When two of the greatest pugilists in modern boxing history clashed in 2015, the world stood still. Floyd Mayweather Jr. vs. Manny Pacquiao wasn’t just a sporting event—it was a spectacle. Dubbed the “Fight of the Century,” the bout broke revenue records and reportedly netted Pacquiao a staggering $125 million. But even that eye-watering paycheck couldn’t silence the quiet sting of regret that still lingers for the Filipino icon.

The clash in Las Vegas was marketed as a battle for the ages. But behind Pacquiao’s steely gaze and relentless southpaw rhythm, there was a secret he tried to keep buried—a torn rotator cuff suffered just weeks before the bout. While fans saw a poised and focused fighter step into the ring, what they didn’t see was the pain lurking beneath the gloves. And years later, that is the moment he wishes he could rewrite.

The resurfaced quote, originally shared in a 2020 interview with Business Insider’s Alan Dawson, revealed the boxing legend’s haunting reflection. “If I could change one thing in my career,” said arguably one of the most beloved champions of the sport, “I’d have asked to postpone my 2015 fight against Floyd Mayweather after hurting my shoulder in training.”

The injury, which had already been whispered about post-fight, was confirmed to have occurred two weeks prior to the mega bout. The Filipino senator-turned-sportsman elaborated in his conversation with The Athletic, saying he initially hoped to manage the pain without surgery. “I thought it was going to be okay and that I’d be feeling better without an operation,” he admitted. But once the bell rang, hope clashed with harsh reality.

“My injury worsened after the third round,” he continued. “Pushing for that important fight to happen as scheduled is my biggest regret.”

While the unanimous decision that crowned Mayweather the victor was never in dispute, the context of Pacquiao’s physical state paints a more nuanced picture of the night. ESPN had reported, even in 2015, that his longtime trainer Freddie Roach and promoter Bob Arum considered postponement—but the show went on.

Since that night, the two fighters have flirted with the idea of a rematch, stoking fans’ hopes through cryptic social media exchanges. In 2018, the undefeated American even posted a video alongside his old rival, teasing, “I’m coming back to fight Manny Pacquiao. Another nine-figure payday on the way.” But as fast as the promise was made, it faded.

Mayweather, whose post-Pacquiao exploits include a flashy (and financially flush) crossover win against UFC’s Conor McGregor in 2017 and a surreal exhibition demolition of kickboxer Tenshin Nasukawa in 2018, has made his stance clear in recent years. In a no-nonsense statement to Fight Hype, the five-division world champ shut down rumors of a true comeback: “I’m not boxing no boxers, at all, none… I’m retired and I love my life.”

He added with signature bravado, “If I see an opportunity where I can entertain and have a little fun and make $600 million, why not?”

But for the man from the Philippines—who fought with the weight of a nation on his back and one arm seemingly tied—no price tag can undo what he calls his greatest misstep. 

The Making of a $600 Million Super-fight: How Mayweather vs. Manny Pacquiao Finally Happened

It’s hard to believe, but a full decade has passed since Floyd Mayweather Jr. and Manny Pacquiao finally stepped into the ring for what would go down as the most lucrative boxing match of all time. With over $600 million generated—including 4.6 million U.S. pay-per-view purchases through HBO and Showtime—the May 2, 2015, clash became more than just a sporting event. It was a cultural phenomenon. So massive was its impact that the Philippine parliament literally hit pause, allowing politicians to fly to Las Vegas to witness history at the MGM Grand Garden Arena.

The match itself, however, left many wondering what if. Despite being billed as the “Fight of the Century,” the actual contest—won convincingly by Mayweather via unanimous decision (116–112, 116–112, and 118–110)—lacked the fireworks fans had hoped for. The American masterfully controlled the distance, making the fight more a tactical clinic than a toe-to-toe war. Both fighters entered the ring as reigning welterweight champions—Mayweather at 38, Pacquiao at 36—but the timing, many say, was far from ideal.

Talks for this clash had actually begun back in 2009 when both were arguably in their primes. But it wasn’t until the undefeated “Pretty Boy” Mayweather felt the time was right that it became reality. Negotiations were marred by disagreements over purse splits, promotional hurdles—Pacquiao was with Top Rank and Bob Arum—and most infamously, accusations of doping from Mayweather’s camp. “If he agrees to a blood test 30 days before the fight, it’s on,” Mayweather declared at the time. Pacquiao threatened a defamation lawsuit, stating he would do several blood tests—just not so close to fight night, fearing it would weaken him.

Still, the stars aligned unexpectedly in 2015. While in Miami for the Miss Universe pageant, Pacquiao’s return flight got cancelled due to bad weather. So, he went to a Miami Heat game—coincidentally attended by Mayweather. What followed was a brief courtside conversation that would change boxing history. That same night, they met in Pacquiao’s hotel room and hashed out final details: drug testing terms, ring-walk order, promotional billing. Mayweather personally phoned Showtime Sports to green light the deal, and soon after, the fight was officially on.

By the time the opening bell rang, front-row tickets had skyrocketed to $180,000, and luxury weekend packages were sold to the ultra-elite. Celebrities from Prince and Robert De Niro to Beyoncé, Michael Jordan, and even Donald Trump packed the venue. In many ways, it was everything fans had ever dreamed of—just five years too late.