Jake Paul likes to call himself a “disruptor.” It’s a hard label to argue against.

Maybe it’s boxing’s fault for being so eminently disrupt-able, for being a professional sport with almost no barrier to entry, but Paul deserves credit for being innovatively exploitative.

He thinks outside the box. He’s crazy like a fox. (He’s a walking Sam I Am monologue, basically.)

When it comes to making money, Paul knows what the hell he’s doing.

Reports mixed with speculation have him earning in excess of $50 million for his Netflix fight Friday night against Anthony Joshua under the apparently unconcerned eye of the Florida Athletic Commission.

And if Joshua is making a paycheck anywhere in that same vicinity — and it would appear he is — then he is the ultimate beneficiary of Paul’s disruptive behavior.

One of the top heavyweights of his era facing a relatively undersized and inexperienced celebrity in a fight that counts on his record and could very realistically earn him a million dollars for every second the fight lasts?

It’s an assignment that should make every past heavyweight champion bitterly jealous.

Joshua just happens to be the right ex-champ in the right place at the right juncture on the stupidest timeline.

But what if prior legends of the ring had stumbled into living through idiocracies of their own similar to what’s become of the world in 2025?

Enjoy this journey backward in the time machine had “heavyweight champ fights unqualified celebrity” been an option available throughout history …

John L. Sullivan vs. Mark Twain

As a testament to just how different the world was when “The Boston Strong Boy” reigned in the 1880s, I searched for a list of the biggest celebrities of the time and the top name on the list was a writer. (And a writer who, as best I can ascertain, had not a single “Gotcha Hat” tattoo on his body.)

Sullivan once said of his entry into athletics, “I threw my books aside and gave myself up to it,” so Sullivan vs. Twain is, in some ways, a referendum on books.

It’s also a referendum on mustaches, and whether the superior lip curtain curls upward, as Sullivan’s did with a touch of wax, or downward, walrus-style, as Twain’s did.

Sullivan famously boasted that he could “lick any man in the room,” and had he lived long enough, he might have had the chance to lick Twain, for a postage stamp with the Adventures of Huckleberry Finn author’s face on it was issued in 1940.

In the ring, the licking would have been just as easy. Twain was a writer, not a fighter, and though he wouldn’t have been at a massive height disadvantage against Sullivan, he was a mere welterweight in his prime, giving away 50 or 60 pounds to the champ.  

About the best move for Twain would have been to read aloud controversial, race-related passages from his most famous books during the fight, so that future book-banners might be compelled to burn all footage of his inevitable one-sided beatdown at the hands of Sullivan.

Jack Dempsey vs. Charlie Chaplin

It’s The Champ vs. The Tramp. You’re not gonna beat that for a tagline that looks good on a fight poster.

The fight itself, however? Chaplin checked in at 5-foot-5 and about 135 pounds, meaning he and Dempsey standing next to each other would look … well, a lot like Paul standing next to Joshua.

The important thing is that Chaplin was a white guy, meaning Dempsey would be willing to defend the heavyweight title against him.

For what it’s worth, Albert Einstein rose to fame alongside Chaplin and Dempsey in the 1920s so I considered him for the celeb opponent slot, but I can’t see Dempsey’s people agreeing to fight Einstein. There would have been too much risk that Einstein could have come up with an obscure equation between rounds proving that, under the present physical conditions, Dempsey doesn’t exist, resulting in a no-contest.

So Dempsey vs. Chaplin it is, a silent-film mismatch — with crude, unrealistic punch sound effects added after the fact for future airings on ESPN Classic.

Joe Louis vs. Humphrey Bogart

I was tempted to pair Louis against Adolf Hitler, arguably the most famous man in the world for much of Louis’ title reign, but I didn’t want to run the risk of finding out in the comments below this article that some of our readers are “Hitler wasn’t so bad” types.

So I’m playing it safer with “Bogie,” the biggest movie star of the 1940s.

Bogart served in the Navy, which suggests he probably possessed a modicum of toughness and could whip himself into decent shape. But he would certainly be outsized against “The Brown Bomber,” standing about 5-foot-8 and famously said to have worn lifts while filming scenes with Ingrid Bergman in Casablanca and with his fourth wife Lauren Bacall in assorted films.

An extra inch or two wouldn’t help him against Louis. You know what would help him, though? Appealing to the champ’s sensitive side. As they touch gloves, Bogie declares, “Louis, I think this is the beginning of a beautiful friendship.” And that softie Joe proceeds to carry Bogart to a relatively gentle shutout decision defeat.

