Floyd Mayweather
Mayweather is the most financially successful athlete in history. The boxing legend became a marketing force in his prime and brilliantly managed his career. He earned hundreds of millions of dollars before he retired with an undefeated 50-0 record. But while he was a superb fighter he behaved badly outside of the ring.

‘Money’ served 60 days in jail after a reprehensible act of domestic violence. Meanwhile, his lack of respect for women became even more obvious when he opened a Las Vegas strip club. It’s safe to say that Mayweather considers women to be tools and nothing more. Unfortunately, his generational boxing talent doesn’t mean he’s a nice person (via Bleacher Report).