Witness Brings Smile To 'Whitey' Bulger, Tells Of Extortion

By EDMUND H. MAHONY, emahony@courant.com

The Hartford Courant

7:01 PM EDT, June 14, 2013




The witness was Richard "Dickie" O'Brien, an understated, south shore bookmaker, now 84 and retired to Florida. With his blue blazer, buttoned-down collar and striped tie, O'Brien looked as if he might have arrived in federal court from the yacht club.

The government called him to testify about events in the early 1970s, which was when news reached Bulger's Winter Hill Gang that O'Brien was running his Quincy office independently, meaning that he had been freed by a series of arrests from paying protection, or rent, to Boston's Italian mob, sometimes referred to as The North End.

"Mr. Bulger wanted to talk to me," O'Brien said. "He said, in so many words, 'You are by yourself now.' And he said, 'I think you should be with us.' I said, 'Well, I was with The North End.' He said, 'Forget The North End. If you want to be in business, you are with us.' That was put down as law."

O'Brien said he knew he was not being presented with a choice. He began paying Bulger's gang what would become $2,000 — and in many cases substantially more — every month, until O'Brien himself was arrested in the late 1990s.

"Of course, I had heard about them because their reputation had always preceded them, that they were very capable," O'Brien said.

"What do you mean by capable?" Assistant U.S. Attorney Zachery Hafer asked.

"They had a gang war in South Boston and people were shot," O'Brien said, "And Mr. Bulger ended up on top. You can draw your own conclusions."

"Why did you agree to pay rent?" O'Brien was asked.

"I valued my own life," he said, "as well as those with me."

O'Brien was no newcomer to the gambling racket. He inherited the business from his father and passed it on to a daughter when he retired. Once, when summoned to a meeting with a Bulger associate, O'Brien said he ordered his daughter to call the FBI's Miami office if he was not back in 12 hours. He said he had became suspicious of agents in the Boston office after learning that Bulger was providing sliding glass doors for a home owned by a Boston agent.

But despite O'Brien's apparent distaste for Bulger's violence, he benefited, more than once.


"You are going to go your own way?" O'Brien recalled Bulger saying. "You know, we have a business besides bookmaking. And (the associate) said, 'What's that?' And Mr. Bulger said, 'Killing a..holes like you.'"

Over the opening three days of his trial, Bulger's expression, when visible to the public, has been something between bored and distracted. O'Brien's crack made him laugh, although it was not clear why.

O'Brien and another retired bookmaker, James J. Katz, gave hours of testimony that supported the government's contention that Bulger was part of a racketeering conspiracy that used threats and violence to extort millions of dollars of rent payments from dozens of bookmakers for more than three decades, beginning in the 1970s.

He is accused in the indictment against him of collecting millions more by extorting payments from drug dealers. He is accused of laundering the money in real estate or using it to bribe law enforcement officers. He is charged additionally with participating in 19 murders, four of which were part of the gang's attempt at a hostile takeover of the parimutuel business World Jai Alai in the early 1980s.




The plan, which ultimately succeeded and is responsible for Bulger's trial, was to hit the bookmakers whose extortion payments were a major source of Winter Hill income. The investigators hoped to pressure bookies to cooperate by threatening them with hefty fines and long sentences for gambling and financial crimes.



"I knew that the people who I would testify against had reach," Katz testified Friday. "They could even reach me in jail."




Bulger's lawyers are expected to cross-examine O'Brien when the trial resumes Monday. The government indicted O'Brien on charges of perjury and obstruction of justice before he agreed to testify against Bulger.


Flemmi wasn't around, he said, when Bulger imposed rent payments on him. He was, as O'Brien put it, "on the lam" in Canada. Tipped off by a friendly FBI agent, Flemmi fled an indictment accusing him of setting a car bomb that crippled a lawyer for a government witness.

But later, O'Brien said, Flemmi proved helpful. O'Brien dragged another debtor he identified in court as "Timulty" to a meeting with Bulger and Flemmi. O'Brien said that Bulger and Flemmi took Timulty into an office and asked O'Brien to wait outside.

Timulty emerged, shaken, sometime later.

"He said, 'Will you drive me somewhere where I can get a drink?'" O'Brien said. "And I said, 'Certainly.'"