Whitey Bulger's early life was that of the average kid growing up in the Southie projects. It is natural to try to find a reason for James' criminal behavior, but plenty of kids came up the same way he did and turned out to be honest, hard-working citizens. Some even became victims of this ruthless killer. After his initial stint with incarceration and his bout with the U.S. Navy, he had a chance to redeem himself and turn his life around, but history shows that he did not take that chance. Instead, he got worse . . . far worse.
After an impressive round of bank robberies and hijackings, James "Whitey" Bulger found himself serving time across the United States. He was one of the famous prisoners at Alcatraz for a while. He also served time in Leavenworth. All said, he spent nine more years in jail and was released in 1965. Again, his past was behind him and he had a choice. He made the same one he always made.
At first, Bulger was a relatively small time muscle man, but he was ambitious. He got himself caught up in the infamous Killeen-Mullen gang rivalry and positioned himself to be on the winning side. His first murder likely occurred in 1971 and was Donald McGonagle. Bulger was not exactly a criminal mastermind. He just got by on the skin of his teeth. He had meant to kill Donald's brother Paulie and wound up killing the brother that no one had a problem with. He survived his own stupidity and came out as a member of the Winter Hill Gang out of Somerville, MA.
Whitey Bulger found his way to the top of the crime world in Boston by selling out his peers to the FBI. He caught the eye of John Connolly, an agent who grew up in Southie with Bulger and convinced him to become an informant starting in 1975. Using the FBI to take out rival mobsters and allegedly escape arrest himself (rumor has it that the FBI tipped him off on raids more than once), Bulger climbed to the very top of the ladder. It was during his rise to the top and his time there that Bulger was involved in at least 11 murders. Even his connections could not save him and he went on the run starting in 1994.