A 50-0 record, a champion across four weight classes, and retired by age 40 with a bank account most athletes only dream of, Floyd Mayweather did what no boxer has managed to replicate. With an estimated net worth of $500 million, ‘Money’ Mayweather isn’t just the most successful boxer inside the ring; he’s the richest in the sport’s history. The Grand Rapids native shared the ring with nearly every major name of his generation, including Manny Pacquiao, Miguel Cotto, Ricky Hatton, Oscar De La Hoya, Juan Manuel Marquez, Shane Mosley, and even Saul ‘Canelo’ Alvarez. Sure, critics argue some of those opponents were past their prime, but the wins still count.But even a near-perfect career has its what-ifs. Despite his meteoric rise and mind-blowing earnings later on, Floyd Mayweather admitted he does have one big regret. And surprisingly, it has nothing to do with ducking fighters or missed superfights. When he began his pro career in 1996, Floyd Mayweather signed under Bob Arum’s Top Rank Promotions. And while it gave him a platform to build on, he wasn’t earning anywhere close to what he believed he deserved. That early pay gap stayed with him, fueling the mindset that would later turn him into not just a fighter, but a promotional powerhouse.Even though Floyd Mayweather entered the pro ranks with a bronze medal from the 1996 Atlanta Olympics, his early earnings were anything but golden. In fact, for his second professional fight, a second-round stoppage of Robert Apodaca, ‘Pretty Boy’ pocketed less than $3,000. While his pay steadily increased during his time with Bob Arum’s Top Rank, it never came close to reflecting the star power he knew he could command. By the time he beat Arturo Gatti in 2005 to claim the WBC super lightweight title, Floyd Mayweather already had enough. Looking back, he didn’t mince words. While speaking to FightHype back in 2018, he admitted, “The worst thing I ever did in my career was sign with Top Rank…. because I was destined to be big anyway. I was destined to be a superstar anyway.”That breakaway came at a steep cost, $750,000, to be exact. But for Floyd Mayweather, it was an investment in himself. Once free, he launched Mayweather Promotions and took full control of his career trajectory. The move paid off almost instantly. A year later, Money Mayweather headlined a mega-fight against Oscar De La Hoya and banked a jaw-dropping $25 million purse. From that moment on, the blueprint was set: build your brand, control your business, and cash in like never before.And cash in he did. The numbers only got wilder, huge paydays for Shane Mosley, Victor Ortiz, and Saul ‘Canelo’ Alvarez followed. But it was his final stretch that truly cemented the “Money” legacy. Mayweather reportedly earned $180 million for his historic bouts against Manny Pacquiao and a whopping $280 million against Conor McGregor. Yet despite those blockbuster paydays, fans were taken aback to hear a rare note of regret in Floyd Mayweather’s voice as GiveMeSport recently reshared a snippet of the interview on Facebook.Floyd Mayweather’s paycheck confession ignites controversyWhile many still celebrate Mayweather as a boxing genius, others didn’t hold back in their criticism. “He should regret all of his fixed fights,” one user commented bluntly. The sentiment echoes a broader frustration: when Jake Paul cherry-picks his opponents, critics call him an “influencer boxer” who doesn’t understand the sport. But when Floyd Mayweather, a 50-0 legend, does the same, or so they claim, it’s seen as strategy, not spectacle. For some fans, this double standard is hard to digest, especially now that Mayweather is profiting more in retirement than many boxers make in a lifetime.Then came the deeper jabs. “When he paid to win the fight,” another fan wrote, drawing a parallel to the November bout between Jake Paul vs. Mike Tyson. Many speculated that the “Baddest Man on the Planet,” only stepped into the ring for a massive payday, reportedly $20 million. Jake Paul, in turn, walked away with $40 million and a résumé boost. While there’s no concrete proof that the fight was staged, fans were quick to compare that spectacle to Mayweather’s business-driven career, suggesting that Floyd Mayweather may have manufactured his spotless record just as strategically.One fan made a particularly biting point: “No rematches.” It’s true, Floyd Mayweather, for all his accolades, never ran it back with any of his opponents, except José Luis Castillo and Marcos Maidana. Even after the blockbuster 2015 fight with Manny Pacquiao, which grossed more than $600 million, a rematch never materialized. When asked, Mayweather cited his unwillingness to work with Bob Arum. Whether that was a valid business stance or an excuse to avoid risk is still debated. But the fact remains, Floyd Mayweather never gave fans the sequels they often craved, leaving some to argue he played it safe rather than prove his dominance a second time.The backlash wasn’t just about strategy, it was personal. One user even mocked, “He should have sold running shoes,” accusing Mayweather of running from real challenges in the ring. Others just shrugged it off, with a final commenter writing, “Who cares.” It reflects how polarizing the man really is. To his fans, Floyd Mayweather is the GOAT, a defensive genius who played the game of boxing better than anyone ever has. To his critics, he’s a businessman in gloves, more concerned with protecting his brand than pushing his limits.Which brings us to Manny Pacquiao, arguably the perfect foil to Mayweather. Unlike Floyd Mayweather, PacMan fought across multiple eras, took risks, embraced rematches, and wasn’t afraid to suffer defeat in the pursuit of greatness. His career was about challenging the best, often at their best, which is why many fans still hold him in such high regard, even if his record isn’t flawless. With that said, what are your thoughts on Floyd Mayweather’s recent confession?The post $500M Rich Floyd Mayweather’s Biggest Regret Earns Him No Respect From Boxing Fans appeared first on EssentiallySports.