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Theo Epstein Says Goodbye to the Cubs

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It’s been nine years, but Theo Epstein has made his decision to say goodbye to the Chicago Cubs. The announcement came yesterday, however, the writing had been on the wall for a while. Although somewhat surprised, I wasn’t shocked. GM Jed Hoyer has been named as Theo Epstein’s replacement and will assume the title and duties on Friday, November 20th.

A few months back, news leaked that Theo Epstein wouldn’t be seeking a contract extension, with his current contract set to expire after the 2021 season. Epstein left himself an out, however, never officially committing to stay with the club past 2020.

When Steve Cohen came into the Mets’ organization as their new owner, the first thing he did was cleaned house. I surmised at that point that Theo Epstein would be leaving Chicago to join the Mets, but subsequently learned that the Cohen had already named Sandy Alderson as his new president of baseball ops. Nxet, I was told that Alderson wasn’t so much a choice, but rather, was named due to a lack of options.

The Phillies were also seeking a man of Epstein’s caliber, but apparently Theo Epstein isn’t going to the City of Brotherly Love either.

Theo Epstein on Leaving the Cubs

“For the rest of my life, I will cherish having been part of the great Chicago Cubs organization during this historic period. All of the things that have made this experience so special — the fans, the players, the managers and coaches, ownership, my front office colleagues, the uniqueness of the Wrigley experience, the history — make it so tough to leave the Cubs. But I believe this is the right decision for me even if it’s a difficult one. And now is the right time rather than a year from now. 

“The organization faces a number of decisions this winter that carry long-term consequences; those types of decisions are best made by someone who will be here for a long period rather than just one more year. Jed has earned this opportunity and is absolutely the right person to take over this baseball operation at such an important time.”

Questions About Theo Epstein’s Decision

The Cubs were initially under the impression that Theo Epstein would complete his contract, so what changed?

For the last couple of seasons, owner Tom Ricketts has been reluctant to go over the luxury tax threshold again. Last winter was a near catastrophy, losing key players such as Brandon Kintxler and Nicholas Castellanos.

For the last two years Theo Epstein has vowed that changes were coming, but the Cubs did nothing to interrupt the remainder of the core that won them the World Series title in 2016. There’s just one problem: That core has had – for the most part – a steady decline in performance since winning it all in 2016.

Could it be that Ricketts wants to tank the team and that Theo Epstein wants no part of it? After all, as it stands now (including arbitration estimates) Ricketts only has roughly $33.6M to work with this year, if he wants to stay under the luxury tax. Epstein has a knack for building winning teams and was left hanging out to dry last year after the Ricketts’ family closed their checkbook.

Nicholas Castellanos wanted to stay. Brandon Kintzler wanted to remain a Cub, but no money was made available to Theo Epstein for either player. Kintzler was, by far, the best arm in Chicago’s bullpen in 2019, and the Cubs would only offer him $1M on a one-year deal. Negotiations eventually raised the offer to $1.5M, but when the Marlins offered double that figure, Kintzler migrated to Miami.

As it stand now, the core has little trade value, especially after a bad 2019 season and subpar performances at the plate (by most) in 2020. Kris Bryant – the Cubs’ golden child – batted all of .206 in 2020, posting a WAR of 0.3. Not exactly prime trade bait.

It would appear that the plan may be to completely revamp -aka demolish -the team, leaving Theo Epstein to make the statement, ““The organization faces a number of decisions this winter that carry long-term consequences; those types of decisions are best made by someone who will be here for a long period rather than just one more year.” Ironically, Hoyer’s contract is set to expire after the 2022 season, so it’s not like he’s currently in a position to lead the next wave of Cubs. Will Hoyer get an extension? It all depends on what he can accomplish in just a pair of seasons.

So, What’s Next for Theo Epstein?

Epstein has already vowed to take the 2021 season off, in order to spend time with family. He also intends on working with some non-profit orgamizations, as he bides his time.

His ultimate goal? “I do hope and expect to have a third chapter in baseball. But in no shape or form do I expect to do it right away. I envision taking some time to pursue other pursuits. … I do hope to stay engaged in the game. This game is my passion. I care deeply about it. So I’m going to seek out ways to serve the game in the near future, and I’ve already started to pursue a few possible avenues to do that.

Epstein also mentioned wanting to become part-owner of an MLB franchise, the next logical step in a career that has seen Epstein bring two World Series Championships to the Boston Red Sox (2004 and 2007), and, of course, the one in Chicago in 2016.

From every fan in Chicago: Thanks for ending the drought, Theo. God speed.

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Ken Allison is the senior of two MLB Department Heads, as well as a writer and editor for Overtime Heroics. A life-long MLB fan, he's also written for CubsHQ and had the opportunity to try out for the Chicago Cubs in 1986.