10. Mike Tyson
We’re not talking about his November 2020 comeback against Roy Jones Jr. because that was just for fun. However, ‘Iron Mike’s’ actual professional career did go on too long. It was ludicrous to see him lose against Irish journeyman Kevin McBride in 2005 after Danny Williams knocked him out the year before. The legendary heavyweight was no longer a force of nature and fell out of love with the sport.
He definitely stuck around for too long and should have retired after losing against Lennox Lewis or even Evander Holyfield five years earlier. The truth is that McBride didn’t beat Tyson, Tyson beat Tyson. In short, the feared ‘Iron Mike’ was a broken man. It’s easy to say he should have quit earlier for the sake of his legacy and his health. But Tyson knew nothing else and couldn’t pull himself away.