The biggest crossover fights of all time

Sports

Tyson Fury, the greatest heavyweight boxer in the world, will step in the ring on Saturday (2 p.m. ET on ESPN+ PPV) for a meeting with the other greatest heavyweight in the world, Francis Ngannou. But to portray this matchup in Riyadh, Saudi Arabia, as the best vs. the best would be living in a fantasy world. Ngannou may be the baddest man on the planet, but he earned that distinction as an MMA knockout artist. He has never competed in professional boxing.

This weekend’s fight could be more aptly described as the best vs. the rookie with a puncher’s chance. But that doesn’t douse the intrigue. It never has for extravaganzas like this. Fight fans have long argued over what would happen when an elite boxer — the gold standard of prizefighting for much of our culture’s history — was put in the ring with a top-shelf wrestler, karate master, mixed martial artist or someone else who doesn’t abide by Marquess of Queensberry rules.

For generations, it was a hypothetical question. But that is no longer the case, and hasn’t been for years. Before Fury vs. Ngannou, we had Floyd Mayweather vs. Conor McGregor. Before that, we had Muhammad Ali vs. Antonio Inoki. A boxer was Royce Gracie’s first opponent way back at UFC 1. And the Octagon later welcomed three-division world champion boxer James Toney.

Here’s a history of the most notable spectacles we’ve witnessed when boxing takes on other combat sports:


The crossover event often cited as inspiring the sport of MMA

Muhammad Ali vs. Antonio Inoki

June 26, 1976, in Tokyo

This was conceived as a “work,” the pro wrestling term for a match scripted ahead of time, with a predetermined result. The problem was, the promoters planned for Inoki, a wrestling star adored in Japan, to be the winner in his homeland, and Ali wasn’t OK with being told to lose. So it turned into a real fight, although rules were established to prevent Inoki from grappling Ali to the canvas. (Yes, the wrestler was not allowed to wrestle.) As a result, for the better part of a more-painful-to-watch-than-participate-in 15 rounds, Inoki lay on his back and kicked at Ali’s legs while scurrying after him around the ring like an angry crab. But Inoki wasn’t as angry as the fans at Nippon Budokan, who threw debris into the ring and chanted, “Money back! Money back!”

Adding to the night’s mayhem: The closed-circuit telecast also featured an even more bizarre boxer vs. wrassler scrap from Shea Stadium in New York: Andre the Giant vs. Chuck the Bayonne Bleeder. That would be Chuck Wepner, who was one year removed from surviving into the 15th round against Ali and who later would be Sylvester Stallone’s inspiration for “Rocky.” This one had the clear appearance of a work, with every potentially combative engagement conveniently interrupted by the referee. Until the finishing flourish, that is, when Andre picked up Wepner and tossed him over the top rope.


No, actually, this was the one that started it all years earlier

Gene LeBell vs. Milo Savage

Dec. 2, 1963, in Salt Lake City

It all began, as so many things do in the fight game, with a challenge that targeted ego and economics. A writer named Jim Beck wrote a magazine article with the crotchety title “The Judo Bums” in which he offered a $1,000 reward to any judo or karate practitioner who could defeat a boxer. That caught the attention of Gene LeBell, who had won a national judo championship before transitioning to pro wrestling and movie stunts. (He later would be a judo mentor of pre-UFC Ronda Rousey.) LeBell answered the challenge and headed to Utah, where his opponent would be Milo Savage, who had more than 100 pro boxing fights and had once been a ranked middleweight.

The fight occurred at Fairgrounds Coliseum, headlining a televised pro wrestling show billed as “Something New for Sports Fans.” Those who bought a $2 ringside seat or watched from home saw the historic scuffle end violently when LeBell used his judo to throw Savage to the canvas, then choked the boxer unconscious. Savage was a local hero, so the sight of him lying motionless as LeBell paraded around in celebration prompted the crowd to litter the ring with debris. But a statement had been made.


