When Pride was 14, his mother purchased him his first guitar and he taught himself to play. Though he loved music, one of Pride's lifelong dreams was to become a professional baseball player. In 1952, he pitched for the Memphis Red Sox of the Negro American League. In 1953, he signed a contract with the Boise Yankees, the Class C farm team of the New York Yankees. During that season, an injury caused him to lose the "mustard" on his fastball, and he was sent to the Yankees' Class D team in Fond du Lac, Wisconsin. Later that season, while in the Negro leagues with the Louisville Clippers, two players – Pride and Jesse Mitchell – were traded to the Birmingham Black Barons for a team bus. "Jesse and I may have the distinction of being the only players in history to be traded for a used motor vehicle," Pride mused in his 1994 autobiography.