Chicago Cubs: Closing the book on the Joe Maddon era

Sixty men have held the title of manager for the Chicago Cubs in their historic baseball franchise history. Where does Joe Maddon rank among them?

Since 1903, when the postseason was modernized similar to how it is today, only 11 of 60 managers have been able to lead the Chicago Cubs to a postseason berth. Joe Maddon and Frank Chance are the only two managers in the organization’s history to win a World Series.

This list before you is a ranking of the top five managers in the 144-year history of the Cubs. The list is compiled of post-1900 managers. Cap Anson was one of the team’s early managers, leading them from 1879 to 1897. Personally, I would consider putting him in a different class because the managerial duties were not like they are now.

So now, as we approach a new era on the North Side, one led by former catcher and fan favorite David Ross, let’s officially close the book on Joe Maddon – and where he ranks among the all-time greatest skippers in Cubs history.

5). Leo Durocher (1966-1972)

Leo Durocher didn’t lead the Cubs to a postseason berth in his seven years with the club. He did, however, have a positive winning percentage at .504. His seven-year tenure with the team is the third-longest time, only Charlie Grimm (14 years) and Chance (eight years) held the role longer. His 535 wins rank third post-1900 in managerial wins in club history. Durocher, of course, is a member of the National Baseball Hall of Fame.

4). Don Zimmer (1988-1991)

During his four seasons at the helm, Don Zimmer managed some of the greatest Cub players in the organization history include the names of Mark Grace, Andre Dawson, Greg Maddux, Rick Suttcliffe, Ryne Sandberg.

His only trip to the postseason in 1989 led to a National League East title. Zimmer’s 265 wins place him 13th on the all-time win list for the Cubs.

3). Charlie Grimm (1932-1949)

The longest tenure in Cubs history belongs to Charlie Grimm. In 14 years Grimm won 946 games – the most all-time in Cubs history (post-1900).

This manager led the Cubs to three National League championships in 1932,1935 and 1945. Not only is he one of the best managers in Cubs history, but he also was a tremendous player. Grimm played 20 seasons in the league batting .290 average, courtesy of 2,299 base hits.

2). Joe Maddon (2015-19)

Here it is. The moment you’ve been waiting for. While many might consider Maddon the greatest manager in team history, for me, he comes in second. Still, that’s pretty impressive when you look back at what he accomplished in just five years.

After coming to the Cubs in 2015, Maddon wasted very little time making his Cubs known. He led the young team to a staggering 97 wins in his first year – punching a ticket to the postseason in the process. Although their quest for a title fell short, that all changed in 2016.

That year, of course, was nothing short of historic. Chicago won 103 games and brought home the first World Series title in over a century. The entire season was like a never-ending party – capped off with an unbelievable Game 7 victory that will undoubtedly stand the test of time.

Things soured a bit from there – but when you lead the Cubs to a championship, there’s really only one direction to go from there. Chicago reached the postseason in both 2017 and 2018 – winning another division title in the process – but the club faltered in the final year of Maddon’s deal. All told, Maddon finished his time with a record of 471-339 putting him fifth overall for wins in franchise history.

1). Frank Chance (1905-1912)

Chance won four pennants and the two of the three World Series titles in team history. His World Series wins were back-to-back years (1907 & 1908). The Hall of Famer won 768 games out of the 1,176 games he has coached in his career, the second-most in franchise history.

When you led the Cubs to a pair of titles, there’s only one place you can be on a list like this.