Evander Holyfield Names The Heavyweight Who Beat Him That He Regrets Ever Facing

The undeniable legacy of heavyweight legend Evander Holyfield lives on, almost 14 years after he last appeared in the ring.

The 62-year-old from Atmore, Alabama is one of the most accomplished fighters in the history of boxing, winning the undisputed championship in two separate divisions.

‘The Real Deal’ captured the undisputed cruiserweight championship in April 1988 before repeating this feat at heavyweight two years later, with a third-round knockout victory over James ‘Buster’ Douglas.

His campaign at heavyweight saw him pick up wins against the likes of George Foreman, Riddick Bowe and Mike Tyson, as well as participating in two historic showdowns with Lennox Lewis, drawing with ‘The Lion’ in March 1999 before losing in the rematch eight months later.

Despite facing such an array of legendary fighters during his career, there was one man that Holyfield claims he regrets facing.

Speaking to The Big Podcast with Shaq, ‘The Real Deal’ explains why he should have opted against facing Riddick ‘Big Daddy’ Bowe.

“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 locked horns on three occasions in a memorable trilogy. Bowe won their first showdown in November 1992, handing Holyfield his first career defeat in the process. It was revenge for ‘The Real Deal’ just one year later as he recaptured his WBA and IBF heavyweight titles.

Their third and final meeting came in a non-title clash at the end of 1995, as ‘Big Daddy’ stopped Holyfield in the eighth round, putting an end to their bitter rivalry.