From Boston mobster to FBI informant. This might be one of our most interesting guys who had a tragic ending.

Matthews was influential in the Black Mafia and had the most mysterious escape of any mobster in history.

Johnny Boone was the leader of the Cornbread Mafia and arrested for growing marijuana on several farms in Kentucky.

He was loosely connected with the Chicago Outfit, but was a deranged man of torture.

He might have been short in stature but a fearful man you didn't want to mess around with.

Rothstein did more than commit the infamous 1919 White Sox Scandal, he also changed the mobster game forever in New York City.

Small town Alabama went through a crazy mobster time after the Great Depression, led by Hoyt Shepherd.

Sam Bass is another Texas outlaw who was on the right track as a kid but then made some questionable decisions that spiraled to a life of crime and an epic shooting to the death.

We already discussed the Jesse James portion of the James-Younger gang, but now its Cole Younger's turn. See how things turned out for him and the Younger brothers in their robberies and rebellion against the Union. --- This episode is sponsored by ·

Teflon Don has become a recent infamous mobster of the 20th century. Contrary to his nickname, he did eventually get evicted and passed away in 2002.