Chicago Cubs: The definitive guide to the 2020-21 offseason

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Chicago Cubs, Theo Epstein
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Keep Theo Epstein around

According to David Kaplan of NBC Sports, Cubs President of Baseball Operations Theo Epstein will be meeting with owner Tom Ricketts this week to discuss his future with the team (and future departure).

Though it seems certain that Epstein won’t be signing an extension, it’s also possible that Theo could opt to leave during the current 2020-21 offseason. According to the report, the two parties will make a determination a timeline for Theo’s exit at the meeting.

Regardless of outcome and results of the past few seasons, it would be beneficial to keep Theo around for another offseason and regular season. He’s a proven exec who knows how to build a championship team and ensure that they remain a contender even after his departure.

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In addition to having his expertise for the 2021 Major League roster, it would be hugely beneficial to have him around for another year so that he can shape the team for a future rebuild (we’ll get to that later).

Another year of Theo means another year of draft picks, prospect development and front office molding for what it would look like after he leaves.

Even if he doesn’t bring another championship in 2021, he could at least put the Cubs in the best possible situation to rebuild and contend in the future post-Theo era.