Arguably, the seeds for Floyd Mayweather Jr.’s return to the professional ring were sown when Manny Pacquiao was first linked with a 2025 WBC welterweight world title fight against then-champion Mario Barrios.
Pacquiao created a performance that will last through the ages. At 46, he looked back through the years and attacked Barrios with aplomb, with the 30-year-old world champion seemingly stunned and only equalizing a controversial draw late in the fight.
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An insider involved in the production of the Barrios-Pacquiao fight has no illusions about what a strong performance from Pacquiao might mean — both for the Premier League boxing champions organizing the fight and for the Hall of Famer’s possibilities thereafter.
Sources say Mayweather would be an interested party. “It might trigger some thoughts in his mind about a rematch,” they told The Untitled at the time. “[It] Will do big business. “
Although Pacquiao insisted he was only focused on Barrios, he still pushed for a rematch with Mayweather in an interview with The Untitled the week before his comeback in Las Vegas in July.
In July, Manny Pacquiao shocked the sports world with a classic performance against then-champion Mario Barrios.
(Anadolu, Getty Images)
So it was no surprise to learn on Monday that Pacquiao and Mayweather would be boxing again.
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“Floyd and I gave the world one of the biggest fights in boxing history,” Pacquiao, 47, said on Monday when Netflix announced the Sept. 19 rematch. “The fans have waited long enough – they deserve this rematch.
He concluded: “I hope Floyd can endure a loss on his career record and always remember who gave him this loss.”
Mayweather, 49, has never tasted defeat in his entire boxing career, beating a who’s who of elite boxers and box-office heavyweights such as Oscar De La Hoya, Saul “Canelo” Alvarez, Diego Corrales, Arturo Gatti and Conor McGregor.
When he fought Pacquiao in 2015, he defeated Pacquiao with a lopsided decision.
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“I’ve fought Manny once,” Mayweather said Monday. “It will be the same this time.”
Considering the ability Pacquiao still showed against Barrios, it’s obvious why he’s still in the fight. But the timing of Mayweather’s return is intriguing.
Earlier this month, Mayweather sued his now-defunct broadcast partner Showtime and its former president Stephen Espinosa, claiming they concealed and misappropriated the income he earned from boxing with the help of Mayweather’s former adviser Al Haymon. In the lawsuit, Mayweather alleged breach of contract, fiduciary duty and unjust enrichment and sought $340 million in damages.
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In his first statement since the lawsuit became public, Espinoza denied Compas on the Beat’s allegations:
“I’ve spent my entire career representing fighters and making sure they’re paid properly,” Espinoza said. “I’m doing this for the Oscars [De La Hoya]. I did it for Mike [Tyson]. I did this for every fighter developed under Showtime.
“I’m proud of my reputation – it’s a reputation of integrity. I’ve done everything I can to make sure the fighters get every penny they deserve.”
The lawsuit follows an explosive investigation by Business Insider that revealed Mayweather’s alleged vast wealth may have been exaggerated and includes liens, debts, foreclosures and leveraged assets such as properties and private jets. Reports in December painted a chaotic financial picture, alleging Mayweather took out millions of dollars in new mortgages in 2025 while two commercial properties were foreclosed and his Las Vegas strip club complex faced delinquent taxes.
Creditors are reportedly pursuing Mayweather over unpaid jet fuel and a controversial $1.2 million Maybach car, Business Insider reported. He sold his Gulfstream aircraft and his primary home. He has settled more than $28 million in back taxes with the IRS in a lawsuit alleging unpaid luxury goods debts, but his attorneys deny the accusations.
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Former Mayweather promoter Ish Smith commented on Mayweather’s comeback:
“Read between the lines. People don’t come back when they’re almost 50 for the love of the sport. That’s not how boxing works.”
Forbes has long considered Mayweather a billion-dollar boxer, the first fighter in the sport to surpass that financial threshold, primarily through lucrative fights with De La Hoya, Pacquiao and McGregor. He has long guarded a luxurious image, posting photos on Instagram along with millions of dollars worth of cash, sports cars and watches. The Uncrowned King has also seen Mayweather in and out of casinos, placing bets in high-roller blackjack rooms in New York state and pouring cash from his tote to place bets on a major boxing match at the Mandalay Bay sportsbook in Las Vegas.
“The man stole all his money and needs it back,” Smith said.
Claressa Shields, one of the top boxers in the sport and the current undisputed women’s heavyweight champion, commented on Smith’s post.
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“I don’t want to agree with you,” she said.
Boxing is one of the most beautiful sports in the world, but it can also be said to be the most brutal. The game is filled with tales of failed comebacks, as fighters return to the ring for one last roll of the dice, only to find themselves unable to challenge Father Time again as they watch their gamble backfire spectacularly.
Mayweather’s final retirement in 2017 was the opposite. He finished his career with a perfect 50-0 record, amassed generations of wealth, and was guaranteed induction into the International Hall of Fame.
When it comes to combat sports, he’s done.
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The old trope of the penniless boxer exists in the sport, as boxing legends often have to make comebacks against their better judgment. Mike Tyson, the greatest ticket seller in history, filed for bankruptcy in 2003 but was still stopped by Danny Williams in 2004 and Kevin McBride in 2005 – fighters he destroyed in his prime. Nearly two decades later, at age 58, he fought again against a 27-year-old Jake Paul.
Another icon, Evander Holyfield, faced foreclosure and crippling debt only to return to boxing multiple times into his 40s and 50s — most tragically, when he was defeated by MMA legend Vitor Belfort in less than two minutes at a 2021 Triller event.
If even a fraction of the financial accusations surrounding him are proven correct, Mayweather risks falling into boxing’s troubling tradition of being one of the most profitable men in history, controlling the business inside the ring only to be dragged down by the economy outside the ring.
And, against an in-form, more dynamic and ruthless Pacquiao, “Money May” could become the sport’s next great cautionary tale.
