Whitey Bulger was born into a large Irish-American Catholic family on September 3, 1929, in Dorchester, Massachusetts. He was one out of six children in his home at the housing projects Old Harbor. His younger brother, William, would later become president of the Massachusetts Senate for seventeen years. The Bulger’s family didn 't have a lot of money. His father worked as a longshoreman. …show more content…
In 1956, his offenses grew increasingly alarming in a large scale of culminating bank robberies. Ranging from three states between Rhode Island to Indiana. In June of 1956, he was convicted and sentenced to 20 years in federal prison. He ended up serving nine years, including stints in Atlanta, Alcatraz, and Leavenworth. The reason why he ended up in Alcatraz was because during his incarceration, Bulger was accused of conspiring to escape. He was transferred there to serve the remainder of his sentence.
Again the South Boston native returned back to his home town. Whitey then became an enforcer for crime boss Donald Killeen. After Killeen was gunned down in 1972, Bulger joined the Winter Hill Gang, a predominantly Irish American crime syndicate led by Howie Winter. Here he took similar duties with the Winter Hill Gang as an enforcer, but quickly rose up in the ranks. A ruthless, cunning mobster, Bulger sanctioned numerous killings, including the murders of Spike O’Toole, Paulie McGonagle, Eddie Connors, Tommy King and Buddy …show more content…
The people of Boston both feared and respected the man. His criminal career hit new heights after 1975 when he began his partnership with another product out of Old Harbor projects, John Connolly, who also happen to be an agent in the Federal Bureau of Investigation (FBI). John Connolly, who was about 10 years younger than Bulger and who had grown up idolizing him along with Bulger’s brother, William, who became a well-respected politician in Massachusetts. Remaining mindful of the long-standing strictures against informers among the South Boston Irish, Bulger provided Connolly with information that brought successful prosecutions against Boston’s Italian mob. This becomes unbeknownst to even his closest associates, Bulger an FBI informant. This goes completely against everything he taught his gang not to do which is snitch. Connolly soon enjoyed great success in the FBI, but Bulger’s cooperation came at price. The informant relationship quickly turned corrupt, becoming what was later described as a “devil’s deal” and giving rise to the worst informant scandal in FBI