12. Evander Holyfield
The definition of a boxer who couldn’t stay away from the sport. Obsessed by the pursuit of glory and burdened with massive expenses, Holyfield fought on for a long time. The only undisputed two-weight champion in boxing history, it’s also indisputable that he should have retired earlier. At the age of 48, Holyfield finally stepped down from the fight game. He wanted to become a five-time world champion but fell short in that pursuit.
After his controversial WBA Championship loss to Nikolai Valuev, the door finally shut on his title hopes. But he still fought several more times after this point. As boxers get older, their reflexes slow down, and the risk of sustaining damage increases. Every match enhances the possibility of life-changing consequences. That’s what makes it so compelling for fans but also is why fighters shouldn’t stay in the game too long.