It’s been 19 years since Mike Tyson’s last professional fight and 21 years since his last win

It’s been 19 years since Mike Tyson’s last professional fight and 21 years since his last win.

It’s been 28 years since he last held a belt, 34 years since Buster Douglas ended the myth of his invincibility, and 38 years since he became the youngest heavyweight champ ever.

It’s been 25 years since I wrote a cover story for Boxing 99 titled “The Secret of Mike Tyson’s Enduring Popularity.”

That’s right. By 1999, when he was preparing to return from his ear-bite suspension, we were already marveling at the continuing relevance of this mostly used-up boxer who had clearly become more curiosity than colossus.

And thanks to the announcement last week that Tyson will be fighting against Jake Paul on Netflix in front of probably 80,000 fans at AT&T Stadium on July 20, we must confront the reality that Tyson, who will be 58 years old by fight night, remains a phenomenon in 2024.

His grip on the paying public was unique, if not quite unprecedented for an aging boxing icon, during the final phase of Tyson’s pro boxing career. That grip is ludicrous and fully unprecedented now. There has never before been a boxer who could fill a stadium while pushing 60.

But no rules have ever applied to “Iron Mike.” He was a fireball that burned so bright the myth engulfed the reality, then crashed so destructively that the rubbernecking ensured he would never “fade into bolivian.”

Tyson had one of the shortest primes of any great heavyweight champion. But he’s had the longest tail, by far.

The Jake Paul phenomenon is weird — to go from Disney Channel star and YouTuber to boxing pay-per-view headliner would be impossible to wrap our heads around if we hadn’t watched it unfold step by step.

But somehow Paul identified the one boxing phenomenon weirder than his own. And the result will be, like it or not, the most watched boxing match of the year, probably of the decade, possibly of the century.

How is this possible? How is Tyson’s popularity still enduring 25 years after I first scratched out an article over scratching my head about his staying power?

It starts with understanding what he meant to the children of the 1980s. I was 10 years old, and not a boxing fan at all, when my January 6, 1986 copy of Sports Illustrated arrived in the mail with that gold-toothed smile flashing at me, the headline “Kid Dynamite” in the upper right corner, and on the lower left, the line, “Mike Tyson: The Next Great Heavyweight — And He’s Only 19.”

I’d never heard his name before. Serious boxing fans certainly had — Tyson was 15-0 with 15 KOs, including 11 in the first round, by the end of 1985. But this was my introduction to him. I remember reading with fascination the detail about his 20-inch neck and discussing with my brothers how crazy that sounded (none of us understood that such a measurement was of circumference not length — and back then, there was no internet, so you only knew what you knew and then you asked your brothers who were just as stupid and sheltered as you).

That SI article was a key cog in the mythmaking of a generational athlete for the generation that was most impressionable at the time.

And then Tyson proceeded, for a few years anyway, to live up to all the myths, all the hype. He won a piece of the heavyweight title at 20 and was a few days shy of 22 when he knocked out Michael Spinks in 91 seconds to claim the lineal title.

Outside the ring, he was the end boss in a major video game with his name in the title, he was the subject of a hit Fresh Prince song, and he married a Hollywood starlet.

He was Gen X’s Muhammad Ali, except his calling card was sensationally violent knockouts, not fancy footwork. He was all stinging, no floating. And that meant that, to anyone lacking a deep understanding of the Sweet Science, it was a foregone conclusion that Tyson would kick Ali’s ass.

And for a lot of people, that belief would never go away. It proved itself to be almost like a religion, a kind of blind faith. As he transformed from boxing’s Michael Jordan in the ‘80s (the ultimate athletic dynamo) to boxing’s Michael Jackson in the ‘90s (the ultimate tabloid freakshow), the Tyson fans still saw him as that KO king from the previous decade.

“There will always be people who believe he can recapture what he once was,” then-HBO analyst Larry Merchant told me for that 1999 article. “Remember, this is an athlete who makes the front page as well as the back page, something that’s rare in any sport. There will always be a sort of morbid fascination with Tyson. He simply evokes an emotional reaction that’s difficult to deny.”

