Which Chicago Cubs managers have been ejected the most?

Most managerial ejections in Cubs history: #2 – Charlie Grimm

Managing 14 years and 1,737 games, only Cap Anson has managed more games for the franchise than Charlie Grimm. Serving as both a player/manager and just manager, Grimm won three pennants as the team’s skipper. He was ejected 19 times as a Cubs manager.

Grimm was not making ejections frequent however, the most he ever got tossed in a season was four in 1934. Other than that he was typically ejected roughly twice a year. He accumulated the 19 ejections from managing the team for so long.

It is worth noting he was ejected in Game3 of the 1935 World Series for “bench jockeying”. In fact, four guys (two from each team) were ejected that game, Grimm being one of them.