Before Mayweather-McGregor: History's Most Famous, Notorious Crossover Fights

Frank Franklin II/Associated Press

August 26's Floyd Mayweather Jr. vs. Conor McGregor bout has captured the world's attention in a way few fights have, but while it may feel like a once-in-a-lifetime matchup, "what if" questions involving different combat sports disciplines are a 100-year-old tradition. 

From spectators clamoring for a match between wrestling legend Ed "Strangler" Lewis and elite pugilist Jack Dempsey in the 1920s, to the mixed rules contests in the 1960s and 1970s that planted the seeds of MMA, fans have always been willing to line up to find out what would happen if a boxer faced off with an opponent from another fighting style.

With The Money Fight quickly approaching, let's take a look back at the various contests that have pitted boxer against martial artist. Some of these have taken place in 56,000-seat arenas. Some have happened in smoky local theaters. All of them, however, have given an answer to the "what ifs" of the time.

Salt Lake City, 1963

The Setup

"Judo" Gene Lebell is a familiar name for hardcore MMA fans. The grappling pioneer established himself as one of the best American judoka of his era, and that success led him to big places. Over his many years in combat sports, he has been seen alongside top fighters in all disciplines, going from taking Bruce Lee's kicks on screen to reffing fights for Muhammad Ali to mentoring Ronda Rousey.

Milo Savage, on the other hand, is not remembered by many. A middling journeyman boxer, he never quite broke through into the big time, coming up short every in every attempt to knock off higher-end opposition. He entered this one-off, mixed rules contest with a 49-46-10 pro record, and functionally retired from there. 

The Result

In the 1960s, the U.S. mainstream didn't know what to make of the martial arts. Kicks, trips and throws were a mystery to many Americans and even then, few boxing fans would have believed there were other styles of combat as effective as the one used by Ray Robinson, Rocky Marciano and Joe Louis.

With that in mind, sports writer Jim Beck ran an article in Rogue magazine titled "The Judo Bums," offering a cash reward to anyone who could prove a martial artist could defeat a boxer.

Legend has it that the martial arts community was irked by this and tasked Lebell with answering the challenge. Facing Savage in a unique mixed-rules contest, he silenced any doubters of judo's effectiveness by choking the boxer unconscious in the fourth round.     

Tokyo, 1976

The Setup

Neither man needs an introduction in their respective fields. Muhammad Ali is possibly the greatest boxer of all time and was a pop culture icon via his gift of gab and social activism. Antonio Inoki is one of the most influential professional wrestlers of all time and applied his legitimate hook-and-shoot skills to the squared circle, pioneering "strong style" wrestling.

The Result

When Ali and Inoki put pen to paper, they signed for a worked pro wrestling match. However, Ali's camp demanded a new set of rules out of fear Inoki would turn the match into an unscripted bout. Those turned out to be very, very silly rules.

Among those stipulations was that Inoki could only throw kicks below Ali's waist with one knee touching the canvas—a rule added two days before the match. While that was meant to force Inoki into standing and giving Ali an easy knockout, it instead resulted in Inoki baseball sliding to the ground and kicking Ali's leg for 15 agonizingly slow rounds.

The outcome was officially a draw, but the fact that Inoki landed over 100 kicks to Ali's six punches speaks to who really won the contest.

Tokyo, 1991

The Setup

Muhammad Ali vs. Antonio Inoki was not well-received by the Western public, but Japan's fascination with the boxer vs. wrestler matchup didn't die in 1976. Fifteen years later, a do-over was booked with the best substitutes available.

In place of Ali was Trevor Berbick, the man who sent the legend into retirement a decade earlier. In place of Inoki? Nobuhiko Takada, the shoot-style wrestler behind UWFi whose stiff, realistic brand of wrestling gave him a reputation as one of the toughest men in the business.

The Result

Both Ali vs. Inoki and Takada vs. Berbick were defined by leg kicks, but while Ali attempted to deal with the crab-walking Inoki, Berbick simply left the ring in a huff. Indeed, after absorbing kick after kick to the thigh with no defense beyond complaints to the referee, Berbick stepped through the ropes and was unceremoniously disqualified in a scene that was undoubtedly frustrating for the paying customers...but is amusing in retrospect.

Denver, 1993

The Setup

UFC 1 was a martial arts flick brought to life, bringing together representatives from a number of different combat sports to determine which fighting style was the best.

Representing boxing? Art Jimmerson. Entering the Octagon with a 29-5 pro record, 15-fight winning streak and just one glove, he sought to show that the sweet science was the one style to rule them all.

Representing Brazilian jiu-jitsu? Royce Gracie. Sent by his family to bring the "Gracie Challenge" north of the equator, he was tasked with promoting BJJ by submitting significantly larger men.

The Result

Jimmerson, quite frankly, had no idea what he was in for at UFC 1.

After some early pawing, Gracie shot for a single-leg takedown and took full-mount position without any trouble. After trying and failing to buck his way out from underneath the Brazilian, Jimmerson tapped out before Gracie even had the opportunity to start working for a submission.

Nagoya, Japan, 2003

The Setup

Eric "Butterbean" Esch was a boxing oddity in the late 1990s, working his way up to a 77-10-4 record in four-round super heavyweight fights while standing at 5'11", 425 pounds. There was a distinct carnival appeal to Esch as a competitor, and that opened the door for numerous novelty fights, even when his reputation was at its peak.

