“Vs. Mike Zambidis – Cancelled,” “vs. Manny Pacquiao – Cancelled”—that is what a search for Floyd Mayweather‘s upcoming schedule currently reveals. With much fanfare, the 49-year-old former undefeated world champion had announced a comeback months ago. But his path back has been entirely uphill since then.

A string of lawsuits has put Floyd Mayweather in a troubling situation, with his legal woes and financial duress becoming a major point of discussion and derailing the fights he had lined up. However, despite the grim realities, the former world champion remains upbeat. After securing a favorable outcome in court recently, the latest development has him entering a new collaboration.

“It is good to go through certain situations so that you can find out who is really there for you,” Floyd Mayweather said as he welcomed Leo McManus to his gym. “It takes the real thing, just in life, you know… Loyalty is not an action; it’s a lifestyle. Stay focused, stay positive, and just keep believing.”

The precise details surrounding the linkup between the boxing legend and the founder-CEO of the adult content platform ‘Baddies.Com’ remain unclear. However, as the footage of the meeting, shared via an Instagram post, rolled, a hint emerged when a media member interacted with McManus.

When asked whether he would potentially be promoting the Pacquiao fight, the Baddies founder replied, “Something like that, man.”

There may be a reason why Mayweather pressed on the loyalty point. It largely stems from the recent developments surrounding a major lawsuit he filed against his former business associates.

Two months ago, Mayweather filed a case against Jona Rechnitz, his former investment manager, and Ayal Frist, a real estate adviser, in a New York State court for allegedly cheating him over a couple of years.

The $175 million civil lawsuit saw Mayweather’s team claim that the accused had betrayed their trust. It includes allegations of siphoning off $100 million worth of jewelry to secure a loan without seeking prior permission, a missing Gulfstream IV private jet, and real estate investments funneled into accounts operated by the defendants.

Months earlier, in February, around the time he announced his comeback, Mayweather surprised everyone by filing a $340 million case against his former broadcast partners, Showtime, and its then president, Stephen Espinoza, for allegedly siphoning off millions worth of his fight purse into hidden accounts.

Meanwhile, Mayweather himself faces a breach of contract lawsuit filed by CSI Sports.

Floyd Mayweather’s comeback dreams tested by mounting legal battles

Seeking damages worth $4.65 million from the former five-division champion, the sports promotion filed a case in a New York federal court, claiming Mayweather failed to honor the contract, which included the Mike Tyson exhibition and the professional rematch with Pacquiao, by signing separate deals with other parties and negotiating a Netflix deal for the Pacquiao fight and an additional exhibition against Mike Zambidis.

Much to Mayweather’s relief, the court denied CSI’s emergency request seeking a temporary restraining order to halt his exhibition against Zambidis, scheduled for June 27 in Athens, Greece. While the last-minute legal hassle led to confusion surrounding the ticket sales, the fight was eventually cancelled, with the broadcaster DAZN removing it from its schedule.

While the CSI’s breach of contract case remained active, the court’s intervention allowed Mayweather to proceed with the Zambidis exhibition and reschedule it to a later date.

Though small, the legal win likely injected some confidence into Mayweather, whose reputation has suffered significantly over the past few months.

It remains to be seen how Mayweather navigates his way through legal challenges before finally making his ring return.

Given that his team should come up with a new date for the Zambidis exhibition within the next thirty to forty-five days, the attention has now shifted to the Pacquiao fight.

Reports indicate the rematch between the two boxing legends, who first met back in 2015 in a record pay-per-view-churning clash, is likely to take place by January 2027, only if there are no further issues.

The delay has now forced Pacquiao to look for a fight, likely an exhibition, to keep him sharp. That adds to the pressure on Mayweather, given he has not only to deal with legal problems but also prepare for the much-hyped comeback fight, which, as of now, still appears uncertain.