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    Kevin Cullen

    Courtroom tales bring Whitey’s reign of fear into focus

    For the first few days of his trial, Whitey Bulger had been sitting at the defendant’s table wearing bad clothes and a blank expression. He looked like some guy waiting for a bus at South Station.

    But on Friday he smiled. He smiled at Dickie O’Brien, a bookie he used to shake down.

    Dickie is 84 now and arrived at the federal courthouse in a wheelchair. But he still has his fastball and told some great stories, stories that even made Whitey smile.


    Dickie grew up in Quincy and his dad was a bookie, so he was a bookie. Father and son had an office in the South End, and they had a team of agents who took bets all over town. But the guy they used to lay off their bets to got pinched and sent to prison, so a buddy told Dickie O’Brien to go see one Raymond L.S. Patriarca in Providence.

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    Patriarca was the head of the New England faction of that fine fraternal organization known as La Cosa Nostra, more commonly the Mafia.

    “It was a short meeting,” Dickie recalled. “It was the day Jimmy Hoffa got arrested and they were up in arms.”

    As upset as he was about the arrest of his favorite Teamster, Patriarca carved out some time for the earnest young Irish bookie. He was so impressed with Dickie that he set up a meet for Dickie with the Angiulo brothers, who ran the North End of Boston for the Mafia.

    They met at Jerry Angiulo’s bar, Jay’s, but Jerry wasn’t there. Instead Dickie met with Peter Limone and Larry Baoine.


    “Larry was a very capable man,” Dickie said, capable meaning Larry was capable of killing anyone at the drop of a hat.

    The Mafia guys were more than willing to take Dickie’s lay-off bets and, as he put it, “if there was a problem they would straighten it out.” Meaning if anybody gave Dickie any trouble, the Mafia would kill them.

    But everything went pear-shaped when all the Italians in the North End got lugged. Peter Limone and three other guys were framed by the FBI for a murder they didn’t do.

    “Peter served 30 years,” Dickie told the prosecutor, Zach Hafer, and the rest of us.

    So Dickie was independent, but not for long. Some guy called him and said he had to meet some guys at Kimberly’s, a bar in Quincy that had its share of wiseguys. So Dickie walks into Kimberly’s and he’s staring at the Winter Hill Gang: Howie Winter, Johnny and Jimmy Martorano, and Whitey Bulger.


    At this point, Hafer asked Dickie to identify Whitey. Dickie pointed to the defendant’s table and he smiled and Whitey smiled. They know the drill.

    At that meeting in the 1970s, Whitey told Dickie, “You’re by yourself. You should be with us.”

    “I was with the North End,” Dickie replied.

    “Forget the North End,” Whitey told him. “You’re with us.”

    It wasn’t negotiable.

    “Their reputations preceded them,” Dickie said, which means they killed people who defied or angered them.

    So Dickie was with the Hill. Not that they did anything for him. If somebody didn’t pay him, that was his problem. They just collected rent from Dickie.

    One of Dickie’s bookies got too ambitious. “I’ll go my own way,” he said.

    Whitey told the ambitious young bookie he could not go his own way. “We have a business beyond bookmaking,” Whitey told the ambitious young bookie.

    “Oh, yeah,” the guy replied. “What’s that.”

    “Killing [expletives] like you,” Whitey replied.

    The guy changed his mind and kept paying Whitey rent.

    Whitey was cute, Dickie said. Whenever Dickie delivered the rent, Whitey wouldn’t pick it up in Dickie’s presence. Dickie would leave it on a table at Triple O’s, the dive bar on West Broadway in Southie that Whitey used as his lair, or the liquor store down at the rotary across from the Old Colony projects. If Stevie Flemmi, Whitey’s partner in crime, was there, he’d pick up the money. Whitey never did. Cute.

    Dickie paid Whitey and Stevie rent for 14 years, topping off at $2,000 a month, until he moved to Florida in 1993.

    But he wasn’t done with them. One of Dickie’s six daughters took over the bookmaking business; like father, like daughter. His daughter was going out with a guy who worked at Steve Flemmi’s bar. The guy flew down to Florida and told Dickie O’Brien and his daughter to be very careful, because a bunch of bookies in Boston had rolled on Whitey and Stevie and were going before a grand jury.

    Obviously, the fear was that Dickie O’Brien might roll, too.

    So one night, Dickie’s wife is giving a speech at the local PTA in Florida and she looks up and who’s looking at her but Johnny Martorano, the Winter Hill hit man who had gone on the lam 15 years earlier. Johnny said they needed to have a meet with Stevie Flemmi. Dickie was unnerved, but at least Johnny would be with him.

    “I liked John,” Dickie O’Brien said. “I considered him a friend.”

    But Dickie wasn’t stupid.

    Before he left for the meeting with Stevie, Dickie O’Brien told his daughter, “If I don’t come home, go to the FBI. Don’t go home. Go to the FBI.”

    Actually, if Steve Flemmi killed Dickie O’Brien that night, going to the FBI would have been a waste of time. They were still busy covering up for their informants, Whitey and Stevie.

    “That goddam Chico,” Flemmi complained to Dickie O’Brien about Chico Krantz, the biggest bookie in Boston who became a government witness. “He turned over. I should have taken care of him when I had the chance.”

    Dickie spent the meeting trying to reassure Flemmi that he was the last person who would turn on them. Basically, Dickie O’Brien asked them to trust him, asked them not to kill him.

    At that very moment, from the stand, Dickie O’Brien looked at Whitey Bulger.

    And Whitey wasn’t smiling anymore.

    Kevin Cullen is a Globe columnist. He can be reached at