Now 80, there's a $2 million price on his head and some think he may never be found.
Like many famous criminals of his stature, he's inspired books and films, including Jack Nicholson's character Frank Costello in Martin Scorsese's 2006 film "The Departed."
His complex relationship with his brother William Bulger, a former president of the Massachusetts state senate, was the inspiration for the Showtime series "Brotherhood," which lasted three seasons.
Joanne Chesimard, aka Assata Shakur, was a New York City newspaper headline staple in the 1970s. A former member of the Black Liberation Party and the Black Panthers, Shakur was convicted of multiple felonies, including armed robbery, attempted murder and murder for her involvement in a shootout with police. She was sprung from prison in 1979 by sympathizers and has been living under political asylum in Cuba since 1984.
Shakur has been the subject of documentaries and made a hero by such hip hop stars as Common, Public Enemy, Mos Def and her stepnephew Tupac Shakur.
Heavyweight boxing champion Jack Johnson suffered more deeply from racism than any blow he may have felt in the ring during his turbulent career in 1908-1910. He won fights while newspapers vilified him, crowds shouted cruel epithets at him and people called for a "Great White Hope" to defeat him.
Though wildly controversial, he was a huge star in his day and made headlines for racing cars, his vibrant social life and roles in early film and radio. However, his involvement with two white women, one of whom he married, landed him in jail in 1913 under the Mann Act. He fled to Mexico with his wife and did not return until 1920. He served a year in jail and left prison a hero to his many admirers.