4. Chuck Prince
Chuck Prince is the former CEO of Citi Bank and was one of the key players in building it into one of the largest banks in the world. Unfortunately, he also played a critical role in its downfall as well. Known for its expansive structure that included investment banking, high-street banking, and management for wealthy clients, Citi would eventually drift into subprime mortgage territory. When profits began to tank in 2007, Prince continued to forge ahead—but when the subprime business surfaced, he was ousted when the bank took a multi-billion dollar loss. Don’t feel too bad for him though, he received a nice $140 million payout.