5 Troubled Childhood
Nicknamed “Whitey” for his white blonde hair, Bulger was one of six children born to Catholic Irish-American parents in Dorcester, Massachusetts. Growing up in the South Boston projects, Whitey was a criminal before most of us hit puberty. He legitimately ran away with the circus when he was just 10 years old, and notched his first arrest at age 14 when he was caught stealing. His early arrest record included larceny, forgery, assault and battery, and armed robbery, and he served a total of five years in a juvenile reformatory.
4 Time in the Service
After serving his time as a youth, Bulger joined the US Air Force in 1948. His service to our country wasn’t exactly exemplary though, as he wound up in military jail for assault on several occasions, and was also arrested for going AWOL in 1950. In spite of his less than admirable record though, Bulger still somehow managed to earn an honorable discharge from the Air Force in 1952. Because apparently in order to be deemed “honorable” by the Air Force, you just have to not attack TOO many people.
3 Young Outlaw
After returning home to Boston, Whitey quickly embraced a life of crime. This time around his charges became more serious though, including a string of bank robberies that spanned from New England to the Midwest, and by 1956 he was sentenced to serve 25 years in federal prison. Spending time in several locations, including Alcatraz, Bulger served just nine years before he was released and headed back to Boston to REALLY get things going. Good call on the early release, American prison system!
2 The Boss
Bulger really hit his stride in the 1970s, when he became a preeminent figure in the world of Boston organized crime. He quickly rose to prominence, due in no small part to the fact that he was serving as a secret informant for the FBI, tipping off authorities on the misdeeds of his rivals while building an even more powerful crime syndicate of his own. Bulger was a fixture atop the Boston crime scene for 25 years, until he was forced to flee in 1995 after the DEA and Massachusetts State Police indicted him following an investigation into his gambling operations.
1 Life at the Beach
After his disappearance in ’95, Whitey Bulger made a steady climb up the FBI’s Most Wanted list; cracking the top ten in 1999 and at one point reaching as high as number two, behind only Osama bin Laden. And despite the best efforts of the FBI and a $1 million reward for information leading to his arrest, he managed to duck authorities for an unbelievable 16 years before his capture in 2011. Whitey Bulger was eventually found living with his long-time girlfriend in Santa Monica, California at the age of 81, and was said to still be pursuing a life of crime. But as the saying goes, “You can’t teach an old dog to not be a crime lord.”