Floyd Mayweather, the boxer who amassed earnings exceeding $1 billion during his career, now finds himself battling a series of financial and legal challenges outside the ring.
The American boxing icon faces lawsuits from multiple directions whilst simultaneously pursuing his own legal action against others.
In April, the Internal Revenue Service presented Mayweather with a tax demand of $7.3 million for unpaid taxes spanning 2018 to 2023.
This substantial bill arrives alongside several other legal disputes that have emerged in recent months.
Floyd Mayweather is renowned for his lavish lifestyle but the bills appear to be catching up with him
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The 47-year-old, who earned approximately £250 million from his 2015 victory over Manny Pacquiao and another £200 million defeating Conor McGregor in 2017, appears to be facing a dramatic reversal of fortune.
In February, the boxing legend was hit with legal action over more than $330,000 in outstanding rent for his luxury New York apartment.
That same month, Miami-based AJ's Jewelry filed a $1.4 million lawsuit against Mayweather, claiming he failed to settle debts for 27 watches and 15 chains, with cheques allegedly bouncing.
The legal troubles continued into April when Jet Set Aircraft launched proceedings against the former champion over an unpaid $105,690 charter flight to Turks and Caicos from September.
The private jet company is pursuing the full flight cost plus punitive damages to be determined at trial.
Manny Pacquiao and Floyd Mayweather II could go down in boxing folklore | GETTYThese mounting debts paint a stark picture for a fighter once known by the nickname "Money" and famed for his extravagant displays of wealth.
With his financial pressures mounting, Mayweather is scheduled to face Pacquiao again on September 19 at Las Vegas' £1.9 billion Sphere venue.
Jas Mathur, chief executive of Manny Pacquiao Promotions, confirmed negotiations remain ongoing despite Mayweather's attempts to alter the terms.
Floyd Mayweather, pictured here in his Bugatti, is set to face Manny Pacquaio later this year
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"The fight is still on, it's not cancelled, we're in negotiations," Mathur told SunSport. "There's a few points that were in the initial contract that Floyd wants to renegotiate and we've made a lot of headway in this last week."
Mathur dismissed any suggestion the bout could become an exhibition rather than a professional contest.
"There's no exhibition happening, this is a pro fight," he stated. "Floyd does have a tendency sometimes to think that he can change things in his favour later down the road."
Crucially, Mathur has revealed that Mayweather has already drawn an advance on his fight purse.
Floyd Mayweather is also set to face Mike Tyson, though explicit details on such a blockbuster fight are rare
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"Floyd needs to fight. Yes, he 100 per cent needs to fight," Mathur added.
According to Business Insider, Mayweather's financial difficulties have forced him to offload assets including a private jet and properties in Beverly Hills and Miami.
Despite these sales, the boxer continues to display his remaining wealth through social media posts featuring luxury travel and holidays.
Mayweather is also pursuing his own legal battle, having filed a $340 million lawsuit against broadcaster Showtime in February, alleging fraud and breach of fiduciary duty.
The suit claims revenue owed to Mayweather was redirected to his former advisor Al Haymon, though Haymon was not named as a defendant.
Meanwhile, a previously announced exhibition against Mike Tyson, initially set for 2026 in Africa, remains in limbo with no confirmed date, though sources suggest it could potentially proceed in late May.