Former Boston Bookie Takes Court Back In Time In Bulger Case

Former Boston Bookie Takes Court Back In Time In Bulger Case

James “Whitey” Bulger (aged 83) was the leader of the Winter Hill Gang in Boston for years before going on the run in 1994 after an FBI agent let him know that the agency was on to him in regards to a pending RICO Act (Racketeer Influenced and Corrupt Organization Act) indictment. The Winter Hill Gang was an Irish crime group established in the 1950s which Bulger took over in 1979. His federal case—based on his involvement in the deaths of 19 people as well as several other charges—began this week and today saw former Boston-area bookie Richard O’Brien (aged 84) testify for the prosecution of Bulger’s involvement with the gang as well as to his character. 

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Richard O’Brien went into one incident involving Bulger and someone who owed him money. After scoffing at the notion of paying Bulger, the former crime boss told the man “We have a business besides bookmake.” When the man asked what business it was, Bulger supposedly answered, “Killing **** like you.” Bulger laughed at the recollection as if hearing a humorous story from the good old days. O’Brien also went into how he came about being a part of the Winter Hill Gang saying that he was an unaffiliated bookmaker—meaning he had no links to any particular group. He stated that Bulger said to “Forget the North End,” and that if he wanted to remain in business he would have join them. “Their reputation preceded them.” O’Brien said of the Winter Hill Gang.

O’Brien said in the 14 years he worked with Bulger, he paid the group roughly $2,000 a month in case as rent saying that he valued his life and those with him—friends and loved ones. Sometimes he would pay more because since Bulger and his partner Stephen “Rifleman” Flemmi would impose “taxes” for a number of arbitrary reasons. Bulger got the money through Flemmi to keep his own hands clean suggested O’Brien.

He left the business—and his association with the Bulger’s group—in the early 1990s. The bookmaking firm was left in the hands of one of his daughters.  A few years later while staying in Florida he said that he was called back to Boston for a meeting with “Rifleman” Flemmi. The premise of the meeting was to discuss rumors of a “father and daughter team”—obviously meaning he and his daughter—talking with the FBI about their activity. Before heading into the meeting he told his daughter, “If I’m not back in 12 hours go to the FBI in Miami. Don’t go home (Boston). Don’t go to the FBI there.”

It’s expected that Richard O’Brien will continue to testify today. Bulger’s legal team is looking to paint the FBI and federal prosecutors unfavorably by saying they allowed for Bulger to act as he wished and were in league with him. Massachusetts State Police Colonel Thomas Foley (retired) mentioned that the FBI ran a shoddy ship and that the agency “put a higher priority protecting their informants,” than public safety.

During cross defense attorney Hank Brennan asked Foley about how legitimate James Bulger’s FBI informant file is and his reasons for using the file if he didn’t trust the agents he worked with. Foley stated that there were other sources, but that he never bothered to check into the integrity of the FBI file as a whole.

The defense is also looking to show that Bulger was never working with the FBI as a paid informant and was using dirty agents for information. In an HLN interview with Ryan Smith, former Winter Hill Gang associate and drug dealer John “Red” Shea said that Bulger worked with the FBI while spouting the code of silence to the rest of his group.

The entire trial could take around three months as there is quite a bit of information to go over during James “Whitey” Bulger’s run of the Winter Hill Gang and the murders. These include the nature of FBI corruption and far it goes as well as the inside workings of the Irish mob. Expect some former members and associates, more law enforcement, and maybe even family who weren’t directly involved with the workings of the mob, but were probably aware of what was going on. The main event of the trial would be Bulger himself testifying.

Prior to his capture, Bulger was hiding for 16 years and living in Santa Monica under a false name. He was staying with his long-time girlfriend Catherine Greig when he was captured two years ago. Greig had been wanted by the FBI since 1999 while Bulger was in the FBI’s Most Wanted Fugitives. While on the run, he had been sighted throughout North America and the UK.

During his July 2011 arraignment he pled not guilty to charges of 19 murders and 13 other accounts. Greig was sentenced to eight years for “conspiracy to harbor a fugitive”, identity fraud, and conspiracy to commit identity fraud.

While Bulger was on the run, his brother William “Billy” Bulger—former Democratic Party Senator of Massachusetts and former President of the University of Massachusetts—testified before the U.S Congress in 2002. Of his brother’s criminal past and what he thought Bulger did for income he stated that he figured Bulger was involved in gaming (gambling) and possibly illegal work that wasn’t “all that violent”. He also mentioned that Bulger had regular jobs. He went on to mention that he did talk to Bulger via pay phone. As a result, former Governor and 2012 Republican presidential candidate Mitt Romney forced William Bulger to step down from his position as president of University of Massachusetts.

William Bulger wasn’t the only Bulger brother involved in politics who lost his position as a result of communicating with James Bulger while he was on the run. John “Jackie” Bulger, a retired judge in the state, was convicted of perjury to two grand juries in 2003.

With some 78 witnesses scheduled to be called by the defense and 50 potential witnesses revealed earlier this week, both brothers could possibly be brought in based on their previous confessions in public record. Catherine Greig has turned down speaking before court.


Starting with Kabir News in 2013, James has focused on tech, gaming, and entertainment. When not writing, he enjoys catching up on sci-fi and horror shows and comics. He can be followed on Twitter @MetalSwift.

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