Mike Tyson identified Donovan Ruddock as the hardest opponent he ever shared the ring with.
While Tyson is famously remembered for his rivalries with Evander Holyfield and Lennox Lewis, he maintains that Ruddock’s unique power was on a completely different level. The two engaged in two brutal fights.
Tyson walked away with a seventh-round TKO in their 1991 fight, but the victory was marred by controversy. When the referee waved the fight off, Ruddock’s team erupted, leading to a massive in-ring brawl. The “premature” stoppage was so heavily disputed that the public demanded an immediate repeat.
To settle the score, the pair met again just three months later. Tyson ultimately secured a unanimous decision, but the physical toll was immense. “Iron Mike” left the arena with a ruptured eardrum, while Ruddock endured a fractured jaw and significant facial trauma. According to Tyson, being hit by Ruddock didn’t just cause pain—it effectively shut down his senses.
“Yes, Ray Ruddock … You’re talking about when you were like whoa. When you get hit, it doesn’t hurt anymore. It’s just numb. You just hear the bell ringing — bong,” Tyson said
As for his boxing future, Tyson has been linked with a fight against Floyd Mayweather. Reports indicated that an exhibition will take place in March. However, Mayweather announced a fight with kickboxer Michalis Zambidis for June, raising doubts over whether it will happen. Tyson’s last fight was a 2024 loss to Jake Paul. Reports indicated he earned a minimum of $20 million for that fight. Tyson admitted he has made more money in the late stage of his career than he did when he was fighting at his peak.
“I made more money in my 50s than I did in my 20s. That’s really interesting. From that perspective, I’m [about to be] 60 years old. The money doesn’t mean anything. The people I love, I can take care of. This is going to be some good stuff, right?” he said. “I’ll be three fights in, so I’m already over my jitters. This is going to be the best one. … If these people stop giving me money, yes, this will be the last one,” Tyson said
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