The biggest-selling crossover of all, inspiring more MMA fighters to try boxing

Floyd Mayweather vs. Conor McGregor

Aug. 26, 2017, in Las Vegas

Mayweather was two years into his retirement from boxing at 49-0, after winning championships in five divisions. McGregor was the UFC lightweight champion and previously owned the featherweight title, making him the promotion’s first champ to reign in two weight classes simultaneously. What brought these two stars together? You’ll find a clue in Mayweather’s nickname: “Money.” Mayweather was guaranteed $100 million for the bout, McGregor $30 million, and both men pocketed multitudes more than that.

The fight itself? McGregor looked good early, with Mayweather doing little but laying against the ropes. Once Mayweather started fighting, a few rounds in, McGregor started to fatigue and absorb punches. By Round 10, it was one-way traffic, Mayweather delivering a beating, until referee Robert Byrd mercifully jumped in. Cha-ching!


The most successful crossover into MMA by a boxer

Ray Mercer vs. Tim Sylvia

June 13, 2009, in Birmingham, Alabama

The most shocking MMA performance by a boxer, without a doubt, was by three-division world boxing champ Holly Holm, who knocked out the undefeated Rousey in 2013 for the UFC women’s bantamweight title. But by then, Holm had fully transitioned to an MMA career and was in her 10th fight. Mercer, on the other hand, was a relative newcomer to cage fighting when he fought Sylvia. The 1988 Olympic gold medalist boxer and former WBO heavyweight champion had been quickly choked out in his one previous appearance, a 2007 exhibition match against YouTube brawler-turned-MMA neophyte Kimbo Slice. Two years later, Mercer was back in a cage, this time with a more experienced mixed martial artist who had been UFC heavyweight champion not long ago.

Even those who had seen Sylvia get submitted by all-time MMA great Fedor Emelianenko in a mere 36 seconds about a year earlier probably figured Mercer had bit off more than he could chew. Instead, we saw boxing’s greatest moment inside an MMA cage. Mercer threw just one punch, an overhand right that chopped down the 6-foot-8, 310-pound Sylvia like a rotund redwood in 9 seconds.


The most successful crossover into boxing by an MMA fighter

Anderson Silva vs. Julio Cesar Chavez Jr.

June 19, 2021, in Guadalajara, Mexico

Silva, the longtime UFC middleweight champion, was on the short list of candidates for the GOAT in MMA. His 16 consecutive victories still stand as an Octagon record. Silva made his name as one of the sport’s greatest strikers, and he often spoke of a desire to transition to boxing. Now that he was done with MMA, he was looking to box a big-name opponent. He found him — sort of — in Chavez, who a decade earlier had owned the WBC middleweight title but was best known as the son of Mexican legend Julio Cesar Chavez Sr.

Chavez was living through troubled times, including drug-test failures and weigh-in misses. Still, he was expected to easily handle the inexperienced Silva. But that’s not how things went down. Silva was the aggressor throughout, and while he did not dominate the bout, he did enough to earn a stunning split-decision victory.


Other MMA ventures by boxers

Trevor Berbick vs. Nobuhiko Takada

Dec. 22, 1991, in Tokyo

Berbick, a former WBC heavyweight champ who had fought Muhammad Ali (win) and Mike Tyson (loss), traveled to a sumo hall for this boxer-vs.-wrestler match that, to his shock and horror, turned into kickboxing. In the opening seconds, Takada, a pro wrestling star, landed a kick to the lead calf, and Berbick turned to the referee in protest. Berbick pointed to his torso, apparently claiming that kicks to the legs were against the rules. But the ref was unmoved. Takada kept kicking, and Berbick kept protesting, while not throwing a single punch. After absorbing more than a dozen leg kicks in less than a round, Berbick just turned and hobbled out of the ring. Fight over.

Matthew Saad Muhammad vs. Kiyoshi Tamura

May 8, 1992, in Tokyo

Saad Muhammad had once been WBC light heavyweight champion, and he later would be inducted into the International Boxing Hall of Fame. But his boxing career had ended sadly, with just one win in his last nine bouts. Desperate for a payday after declaring bankruptcy, Saad Muhammad stepped in with Tamura, a submission fighter who later would score MMA wins over Renzo Gracie, Pat Miletich and others. Tamura needed just 34 seconds to choke out the fish-out-of-water boxer.

