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Come Fan with UsMonday, June 29, 2026

Rumor: Theo Epstein Leaving Red Sox For Cubs

According to Joel Sherman, the word around baseball is that Red Sox GM Theo Epstein will leave the Sox to run the Cubs this winter. Would the Boston native even consider such a move? And if so, why?

What do you think? Is this just a terribly irresponsible rumor? Or the precursor for a Beantown bombshell?

I am shocked, but in last 36 hrs every exec talk to says believe #Redsox will give permssion and Theo will go to #Cubs to be GM
Oct 01 via TweetDeckFavoriteRetweetReply

This qualifies as a solid rumor, right? Granted, we don’t know if “every exec talk to” means eight general managers, or two Assistants to the Traveling Secretaries and one Administrative Aide, Minor League Operations.

But in my mind, anyway, Sherman’s not the rumor-mongerer some of his more nationally known colleagues are. I’m not saying this single tweet is the same as a press conference. But whereas yesterday I would have estimated the chance of Theo Epstein leaving the Red Sox as less than five percent, today I would estimate that chance as less than 50 percent but greater than 10 percent.

Why would Epstein leave?

Remember, he’s almost left before. Six years ago, Epstein exited the Red Sox for roughly a month before returning to the fold. Perhaps that was merely a negotiating ploy -- he presumably did well, financially -- but the relationship between Epstein and his bosses has not always been 100-percent highly functional.

I don’t know Theo Epstein anything like well enough to read his mind, but it’s certainly possible that he’s simply ready for a change. I’ve had two great jobs in my life -- before this one, I mean -- but at some point it’s just time to try something different. And what else, really, is there left for Theo Epstein in Boston?

Win a World Series? He’s done that.

Win another World Series? Done that, too.

Which isn’t to suggest that winning a third World Series wouldn’t be wonderful, too.

But what about winning a World Series in Chicago? Couldn’t that be even more wonderful?

Which achievement would be more notable: Winning three World Series with the Red Sox, or ending eternal runs of failure in both Boston and Chicago? If Epstein were to win a World Series with the Cubs, he would become the second-most famous baseball executive in major-league history, behind only Branch Rickey, and without a doubt would wind up with a plaque in Cooperstown.

All of this is rank speculation, of course. But as John Henry once told me, “Life is too dynamic to remain static.”

I don't expect Theo Epstein to work for the Boston Red Sox forever. And maybe the less-than-forever is coming a bit sooner than we figured.

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