And when his boxing career started slowing down in 2002? Well, things turned into a circus fairly quickly when he decided to transition to MMA at 2003's Dynamite!! year-end mixed-sport card.

His debut opponent? Grappling specialist Genki Sudo.

The Result

At times, Japanese MMA more closely resembles classic Nintendo game Punch-Out!! than it does a serious athletic contest. Sudo vs. Butterbean is a great example of that.

For four minutes, the spindly lightweight Sudo danced around the 400-plus-pound Butterbean, flicking leg kicks and avoiding any damage. An ankle pick and quick transition to a leglock in the waning seconds of the first round revealed a clear path to victory for Sudo, and he made the most of that in the second.

Shortly after the bell, he ran the ropes pro wrestling-style and let loose a flying kick. Butterbean wasn't harmed from the strike but was baited into following Sudo onto the canvas. That proved to be a grave mistake as Sudo quickly found a foot, grabbed hold and began twisting.

The tapout via heel hook followed shortly thereafter, and Esch was cemented as a sideshow on the international MMA circuit.

Birmingham, Alabama, 2009

The Setup

Tim Sylvia's relationship with MMA fans is complicated. Despite being a two-time UFC heavyweight champion, he was maligned for a number of reasons including boring fights, a failed drug test and the simple fact that he wasn't Fedor Emelianenko, the actual top heavyweight at the time.

There was actually some celebrating when he left the UFC for the independent circuit in 2008. Those hurrahs turned into angry message-board posts, however, when Sylvia was steamrolled in an MMA bout by former WBO heavyweight champion and 1988 Olympic boxing gold medalist Ray Mercer.

The Result

The build to the fight was a strange one. Not just because it was a 48-year-old boxer making his MMA debut against a former UFC champion, mind you. The contest itself was odd as it bounced from MMA bout, to boxing match, to boxing match inside an MMA cage, back to a regular MMA bout.

Ultimately, however, the rules mattered little as Mercer prevailed in emphatic fashion by scoring a vicious one-punch knockout just nine seconds into the fight. Sylvia would later claim the repeated rule changes shifted his focus and that Mercer's smack talk got under his skin, but the damage was done to both his career and MMA's street rep.    

This photo is basically the entire fight.Josh Hedges/Zuffa LLC/Getty Images

Boston, 2010

The Setup

Five-time UFC champion Randy Couture was a dangerous man, even deep into his 40s. One of the people who got to experience that firsthand was James Toney. A 22-year boxing veteran in a career tailspin by the time he stepped into the Octagon, Toney entered with few questioning his striking skills. However, many wondered how seriously the pugilist was taking the contest. Unfortunately, any and all doubts were confirmed when the cagefighting legend steamrolled him.

The Result

Officially, Couture got the win at 3:19 of the first round. In reality, he got the win at 0:16, when he shot for an ankle pick and immediately stepped into full-mount position. Toney was hopelessly out of his depth on the ground with the accomplished wrestler, and it showed as Couture pounded on him, flowed from position to position and eventually sunk the fight-ending arm triangle.

Toney never returned to the cage.

Holly Holm is the most successful boxing-to-MMA convert.Jeff Bottari/Zuffa LLC/Getty Images

Melbourne, Australia, 2015

The Setup

While Mayweather vs. McGregor has opened up the discussion about how mixed martial artists hold up in boxing, people wondered for years about what would happen if a high-end boxer committed to MMA full time.

Holly Holm was the first to really take that plunge. Making her in-cage debut in 2011, she juggled boxing and MMA for years, adding to her collection of belts in the ring while working her way up the rankings in the cage.

In 2015, she made her UFC debut and nearly nine months later, she was holding gold.

The Result

At UFC 193, Holm posted one of the most impressive all-around performances in UFC history, sticking-and-moving circles around Ronda Rousey before putting her to sleep with a picturesque head kick. While Holm went on an ugly three-fight losing skid from there, that victory lives on as one of the most memorable moments in UFC history.

Granted, the Holm of today isn't a pure boxer the way others on this list are. Her deadliest offensive tool is her sneaky head kick, and the sweet science isn't what taught her how to avoid takedowns.

Still, her boxing base shines through in her overall game. While the experiment still needs a larger sample size to be a confirmed a success, Holm gives cause to be intrigued by other talents who make the jump.

Phoenix, 2016

The Setup

When UR Fight made the move to launch its new internet pay-per-view service, it made the bold move of doing a mixed card that included "superfights" in four different combat sports. The biggest name involved was veteran boxer Roy Jones Jr., and UR Fight had a unique way of promoting his bout: giving fans the chance to be his opponent.

The selection process is something of a mystery, but the "winner" was 6-3 MMA journeyman Vyron Phillips. Looking at how the fight went, though, there wasn't much that distinguished him from any other fan.

The Result

After the first exchange, it was obvious how this match would go. Jones would do whatever he felt like. Phillips would try in vain to counter. The only question was how long it would take for the actual boxer to end it.

He found his timing early, picked where the fight took place, tagged Phillips at will and effortlessly dodged every punch thrown at him. The knockout came in the second when Phillips attempted an ill-advised lunging right hand and ate a vicious pair of hooks from Jones that left him stiff on the canvas.