Roger Federer

Net worth: $550 million. Federer retired in 2022 but his earnings accelerate in retirement. He holds equity in On Running (IPO'd in 2021 at $6 billion valuation — Federer's stake worth an estimated $300 million), Uniqlo ($300 million, 10-year deal), Rolex, Mercedes-Benz, and Credit Suisse partnerships. He won 20 Grand Slam titles and earned $130 million in prize money — less than a quarter of his total wealth. Federer proved that athlete branding built on elegance and longevity outearns branding built on controversy. The most marketable tennis player in history.