Cubs Rumors: Could Theo Epstein leave the team this week?

After nine years and a fantastic run with the Chicago Cubs, could Theo Epstein’s time with the club be over?

It’s something most Chicago Cubs fans have known for a while but probably filed away in the reserve memory banks as something that might happen in the distant future. It’s also something that most fans are probably not very eager to see become a reality. That something, of course, is the possibly imminent departure of President of Baseball Operations, Theo Epstein.

Sure, there are fans out there who have been secretly (or overtly) pining away for that day, hoping for some secret baseball white knight to ride in and magically “save” an organization that has been better over the last six years than at any point in any fans’ lifetime. Most, I suspect, understand what Epstein has meant and brought to a franchise deemed “lovable losers” for the better part of, well, all of my time on this Earth.

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As David Kaplan reported yesterday, Epstein will meet with Cubs Chairman Tom Ricketts this coming week to discuss plans for Cubs baseball going forward. Typical and not unexpected at all. What was a bit surprising, however, was the more than the insinuation that one of the possibilities that might come up would be a transition of power to GM Jed Hoyer and departure from the Cubs a bit sooner than some may have thought.

While the feeling that Epstein might be done when his current contract runs out after next season is not a new one, up until now, basically no one had said he might leave before that contract was done.

That’s precisely what Kaplan flat out said in his article as his sources have said there is the possibility that the discussion might be about leaving this year rather than see the contract all the way through. Note, this is only a slight possibility according to those sources, but wow.

What’s the thinking behind this idea? Well, if the Cubs plan on having Hoyer take over, it matters little if that transition occurs right now or in a year. Epstein doesn’t have to get him “up to speed” or transition throughout the year. Hoyer already knows how to run things, is more than adept at doing them, and has been with Epstein for nine years in Chicago. He also knows a thing or two about picking up the pieces when Epstein leaves as that’s precisely what he did in Boston in 2011 and then won another title in 2013 there. I’ll take that in Chicago.

Epstein may be feeling deflated after this rough 2020 season (or entire run with the Cubs) or may think that the timing is right to move on before time runs entirely out on this group of core guys in Chicago. It would also mean he doesn’t have to helm a trade of Kris Bryant, Kyle Schwarber, Javier Báez, or Willson Contreras. He also won’t have to decide on Jon Lester or Anthony Rizzo. When put that way, he could never be at fault for any bad decisions in there. Not that he has ever run away from decisions, but he no doubt some pretty close and even personal connections to many in that group.

He may also see possible openings in New York and Los Angeles as interesting landing spots should he be able to work it out so that his time with the Cubs end this year rather than next when those jobs would probably be filled long term. Regardless of the possible outcomes, all good things must come to an end; that means that whether it’s this offseason or next, Theo Epstein will almost definitely not be with the Cubs to open another window of contention. And, despite the naysayers, haters, and those critical of his job the last few years, that’s a damn shame.

Just as last year was the end of an era of greatness with former manager Joe Maddon, time is running out on the architect of this era of Cubs baseball. Time will assuredly be more kind to both when we look back on them in a decade or two without the sting of heartbreak or disappointment to cloud our judgment.