Stede Bonnet was a wealthy landowner who walked away from his family to buy a boat and become a really bad Pirate of the Caribbean. Blackbeard ran into him, took his ship, decided for some reason he kinda liked the guy, taught him a few things about piratin’, then went his own way. Bonnet did better after that, but he was eventually captured and hanged.

https://en.wikipedia.org/wiki/Stede_Bonnet

Were you looking for a story of inspiration and success instead of history’s worst midlife crisis? If so, oops.