Crutchfield began his career with the Birmingham Black Barons in 1930 but the following year moved to the Indianapolis ABC's. When the team ran into financial difficulties, he left to play with the Pittsburgh Crawfords, where he remained for the next five years. Teamed with Ted Strong and Cool Papa Bell, they formed what is considered the best outfield in the Negro Leagues. During this time, his performance earned him three appearances in the East-West All-Star game. In the 1935 game, Crutchfield made an astonishing catch when he chased down a long drive and leapt in the air, catching the ball in his bare hand. In 1941 he was named an All-Star again, this time as a member of the Chicago American Giants.
Renowned for his personality, Jimmie Crutchfield exemplified the "team player" who was a stable and positive influence on the field and in the clubhouse. After his baseball career was over, he went to work for the United States Postal Service.
Jimmie Crutchfield died in Chicago in 1993 and was interred in the nearby Burr Oak Cemetery, Alsip, Illinois.