Art Jimmerson vs. Royce Gracie

Nov. 12, 1993, in Denver

This was at historic UFC 1, where every bout was a crossover bout. Eight fighters from disciplines ranging from sumo to taekwondo showed up at a half-filled McNichols Sports Arena to take part in the one-night tournament. Representing boxing was Jimmerson, a ranked cruiserweight on a 15-fight winning streak. His most notable attributes at this event were his hands, but not for the pugilistic reasons you might imagine. Jimmerson left his mark on UFC history by wearing just one boxing glove. The plan was to jab with the gloved left hand, then get the knockout with his bare-knuckled right. Instead, the only use he got out of his bare hand was to tap out barely two minutes into the one-sided bout, overwhelmed by Gracie and his then-mysterious discipline of Brazilian jiu-jitsu.

James Warring vs. Renzo Gracie

Oct. 17, 1995, in Charlotte, North Carolina

Gracie was actually the third MMA foe for Warring, a former IBF cruiserweight boxing champ and a one-time kickboxing world titlist. All three of those MMA matches came in this one-night tourney. Warring won his first two fights of the evening, beating kickboxer Jerome Turcan and MMA fighter Erik Paulson before meeting Gracie in the final. Two years after cousin Royce had put jiu-jitsu on the global map, Renzo showed off the martial art’s dominance once again, choking out Warring in less than three minutes.

Imamu Mayfield vs. Kazuyuki Fujita

Dec. 31, 2003, in Kobe, Japan

Mayfield, a former IBF cruiserweight boxing champ, had time on his side in this bout. The rules allowed for just 20 seconds of ground fighting whenever Fujita got the fight to the canvas. That was not enough time for Japan’s one-time Greco-Roman wrestling national champion to work toward a submission. Eventually, Fujita figured that out and instead clamped on an arm triangle choke while he and the boxer were standing. That got him the submission.

Ray Mercer vs. Kimbo Slice

June 6, 2007, in Atlantic City

Mercer signed up for an exhibition against Kimbo, the backyard brawler and YouTube sensation who was just a few months away from launching a pro MMA career. “Merciless” Ray, 46, apparently was expecting a boxing match, but the spectacle was slated as an MMA bout, and Kimbo embraced the “mixed” part. He immediately took Mercer to the canvas, and even after the boxer stood back up, Kimbo kept him in a clinch, landing knees to the body and elbows to the head. Barely a minute in, Kimbo took Mercer back to the canvas and finished him with a guillotine choke.

Mia St. John vs. Rhonda Gallegos

Jan. 26, 2008, in Honolulu, Hawaii

Before becoming a super welterweight and lightweight world champion and one of the pioneers of women’s boxing, St. John had been a taekwondo black belt with a 27-1 record. So she was not entirely out of her element when she fought her one and only MMA fight. That showed immediately, as she overwhelmed Gallegos with kicks before landing a big right hand for a 44-second knockout.

James Toney vs. Randy Couture

Aug. 28, 2010, in Boston

Fifteen seconds. That was how long Toney, the former three-division world boxing champ, was able to fight while standing up — you know, like a boxer is trained to fight. After that, he was flat on his back, courtesy of a Couture ankle pick takedown. As the UFC 118 crowd at TD Garden chanted “UFC! UFC!” the 42-year-old Toney was defenseless. Couture, 47, delivered a ground-and-pound beatdown for a couple of minutes before locking up an arm-triangle choke. Toney quickly tapped out, as he was on the verge of living up to his “Lights Out” nickname.

Ricardo Mayorga vs. Wesley Tiffer

May 13, 2013, in Managua, Nicaragua

Mayorga, the volatile former two-division world boxing champion, had planned to make his MMA debut three years earlier, but a Don King injunction prevented that bout from taking place. Finally, in his home country, Mayorga made it to a cage. He was dominated on the canvas, but initially was awarded the win after his knee to the spine rendered Tiffer unable to continue. But the Nicaraguan commission later overruled the result because of the illegal knee — and because Mayorga had weighed in 20 pounds over the limit. Mayorga would fight three more times in MMA, all losses.

