Floyd Mayweather Never Wore the Same Pair of Underwear Twice. Now He Might Be Broke.
Floyd Mayweather Never Wore the Same Pair of Underwear Twice. Now He Might Be Broke.
The Mayweather-Pacquiao rematch is falling apart, and the reason tells you everything you need to know about where Floyd Mayweather is in 2026.
The fight was announced on February 23. Netflix. The Sphere in Las Vegas. September 19. A professional bout, sanctioned and on the record. Mayweather’s 50-0 would be on the line for the first time since he beat Conor McGregor in 2017. It was supposed to be the biggest event in combat sports this decade.
Then Floyd started talking.
On March 29, Mayweather told the world the fight would actually be an exhibition. Not a real fight. Not on his record. Just a show. Pacquiao’s camp responded immediately. His promoter, Jas Mathur, pointed to the signed contracts and said Mayweather had agreed to a professional fight. Three separate contractual agreements, all for a sanctioned bout. Mathur put it plainly on Instagram: “Men lie, women lie, executed binding agreements don’t.”
Reports say Mayweather has already taken a cash advance on his purse. He got paid. And now he wants to change the terms.
This is the part where you need to understand how Floyd Mayweather spends money.
The Spending
Floyd Mayweather has never worn the same pair of underwear twice. According to a 2013 ESPN The Magazine profile, he buys new boxer shorts constantly, wears them once, and throws them away. He spends roughly $6,500 a year just on disposable underwear.
His shoes get the same treatment. He wears a pair once and leaves them behind in hotel rooms for housekeepers.
He employed a private chef who was paid $1,000 per meal. He employed someone whose entire job was to sanitize his cars every single day. He would not get in a vehicle unless it had been detailed that morning.
His car collection includes five Bugattis, sixteen Rolls-Royces, a $4.8 million Koenigsegg CCXR Trevita with diamond-coated carbon fiber bodywork, and 33 Mercedes-Benz from the same dealership. The total value has been estimated at over $40 million.
He owns two private jets. The first cost $50 million. The second has gold cup holders, a gold sink, and gold accents throughout.
He carries cash. Not wallet cash. Duffel bag cash. He once posted a video of himself stacking piles of money across a hotel bed before stuffing them into a bag. A million dollars. Walking-around money for Floyd.
His watch collection includes an $18 million Jacob & Co. “Billionaire” watch and a $1.1 million Hublot Big Bang. He once saw four watches, each priced at $250,000, couldn’t decide which one to buy, and bought all four.
In total, Floyd Mayweather has earned more than $1 billion from boxing. Some estimates put it closer to $1.7 billion when you include revenue generation from his fights. He earned $250 million for fighting Pacquiao the first time in 2015. He earned $275 million for fighting McGregor in 2017.
No boxer in history has made more money.
The Cracks
In July 2017, just weeks before the McGregor fight, documents revealed that the IRS had filed a lien against Mayweather for $22.2 million in unpaid taxes from 2015. An additional $7.2 million lien from 2010 was also unresolved.
Mayweather’s legal team filed a petition with the U.S. Tax Court asking for a temporary reprieve. Their argument: Mayweather had substantial assets, but they were “restricted and primarily illiquid.” He needed time. Specifically, he needed the McGregor fight purse to land before he could pay.
The man who carried a million dollars in a duffel bag was telling the IRS he didn’t have the liquidity to cover his tax bill.
Conor McGregor, never one to miss an opening, said it publicly: “The reason he has accepted this fight to come out of retirement is because he has to. He’s in a dire situation.”
Mayweather paid his taxes after the McGregor fight. But the question lingered. If you earn over a billion dollars and still owe the IRS $30 million, where is the money going?
The answer was always right in front of everyone. Underwear. Shoes. Bugattis. A $50 million jet. An $18 million watch. A thousand-dollar meals. Five hundred dollars to detail a car that sits in the driveway.
The Exhibitions
After beating McGregor in August 2017 and pushing his professional record to 50-0, Mayweather retired. Then he started doing exhibitions.
