Willie Sutton
Willie Sutton spent roughly four decades robbing banks and stores, becoming famous for disguises and repeated prison escapes. Arrested for the final time in 1952, he owed multiple life sentences and more than a century in additional prison time.
Doris Payne
Doris Payne built an extraordinarily long career as a jewel thief, using charm and misdirection rather than violence. Over nearly 70 years, she used dozens of aliases and stole more than $2 million worth of jewelry.
Allen Stanford
Robert Allen Stanford orchestrated a 20-year investment fraud involving Stanford International Bank. A federal jury convicted him in 2012 after prosecutors said he misappropriated $7 billion to support personal businesses and an extravagant lifestyle.
John Dillinger
During an astonishingly concentrated criminal career in the 1930s, John Dillinger and his gangs robbed banks, plundered police arsenals, and carried out multiple jailbreaks. The FBI says his gang’s spree between 1933 and 1934 terrorized the Midwest.
Rita Crundwell
Rita Crundwell stole more than $53 million from the city of Dixon, Illinois, where she served as comptroller. Her fraud continued from 1990 until its discovery in 2012, and she later received a lengthy federal prison sentence.
Bartholomew Roberts
Known as Black Bart, Bartholomew Roberts was among history’s most successful pirates, plundering more than 400 ships between 1719 and 1722. His extraordinary criminal career ended when Royal Navy forces confronted him in 1722.
