Floyd Mayweather's planned exhibition match against Mike Tyson — originally scheduled for Saturday, April 25 in the Democratic Republic of Congo — is in serious doubt. And it is only one of three high-profile 2026 bouts on his calendar that are now tangled in contractual and financial problems.

According to Complex, the fight has gone quiet in the final lead-up, with limited public updates from either side. Tyson advisor Amer Abdallah told Boxing News the contract is still in place. "There is a contract in place. Details will come out soon. But I believe the fight will happen," he said. But no broadcaster has been confirmed, no promotional rollout has occurred, and Tyson himself effectively signaled the fight was off last month when he disclosed he was nursing a hand injury.

On Tuesday, Mayweather confirmed his next appearance will instead be a June 27 exhibition against Greek kickboxing legend Mike Zambidis in Athens, per GB News. "IT'S OFFICIAL," he wrote on X. "History will be made."

The Tyson issue is only one thread of a much bigger mess. The IRS filed a $7.3 million tax lien against Mayweather last month for unpaid taxes tied to 2018 and 2023, according to Complex. This is not his first time at bat with the IRS: he previously settled with the agency for $22.2 million tied to his 2015 taxes, the year of his first Pacquiao fight.

The 49-year-old retired champion is also facing multiple civil lawsuits. Among them: a $105,690 unpaid private jet charter, a reported $900,000 loan default, and nearly $338,000 in unpaid rent for a Manhattan luxury duplex at the Baccarat Hotel and Residences. Two Miami jewelers are suing him — one alleging he walked away with luxury watches and gold chains worth roughly $1.675 million after paying only $300,000, and another alleging unpaid amounts tied to nearly $3.9 million in jewelry.

Mayweather has been filing lawsuits of his own as well, including a $340 million suit against Showtime Networks over what he claims are misappropriated funds from his fight earnings, and a complaint against a Las Vegas dealership over the sale of a $1.2 million rare Maybach.

The bigger fight on Mayweather's 2026 calendar is a September rematch with Manny Pacquiao at The Sphere in Las Vegas, set to stream on Netflix. That, too, may be in legal trouble. Pacquiao's team has said Mayweather signed for a professional bout but is now attempting to reclassify it as an exhibition. "For me, he cannot get out of this contract," Pacquiao told Inside the Ring. "He will face a lot of consequences if he fails this commitment."

Pacquiao Promotions CEO Jas Mathur told ESPN Mayweather signed three separate agreements between October and December 2025 — all subsequently merged in January 2026 — and took advance money and a loan against the fight purse. Mayweather is now facing potential nine-figure damages if he is found in breach.

Despite earning more than $1.2 billion across his career and retiring with a perfect 50-0 record, Mayweather has remained active through exhibitions since 2017, facing opponents ranging from Logan Paul to John Gotti III. What he has never faced is a stretch quite like this one.