Roger Federer may be one of the greatest tennis players of all time, but his most lucrative move didn’t come on the court. It came from a smart investment in the Swiss sneaker brand On Holding. While Federer earned over $130 million in prize money from 20 Grand Slam wins, his estimated 3% stake in On is now worth at least $500 million, according to Bloomberg. In 2018, Federer signed a $300 million deal with Uniqlo. Since Uniqlo doesn’t make shoes, it gave him the freedom to explore other footwear deals. He discovered On through his wife, connected with the founders, and collaborated on a line of performance sneakers. As the brand’s popularity surged—especially in the U.S.—its valuation jumped past $17 billion. Federer’s success mirrors other billionaire athletes like Michael Jordan and LeBron James, who also turned fame into equity. But Federer’s approach has been quieter. He avoids short-term endorsements and stays selective with public appearances, choosing long-term partnerships that align with his values. He works with trusted advisors to grow his brand and investments thoughtfully. Federer’s story shows that smart business moves can be even more rewarding than championships. He’s built a legacy far beyond the tennis court.