The man that many of his Santa Monica neighbors were shocked to hear was a notorious gangster appeared in court as being old, hunched over, even harmless. Those from his neighborhood in South Boston called him a “genuine ‘Southie’”; people even thought him to be a Robin Hood-type figure.

Tom Foley, an organized crime investigator for the Massachusetts State Police, however, warns people to think otherwise. CNN reported that Foley expressed, "The guy is a sociopathic killer...He's one of the hardest and cruelest individuals that operated in the Boston area. He's a bad, bad, bad guy.”

Aside from the 19 murders he’s believed to have a hand in, Bulger is “accused of using violence, force and threats to shake down South Boston's bookmakers, loan sharks and drug dealers,” CNN reported. His gang, the Winter Hill Gang, was notorious for laundering money through liquor stores, bars, and other establishments throughout South Boston.

Their group started in 1972 and was originally made up of “splinters” from other gangs. Although the leader was Howard T. Winter at first, Bulger ran it with Flemmi during his his peak as a mobster, in 1979. Once Bulger joined the gang, he also began informing for the government.


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Over the years, Bulger has been so hard to catch because of former FBI agent John Connolly, who has acted as a sort of protector over Bulger. During the winter of 1994-1995, police had delegated arresting responsibilities to take down their rampant mob scene; Foley would get Stephen “Rifleman” Flemmi (Bulger’s right-hand man who is now serving life in prison), and the FBI would take down Bulger. Because of Connolly’s protection over him, Bulger went free. Connolly is now serving 40 years in prison for slipping information to Bulger about his case.

However, it wasn’t just Connolly that protected Bulger from prison. According to Dick Lehr, a Boston Globe reported who co-wrote the book, “Black Mass: The Irish Mob, the FBI, and a Devil’s Deal,” Bulger is a “master of strategy.” Apparently, while in prison, Bulger had done his fair share of research on military history and “learned how to work the system,”
according to CNN.

For Bulger, “working the system” meant that he could build up his mafia empire while still gaining the trust of the government, which he got ample time to do; Bulger was released from prison early for participating in CIA-sponsored mind control experiments with LSD.

And so it came down to present day. After years of hiding, police finally arrested Bulger and  his longtime girlfriend, Catherine Geiger, and they don’t have any intentions of compromising their arrests. CNN writes that, “anything Bulger might promise to reveal about the corruption that coddled him while he built a crime empire pales in comparison to the lives he allegedly took between 1973 and 1985,” but it hasn’t been reported that Bulger has tried to do any of that. After being read a “stack of charges as thick as a small-town phone book,” Bulger thanked the courtroom and said that he was aware of all of them.

CNN sums up Bulger’s life with, “James ‘Whitey’ Bulger left Boston 16 years ago in the dark of night, a brash high-echelon FBI snitch one step ahead of a racketeering indictment. He returned last week under the glare of camera lights, a stooped 81-year-old man in shackles.”