Chicago Cubs: Will Theo Epstein stick around after his deal expires?

With less than two years left on his current contract, it’s time to consider whether or not Theo Epstein will stick with the Chicago Cubs long-term.

There’s little left for president of baseball operations Theo Epstein to accomplish at the helm of the Chicago Cubs organization. He turned around a club laden with overpriced, aging veterans and no impact prospects in the system, guiding them to the most successful stretch in more than a century – including that long-coveted World Series title.

Now, Epstein – along with the rest of baseball – is coming to grips with the ongoing COVID-19 pandemic and its impact on the sport, a challenge no one could have possibly envisioned.

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"“And, I think at the end of the day, all of us have a moment before you put your head on a pillow where you realize just how much has changed, and just what we’re all dealing with, and the potential consequences for society as a whole if we don’t pull together and handle this in the best possible way,” he told MLB.com. “We’re all in this together.”"

With players now either at home or working out on their own at or near the team’s complex in Mesa, Arizona, there’s little else Epstein can do at this point in time. Now, it’s a matter of taking precautionary measures and waiting it out the best we can.

But at some point, there will be baseball again. When America’s pastime returns, it seems likely Epstein will have under a year-and-a-half remaining on his current deal as the head of the Cubs’ baseball operations department.

He’s got his handpicked manager and heir to Joe Maddon in David Ross. The core he largely drafted and signed remains intact, despite rampant rumors and speculation in recent months. Does Epstein and this group have enough left for one more improbable run deep into the postseason?

Perhaps.

Regardless of how this or next year’s iteration of the Chicago Cubs perform, though, Epstein may simply decide it’s time for a new challenge. He’s ended not one, but two, lengthy championship droughts, stomping out curses in both Boston and Chicago. He’s laid the groundwork for long-term success on the North Side, either for himself or his successor. Why stick around?

Epstein remained mum on his future prospects during the offseason, refusing to weigh in on either side of the debate.

"“I’m just thinking about the Cubs and what’s in our best interest,” Epstein said. “What’s in our best long-term interest. What’s important to Tom and his family. That’s a really sustained period of winning. We’ve pulled that off so far, but I don’t think anyone wants to see it abruptly end at a certain point. It’s important to take a long view regardless of (my own status).”"

There’s no telling which course of action Epstein will pursue when his deal concludes. Will his heir apparent, Jed Hoyer, take the reins? That definitely seems like a possibility. Then again, given the losses the front office has suffered of late, with multiple other clubs prying away top talent like Scott Harris heading to San Francisco, maybe Epstein opts to stick around for a few more years, ensuring an even longer run of success.

One thing’s for sure. Epstein is likely destined for Cooperstown. If he can bring another ring to the Friendly Confines before his tenure draws to a close, you might as well start casting his plaque – because it’d be a done deal.

With less than two years left on his current contract, it’s time to consider whether or not Theo Epstein will stick with the Chicago Cubs long-term.

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