WHITEY BULGER served as boss of Boston’s Winter Hill Gang from 1972 to 1994. While leading the vicious mob outfit, he was also a key FBI asset, informing on his rivals in order to weaken them and consolidate power.

He is shown here for his 1953 arrest for armed robbery and truck hijacking, for which he served nine years, including a brief stint at Alcatraz. There are MANY mugshots of Whitey Bulger to choose from, so I went with the one where he is allowed to wear a stylish hat for some reason.

Bulger went on the run in 1994 after one of his allies in the FBI tipped him off to an impending RICO indictment, and he managed to successfully evade the law for an impressive sixteen years before his arrest in 2011. Convicted on 31 counts of racketeering and 11 murders, Bulger was sentenced to two consecutive life terms. In 2018, the 89 year old was beaten to death by fellow inmates.