3. James Whitey Bulger
James Bulger was nicknamed Whitey due to his light blond hair, and he was one of the most ruthless criminals who also became the boss of the Boston’s Winter Hill Gang. The Winter Hill Gang was a group of criminals and Bulger was responsible for crimes such as extortion and arms trafficking. This gangster went into hiding in 1994 but wasn’t arrested until 2011 at the age of 81.