1. Born into an Catholic Irish-American family of six children and two low class working parents, James "Whitey" Bulger didn't waste any time before ensuing his career in crime. Growing up as a young kid Whitey always had dreams of "running away with the circus" and he did just that at the age of 10. He began to get into street fights and stealing and quickly at the age of 13 was when he was first charged and arrested for delinquency and stealing. Things would only escalate from here. He is pictured out front a South Boston home around the time where he first joined a local street gang, then referred to as the "Shamrocks", where he would start building his criminal reputation with charges like armed robbery, battery and assault, larceny, and forgery. He eventually would be charged for these crimes and was put into a juvenile reformatory …show more content…
The image above is at the crime scene where Whitey's hit man, John Mataorano walked up to Roger Wheeler and shot him in the parking lot of his country club. This will soon become the biggest mistake of Whitey Bulger's criminal career. This assasination caused a lot of drama within the Winter Hill Gang, it resulted in Whitey and Flemmi's cover being broken and the rest of the affiliates of the gang felt as if they had been betrayed by their leader in Whitey as well as Flemmi. The man speaking in the video above is, Kevin Weeks who was Whitey's to be predecessor. He is "ratting" on Whitey for all the murders that had been pinned on either him or other Winter Hill Gang members when Whitey was responsible. In 1994 the DEA, Boston Police, and Massachusetts State Police all joined forces and began to investigate the gambling operations of Whitey