Rocky Marciano vs. Elvis Presley

Could the “King of Rock n’ Roll” also be the king of the ring? At least for the first time in this article we don’t have a terrible size mismatch, as Elvis stood six feet tall and weighed about 170 in his prime (allegedly double that in his later days), compared to 5-foot-10 and about 185 pounds for “The Brockton Blockbuster.”

Also, we know Presley had good footwork, and Marciano never had to chase down an opponent with Elvis’ hip-swiveling abilities.

But that’s about where the check marks in the Elvis column end. One decent Suzy Q from Marciano, and Presley woulda been all shook up.

It’s a win for Rock, a loss for rock, and a big dent in the client management reputation of the Colonel.

Young Muhammad Ali vs. all four Beatles

On February 18, 1964, with Ali (then Cassius Clay) preparing to challenge Sonny Liston and the Beatles in Miami for their second appearance on The Ed Sullivan Show, the Fab Four and the original GOAT famously met and took iconic photos together. They all got along wonderfully at the time — but the seeds for a grudge match would be planted three years later, when the lads from Liverpool put Liston and not Ali on the Sgt. Pepper’s Lonely Hearts Club Band album cover.

Look, prime Ali vs. any singular Beatle would obviously be a mismatch. But Ali vs. John, Paul, George and Ringo all at the same time?

Yeah, still a mismatch.

Result: Ali KO (Fab) 4.

Older Ali vs. Sylvester Stallone

A champ-vs.-celeb fight wouldn’t come much more marketable than this.

Stallone, inspired by watching Chuck Wepner almost-kinda-sorta give Ali a fight, writes the script for Rocky, in which Stallone’s character very much does give the Ali-esque Apollo Creed a fight. The movie wins Best Picture at the Oscars, launches “Sly” to stardom, and by 1979, Rocky Balboa is beating Creed in the rematch and Ali is ready to be taken in real life.

Could people convince themselves the actor who learned how to fake fight could beat the badly faded Ali? Your instinct might be to say no, but … remember that Jake Paul is only a +700 underdog against Anthony Joshua when most people who understand boxing wouldn’t bet him at +7000.

Even though Ali was a shell of himself by the end of the ‘70s, this would still be a gross mismatch in his favor. The training montages would be fantastic, though.

Mike Tyson vs. Michael Jackson

I had a few good options for ‘80s celebs to match against “Iron Mike”: Arnold Schwarzenegger, Eddie Murphy, Prince, Michael Jordan. But “The King of Pop” is the pick for one reason: so we can all pause and picture him wearing just one boxing glove.

On paper, this looks like the scariest mismatch of this whole exercise, but it might be fun to see how long MJ could moonwalk away from Tyson before getting tagged. In the end, though, Tyson is landing the kind of punches that would make plastic surgery a “need” rather than a “want” for Jackson.

Yeah, this is not a thriller. This is bad. And dangerous.

Maybe Michael could save himself and tag Bubbles in.

The Klitschkos vs. The Kardashians

Much like Jake Paul, the Kardashians are uber-famous and nobody knows quite why. 

As with Ali vs. the Beatles, there is a numbers game to consider here. Vitali and Wladimir are but two Klitschkos. Against Kim, Kourtney, and Khloe, as well as Jenners Kendall and Kylie, plus mom Kris and, what the hell, let’s throw in Caitlyn Jenner, this could start to get interesting. (And, hey, Caitlyn was once a world-class athlete.)

In all seriousness, the Klitschkos are honorable men who refused to fight each other because of a promise to their mother. Something tells me they wouldn’t punch a woman either, meaning this fight could go the distance with the Kardashians winning an upset decision based on greater activity.

So there you go — I picked the celeb side to win one of these matchups. Ridiculous? Perhaps.

But we live in utterly ridiculous times. As Friday night’s festivities will make abundantly clear.

Eric Raskin is a veteran boxing journalist with nearly 30 years of experience covering the sport for such outlets as BoxingScene, ESPN, Grantland, Playboy, and The Ring (where he served as managing editor for seven years). He also co-hosted The HBO Boxing Podcast, Showtime Boxing with Raskin & Mulvaney, The Interim Champion Boxing Podcast with Raskin & Mulvaney, and Ring Theory. He has won three first-place writing awards from the BWAA, for his work with The Ring, Grantland, and HBO. Outside boxing, he is the senior editor of CasinoReports and the author of 2014’s The Moneymaker Effect. He can be reached on X, BlueSky, or LinkedIn, or via email at RaskinBoxing@yahoo.com.