He knocked out Japanese kickboxer Tenshin Nasukawa in the first round on New Year’s Eve 2018 in Japan. He went eight rounds with YouTuber Logan Paul in June 2021 in a fight with no official decision. He fought Deji, John Gotti III, and a string of opponents who had no business sharing a ring with one of the greatest boxers who ever lived.
Eight exhibitions since retirement. Each one a payday. None of them on his record. None of them a risk to the 50-0.
The exhibitions told a story on their own. Either Floyd Mayweather loved the spotlight too much to walk away, or he needed the money too much to stop.
The Rematch
That brings us to the Pacquiao rematch and the contract dispute that’s trending right now.
Mayweather and Pacquiao first fought on May 2, 2015. It was the biggest event in boxing history. 4.6 million pay-per-view buys. Over $600 million in total revenue. Tickets averaged $4,451 each at the MGM Grand. Mayweather won a unanimous decision. It was, by every financial measure, the most lucrative 36 minutes of sports ever broadcast.
Eleven years later, they’re supposed to do it again. The rematch was announced for September 19, 2026, at the Sphere, streaming on Netflix to more than 325 million subscribers worldwide. Unlike the first fight, there would be no pay-per-view price tag. The whole world could watch.
The fight was announced as a professional bout. Mayweather’s 50-0 record would be on the line against Pacquiao’s 62-8-3. Pacquiao, now 47, came back from retirement in 2025 and fought WBC welterweight champion Mario Barrios to a majority draw in Las Vegas. He proved he could still compete. Mayweather, who will be 49 on fight night, hasn’t fought professionally since McGregor.
Then Mayweather pulled the move that has everyone talking. He said it’s an exhibition now. Not a real fight. His record won’t be at risk.
But the contracts say otherwise. Pacquiao’s camp says Mayweather signed three separate binding agreements for a professional fight. And Mayweather reportedly already took a cash advance on his purse.
He got the money. Now he wants to change the fight.
What This Is Really About
There are two theories.
The first is that Mayweather is protecting his 50-0 record. He’s 49 years old. Pacquiao proved against Barrios that he can still fight at a competitive level. A loss to Pacquiao would destroy the undefeated legacy that Mayweather has spent his entire career building. By making it an exhibition, he keeps the money and keeps the zero.
The second theory is that Floyd Mayweather needs the money more than he needs the legacy. He’s done eight exhibitions in six years. He asked the IRS for a reprieve in 2017. He took a cash advance on a fight purse before the fight was finalized. The man who earned over a billion dollars might have spent his way through most of it, and the exhibitions and the rematch are the only thing keeping the lifestyle afloat.
The truth is probably somewhere in between. Mayweather wants the payday without the risk. He wants Pacquiao money without putting the zero on the line. And the fact that he signed a professional fight contract and then tried to back out of it suggests that either he didn’t read what he signed, or something changed between February and March that made the risk suddenly feel too real.
The Underwear and What It Means
Floyd Mayweather made more money from boxing than any human being in history. He never wore the same pair of underwear twice. He never wore the same shoes twice. He carried a million dollars in cash in a duffel bag for fun. He bought a $4.8 million car with a body that shimmers like it’s covered in diamonds. He paid his chef a thousand dollars to make dinner.
And today, his biggest fight in a decade is falling apart because he signed a contract for a professional fight and then decided he’d rather it be an exhibition.
The man they call “Money” got the advance. Now the question is whether he’ll step into the Sphere on September 19 and actually fight. Not spar. Not exhibit. Fight. With the 50-0 on the line and the whole world watching on Netflix.
If he does, it will be the most interesting boxing match in years. If he doesn’t, it will be the most expensive breach of contract in boxing history.
Either way, Floyd Mayweather is still Floyd Mayweather. He will wake up tomorrow, put on a brand new pair of underwear, and figure out how to get paid.
A longtime sports reporter, Carlos Garcia has written about some of the biggest and most notable athletic events of the last 5 years. He has been credentialed to cover MLS, NBA and MLB games all over the United States. His work has been published on Fox Sports, Bleacher Report, AOL and the Washington Post.
