James Whitey Was A Crime Figure In Boston's Crime

James “Whitey” Bulger could just be considered another troubled soul caught up in the wrong things, but he is one of America's most notorious and ruthless mob bosses. From 1975 to 1990, he served as an informant, tipping off the police and giving information about La Cosa Nostra, an Italian gang, while building his own crime network. After fleeing Boston in 1995, Bulger landed on the "Ten Most Wanted Fugitives" list and lead the FBI on a sixteen year manhunt. Hailing from South Boston, Whitey entered a lifetime of crime at a young age and had become a prominent figure in Boston's organized crime scene by the late 1970s.

James Joseph Bulger Jr. was born in Dorchester, Massachusetts on September 3, 1929 - a month before the stock market crash.

Whitey would show up during the late afternoon for a few hours, poked around private offices, and then would go to his real job in the South Boston rackets (Whitey 172). Eventually he stopped showing up for his job entirely and became a bookmaker and loanshark for Donald Killeen, the leader of dominant Irish mob. On May 13, 1972, Donald Killeen was killed by rival gang, the Mullens, after leaving his son’s birthday party. The Killeens and Mullens came to a truce with Howie Winter, of the Winter Hill Gang, as the overall boss. Whitey quickly rose in the ranks of the Winter Hill Gang. A cunning and ruthless mobster, Whitey arranged numerous killings, including the murders of Spike O'Toole, Paulie McGonagle, Eddie Connors, Tommy King and Buddy Leonard. Whitey had become one of the most prominent figures in Boston’s organized crime scene by 1979. The same year, Howie Winter was arrested for fixing horse races. Whitey moved into the leadership role of the gang ("Whitey Bulger Biography"). When he took over, Whitey decided that his gang would “follow the Mafia way and start charging “rent” to loansharks, drug dealers, bookmarkers, or anyone else who worked in their territories.” Over the next sixteen years, he gained total control of these activities. Whitey established a fearsome reputation both within and beyond the criminal underworld

FBI Agent John Connolly approached Whitey in 1975 claimed the gang and him had a common enemy - La Cosa Nostra. Connolly promised to protect Whitey and the Winter Hill Gang if they fed him information on La Cosa Nostra. Connolly told Whitey, “The only thing you cannot do is kill people,” (Whitey 202). Both groups benefited from the agreement, the FBI was able to take down the Italian gang and Bulger essentially became the king of Boston. Manipulating and taking advantage of his brother Bill's stature in the Massachusetts State Senate and childhood friendships that linked him to other members of the police force, Whitey simultaneously built up his criminal empire even more. Over time Whitey’s corrupt relationship with his Connolly, and the FBI deepened further. Connolly kept Whitey updated on other authorities’ investigations into the Winter Hill Gang’s operations. By the 1990s the compromise between the FBI and Whitey had become apparent to local and state police. They launched an investigation with FDA. In January of 1995, Whitey and other associates were charged with multiple counts of racketeering and extortion. Connolly informed the men in advance of the indictment and Whitey fled Boston. He was never seen again until sixteen years