Dick O'Brien was a Boston bookmaker. He learned the business from his father and learned it well. Dick O'Brien paid his debts fast and for that he got a lot of action. He had at least 30 agents under him at any given time and kicked up to the Italian mob.
"You're by yourself now?"' O'Brien recalled Bulger asking him.
"I said yes," O'Brien said. "He told me 'You should be with us.'"'
"I said I was 'with the North End,'"' O'Brien said. "He said, 'Forget the North End, you're with us. If you want to be in business, you're with us.'"'
A prosecutor asked O'Brien if he felt he had a choice in Bulger's demand.
"No, like I said, his reputation preceded him," O'Brien told the court.
That reputation, jurors heard from bookies, was a murderous one. So for the next 14 years O'Brien paid "rent" to what prosecutors claim was Bulger's Winter Hill gang in varying amounts from $200 to $2,000 with surcharges added for wiretap sweeping and lawyers. In exchange, Bulger would "straighten out" any of his agents that didn't want to pay.
O'Brien described bringing one agent that owed him money to the Lancaster Street garage where Bulger held court , the same garage where Massachusetts State Police efforts to bug were thwarted by the FBI, two former state police commanders testified this week.
"The guy had run up a considerable amount of make-up [money owed] and then for reasons only known to him he disappeared, stopped calling. That's a no-no in the business. You don't just get paid thousands of dollars and throw your hands up and walk away,"' O'Brien testified.
O'Brien said brought the agent to Lancaster Street to meet with Bulger. There Bulger scowled at the terrified agent saying: ""You know we have a business that's not bookmaking too?" And he responded 'What's that?' Bulger said 'Killing a**holes like you," O'Brien testified.
Bulger snickered when O'Brien recalled the threat.
The third day of testimony in the Bulger case centered around two elderly bookmakers – O'Brien, 84, and James Katz, 73, who said he, too, paid rent to the Bulger gang.
Bulger, 83, is being tried on a 32 count indictment charging him with racketeering, bookmaking, money laundering, weapons charges and 19 murders.
"You had to comply,"' Katz testified. If you didn't you could "wind up in the hospital."
Katz added: "At that time there were a lot of murders and beatings."
Defense attorney J.W. Carney worked to discredit Katz by ticking off a list of roughly two dozen Boston mobsters prosecuted with the help of Katz's testimony in order to gain his freedom. With each name read Carney asked Katz if he had provided information against the person. With each name, Katz answered: "Yes."
Carney then pointed out that the cooperation earned him a new apartment courtesy of the federal government, which spent $85,000 relocating Katz and his wife.
"That's the money they spent on me to get me situated, an apartment, furniture," Katz said.
For the third day in a row Bulger was stone-faced throughout much of the testimony. At one point O'Brien grinned when asked if he saw Bulger in the courtroom. He pointed and said, "Yeah, he's right there."
"Whitey" Bulger Depicted as Fearsome Murderer
Cross-examination of O'Brien will start Monday's court proceedings in the Bulger case, which is coming 18 years after he was indicted. Prosecutors said that he was tipped off to a looming indictment by a corrupt FBI agent John Connolly. Among the witnesses expected Monday is confessed hitman John Martorano.
O'Brien said whispers about the Boston FBI's relationship with Bulger started in the 1990s. He described Bulger asking him if he could "get his friend a good deal on windows." O'Brien had connections and did, but was surprised to learn the windows were being installed in a condominium owned by FBI agent: John Connolly.
"I was sort of raising my eyebrows at that one, but we put the windows in," O'Brien testified.
Still, O'Brien didn't trust the Boston FBI so when he on his way to a meeting with Bulger henchman Stevie Flemmi in Florida he told his daughter:
"If I'm not back in 12 hours, go to the FBI in Miami. Don't go home to the FBI."