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Come Fan with UsMonday, June 22, 2026

Theo Epstein Compensation Talks Between Cubs, Red Sox Hit Snag

Maybe “snag” isn’t the best word. “Snag” can be interpreted as “impasse”, and this situation isn’t nearly that severe. But here’s Alex Speier, on John Dennis’ report:

WEEI's John Dennis is reporting that the initial day of negotiations between the Red Sox and Cubs regarding the compensation that Chicago would send to the Sox in order to hire GM Theo Epstein revealed a gap between the sides.

Reports came out Wednesday that Theo Epstein and the Cubs had agreed to a five-year contract. Given that Epstein is still technically under contract with the Red Sox, that means the Red Sox are entitled to some form of compensation. The Cubs are aware of this, and they’re trying to hash it out, but perhaps unsurprisingly, the Cubs and the Red Sox have different values in mind.

According to Dennis, the Red Sox are looking for prospects. The Cubs, meanwhile, would prefer to send cash. Cash, after all, can’t come back to hurt you by developing into a big leaguer and batting .300 with 30 home runs. Not directly. It can most definitely do that indirectly. Anyway.

As Dennis notes, this was the first day of talks. It shouldn’t come as a shock that the Cubs and Red Sox didn’t reach an immediate agreement. It could take a little while before a compromise is reached, or somebody caves.

But eventually, barring a complete surprise, this’ll get done. The Cubs will send something or some things to the Red Sox, and Theo Epstein will officially take over as Chicago’s general manager. Right now it’s just about the little details, and the little details are unlikely to bring the whole thing down.

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