The incredible fall of boxing's first billion-dollar man behind bombshell Netflix comeback fight

Former Mayweather Promotions fighter Ishe Smith summed it up best when Floyd Mayweather announced he's returning to pro boxing in a rematch against Manny Pacquiao earlier this week.

"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," Smith wrote on X.

"Mans tricked all that money off and needs to come back."

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The overwhelming sense from those connected to the sport is that Mayweather needs to fight again, which is damn near unbelievable considering the amount of money he's made.

Forbes named Mayweather as the sport's first billion-dollar boxer in 2017, with the Michigan native surpassing that number through money-spinning matches against Oscar De La Hoya, Pacquiao and Conor McGregor.

He's long projected an image of immense wealth, posting photographs to social media of himself alongside wads of cash, fast cars and watches worth millions of dollars.

Mayweather spent more than a decade as arguably the biggest American star in boxing, and he beat Manny Pacquiao in 2015 in the richest fight in boxing history at the time.

His superb defensive skills and quick hands were his ring strengths, but his stardom and wealth proliferated largely because of his "Money May" anti-hero persona.

But of late, there's been some indication that Mayweather has been experiencing financial trouble.

Earlier this month, he sued his former broadcast partner, Showtime, and its ex-president Stephen Espinoza, alleging he is owed $US340 million.

Mayweather's intricate suit appears to fault the network for not protecting the boxer from the business practices of his longtime financial advisor, Al Haymon, with claims revenue was concealed and diverted from his earnings through boxing.

The legal action follows a report from Business Insider in December that suggested Mayweather's vast wealth may be overstated.

The report pointed to liens, foreclosures, debt, leveraged assets like property and a private jet, where creditors reportedly chased Mayweather over unpaid jet fuel.

Business Insider reports that 2025 was a tough year for the boxing great, claiming Mayweather took out millions in new mortgages in 2025, while two commercial properties were foreclosed, and his Las Vegas strip-club building also has unpaid taxes.

Additionally, it's understood he was also pursued over a disputed $1.2 million Maybach vehicle and sold his Gulfstream plane as well as major homes.

The report states the undefeated legend settled more than $US28 million in back taxes, while facing lawsuits alleging unpaid luxury debts. His lawyer rejects these claims.

Unfortunately, boxing has many cautionary tales that involve fighters returning to the blood sport because they'd blown their huge earnings.

But Mayweather seemed to have bypassed the demise that has followed champions of yesteryear.

His last retirement in 2017 drew the curtain on a 50-0 career, having defeated Conor McGregor and making a motzer while doing it.

But now his story seems eerily similar to that of Mike Tyson who filed for bankruptcy in 2003 but returned to lose to Danny Williams in 2004 and Kevin McBride in 2005 — fighters he would have demolished in his prime.

Almost 20 years later, he did it again at the age of 58 to fight a 27-year-old Jake Paul.

Now, he's going to fight Mayweather in April.

Another icon of the sport, Evander Holyfield, also faced financial issues and heavy debts to return to the ring in his late 40s and 50s. There are countless more.

A report by the Daily Mail, further illustrates Mayweather's financial woes.

It claims he's being sued by a Miami jeweller for over $US1.375 million.

It's understood Mayweather visited AJ's Jewelry twice in August last year and picked up 27 watches and 15 chains worth $1.675million, according to the latest lawsuit.

But the claim alleges he only paid $US300,000, while five cheques for the remainder are said to have bounced.

Mayweather is also involved in a New York lawsuit claiming the retired fighter owes $US330,000 in unpaid rent and damages on a $US24 million leased Manhattan penthouse.

That comes after another Miami jeweller filed a federal lawsuit against Mayweather in the Southern District of Florida in January, alleging the boxer failed to uphold a 2024 settlement agreement over $US4million worth of watches and jewellery.

In the case of AJ's Jewelry, the complaint states Mayweather was a regular and trusted customer for 17 years.

The company had repeatedly contacted the boxer in writing and on the phone.

"Each time Mayweather acknowledges the debt owed and promises to pay for the jewellery, then never sends the monies owed,' the lawsuit stated.

"Mayweather either knew or should have known these representations were false when he made them."

The firm is demanding the jewellery back plus compensation and damages in a jury trial.

Mayweather's money problems also surfaced earlier this year when it was revealed he is being sued by the owners of the five-bedroom Manhattan penthouse he leased for $US100,000 a month.

The owners allege he failed to pay a total debt of $US330,000 in back rent by a deadline of December 2025.

Mayweather moved into the exclusive Baccarat Hotel and Residences in late 2024. But stopped paying rent in July last year.

During that time, Mayweather posted photos of himself on a private jet surrounded by stacks of cash and captions such as: "I just be minding my business."

In fact, his social media activity and posting of large volumes of money has been mentioned in the lawsuits against him.

Miami jeweller Leonard Sulaymanov alleges Mayweather was flaunting his lifestyle while also failing to pay the $US4 million owed.

"After the settlement was reached Mr Mayweather and Mr Rechnitz enjoyed a multi-million-dollar birthday week in Miami and bragged about it in newspapers and to media outlets," the filing states.

"Then on June 30, 2025, while failing to make a second instalment,' they were 'enjoying a vacation in the South of France and bragging about how much money they were spending."

The lawsuit referenced photos of Mayweather around money and accused the boxer of a "cavalier attitude about court cases, settlements, contracts and monetary obligations."

The lawsuit also stated, "Later… Mr Mayweather boasted about having a $400,000 Richard Mille watch on, while again ignoring his legal and contractual obligations."

Like Tyson and Paul did last year, Mayweather and Pacquiao are expected to pocket tens, if not hundreds of millions from this looming Netflix bout.

How long that will last, is anyone's guess.