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Humorous Jolly Cholly Grimm was a line drive, spray hitter and collected 2299 lifetime hits, including 394 doubles and 108 triples. In 1920, Grimm became the Pittsburgh Pirates regular first baseman, he batted only .227 but led the NL in fielding. The happy-go-lucky Charlie Grimm's batting average rose to .274 the next season, but his superior fielding range and sure hands were his lifelong trademarks. In 1923, he put together a 23 game hitting streak , batted .345 along with 99 RBIs and led the league in fielding again. He was traded to the Chicago Cubs after the 1924 season and became instantly popular with his Jolly demeanor. Charlie Grimm won a total of nine fielding titles. In 1931, he hit .331 with 33 doubles and fanned only 29 times in over 500 at bats. In 1932, his eighth year in a Cub uniform, he became a player manager and led them to a pennant. The Cubs won the pennant again under his leadership in 1935.
In mid-1938, he resigned. Gabby Hartnett became manager and Jolly Cholly Grimm called the games from the radio broadcasting booth. The Cubs rallied and won another pennant. In 1944, Grimm returned as the Cubs' manager and the team responded by winning another pennant in 1945. He was dropped by the Cubs and then managed in the minors, leading a Milwaukee team to the minor league championship. Charlie Grimm became the Boston Braves manager in 1952 and when they moved to Milwaukee the next season, Grimm stayed on for 3 more seasons, leading the Milwaukee Braves to two second place finishes. He returned to the Cubs and worked in their front office for 15 years. After his death in November of 1983, his window was permitted to scatter his ashes over Wrigley Field. Baseball History