Year born: 1983
Hometown: Fort Myers, Florida
Career: 2020-present
Bottom line: One of two players in their 40s in the Top 15, Ryan Sherry grew up in Florida and played tennis for the University of Florida. While Sherry’s pickleball success is something to commend, it pales in success to his accomplishments in the business world.
Sherry is one of the co-founders of Legacy Pro Sports, which helps NFL players file disability claims following the end of their pro careers. Through 2023, that includes over 5,000 players and more than $200 million in disability benefits paid out.
Sherry also gave an all-time interview after winning the North Carolina Open in 2022.