When it comes to crime, Whitey Bulger is the rockstar of Boston. He is famous enough to have been glamorized in films loosely based on his success, such as "The Departed." However, to be fair to the people he victimized over his decades long "career," he was a very bad guy, according to his 2013 convictions. In fact, he spent most of his life on the wrong side of the law, as evidenced by his teenage years.
James "Whitey" Bulger was born on September 5, 1929 in Dorchester. He would grow to revere the neighborhood where he grew up and was thought of by some as a Robin Hood type, but the truth is that he was an opportunistic, murderous criminal. He got his nickname from the white-blonde hair he had in his youth. It was no remark on his character.
As could be expected by his eventual career choice, Bulger was trouble as a kid. It could not have been his upbringing, as his younger brother grew up to be the President of the Massachusetts State Senate, a career his brother destroyed by contacting him as a fugitive. Whatever drove him to crime, he met with his first legal resistance at the age of 14, when he was arrested for theft. He would go on to rack up charges of assault and battery and even armed robbery. He was caught and jailed for forgery before he became a man and put in juvenile "reform" for five years.
James Bulger had the chance to straighten up when he joined the Air Force, but he blew it. He was locked up in a military prison for assault and eventually, through some miracle, got an honorable discharge. It was the only time the words honorable and James Bulger would appear in any official capacity. The man went on to become the most prominent criminal in Boston history and evade capture for decades.