Some stronger skippers have led the Chicago Cubs in the franchise’s history, but who are the best managers in organizational history? The club hired Craig Counsell back on November 13 as the 56th manager in the team’s history. He hopes to make this list one day and has a track record. Until the long-time Brewer manager can make his mark in Wrigleyville, he’ll have to get in line to see if he can top any of the following three individuals below.
3. Charlie Grimm
Managing the team from 1932-1949 (while returning for one last season in 1960), Grimm won 946 games in his time leading the Cubs. Known as “Jolly Cholly,” Grimm won three pennants, with two being as a player/manager. The Cubs’ last pennant before 2016 came in 1945 when Grimm was the manager.
Grimm saw plenty of success as a player in twelve seasons with the Cubs. He possessed a .296 batting average and slugged .405 in over 1,300 games from 1925-1936.
He led the Cubs to 100 wins in 1935. This was just the fifth time the club won over 100 games in a season in franchise history. Grimm’s winning percentage as a Cubs manager sits at .547, eighth best in the history of the club. Despite winning three pennants, Grimm could never capture a title in all his years running the ship on the north side of Chicago.
2. Frank Chance
Winning 768 games in just eight seasons as the Cubs’ skipper, Frank Chance slots in at number two on this list. When doing the math, Chance won an average of 96 games per season in his tenure. He possesses the highest winning percentage amongst all Cubs managers, with a .664 mark.
Chance led the Cubs to back-to-back World Championships in 1907 and 1908. He guided them to four pennants, making four World Series in five years (1906-1908, 1910). The Hall of Famer was at the wheel for four 100-win seasons in the eight he managed for the Cubs.
Making four World Series in five years is an impressive feat, and it made Chance one of the most successful skippers in team history.
1. Joe Maddon
There is 100% recency bias involved here, and that is ok. While Maddon didn’t win back-to-back world titles like Chance did, there is something to say about a man who captained the ship of the group that snapped a 108-year curse. In five seasons as manager, Maddon won 471 games, good for the fifth most from a skipper in franchise history. Maddon’s .581 winning percentage is also the third-best in the team’s history.
The way Maddon flipped the culture of this organization took more effort than anyone could have ever imagined. It took a special someone to turn the loveable losers into the pinnacle of the sport, and Maddon did just that. He’ll never have to buy a meal in Chicago again, and Cubs fans everywhere are forever in debt to him. That alone makes him a worthy candidate, being the best manager of all time for the Chicago Cubs.
Despite the many years of pain and suffering we’ve seen from the Cubs in history, these three men played a huge factor in some of the organization’s happier times. We have three world titles and eight pennants between Grimm, Chance, and Maddon. Without the three “best managers,” who knows how many titles or pennants the club would have?
Main Photo Credits: Jeff Curry-USA TODAY Sports
