...
But I think I found the all-time winner in this category in a Forbes article about billionaires who lost some or all of their fortunes in 2008. Before you read about him, allow me to describe the conversation that the universe had with his soul before he was born. I think it went something like this:

Universe: I've decided to make you a billionaire.

Soul: Woo-hoo!

Universe: But you will lose more than half of it in one year.

Soul: I guess that's still okay. That's still a lot of money.

Universe: And you'll probably go to jail for two years.

Soul: Dang. I knew there was a catch. Still, it's only two years.

Universe: Actually, that's not the catch.

Soul: Uh-oh.

Universe: Your name will be Anurag Dikshit.

Soul: Ha ha! Good one. Seriously, what will my name be?

Universe: We're done here, Dikshit.

http://finance.yahoo.com/banking-budgeting/article/106352/Billionaire-Blowups-of-2008