Hedge fund manager Kyle Bass made a killing when the mortgage bubble popped. He wasn’t as lucky with the oil bust.

Reassured in part by a March 2015 meeting with energy investor T. Boone Pickens, who said the glut of crude wasn't going to overwhelm the country's ability to store it, Bass began buying shares of oil producers like Concho Resources and Whiting Petroleum. It was a big mistake. Energy prices collapsed anew, extending what has become Bass's worst streak since he launched Hayman Capital Management a decade ago.