Tyson vs. Holyfield: The Anticipated Trilogy
The long-anticipated third match between boxing legends Mike Tyson and Evander Holyfield was closer to happening than many fans might have realized, especially in 2021. Following negotiations that suggested both fighters had reached an agreement, boxing enthusiasts were on the edge of their seats for what promised to be a legendary trilogy. Instead, Tyson diverted his attention to a bout with Roy Jones Jr., which turned out to be a decision that would ultimately derail plans for a fight that fans had been craving.
Record-Breaking Exhibition and Disappointment
Tyson’s exhibition match with Jones occurred in late 2020, shattering pay-per-view records for its format. Yet, the interest for a Tyson-Holyfield encounter was palpable enough that experts believed it could have surpassed two million PPV sales—far eclipsing the 1.5 million generated by Tyson’s fight against Jones. Holyfield expressed disappointment that Tyson chose to prioritize Jones beforehand, expressing frustration over the lack of genuine attempts to make their highly-anticipated showdown a reality.
“My team made strong efforts to finalize this fight, but we were met with nothing but obstacles,” Holyfield remarked. “Now it’s clear why Tyson felt the need for a preliminary bout before contemplating a clash with me.”
Although Tyson’s matchup with Jones was deemed successful, Holyfield maintained that his legacy would demand nothing less than a fight between the two titans.
“A matchup with Tyson would have been a global sensation, whereas Jones was merely a regional contender,” Holyfield stated, asserting the unique significance of their rivalry.
The Final Opportunity
After months of waiting for Tyson to commit to their trilogy, Holyfield opted to step into the ring against former UFC champion Vitor Belfort in September 2021. The outcome of that bout was swift and brutal, with Holyfield enduring a knockout in just 109 seconds. This devastating defeat effectively stamped out the remaining hopes for a Tyson-Holyfield III fight, sealing the fate of their storied rivalry.
In a heartfelt message just before the bout with Belfort, Holyfield had pleaded, “Stop making excuses. This fight is essential for our legacies. The world is eager; the ball is now in your court. I’m prepared for this challenge.” Unfortunately for him, Tyson did not respond, and with one swift KO, the opportunity for closure—and the chance to rewrite boxing history—slipped away.
