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Come Fan with UsMonday, June 22, 2026

If Theo Epstein Leaps, He’ll Only Be Human

As much as everyone might want Theo Epstein to stay in Boston, his head or his heart might be ready for a change. And running the Chicago Cubs would certainly be a change.

Theo Epstein is going to run the Chicago Cubs? This is really happening?

Maybe. Here’s the beginning and the end of Peter Abraham’s late-Tuesday report (and you just have to hope he’s getting at least a few hours of sleep every night while everything’s going down) ...

Major league sources said tonight that no deal is in place for Theo Epstein to join the Chicago Cubs in an upper management capacity. But a resolution is expected in the coming days.

Epstein is weighing the decision and is not necessarily a lock to leave the Red Sox after nine seasons. But his interest in the Cubs has progressed to a point where the expectation is that he will leave.

--snip--

The Herald reported tonight that Epstein is on the cusp of leaving for the Cubs. But along with the Globe, ESPN and Comcast Sports New England are reporting that is not quite the case yet.

Well, that depends on how one defines cusp, right? If Theo Epstein is 75 percent sure that he’s leaving the Red Sox, is that cuspy? What about 90 percent? The definition of cusp, in this case, is up to the writers and their editors, because nobody can really know what’s happening inside Theo Epstein’s head.

Here’s what I think, though ... I think if Epstein leaves the Red Sox, it will be for more money, and for the chance to make moves without checking first with Larry Lucchino, and for the chance to escape the crushing pressure of the Everestian expectations that he, of course, has helped create.

People who think Theo Epstein can’t leave are projecting ... He’s making good money, he’s guiding his favorite team in his hometown ... How could anyone leave that situation? If I were him, I certainly wouldn’t leave.

Except you’re not him. And if you were him, you might be ready for a new challenge with a new team in a new town.

I’m not saying he’s going to Chicago. I don’t have any idea. Maybe there are some magic words and John Henry knows what they are. I’m just saying that if Theo Epstein leaves Boston and you’re really surprised, you might want to consider brushing up on your human nature. Because they’re absolutely nothing about this situation that’s not absolutely human.

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