Thoroughbred Racing Jockey Shane Sellers Sellers is one of the top jockeys in his profession. His winnings top $100 million. He's ridden two Breeder's Cup winners, and has ridden in 14 Kentucky Derbies. Shane Sellers appears in the upcoming HBO Undercover documentary Jockey. The film delves into aspects of jockey's lives that are not widely known. Jockeys endure a punishing regime of sweating and purging to make weight minimums, and many work without contracts and health insurance.