The seeds for Floyd Mayweather Jr.’s return to a professional ring were arguably sown when Manny Pacquiao was first linked to a WBC welterweight world title fight against then-champion Mario Barrios in 2025.
Pacquiao produced a performance for the ages. At 46, he rolled back the years and attacked Barrios with such aplomb that the 30-year-old world champ seemed shell-shocked and was only able to split a controversial draw after rallying late.
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An insider involved in the making of Barrios vs. Pacquiao was under no illusions what a strong performance from Pacquiao might mean — for Premier Boxing Champions, who organized the show, and for the Hall of Famer’s possibilities thereafter.
The source said Mayweather would be one interested party. “It would probably trigger something in his head for a rematch,” the source told Uncrowned at the time. “[It] would do big business.”
Though Pacquiao insisted he was focused only on Barrios, he nonetheless pushed for the Mayweather rematch when speaking to Uncrowned that week in July ahead of his Las Vegas comeback.
Manny Pacquiao shocked the sports world with a vintage performance against then-champ Mario Barrios in July.
(Anadolu via Getty Images)
And so it was no surprise to learn Monday that Pacquiao and Mayweather will square off once again.
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“Floyd and I gave the world what remains the biggest fight in boxing history,” Pacquiao, now 47, said upon Monday’s announcement of a Sept. 19 rematch on Netflix. “The fans have waited long enough — they deserve this rematch.
“I want Floyd to live with the one loss on his professional record and always remember who gave it to him.”
Mayweather, 49, boxed his whole career without ever tasting defeat, beating a who’s who of elite fighters and box-office names like Oscar De La Hoya, Saul “Canelo” Alvarez, Diego Corrales, Arturo Gatti and Conor McGregor.
He beat Pacquiao by a lopsided decision when they threw hands in 2015.
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“I already fought and beat Manny once,” said Mayweather on Monday. “This time will be the same result.”
Considering the ability Pacquiao displayed against Barrios, it’s clear to see why he is still in the game. But the timing of Mayweather’s return is intriguing.
Earlier this month, Mayweather sued his now-defunct broadcast partner, Showtime, and its ex-president Stephen Espinoza, claiming they, with the help of Mayweather’s former adviser, Al Haymon, concealed and diverted revenue from his earnings through boxing. In the suit, Mayweather alleges breach of contract, fiduciary duty and unjust enrichment, seeking $340 million in damages.
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In his first statement since the suit went public, Espinoza denied the accusations to Compas on the Beat:
“I spent my entire career representing fighters, making sure they were getting paid appropriately,” said Espinoza. “I did that for Oscar [De La Hoya]. I did that for Mike [Tyson]. I did it for every fighter who was developed under Showtime.
“I’m proud of my reputation — it’s one of integrity. And I’ve done everything to make sure a fighter got every penny they deserved.”
The suit follows an explosive investigation from Business Insider that suggests Mayweather’s supposedly vast wealth may be overstated, noting liens, debt, foreclosures and leveraged assets like property and a private jet. The December story painted a messy financial picture, alleging Mayweather took out millions in new mortgages in 2025, while two commercial properties were foreclosed, and his Las Vegas strip-club building faces tax delinquency.
Creditors reportedly chased Mayweather over unpaid jet fuel and a disputed $1.2 million Maybach vehicle, Business Insider reported. He sold his Gulfstream plane as well as major homes. He’s settled more than $28 million in IRS back taxes, amid lawsuits alleging unpaid luxury debts, though his lawyer rejects these claims.
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Former Mayweather Promotions fighter Ishe Smith had plenty to say on X about Mayweather’s comeback:
“Read in between the lines. People don’t come out of retirement for the love of the game at damn near 50. That’s not how boxing works.”
Forbes long proclaimed Mayweather as a billion-dollar boxer — the sport’s first fighter to surpass that financial threshold, largely through money-spinning matches against De La Hoya, Pacquiao and McGregor. And he has long projected a lavish image, posting photographs to his Instagram alongside wads of cash, fast cars and watches worth millions of dollars. Uncrowned has also seen Mayweather in and around casinos, betting in a high-roller blackjack room in New York state and dumping cash from a holdall bag to bet on a big boxing bout at the Mandalay Bay’s sportsbook in Las Vegas.
“Mans tricked all that money off and needs to come back,” Smith said on X.
Claressa Shields, one of the sport’s top pound-for-pound fighters and the current undisputed women’s heavyweight champion, commented on Smith’s post: “I hate to agree with you smh.”
Boxing is one of the most beautiful sports in the world, but it’s also arguably the most ruthless. The game is littered with unsuccessful comeback tales, with fighters returning to the ring for one last throw of the dice only to find they can no longer defy Father Time as they watch their gamble spectacularly backfire.
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Mayweather’s final retirement in 2017 was the antithesis of this. He drew the curtain on a 50-0 career, having accumulated generational wealth ahead of a guaranteed induction into the International Boxing Hall of Fame.
When it came to combat sports, he’d completed it.
Well-worn tropes of penniless fighters exist in the sport because of the frequency in which boxing’s legends have had to come back against their better judgement. Mike Tyson, an all-time great ticket-seller, filed for bankruptcy in 2003 but still returned to get stopped by Danny Williams in 2004 and Kevin McBride in 2005 — fighters he would have annihilated in his prime. Nearly two decades later, he did it again at the age of 58 to fight a 27-year-old Jake Paul.
Evander Holyfield, another icon, faced foreclosures and heavy debts only to repeatedly return to the ring in his late 40s and 50s — the saddest of which saw him get beat down in less than two minutes by an MMA legend, Vitor Belfort, in a 2021 Triller fight.
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If even a fraction of the financial allegations swirling around him prove true, the fighter formerly known as “Pretty Boy Floyd” risks drifting toward this uncomfortable boxing tradition as an all-time great earner who mastered the business inside the ring, only to be drawn back by the economics outside of it.
And, against an in-form, more active and merciless Pacquiao, “Money May” could become the game’s next great cautionary tale.
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