Claressa Shields vs. Brittney Elkin

June 10, 2021, in Atlantic City

Shields has committed herself to an MMA career in addition to being an undisputed middleweight boxing champion, so she may not qualify as a dip-the-toe-in crossover fighter. The same could be said for Amanda Serrano and Heather Hardy, championship-level boxers who’ve also pursued MMA careers, not one-off appearances. But let’s include Shields’ first foray into the PFL cage. The two-time Olympic boxing gold medalist had a rough start, taken to the canvas and held down by Elkin for two rounds. But when Elkin went for a takedown in Round 3, Shields stuffed the attempt and wailed away with punches until the referee waved off the bout. “Oh my God!” a smiling Shields exclaimed repeatedly as she celebrated with her Jackson Wink MMA coaches.


Other boxing ventures by MMA fighters

Tenshin Nasukawa vs. Floyd Mayweather

Dec. 31, 2018, in Saitama, Japan

Nasukawa had fought in a few MMA matches but was essentially a kickboxer. If anything, that should have helped the 20-year-old in this boxing exhibition, in that he wasn’t a grappling-first fighter who’d have to leave his strongest skill back in the locker room. It didn’t matter. Mayweather, 41, toyed with Nasukawa, knocking him down three times in two minutes before the mismatch was waved off. Nasukawa was in tears afterward as “Money” Mayweather headed home with a reported $9 million payday.

Ben Askren vs. Jake Paul

April 17, 2021, in Atlanta

Purists might question whether an MMA fighter facing Paul qualifies as a “boxing venture.” But let’s go with it. This was the beginning of Jake Paul vs. MMA. After already having had a pair of pro boxing matches against a YouTuber (AnEsonGib) and ex-NBA player (Nate Robinson), Paul took on Askren, a former Bellator and One champ as well as U.S. Olympic wrestler. “Funky” Ben had absolutely no standup skills, and it showed. He was knocked out in less than two minutes.

Tyron Woodley vs. Jake Paul I

Aug. 29, 2021, Cleveland

This second Paul bout against an MMA fighter evolved out of the first. Woodley, a former UFC welterweight champion, was in the corner of Askren, his former wrestling teammate at the University of Missouri. Woodley had words backstage with the Paul team, leading to a callout and this fight. It wasn’t a thing of beauty, but at least it was mildly competitive, ending in a split-decision win for Paul.

Vitor Belfort vs. Evander Holyfield

Sept. 11, 2021, in Hollywood, Florida

Originally, this was to be a boxing match between Belfort, the former UFC light heavyweight champion, and a different legendary former boxer, Oscar De La Hoya. But a week before fight night, the 48-year-old De La Hoya withdrew for health reasons, and in stepped Holyfield — a month short of turning 59. With former President Donald Trump and MMA star Jorge Masvidal providing commentary on the Triller broadcast, the exhibition bout was mercifully brief, as Belfort, 44, scored a TKO over the wobbly shadow of Holyfield in 1:49.

Tyron Woodley vs. Jake Paul II

Dec. 18, 2021, Tampa, Florida

The only rematch in the boxer-vs.-nonboxer oeuvre came about because of popular demand. Just kidding. According to Paul, the first fight had drawn 500,000 pay-per-view buys. So why not return to the well? As it turned out, this bout produced Paul’s greatest highlight, a one-punch faceplant KO of Woodley.

Anderson Silva vs. Jake Paul

Oct. 29, 2022, in Glendale, Arizona

More Paul? Ugh. OK, at least he finally faced an MMA fighter who knew how to strike. Silva should have been Paul’s toughest opponent, if only because of the former UFC star’s win over Chavez. But Paul controlled the fight, even scoring a knockdown in the final round, to take a unanimous decision.

Nate Diaz vs. Jake Paul

Aug. 5, 2023, in Dallas

Diaz carried more star power into this bout than anyone Paul had faced. But that was all Diaz brought, as Paul got a knockdown and another dominant decision win. Is there anyone left in MMA for Paul to box? Maybe the whiskey mogul from Dublin? Anyone interested?

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