Quick explanation of how this list got generated: The first three entries on the list are used to demonstrate the growth of boxing and are not necessarily one of the biggest paydays in history, but they are close. The next 15 entries are based on the estimated winnings of a single boxer from a single match pro-rated for inflation in today’s dollars.
18. Gene Tunney VS Jack Dempsey – (1927) $13,700,000 pro-rated ($990,000) in “The Battle of the Long Count”
This was the first big sporting event the world had ever seen. Over 100,000 fans packed Chicago’s Soldier Field to witness the fight that was the first to crack the million-dollar mark, grossing over $2.7 million (roughly $40 million in today’s money) without Pay Per View or television. The next million-dollar sporting event to follow this one? It was five decades later, and it required the charismatic, bigger than life Muhammad Ali. It was estimated that 3 out of every 4 people tuned into their radio stations to listen in. Even though Tunney was the heavyweight champion, it was Dempsey, the biggest celebrity (let alone athlete) of his time, that drew the fans and generated the revenue. Alas he only received half as much as Tunney.
Even Al Capone got into the action, betting $50,000 ($700,000 today) for Dempsey to regain his title that he lost one year earlier. The amount of money wagered for Dempsey and the caliber of people betting led to fears that the fight was fixed, forcing the referee to be changed at the last minute.
As big as the fight was, the finish was tainted as Tunney won by decision after being knocked down and supposedly out for the count by Dempsey. In the heat of the moment, Dempsey took 6 seconds to go to his corner, allowing Tunney 16 seconds instead of 10 to get back on his feet. In Dempsey’s fairness, this was the first fight ever where boxers were required to go back to their corner after knocking down their opponent. In the past, all Dempsey had to do was stand over his opponent, ready to greet him with a vicious right hand that would promptly knock him out. That mistake cost Dempsey the Crown in the final fight of his career.
17. Muhammad Ali VS Joe Frazier I – (1971) $14,800,000 pro-rated ($2,500,000) in “The Fight of the Century”
This is the fight that made boxing the biggest event in the world once again, after five decades since Jack Dempsey had passed. It wasn’t just a fight, but a statement between the radical chic and the establishment. Muhammad Ali, who refused to join the U.S. Army, represented the new protest generation with his lightning quick speed, while the “Ugly” Joe Frazier, as coined by Ali himself, was seen representing the system that needed to be brought down. Frazier would later state that if he did not get exempted from the war due to his wife and kids, that he would have gladly served a country that was so good to him. This time around, the establishment won as the undefeated Frazier won a unanimous 15 round decision, giving Ali the first loss of his career, and removing the crown he held for seven years. The deciding blow was a left hook, as seen above, in the last round that sent Ali down to the canvas.
The buildup to the fight was so intense that it ushered in the Pay Per View era, as an estimated 300 million people in 50 countries worldwide spent up to $15 ($90 today) to see the match on closed circuit TV. More people saw the fight than the landing on the moon two years earlier, which was broadcast for free.
16. Muhammad Ali VS George Foreman – (1974) $24,400,000 pro-rated ($5,000,000) in “The Rumble in the Jungle”
The man might have recently passed away, but every single one of us, even non boxing-fans, has heard of ‘the Rumble in The Jungle’. This is the fight that Ali won by using the “Rope A Dope”, largely relying on the ropes; thus, allowing the bigger Foreman to tire himself out by throwing punches that continually missed while Ali continually attacked with punches to the face, until a visibly swollen Foreman fell to the canvas in the 8th round, after receiving a 5 punch barrage, then a left-hook, followed by a right. Foreman did get up after 9 seconds, only to have the ref stop the fight. Ali would later complain that he missed “pretty girls and ice cream”.
Don King, the legendary promoter of the fight somehow did not have money to stage this fight, so he went searching for the money. Finally, the money came from Zaire’s (now the Democratic Republic of Congo) dictator Mobutu Sese Seko, who put up the prize money of $5 million to each fighter. The dictator, so eager to put his country on the map, made this into a 3-day celebration featuring legendary acts of the time, like James Brown and B.B King. Too bad this fight didn’t do for his country what it did for boxing.
