Holyfield made history as the first fighter to become undisputed champion at both cruiserweight and heavyweight. He grabbed the heavyweight crown from James 'Buster' Douglas in 1990 and defended it against big names like Larry Holmes and George Foreman.
But it was his rivalry with Riddick Bowe that left a lasting mark. In a recent chat with DJ Vlad on YouTube, Holyfield opened up about his regrets.
"Don't become friends with nobody you're gonna have to compete with," Holyfield recalled his mother saying. "You tell them things that you shouldn't because you all talk about everything."
Holyfield and Bowe go way back. They were friends when Bowe was Holyfield's sparring partner as an amateur. Holyfield even helped Bowe with his son and shared his money with him.
But that friendship came back to bite Holyfield. He realized Bowe used their closeness to his advantage when they fought.
Their rivalry turned into one of boxing's greatest trilogies. Bowe won the first fight in 1992, taking Holyfield's undisputed title. Holyfield got his revenge in 1993, reclaiming the heavyweight crown. Bowe won their final showdown in November 1995.
Looking back, Holyfield wishes he'd kept his distance. He learned the hard way that in boxing, sometimes it's better to keep your friends close and your opponents at arm's length.
That 1990 fight Holyfield regrets changed the course of his career. It's a reminder that in the fight game, the toughest battles often happen outside the ring.