Brien recalled a time in the 1960s, after he left Boston University to follow his father into the family bookmaking business, when the late New England Mafia don Raymond L.S. Patriarca personally intervened as other bookmakers tried to steal his business. He said he gave monthly payments, known as rent, to the local Mafia for years, then became independent, not paying anyone, when a wave of federal prosecutions left the Boston mob in disarray.

Then in the 1970s, O’Brien testified, he was among a group of bookmakers who were summoned to a meeting with the Winter Hill Gang at Kimberly’s bar on Wollaston Beach in Quincy. He said Bulger showed the bookmakers an article in the now-defunct Boston Herald American that said people in South Boston were rounding up South Shore bookmakers.

O’Brien said Bulger, referring to the Mafia, told the bookmakers, “Forget the North End; if you want to be in business you’re with us.”


Bulger’s reputation had preceded him, said O’Brien. “There were gang wars in South Boston, people were shot and Mr. Bulger ended up on top. So you can draw your own conclusions.”

O’Brien said he paid rent to Bulger and his partner, Stephen “The Rifleman” Flemmi, from 1978 to 1992, initially about $200 a month and eventually as much as $2,000 a month. But he said he was frequently required to pay surcharges to cover costs the gang incurred if someone was arrested or caught on a wiretap.

On one occasion, O’Brien said, he was ordered to bring another bookmaker to a garage on Lancaster Street in Boston for a meeting with Bulger and Flemmi. O’Brien said he was told to wait outside, but he knew the other bookmaker was frightened because after the meeting he asked, “Will you drive me someplace so I can get a drink?”

The story drew amusement from Bulger, who chuckled softly, then quickly covered his mouth.

Bulger, who was captured two years ago in Santa Monica, Calif., after 16 years on the run, is charged in 32 counts of a racketeering indictment that includes allegations that he participated in 19 murders, extorted bookmakers, drug dealers, loansharks, and businessmen, laundered criminal profits, and kept an arsenal of weapons.

Earlier Friday, another bookmaker, James Katz, 72, testified that after being sentenced to four years in prison for gambling, money laundering, and wire fraud, fined more than $1 million, and ordered to serve another 18 months for contempt, he agreed in 1994 to cooperate against Bulger. In exchange, the government reduced his sentence to probation and put him in the federal witness protection program for two years.

Katz said he made monthly payments of $1,000 during football season and $500 a month the rest of the year to people associated with Bulger, most of the time to Flemmi.

Katz said he only met Bulger once, but knew of the Winter Hill Gang’s reputation. “In those days, it was murder and a lot of beatings,” Katz said.

Milton J. Valencia of the Globe staff contributed to this report. Shelley Murphy can be reached at Follow her on Twitter @shelleymurph.