14. Name: Joseph P. Kennedy, Sr.
Net worth: $400 million
Crimes: Bootlegging and illegal alcohol sales
About: Most think of the patriarch of the famed Kennedy clan as a legitimate businessman, but he started out as bootlegger. During the US’s post-WWI Prohibition era, Kennedy partnered with Frank Costello, then-head of the Luciano crime family to arrange smuggling alcohol into the US for easy distribution during the period.