15. Sugar Ray Leonard VS Marvin Hagler – (1987) $25,400,000 pro-rated ($12,000,000)
The new media king was Sugar Ray Leonard, the gold medal winner at the Montreal Olympics in 1976. Sugar Ray had other’s in the lower weight divisions that made the non-heavyweight fights the glamour events of the eighties, one of whom was Marvelous Marvin Hagler. In a matchup that many say was 5 years in the making, Sugar Ray won a split decision that might be the most controversial of its time. Depending on who you asked, either Hagler won by a landslide or Sugar Ray won by a landslide. Either way, Leonard floated around the ring, while waiting for Hagler to throw those ferocious punches at him, prompting Hagler to tell his opponent to ”fight like a man”, and Sugar Ray to tell his opponent to “punch instead of push” and to later tell the media: “People said I lost the zip, but my hands are just as fast as they were when I was 20 years old!”.
14. Sugar Ray Leonard VS Donnie Lalonde – (1988) $26,400,000 pro-rated ($13,000,000)
Sugar Ray just wanted to win the crown in every division possible, and in his third fight after retiring, decided to go after the light heavyweight crown by fighting the current champion, Donnie “Golden Boy” Lalonde. The vacated super middleweight crown was also up for grabs in this fight. This was Lalonde’s second title defense but only the 3rd fight in 7 years for Leonard, including a 19-month hiatus from his last fight against Marvin Hagler. It seemed that time only made fans hungrier more for Sugar Ray, as he could command any payday he wanted including the unheard $13 million he received for this fight. Of course, the reigning champ received much less.
Leonard’s chances to win seemed dim in the 9th round when he received 31 straight punches from Lalonde, most of them weak but more than enough to tilt the scorecard. The round turned quickly as Leonard launched three hooks to Lalonde’s head, followed by an endless battery of assaults that dropped the champ down to the ground. Lalonde eventually got up, raised his hand and told Leonard: “You win”. With the fight, Leonard became the second boxer to win 5 weight divisions, a few days after Thomas Hearns accomplished the same goal, setting the stage for the last of Sugar Ray’s great fights one year later.
13. Manny Pacquiao VS Juan Manuel Marquez III – (2011) $26,700,000 pro-rated ($25,000,000) in “The 25th Round Begins”
This was the third fight between the two stars, and the long awaited return of Manny Pacquiao to HBO. Up for grabs, the welterweight title. The fight was up against the major league baseball playoffs, so the promoters required a 4-day, three continent tour just before the fight in order to get the return they hoped for. The fight did make the money as both fighters gave everything they had for 12 rounds, each one refusing to go down while taking punch after punch. In the end, all fans had to rise to their feet, as it appeared to everyone that their favorite boxer had won as the fight appeared to be a draw. The judges awarded the crown to Manny, prompting Marquez’s fans to throw all sorts of things towards the stage. In the end though, the judges did not think it was that close, as two judges awarded the fight to Manny while the third judge called it a draw (later apologizing for missing the mark on that decision), making Marquez’s fans just seem all that much angrier for nothing.
12. Sugar Ray Leonard VS Roberto Duran – (1980) $29,100,000 pro-rated ($10,000,000) in “The No Más Fight”
It seems all major fights now are in Vegas, but at that time they were set in all sorts of obscure places and still made money. This was the second of three fights between the superstars, as Sugar Ray tried to regain the welterweight crown he lost to this same man a few months earlier in Montreal. In the first fight, Duran outlasted Sugar Ray by getting the superstar off his game. In this fight it was Duran that seemingly gave up in the eighth round as he turned towards the ref and proclaimed: “No más” (No More In Spanish), and then walked off the ring seemingly in one piece.
