Heavyweight great Evander Holyfield once admitted that he regretted facing one of his legendary rivals.

‘The Real Deal’ is often regarded as being one of the greatest heavyweights of all time, although he enjoyed a great deal of success in the cruiserweight division prior to his campaign at heavyweight.

Holyfield captured the undisputed cruiserweight championship back in April 1988 when he stopped Puerto Rico’s Carlos De Leon in the 8th round of their showdown at Caesars Palace in Las Vegas.

He later made the move up to heavyweight where he would go on to reign as the undisputed champion with a historic victory over James ‘Buster’ Douglas in October 1990, becoming the first fighter in boxing history to achieve this feat at cruiserweight and heavyweight.

Speaking on the Big Podcast with Shaq, ‘The Real Deal’ admitted that he regretted going ahead with a bout against former rival Riddick Bowe, who he would end up facing on several occasions during his career.

“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.”

Bowe and Holyfield produced one of the greatest rivalries in heavyweight boxing history, facing each other three times between 1992 and 1995.

‘Big Daddy’ defeated Holyfield twice, getting the better of his countryman in their first clash before stopping him in the 8th round of their trilogy encounter in November of 1995.