Chicago Cubs window could close after 2021

CHICAGO, ILLINOIS - SEPTEMBER 07: President of baseball operations Theo Epstein of the Chicago Cubs watches the game between the Chicago Cubs and the St. Louis Cardinals at Wrigley Field on September 07, 2020 in Chicago, Illinois. (Photo by Nuccio DiNuzzo/Getty Images)
CHICAGO, ILLINOIS - SEPTEMBER 07: President of baseball operations Theo Epstein of the Chicago Cubs watches the game between the Chicago Cubs and the St. Louis Cardinals at Wrigley Field on September 07, 2020 in Chicago, Illinois. (Photo by Nuccio DiNuzzo/Getty Images) /
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The Chicago Cubs are set to enter 2021 with a team that is on the verge of a major transition.

The Chicago Cubs window of contention is still open, but just barely. They had managed to reach the postseason, shrugging off a disappointing 2019 campaign to win the NL Central by four games over the second place Cardinals. Chicago rode a solid pitching staff to overcome their offensive shortcomings, until those issues with the bat came to a head in their being swept by the Marlins.

Those issues may come to a head soon. Several key pieces of the lineup – Javier Baez, Kyle Schwarber, Anthony Rizzo, and Kris Bryant – are all slated to be free agents after the season. Chances are, the Cubs will not be able to keep all of those pieces on the roster.

To further complicate matters, Cubs president Theo Epstein’s contract comes to an end after the season as well. At this point, it is expected that he will also depart, working with ownership to create a smooth transition with new leadership.

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The Cubs already face some questions heading into the offseason. Both Jon Lester and Jose Quintana are free agents, leaving two holes in the rotation. Closer Jeremy Jeffress is also slated for free agency this offseason, leaving a possible hole given the struggles of Craig Kimbrel.

It is possible that we have already seen the end of the Cubs run of dominance. Epstein and general manager Jed Hoyer built a contending franchise, ending the Curse of the Billy Goat in 2016 and turning the Cubs into a perenial playoff contender. But the roster is about to undergo a significant change.

With teams looking to cut payroll due to revenue losses in 2020, it may not be a surprise to see Chicago look to the future. Any of those impending free agents could be dealt. Willson Contreras, a potential free agent after 2022, has been the subject of trade rumors as well. The Cubs could see a lot of change in the next year.

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The Chicago Cubs still appear to be capable of contending in 2021. However, their window may be closed once that season comes to an end, as they are about to enter a major transition.