The diminutive 5' 7" Crutchfield began his 15-year career with the Birmingham Black Barons in 1930. As a rookie outfielder for the Black Barons he earned a spot in the everyday lineup with his solid fielding skills and realible performance at the plate. Although he demonstrated little power as a hitter Crutchfield was an excellent slap hitter with the ability to place the ball in play behind runners on the basepath. In addition to compiling impressive rbi totals he always maintained a respectable batting average near .300 throughout his career.
After a brief stint with the Indianapolis ABCs Crutchfield jumped to the Pittsburgh Crawfords joining Cool Papa Bell and Ted Strong to form the finest outfield in the Negro Leagues. While with the Crawfords Jimmie's performance earned him three trips to the East-West All-Star game.
As the Crawfords dynasty began to crumble in the mid-1930s Crutchfield moved on, first to the Newark Eagles and then to the Chicago American Giants. In Chicago his affable personality and consistent willingness to interact with fans at the ballpark made him a favorite with the local regulars. In 1941 he was again honored by election to the West squad in the East-West game.
As a player Crutchfield never rose to "league leading" stature in any single category, yet demonstrated better than average skills in almost every aspect of play. He was, in essence, the epitome of the well-rounded ballplayer - a solid everyday performer. He did, however, possess one exceptional talent - the ability to make friends wherever he went and to serve as a unifying force on every team on which he played. Cool Papa Bell once observed that "Jimmie was the best team player in baseball. If he never played in a game he would still have been an important part of any baseball team. He cheered you up when things weren't going too good whether you had troubles on or off the field. You always knew you could count on Jimmie to be on the bright side of everything."