Charlie Grimm earned the nickname "Jolly Cholly" for his good-natured personality and humor, but few were more competitive as a player and manager. Grimm became one of the best fielding first baseman of his era for the Philadelphia Athletics, St. Louis Cardinals, Pittsburgh Pirates and Chicago Cubs.
Grimm twice managed the Cubs. He coached the Milwaukee Brewers in the American Association in 1950 and caught the eye of Boston Braves' owner Lou Perini. Grimm managed the Braves in Boston for a season and then became the first manager of the Milwaukee Braves. He remained with the team from 1953-56.
Grimm later became part of the Cubs' experimental College of Coaches. He ended his time in baseball in the broadcast booth.