Chicago Cubs: Charlie Grimm 1932-1949, 1960
Long ago, in an era of baseball far far away, the great Charlie Grimm led the Cubs as their managerial face. The era of baseball was a different landscape, with Grimm serving a utility role as both a player and the manager.
An insanely good first baseman, and one of the best in the games’ history, Grimm replaced Rogers Hornsby as the club’s manager midway through the 1932 season. During his inaugural year, Grimm played 107 games for the Cubs and helped lead them to an 86-68 record, and a third-place finish.
After back-to-back winning seasons, Grimm led the Cubs to a National League Pennant in 1935 as the club finished 100-54. During that season, Chicago led the all of baseball in ERA, led the N.L. in batting average, and runs scored. A successful two more seasons saw Grimm lead with 87 wins and 95 wins, respectively.
Gabby Hartnett replaced Grimm partway through the 1938 season with the team sitting at 45-36. They won the pennant that season under Hartnett. Three years later, in 1941, Grimm once again joined the Cubs, this time as a coach. In 1944 following a tough start, Grimm was tasked as the head honcho where he remained until 1949. His last season came 11 years later, in 1960.
Overall, Grimm finished his managerial career in Chicago with a very successful 946-782 record. He led the team to three pennants. In a different age of baseball, Grimm was able to be great for the Cubs and remains as one of the all-time greatest managers to this day.