Although Crowder signed his first baseball contract in 1920, he did not play a full season until 1923, with the Winston-Salem Twins. He did not appear in his first major league game until the age of 27, in 1926. Crowder won only seven games in each of his first two seasons, but finished the 1928 season with a record of 21–5 for the Browns. His .808 win percentage was the best in the American League, and his 21 wins finished fourth best in the league.