By Kelly Kasulis, News Correspondent
Emblazoned in that traffic-cone orange jumpsuit, the “new” and imprisoned face of Whitey Bulger has left Boston wide-eyed as details emerged about how he managed to evade arrest for decades.
Bulger, 84, whose sentence will be announced Nov. 13, is popularly known as the real-life Soprano who led organized crime in Boston through the Irish mob during the 1970s and 80s. Convicted in August 2013, Bulger was ultimately held responsible for 11 of 19 alleged murders and a host of federal racketeering charges.
The FBI Informant
Riddled with controversies, the trial alleged that Bulger ran loose for years because he served as an FBI informant through a complicated and well-documented relationship with FBI Agent John Connolly, giving Connolly piecemeal information about the Patriarca crime family.
Bulger then made headlines in late October when news broke that a witness from his trial, Stephen Rakes of Quincy, died by cyanide poisoning. Rakes was murdered in July and state officials said that his homicide was unrelated.
“People in Boston certainly have lived through this story as it has gradually come to life,” Shelley Murphy, a Boston Globe reporter who has covered Bulger for more than two decades, said. “There have been so many extraordinary details about this case … People wonder how he was able to turn the system on its head, you know, the fact that he was on the FBI’s 10 most wanted list for several years and on the run for 16 years, and yet he was found based on a tip all the way from Iceland.”
Co-author of “Whitey Bulger: America’s Most Wanted Gangster and the Manhunt that Brought Him to Justice,” Murphy said that the most shocking part of the recent trial was that Bulger did not testify for himself despite a not-guilty plea and written letters upholding his innocence.
“In those letters, he vowed to set the record straight, that his associates have lied about him, that the media lied about him, and this was his big chance to set it all straight,” Murphy said. “I thought he would, that he had nothing to lose by testifying.”
Throughout his prosecution, Bulger has widely deflected blame, placing it instead on Connolly, who was sentenced to 10 years in federal prison in 2002 for racketeering.
“[Bulger] has been very adamant that he’s not an FBI informant because, from his perspective, he used the FBI more than they used him,” Murphy said. “Now he’s trying to put all the blame on John Connolly and say that he fabricated the whole [FBI informant] file.”
Connolly covered up a large number of details that could have led to Bulger’s arrest and frequently tipped him off about new investigations, which led to his indictment in 1999. Connolly also faced a first-degree murder charge after John Callahan, a member of Boston’s Winter Hill Gang, was killed as a direct result of information he shared with Bulger.
The Neighborhood Nice-Guy
Bulger, like many previous American gangsters, upheld a falsely noble reputation in his neighborhood for many years, Murphy said.
“This was a guy who, from a very young age, tried to cultivate this reputation as somewhat of a good-bad guy, a gangster with loopholes,” Murphy said. “He cultivated a myth that he kept drugs out of South Boston. Not only did he not keep the drugs out of Southie, but he brought them in. He was the one behind the scenes, orchestrating the supplies … and made a lot of money from that.”
Kevin Weeks, a cooperating witness and past bookkeeper who was close with Bulger until his arrest 1999, said in his autobiography that it was not unusual for Bulger to turn on his own associates.
In Weeks’ autobiography, “Brutal: The Untold Story of My Life Inside Whitey Bulger’s Irish Mob,” he recalled Bulger betraying two associates, Tommy King and Louie Litif.
He wrote that, in 1980, Litif angered Bulger after making an unordered kill and was executed shortly after. Weeks did not know of Litif’s murder until his wedding, and Bulger, sitting at one of the guest tables, pointed to an empty chair and jokingly said, “Say hi to Louie.”
Weeks also wrote that Tommy King was killed for drunkenly shaking his fist at Bulger.
During federal trial, Murphy said that Bulger had a ‘menacin”
“If he wanted you or if you crossed him, he was definitely dangerous,” Murphy said.
The Legacy
Today, Bulger is a candidate for the death penalty in both Oklahoma and Florida as he awaits a sentencing that is less than one week away. In Boston, he has left behind a legacy of violent history and, more recently, tourism. Boston.com published a “mob tour” with accompanying mp3 files, featuring sites in the North End and South Boston where Bulger organized and committed crimes.
“There is a fascination with this sort of underworld history,” said Murphy, who noted that she saw several tour buses stopping outside of Bulger’s Santa Monica apartment while on her Los Angeles book tour. “Whether it’s a fascination cultivated through ‘The Godfather’ or ‘The Sopranos,’ people are intere
Rumors have circulated that Ben Affleck will direct a Warner Brothers movie about Bulger, starring Matt Damon.
