Perhaps Mikhail Khodorkovsky. I’m sure he managed to squirrel away some of his wealth and now lives comfortably in exile, albeit with a huge bullseye on his back. But if your standard is “lose 100% of their wealth” then that almost never happens to anyone, even working class people who declare bankruptcy due to overwhelming debts.

Does Muammar Gaddafi count? He lived like a king with an anime-style cadre of elite female bodyguards, being essentially the emperor of Libya. He died after some soldiers dragged him out of a ditch and summarily executed him.