What does it take to get someone to just walk away? After all, Sugar Ray was known for lightning quick feet, and not killer jabs that gut their opponents in an instant. According to Duran, it was stomach cramps, blaming his manager for an abnormal diet required for his morning weigh-in. His manager’s response: “He quit because he was embarrassed”. The scorecard showed Leonard leading by one on all 3 scorecards at the time. So, you decide what happened.
11. Sugar Ray Leonard VS Thomas Hearns – (1981) $31,700,000 pro-rated ($12,000,000) in “The Showdown”
This was the decade of Sugar Ray, as this is the last of his fights on the biggest money maker list and the first of his fights against the legendary Hearns, the man who later took the glory from Sugar Ray by becoming the first five division champion. The undefeated Hearns went down in defeat after seemingly having won the fight with only one round left. Hearns was winning unanimously between rounds 9 and 12, with Sugar Ray’s legendary trainer proclaiming: “You’re blowing it now, son! You’re blowing it!”. In the 13th round, Sugar Ray received a bit off a wakeup call as he dropped Hearns to the ropes twice with a flurry of shots. By the 14th round, the last minute flurry did not change the fact that all Hearns had to do was stay alive and the match was his. The champ, with his face swollen, sent Hearns to the ropes again with over a minute left in the 14th round, prompting the referee to raise Leonard’s hands as the winner.
In the rematch 8 years later, both men who at that time held multiple belts, fought to a draw in which most pundits felt Hearns was the winner.
10. Evander Holyfield VS George Foreman – (1991) $35,300,000 pro-rated ($20,000,000) in “The Battle of the Ages”
The nineties saw the heavyweights take center stage again, because of one man, Mike Tyson. Holyfield, no slouch himself, benefitted greatly from the new found riches in the heavyweight division and perhaps used this fight as a tune-up to his upcoming rumbles with Tyson himself. Foreman, who along with Ali fought one of the biggest battles ever a few decades earlier, was still a 42-year-old beast who held a perfect 24-0 mark since coming out of his decade long retirement a few years earlier. One would think that the fight was a mismatch, but George held his own, and reminiscent of the first great Rocky Film, Foreman managed to withstand a flurry of punches in the seventh round only to keep holding his ground, until he managed to last the distance against all odds. And just like Rocky, he would become the champion a few years later. The oldest heavyweight champion in history.
9. Mike Tyson VS Peter McNeeley – (1995) $38,300,000 pro-rated ($25,000,000) in “He’s Back”
What happens to a normal human being who is thrown in jail for sexually assaulting his girl? Your life is pretty much going to hell on the job market. What if you are a superstar athlete? Your paycheck just goes through the roof once you get out of jail halfway through your sentence. This is what happened with Mike Tyson. The man had such a ferocious punch and was so feared that once he got back in the ring, the crowd just couldn’t resist no matter what his past looked like. In a tune-up match against what could be called a sparring partner, Mike had one of the biggest paydays in history for a fight that lasted only 89 seconds. Give McNeeley credit. He withstood quite a bit before his manager threw in the towel. For his efforts, McNeeley made $500K with Tyson raking in the rest from a fight that almost grossed $100 million while having nothing to do with a championship.
8. Muhammad Ali VS Joe Frazier – (1975) $40,200,000 pro-rated ($9,000,000) in “The Thrilla in Manila”
Pundits claim this to be the “greatest fight of all time”, but what major Ali fight does not hold that claim? The man was such a legend that every dictator lined up to get him to fight in their country. In this case, it was Ferdinand Marcos of the Philippines, leader of a country that was experiencing three years of martial law, who brought Ali to unite his land in a way that no single man could. It worked, and it also helped out the dictator’s image for a little while longer until he and his wife’s infamous shoe collection were ousted over a decade later.
As for the fight, this was the third and last meeting between these two great boxers, with its moniker being borrowed from the Ali quote: “It will be a killa… and a thrilla… and a chilla when I get the Gorilla in Manila.” It ended with Frazier’s chief second, Eddie Futch, throwing in the towel before the 15th round thus ending his chance to regain the heavyweight title. Some broadcasters felt that deciding blow came in the 13th round when Ali threw two heavy right hand punches that knocked the gum shield flying from Frazier’s mouth and the big man himself was sent flying backwards. After that, the momentum just swung in the champion’s favor.
