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Former world heavyweight champion Evander Holyfield once admitted that he should have never faced one man in particular in a shock claim. ‘The Real Deal’ is widely considered to be one of the best heavyweights of all time, proving his credentials on multiple occasions throughout the course of his decorated amateur and professional careers. Holyfield etched his name into the boxing history books back in October of 1990 when he put on an impressive display to defeat countryman James ‘Buster’ Douglas, capturing the undisputed heavyweight championship and becoming the first fighter to achieve this feat at cruiserweight and heavyweight. He would later produce legacy-defining wins over the likes of George Foreman, Mike Tyson and Michael Moorer before eventually announcing his retirement from the sport shortly after he defeated Brian Nielsen in 2011. Despite conquering a number of legendary heavyweights along the way, Holyfield once revealed that he actually regretted facing former rival Riddick Bowe in an interview on the Big Podcast with Shaq. “Riddick Bowe is the first person that I didn’t listen to what my momma told me. My momma told me not to become friends with people you’re going to compete with. She said you’ll tell them too much. “Riddick Bowe was that guy. I started sparring with him at the age of 18 when he was getting ready to go to the Olympics. I became good friends with him.” Holyfield and Bowe shared the ring with each other on several occasions during the 1990s, producing one of the greatest trilogies in heavyweight boxing history. ‘Big Daddy’ Bowe got the better of Holyfield twice, defeating his countryman in their first clash back in 1992 before he defeated him once again in their third and final showdown several years later.