James Joseph "Whitey" Bulger (September 3rd, 1929 - October 30th, 2018) is the most infamous Irish American mob boss in American history and second on the FBI's Most Wanted List behind Osama bin Laden. He took over the Winter Hill gang in South Boston, Massachusetts after being released from Alcatraz prison in the 1960s. During his prison sentence in the 1950s and 60s, he was subject to LSD experiments by the CIA to test mind control, giving him night terrors for the rest of his life. He was convicted on 19 counts of murder.
Unlike most mobsters, Bulger actually had a mole within the FBI. Corrupt agent John Connolly, also an Irish American, constantly tipped Bulger off about police and FBI bugs, wiretaps and other important information. His younger brother Billy was President of the Massachusetts State Senate.
Tipped one last time in 1995, Bulger went into hiding with his girlfriend Catherine Grieg. He spent 16 years on the run until he was caught in 2011. He was believed to have a relationship with a prison psychologist.
Just hours after he was transferred to a new prison, he was beaten to his death on October 30, 2018.