The Irish American crime boss James ‘Whitey’ Bulger is the only criminal on the FBI’s most wanted list with a bounty on his head bigger than Osama Bin Ladens. The release of new police records show a snapshot of his criminal past before he became the Don of the Winter Hill Gang in Boston.

On May 17, 1955 Whitey Bulger and two other gunmen burst into the Industrial National Bank on Central Avenue, Pawtucket, Rhode Island. A terrified woman described how Bulger waved a long-barreled pistol at the 19 employees and customers and ordered them to the floor.

“All right, lady, I’m not going to hurt you,” he said, sounding like a clichéd mobster movie. “You got a nice bank here.”
The three men, having robbed the bank of $42,000, stuffed into a grocery bag, backed out the door and fled to North California. Later that year they were caught and thus began Bulgers career as a criminal and a fugitive from the law.

The new descriptions of Bulger were released because of the inquisitive mind of Pawtucket Police Chief George L. Kelly III. Having read “The Brother’s Bulger”, a book by Boston journalist Howie Carr, he was reminded of the bank robbery which took place back in 1955. Local officers hunted down the files filled with yellowing pages of interviews and witness statements.

It read like something out of a crime novel. Kelley said “I couldn’t believe the work that went into this case.” The file included a confession from the FBI’s most wanted man, James “Whitey” Bulger. His hand-written confession included a map of the bank and details of the robbery.

They’re casing of the bank and plan for the day of the robbery seems like the perfect plotline for a movie. In a time before hi-tech security of surveillance technology Bulger and his crew, Carl Smith and Ronald Dermody, walked away from the robbery only stopping back at their local residence to change their clothes and divide up the money.

When the FBI eventually caught up with Bulger he spent nine years of a 20 year sentence in the toughest prisons including Atlanta, Alcatraz, Leavenworth and Lewisburg. While in prison he agreed to take part in a drug trial. As part of the experiment he would take LSD. This trial helped to get his sentence reduced.

In 1965 he returned to Boston and rose through the ranks to become one of the nation’s most powerful criminals. Having being the boss of the Winter Hill Gang in Boston it is said that Bulger is responsible for the murder of 19 people and that their empire was worth tens of millions of dollars.

Bulger also knew how to toy with the FBI. He fed agents information and became a high-level informant helping him to knock off any of his rivals. It is now obvious that he played the FBI. On December 23, 2994 Boston FBI agent, John J. Connolly tipped Bulger off that he had been indicted on a host of felonies.

The Feds still haven’t caught him. More than 15 years Bulger is now 80-years-old and a step ahead of his hunters.