While still playing as first baseman, Grimm was enlisted to replace Rogers Hornsby as manager after his dismissal on August 2, 1932. The team was 53-46 at the time, five games back in the standings in second place. In the 55 games that Grimm managed for the Cubs, he rallied them to a 37-18 record for an overall record of 90-64, winning the National League pennant for the first time since 1929. The Cubs were subsequently swept by the New York Yankees in the World Series. The team regressed in the following two seasons, winning 86 games each and finishing in third place. However, Grimm\'s team made a dramatic improvement in 1935, going 100-54. It was the first time the Cubs had won 100 games since 1910 and it was the last until 2016 (along with Grimm\'s only 100-win season as manager). They were bolstered by a 21-game winning streak in September that carried them to a second league pennant in four seasons. In the World Series that year against the Detroit Tigers, they won the first game in Detroit before losing the next three. They rallied to win Game 5 at Wrigley Field, but the Tigers won a walk-off hit from Goose Goslin to win 4-3 and seal the Series. The Cubs went 87-67 for a third place finish the following year (which was Grimm\'s last as a player-manager), but they improved to 93-61 and second place the year after. 1938 was his last season of his first tenure as manager of the Cubs. The team was 45-36 when he was replaced by catcher Gabby Hartnett. As Grimm had done six years earlier, the newly installed player-manager led the Cubs to a dramatic comeback to win the league pennant that season.\n', '

After a sluggish start by the Cubs in 1944 in which the team lost ten in a row after winning the Opening Day game, Grimm was hired to manage the club again. The team finished fourth in the standings with a 75-79 record (the fifth straight losing season for the team). However, Grimm led them to a dramatic improvement the following year, going 98-56 to win the league pennant for the first time since 1938. In the World Series that year, Grimm\'s team faced off against the Tigers once again. It was a hard-fought series, going down to the decisive seventh game at Wrigley Field. The Cubs were trounced 9-3, with six of the Tiger runs coming in the first two innings. It was the last pennant for the Cubs for 71 years. The Cubs went 82-71 the following year, finishing 3rd in the standings. It was the last time the team had a record of .500 until 1963. Grimm finished his last three seasons with losing record (69-85, 64-90, 19-31) before resigning in 1949.\n', '

After his resignation from being manager, he served as the Cubs\' Director of Player Personnel, then the club\'s title for general manager, doing so until February 1950 due to not feeling comfortable in his front-office post. He subsequently was hired to manage a Double A team, the Dallas Eagles of the Texas League.\n', '

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