As for the country itself, it got its own hero four decades later in Manny Pacquiao.
7. Oscar De La Hoya VS Felix Trinidad – (1999) $41,100,000 pro-rated ($28,500,000) in “The Fight of The Millennium”
This fight set the PPV record that took eight more years to break when the loser of this fight, De La Hoya, fought Floyd Mayweather. In a rather close decision, Trinidad won a lackluster fight that did not fulfill the hype that had people yearning to see the greatest welterweight bout since Sugar Ray Leonard defeated Thomas Hearns, two decades earlier. Why wouldn’t it be the greatest ever? Both fighters fought over 30 undefeated matches, with Trinidad the great power puncher, and De La Hoya seemingly being able to do everything. With no clear favorite prior to the match, the outcome was destined to be close and destined to be questioned, no matter what. And it was close with one judge deeming it a draw and two judges giving a one and two-point edge respectively to the champ. Many saw De La Hoya as the winner, prompting even the two promoters, Don King and Bob Arum to verbally scrum after the match with King proclaiming: “Give my fighter credit. He beat your man. You’re trying to manipulate these people. There’s no controversy here…” and Arum telling King to Shut the hell up. This fight should have had a rematch, but it never happened.
6. Floyd Mayweather VS Miguel Cotto – (2012) $41,800,000 pro-rated ($40,000,000) in “The Ring Kings”
We are now entering the era of Mayweather, seen as the greatest pound for pound fighter ever by many and definitely the biggest boxing goldmine in history, as the man seemingly broke one Pay Per View record after another with each fight. This fight was for the light middleweight titles and ended with Mayweather winning by unanimous decision.
Cotto, was no slouch himself, having won his 3 previous title defenses in this division. Despite his prowess, he was still deemed a 6-1 underdog and received one-fifth of the money that Mayweather received. But he gave Mayweather all he had, even seemingly becoming the first boxer to draw blood from Mayweather, prompting the champ to call him the “toughest guy I ever fought”. Despite the bloody nose, the greatest fighter of this era found a way to win.
5. Mike Tyson VS Evander Holyfield 1- (1996) $45,900,000 pro-rated ($30,000,000) in “Finally”
This is not “The Fight” that everyone remembers between the two. This one was relatively clean when Tyson and Holyfield “finally” got to fight six years after the fight was first scheduled. In those six years, Tyson went to Jail, lost his title and got it back. Holyfield meanwhile retired two years earlier due to a heart condition after losing his heavyweight title to Micheal Moorer. Holyfield was seemingly no match against Tyson prior to the match. His 3 bouts since coming out of retirement contained two lackluster wins, one of which was against a less than stellar opponent and one knockout loss to Riddick Bowe. Still he moved up the WBA ranks as the number one contender, likely as a testament to his past.
Tyson, meanwhile won the WBC title in his second post jail fight against Frank Bruno, only to have it stripped from him when he elected to go after the WBA title against Seldon, which he won, instead of defending his WBC title against Lennox Lewis.
The opening round was straight out of a movie, with ferocious back to back punches and furious combat no one had seen in years. In the second round Holyfield, not the power puncher that Tyson was, knocked the champ into a Daze with Tyson later admitting that he had blacked out and had no idea what was going on at that time. The match was Holyfield’s from then on as Iron Mike could not even remember rounds 3 to 6, and finally in round 10, Tyson was saved by the bell after a ferocious barrage by Holyfield. Tyson never once received such punishment from anyone in his career. In the next round, Tyson succumbed to a right from Holyfield and was slammed into the ropes only to be embraced by the referee for protection, and the unlikely happened, Holyfield, the huge underdog won.
