Holyfield's impressive career saw him step into the ring with many of boxing's biggest names. He beat icons like Mike Tyson, George Foreman, and Larry Holmes. He also went toe-to-toe with Lennox Lewis and James Toney. By the end of his run, Holyfield had racked up 44 wins, 10 losses, and 2 draws.
But it's his fights with Riddick Bowe that Holyfield now looks back on with mixed feelings. The two first met when Holyfield was 18, sparring with Bowe as he got ready for the Olympics. They became good friends, something Holyfield's mom had warned him against.
On The Big Podcast With Shaq, Holyfield shared his mother's words:
"Don't become friends with people you're going to compete with, you'll tell them too much."
Looking back, Holyfield admits:
"Riddick Bowe is the first person that I didn't listen to what my momma told me."
Holyfield and Bowe ended up fighting three times. Their first bout in November 1992 saw Bowe win by unanimous decision, handing Holyfield his first loss and taking his undisputed heavyweight champion title. Holyfield got his revenge 12 months later with a majority decision win. But Bowe had the last word in November 1995, stopping Holyfield in the eighth round.
Recently, Holyfield stirred up some controversy by claiming he's the greatest heavyweight of all time, not Muhammad Ali. But regardless of where he ranks, Holyfield's unique achievement as a four-time world heavyweight champ puts him in a class of his own.