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.