21. James Toney
Toney had 92 professional boxing matches. In the end, he lost to 40-year-old journeymen like Charles Ellis and Jason Gavern. No-namers without any future in the sport defeated a legend. ‘The Dark Emperor’ should have retired years before the age of 49, but finally quit the sport in 2017. His toughness was his own worst enemy. In 10 defeats he was never knocked out.

However, a boxer can’t take that many fights and expect to walk away unscathed. It’s not just the matches that cause damage but also sparring in the gym during training. Now, Toney shows signs of CTE which is very sad. When it comes to combat sports athletes, the people around them have a responsibility to try and talk them out of punishing their bodies even more. Toney unquestionably fought on for too long.