4. Evander Holyfield VS Mike Tyson 2 – (1997) $52,400,000 pro-rated ($35,000,000) in “The Sound and The Fury AKA The Bite Fight”
Iron Mike got his chance for revenge, but in this one he was not the bigger draw, as Holyfield cashed in the biggest paycheck. So what does any adult do when he starts losing? Some would say fight harder or change strategies. Not Iron Mike. He decided to bite Holyfield’s right ear in the third round after Holyfield got Tyson in a clinch, removing one inch of cartilage from the champ’s ear. Holyfield started shrieking in pain and the referee called for a timeout not knowing what to do. The referee’s initial reaction was to disqualify the contender, but the ringside doctor cleared Holyfield for battle so the fight ensued with Tyson being deducted a mere 2 points. During another clinch in the third round, Tyson bit Holyfield’s other ear. No damage was done but when the round finished and the bite was discovered, Tyson was disqualified. A brawl ensued prompting heavy security around the referee and Holyfield. Twenty-Five minutes later, as the disruption ended, Holyfield was declared the champ. Tyson was later banned from boxing only to have his license renewed a year later. The two joke about it now and why not, it made both of them a legend and a huge fortune. Too bad neither of them have any of it left.
3. Oscar De La Hoya VS Floyd Mayweather – (2007) $60,200,000 pro-rated ($52,000,000) in “The World Awaits”
This represents the last time anyone received a bigger payday then Floyd Mayweather, as De La Hoya, the 6-division champ was the star of this one. The fight was for the WBC light Middleweight crown. This is the fight that finally eclipsed the live gate record held by Tyson VS. Holyfield, 10 years earlier. The biggest subplot to this fight was whether Mayweather’s estranged father would train De La Hoya. Mayweather Sr.’s asking price was too high and alas, that did not happen. In the end Floyd Mayweather won a split decision and well on his way to becoming the game’s biggest money maker.
Upon Mayweather’s retirement, De La Hoya showed just how much he respected Floyd by telling Floyd in a Playboy article: “Let’s face it: You were boring .. the fight game will be a better one without you in it.”
2. Floyd Mayweather VS Canelo Alvarez – (2013) $82,500,000 pro-rated ($80,000,000) in “The One”
In another grandiose display by the master tactician, Mayweather outlasted Alvarez and won a majority decision in 12 rounds with one judge deeming it a draw, as Floyd was the star this time in what became the most profitable boxing matchup to that point in history. It is no coincidence that one man seems to be involved in all the big bouts in this century. In this fight both men fought not to lose, but except for a few rounds, the match was all Mayweather. It is unfortunate Floyd cannot keep the fighting to the ring, as he has demonstrated a history of domestic violence which has resulted in a 90-day jail sentence and two guilty pleas throughout his life. His last arrest was five years ago.
1. Floyd Mayweather VS Manny Pacquiao – (2015) $180,000,000 in “The Fight of the Century” or “The Battle for Greatness”
So the century is young, and there are going to be several “fights of the century” before the century is out, but this one outdid everything prior to it in hype. The purse was three times higher than any fight before it. Entry level ticket prices were higher than the Super Bowl at $5400. Both fighters made over $100 million with Floyd taking anywhere between $140 million to $180 million depending on who you ask, with Manny raking in at least $96 million. Both deserve the limelight as one is a 5 division champion while the other is an eight division champion. Manny’s star hasn’t shone as bright this year however, as his latest fight didn’t even make enough money to pay his guaranteed salary of $20 million. But who cares, right? Both fighters have earned close to half a billion in their careers.
Mayweather walked away from the fight and retired with a perfect 49-0 mark, tying boxing’s all time mark. But of course, money can lure anyone out of retirement as there is more talk of a 9 figure payday for the 39-year-old boxer in a proposed boxing match against MMA star Conor McGregor, in South Africa. Of course for that kind of money, I would come out of retirement, too.
As for the fight itself, Mayweather won by a unanimous decision in 12 rounds in what critics considered a boring fight. So no one will be talking about the fight until the next big match that makes more money than this one.
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