
Damian Lillard
In 2023, Lillard signed a two-year $122 million extension with the Portland Trailblazers. The basketball star is playing in one of the NBA’s smallest markets but they’re desperate to keep him. That’s why they’ve thrown that much money at the seven-time All-Star. It’s unlikely that he’ll win rings in the Pacific Northwest but he’s still making a fortune.

Lilliard also has major deals with Adidas and Powerade. Many of the most successful basketball players create their shoe lines and Lillard is no exception. Now he’s one of the richest athletes in the U.S. despite being a big fish in a small pond. But that’s how the Oakland native prefers it (via Sportskeeda).