Soon after his released in April of the year 1948, he joined US Air Force where his character was continued. After basic training, he was then stationed as aircraft mechanic first at Smoky Hill Air Force Base located in Salina, Kansas and then in Idaho. He was sentenced to stockade for several of the assault. Additionally, he was also arrested in the year 1950 for going absent without the leave. Later, he received an honorable discharge in 1952 and then he returned to Massachusetts. Based on the grand jury testimony of former associates of Kevin Weeks, US prosecutors have indicted Whitey for nineteen murders. In addition to that, there has also been written the books that are related to Bulger.
During middle 1980s, he started to summon drug dealer from in and around the Boston to his headquarters. In summer of the year 1991, Whitey as well as his three friends came into the possession of winning the Massachusetts Lottery Ticket which had been bought as store he owned. Four people shared the prize of around US$14 million. He was then widely thought to have obtained his share of jackpot illegitimately. In 2006, the character of Frank Costello in the film The Departed is loosely based on Whitey Bulger. His trials have also been based on the 2014 documentary movie called Whitey: United States of America v. James J. Bulger which was made by Joe Berlinger.
There has also been the plan for directed the Whitey Bulger film by Ben Affleck and star Matt Damon. To talk about his personal life biography, Bulger fathered his son Douglas Glenn Cyr during the 12 years common law marriage with Lindsay Cyr who was a waitress as well as a former fashion model who is residing in North Weymouth, MA.
The couple began to live together in 1966. His son Douglas died when he was six years old due to Reye's syndrome after he got severe allergic reaction to aspirin injection. After splitting with Lindsay, he started dating Theresa Stanley who is a South Boston divorcee with several children and began to act like a family. There is no more news found about his wife and married. Apart from that, Bulger has now reached at the age of 85. Besides that, more about him can also be found in different social networking sites such as Facebook, Instagram and Twitter.