James "Whitey" Bulger

James “Whitey” Bulger, currently wanted for $2 million on the FBI’s Most Wanted list, was sentenced to prison for bank robbery in the mid-1950s and served on Alcatraz from 1959 until 1963. Like many big timers, he was a solid con, did his time with a minimum of fuss, stated that he would never again cause his family shame and humiliation and was “anxious to make a new start.”

And that’s mostly what he did. After paroling out of prison in 1965, “Whitey” headed up what became known as the Irish Mafia in South Boston. Murder, extortion, narcotics distribution, money laundering and a whiff of arms smuggling rounded out his resume. During the same time, his  brother, William “Billy” Bugler was a state senator and rose to become the president of the Massachusetts state senate.

“Whitey” was also a Boston FBI informant, ratting out the Italian Mafia. In fact, his unfortunate handler, Special Agent John Connolly, is now serving time for numerous offenses including conspiracy to murder.

Several Bulger colleagues have turned state’s evidence in the last 15 years in exchange for lengthy prisoners sentences, or by now, have paroled out. But not “Whitey.” He went underground in 1995, fading into society as a comfortable senior citizen. He is now nearly 80. Billy Bulger eventually retired from the senate, took a position as president of the University of Massachusetts, but was fired in about 2002 for taking the 5th Amendment on the whereabouts of his brother.

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