June 14, 2013

Witness brings smile to ‘Whitey’ Bulger, tells of extortion

Bookmaker Dickie O'Brien says he had to Bulger's gang a monthly stipend because, “I valued my own life, as well as those with me.”

By EDMUND H. MAHONY The Hartford Courant

BOSTON — James “Whitey” Bulger, whose racketeering trial continues to be the best show in town, finally flashed a smile from his seat at the defense table Friday, although it was unclear from the context whether Bulger found one of his accusers amusing or was simply recalling better times.

click image to enlarge

This courtroom sketch depicts James "Whitey" Bulger during the first day of his racketeering trial in U.S. District Court in Boston, Wednesday, June 12, 2013. At right is defense attorney J.W. Carney, Jr. Bulger faces a long list of crimes, including extortion and playing a role in 19 killings. (AP Photo/Margaret Small)

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, Mass., 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.

He said he once dragged a business associate who owed him thousands of dollars to a meeting with Bulger. After some sharp words from Bulger, the associate agreed to a prompt repayment. But the associate wanted to leave the meeting with some dignity. He told Bulger that after the debt was paid, he would run his own business, however he chose to run it.

“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.

(Continued on page 2)

Were you interviewed for this story? If so, please fill out our accuracy form

Send question/comment to the editors




Further Discussion

Here at PressHerald.com we value our readers and are committed to growing our community by encouraging you to add to the discussion. To ensure conscientious dialogue we have implemented a strict no-bullying policy. To participate, you must follow our Terms of Use.

Questions about the article? Add them below and we’ll try to answer them or do a follow-up post as soon as we can. Technical problems? Email them to us with an exact description of the problem. Make sure to include:
  • Type of computer or mobile device your are using
  • Exact operating system and browser you are viewing the site on (TIP: You can easily determine your operating system here.)