Why does Mike Tyson, a 58-year-old cannabis mogul, think he can defeat an active boxer in Jake Paul, who happens to be 21 years his junior?

‘Can I be honest?’ Tyson asked rhetorically during a recent interview with Esquire. ‘I don’t think he can hurt me.’

An ulcer flareup delayed his matchup with Paul from this Saturday – when the former YouTuber will instead face converted bareknuckle boxer Mike Perry – until November 15.

Regardless, Iron Mike’s confidence has not waned. Asked to compare the November comeback fight with his own 1988 victory over 38-year-old Larry Holmes, and Tyson refused to even consider it. Just 21 at the time, Tyson was already a unified heavyweight champion and entered that fight at a perfect 32-0.

‘Larry Holmes was a legendary fighter who was fighting a champion who was active every day of his life,’ Tyson said. ‘I am fighting a YouTuber… It doesn’t matter how seriously he’s taking it. He is who he is.’

Tyson may be 58, but when he faces Paul on November 15, he'll be fighting a YouTuber
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Tyson may be 58, but when he faces Paul on November 15, he’ll be fighting a YouTuber

Tyson recently suffered an ulcer flareup aboard a cross-country flight from Miami to LA
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Tyson recently suffered an ulcer flareup aboard a cross-country flight from Miami to LA

Obviously a 58-year-old Tyson is not the same man who made mincemeat out of the legendary Holmes with a fourth-round knockout at the Atlantic City Convention Hall back in 1988.

During his interview with Esquire, he admitted ‘I’m an old dude,’ and his wife, Kiki, reminded the Brooklyn native to stay hydrated while training.

‘Baby,’ Kiki yelled, ‘drink your electrolytes more than usual!’

But even as he nears 60 while spending the bulk of his time promoting his cannabis company and podcasting, Tyson is no stranger to the gym these days. He fought the equally ancient Roy Jones Jr. to a draw in 2020, and since then has impressed social media audiences with flattering edits of training footage.

Paul, inarguably, has been more active. He’s 9-1 since becoming a pro fighter in 2020, and has overcome a number of well-known former UFC champions in crossover boxing matches.

Also undisputable: He’s chosen his opponents very carefully. Paul’s first bout against an experienced boxer resulted in his only defeat in 2023, when he dropped a split decision to Tommy Fury, and has yet to face a true talent in the ring. Even Saturday’s fight in Tampa pits Paul against a converted bareknuckle boxer, who hasn’t put on the gloves since 2015.

Tyson sees no similarities between the Paul bout and his 1988 KO win over Larry Holmes
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Tyson sees no similarities between the Paul bout and his 1988 KO win over Larry Holmes

And as busy as Paul has been in the ring, where he’s made millions promoting himself, he’s less than a decade removed from his career as a YouTuber, musical artist, and Disney Channel star. He did not grow up in the ring, like Tyson did at trainer Cus D’Amato’s home in Catskill, New York.

What’s more, Tyson has a few advantages. It’s only an eight-round fight, as opposed to 12, and each frame will last only two minutes rather than three, allowing the 58-year-old the chance to conserve and harness his energy for the right moment.

To some, it raises the question of why Tyson is even bothering with Paul.

‘My wife keeps saying, ‘You don’t have to do this. You don’t have to do this.’ And I’m like, ‘No, I do have to do this,’ ‘ Tyson told Esquire, stressing that his multi-million-dollar purse ‘will not change my life financially in any way.’

‘I’m a glory junkie. I love people thinking about me all day,’ Tyson said. ‘I’d rather live a short life of glory than a long life of obscurity. It’s just who I am.’