Jolly Cholly was an ebullient, fun-loving fellow who frolicked through 20 seasons as a player. He was also a tolerant manager who could coax career-best performances from mediocre players and gave free rein to his stars.
Grimm was the most skillful first baseman of his era. He won nine fielding titles wearing a small mitt and ranging wide of the bag. He broke in with the Athletics in 1916 and won his first regular job with the 1920 Pirates. In Pittsburgh, he teamed with fellow free spirits Rabbit Maranville and Cotton Tierney, to the despair of owner Barney Dreyfuss. The vaudeville team of Gallagher and Shean had a patter song which Grimm, a lefthanded banjo player, appropriated. Once, Grimm snared a sharp grounder, and instead of simply stepping on first, threw the ball to Cotton, shouting, “Have we got him, Mr. Tierney?” “Absolutely, Mr. Grimm,” came the rejoinder as the ball was thrown back to Charlie for the putout. Grimm had a 23-game hitting streak in 1923.
Grimm and Maranville were traded to the Cubs after the 1924 season, and continued their fun-loving ways. In 1932, his eighth year as Chicago’s first baseman, Grimm became manager of a Cub team that had responded badly to Rogers Hornsby‘s stern direction, and captured the pennant with a 14-game September winning streak. They won again in 1935, but in mid-1938 Grimm resigned, saying he couldn’t relate to or control his players. Gabby Hartnett stepped in, and the team rallied to the pennant while Grimm called the games from the broadcasting booth.
Grimm gave up sportscasting in 1941 to return as a Cubs coach, and then had what he described as the most fun of his career, managing Milwaukee of the American Association for Bill Veeck. After three successful seasons, Grimm was back at the helm in Wrigley Field. In 1945 his Cubs won another pennant, one which would have to last Cub fans for decades.
After being relieved as manager in 1949, Grimm moved to the front office, but in 1950 he returned to the minors, again leading Milwaukee to win the Little World Series. Braves owner Lou Perini invited him to manage in Boston in 1952, and when Perini shifted the franchise to Milwaukee the next year, the established local hero, Charlie Grimm, went along to manage. He remained for over three seasons, twice finishing second.
Grimm had a final fling leading the Cubs in 1960, but, after 17 games, swapped jobs with broadcaster Lou Boudreau. He stayed with the Cubs in various front office jobs another 15 seasons. After his death, his widow was allowed to scatter his ashes over Wrigley Field.