Who: Herman Cain
Fail: Once known for his work as CEO of the Federal Reserve Bank of Kansas and board member for a slew of major companies, including Nabisco, Godfather's Pizza and Whirlpool, Cain is currently one of the most controversial Republican presidential nominees. The 65-year-old has recently been slapped with allegations of sexual misconduct. According to the latest claims, Cain reportedly placed his hand up an employees skirt while CEO of the National Restaurant Association.
Redemption: Depends on what side you stand on … Bill Clinton may even give him a high-five.