TMZ Sports reports that retired great Floyd Mayweather Jr. is suing Showtime and its former executive, Stephen Espinoza for $340 million. The lawsuit alleges that for Mayweather's most lucrative fights, including vs. Manny Pacquiao and Conor McGregor, Showtime and Espinoza directed payments to accounts controlled by Mayweather's advisor Al Haymon, instead of to Mayweather himself. What is suspicious about the lawsuit is that Haymon himself was not sued. Should the lawsuit proceed, Haymon would certainly, at the very least, be deposed as a witness by Showtime, if not outright brought into the lawsuit as a third-party defendant.

 

There are independent signs that Mayweather is experiencing financial difficulties. KSNV reported in September that Mayweather was sued by Vegas Auto Gallery over his alleged failure to pay $1.2 million for a Mercedes G-Class SUV. Earlier in 2025, Mayweather was sued in Florida by a man named Jayson Winer, who claims to have been the victim of a $4 million dollar fraud for taking payments in exchange for introducing Winer to Elon Musk, but then failing to make the introduction. A third lawsuit in Florida accuses Mayweather of failing to make payments to Leonard Sulaymanov and JLZ Consulting after "systematically steal[ing] and convert[ing over $4 million worth of] watches and jewelry to their own, without paying the full and fair price for same all to Plaintiffs’ extreme financial loss."