To the “morbid fascination” point: There was a belief among many that Tyson was destined not to live long. You could have gotten fairly juicy odds back then if you’d wanted to bet on him making it to 57. When he got a tattoo on his face in 2003 — long before every rapper, rocker, fighter, and troubled teen were inking up their faces — those odds spiked.

But then he turned a corner. He had a memorable cameo in The Hangover. His illustrated likeness was at the center of a show on Cartoon Network. He became a best-selling author and the star of a one-man show that went to Broadway. He became a podcaster and a pot-caster.

He mellowed. He survived. He thrived. There remains a fascination, but it isn’t morbid. He faded to some extent, but not into bolivian. For my kids’ generation, if you ask them to name a famous boxer from the past, he’s going to be one of the first two of three names spit out.

Oh, and it didn’t hurt that, when he stepped back into the ring for an exhibition fight against Roy Jones at age 54, he looked like he could still fight. He still had some “Baddest Man on the Planet” in him.

And they sold a reported 1.6 million pay-per-views. It was the biggest boxing PPV in terms of U.S. sales since Floyd Mayweather vs. Conor McGregor.

Which brings us to July 20.

Mike Tyson vs. Jake Paul is going to be one of the most viewed boxing matches of our lifetimes. Grumble and groan all you want, but there are some 260 million Netflix subscribers globally, and about 80 million in North America — roughly as many as had HBO (or Max) and Showtime combined last year.

If this fight were on pay-per-view, who knows, maybe a million households would pay, maybe 2 million, maybe 3 million. Because it’s included with a Netflix subscription, it could reach the biggest audience for boxing since … well, since major fights were sometimes live on network TV back when Tyson was first coming up in the ‘80s.

It’s crazy that it will be Tyson attracting this audience.

It’s crazier that he’ll be doing so against someone who was born in between his two fights with Evander Holyfield.

As my BoxingScene colleague Jason Langendorf tweeted, “Whether you like the circus act or not, boxing benefits from s*** like Paul-Tyson. I’m currently in Bumf***, Illinois, and there’s a Karen mom at this roadhouse talking about ‘I don’t care how old he is, Tyson is gonna murder that boy.’”

As my boxing podcast co-host Kieran Mulvaney wrote in his latest BoxingScene column, “boxing fans should be prepared for this being the only fight their friends ask them about for the next several months.”

You won’t be able to get away from it. And the enormity of this spectacle stems from Tyson’s continuing brand value dwarfing that of any other living fighter. Only a rare few athletes could pull off something like this.

If 61-year-old Michael Jordan announced a one-on-one basketball game against 30-year-old Justin Bieber — generally considered good for a celebrity basketball player — it would also generate massive buzz and perhaps a viewing audience in the tens of millions. It would lack the danger factor of a fight between Paul and Tyson — the worst that could realistically happen to Old Man MJ is he twists and ankle or pulls a hammy — so maybe Jordan-Bieber isn’t quite as big as Tyson-Paul. But it’s in the ballpark, because Jordan is the one ex-NBA player who remains bigger than his sport.

Justin Bieber vs., say, Charles Barkley wouldn’t move the needle much at all.

The same goes for Jake Paul vs. Holyfield, even though Holyfield was 2-0 vs. Tyson and ranks comfortably ahead of him on any all-time-great list.

You specifically need Tyson to make an otherwise silly sporting sideshow like this a must-see event. Sure, he lost embarrassingly to Kevin McBride nearly two decades ago. It doesn’t matter. When people close their eyes, they see a knockout machine pulverizing so many Steve Zouskis and Sammy Scaffs.

It’s long been said that for old fighters, punching power is the last thing to go. But with “Iron Mike,” it’s selling power that will be the last thing to go.

And tens of millions of people will be tuning in on July 20 to find out if there’s still some punching power accompanying it.