Whitey Bulger was a boss in organized crime in Boston from the late 1970's to the mid-nineties. He was also an F.B.I informant during the mid-nineties as well, all the while still building his own criminal empire. In 1994, Bulger and an associate named Stephen Flemmi became the target of a joint task force from the DEA, Boston Police and the Massachusetts State Police. They were going to look into Whitey Bulger's gambling business. However, Bulger avoided prosecution by running when his FBI handler and friend, warned him about the investigation. He was finally captured in California in 2011.

Whitey Bulger started his life of crime at the age of fourteen. He was arrested for stealing and his criminal record just blew up from there. Still as a youth he was arrested for various things that included forgery, assault, and even armed robbery. He did some time in a juvenile facility and when he got out, he joined the Air Force but his life of crime didn't stop in there. He was arrested for assault and then was arrested for going AWOL. He left the military in 1952, somehow with an honorable discharge, and moved back to Boston where he began to thrive in a life of crime again.

Whitey Bulger began robbing banks in the mid 1950's from Rhode Island to Indiana and was finally arrested in 1956 and was sentenced to a prison term of twenty-five years in federal prisons and did time in places like Leavenworth and Alcatraz but was finally released after serving only nine years. From there he went back to Boston and eventually became an enforcer for crime boss Donald Killeen. However, in 1972, Donald Killeen was murdered and Whitey Bulger joined a gang called the Winter Hill Gang and quickly rose through the ranks and even sanctioned hits on numerous gangsters including Eddie Connors, Spike O' Toole, and Tommy King.

In 1979, the leader of the White Hill Gang, Howie Winter, was sent to prison for fixing horse races and this left the spot for Whitey Bulger to become the boss. Over the next sixteen years or so, Whitey Bulger controlled a large portion of the gambling, drug dealing and loan sharking in Boston and more than eighteen murders happened under his reign. He remained the boss until he fled to California to avoid arrest and possible prosecution for his crimes and avoided the law until 2011 when he was arrested in his home in California where he also was involved in criminal activities.

His trial finally began in June of 2013 and wrapped up two months later in August. He faced thirty-three counts of criminal activity that included murder, money laundering, and drug dealing, just to name a few. When the trial was over, Whitey Bulger was convicted of thirty-one counts of the thirty-three indictment, including being found guilty of eleven of the nineteen murders he was indicted for. He was sentenced to two consecutive life terms plus five years in November 2013.