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 Page[1] and Cool Papa Bell, they formed what is considered the best outfield in the Negro leagues.

Crutchfield died in Chicago in 1993 and was interred in the nearby Burr Oak Cemetery, Alsip, Illinois,[3] buried in an unmarked grave until 2004 when Peoria, Illinois anesthesiologist Jeremy Krock contacted members of the Society for American Baseball Research to try to get a proper headstone on the grave of Crutchfield, who originally comes from the same town as Krock.

This launched the Negro Leagues Baseball Grave Marker Project of which Dr. Krock still works with today.