Born in St. Louis, Missouri, to parents of German extraction, Grimm was known for being outgoing and chatty, even singing old-fashioned songs while accompanying himself on a left-handed banjo.

He played with the St. Louis Cardinals and appeared in 50 games from June to August while batting .220 while serving usually as the first baseman or pinch hitter.

[6] Grimm played 148 games with the Pirates for 1920, primarily at first base, where he had a .995 fielding percentage in 1,327 innings.

For example, he played 141 games for the Cubs in 1925 and batted .306 while having 159 hits and 76 RBIs, which went well with 38 walks and 25 strikeouts to garner a 13th place finish in voting for Most Valuable Player.

He was the only hitter on the team to bat left-handed, which proved key to the right-handed pitchers for the Athletics, who were not troubled by having Lefty Grove go in the bullpen.

During the season, he recorded his 2,000th hit, doing so on July 6 against the Philadelphia Phillies at Wrigley Field off Snipe Hansen.

While he did not lead many categories in the hitting department, he was a solid fielder in terms of durability, playing 2,131 games in the first base position (owing to twelve seasons of being in the top ten for games played alongside putouts) that ranked third at the time he retired, and his 20,711 putouts are fifth most in MLB history (Eddie Murray is the only player to have passed Grimm since the latter's retirement).

The team was 45–36 when owner P. K. Wrigley moved Grimm to the broadcast booth and named catcher Gabby Hartnett as player-manager.

As Grimm had done six years earlier, Hartnett led the Cubs to a dramatic comeback to win the league pennant that season.

After a sluggish start to the 1944 season which the team lost ten in a row after winning the Opening Day game, Grimm was hired to manage the club again.

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.

He subsequently was hired to manage a Double A team, the Dallas Eagles of the Texas League.

He was highly successful as a manager during each term, winning the regular season American Association title in 1943 and 1951, and the playoff championship in 1951.

On May 30, 1952, Grimm was promoted from Milwaukee to manager of the big league Braves; he would prove to be the last skipper in the history of the Boston NL club.

The next year, they regressed a bit as a team with an 89–65 record for a third place finish (eight games back), but it was the first time that they had consecutive winning seasons since 1947–48.

Wrigley made the novel move of swapping Grimm with another former manager, Lou Boudreau, who was doing Cubs radiocasts at that time.

Grimm had done play-by-play in the past, so he gave it one more go in 1960, before stepping back to the ranks of coaching and then front office duties.

Grimm is one of 29 managers to win 1,000 games and three league pennants, although he is one of five who are not currently inducted into the National Baseball Hall of Fame and is also one of six to not have won a World Series (although each member coached in the 19th century).

Baseball historian Bill James wrote, "One of the biggest surprises to me, when I ranked the managers, was how high up the lists Charlie Grimm was.

He ranks about even with Al López, Whitey Herzog, Tony La Russa, Frank Chance, those kinds of guys.

"[14] After his retirement from baseball, he lived adjacent to Lake Koshkonong, near Fort Atkinson, Wisconsin.