Floyd Mayweather Jr.

Floyd Mayweather Jr.'s 50-0 record includes victories over 23 world champions, yet his seven domestic violence charges and 90-day jail sentence in 2012 stain his legacy worse than any opponent's punch. He earned $275 million from the 2017 McGregor fight alone — 50% more than any other boxer's single purse — but his defensive style averaged just 12 punches per round, 40% fewer than the typical welterweight champion. Mayweather's financial success outperforms #5 Mike Tyson's $300 million career earnings, but his legal record falls short of #7 José Mourinho's redemption arc.