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Come Fan with UsMonday, June 22, 2026

Theo Epstein, Cubs Agree To Five-Year Contract

As the Theo Epstein saga continues, Jon Heyman floated an interesting tweet early Wednesday:

can confirm epstein has deal in place with #cubs. believed to be worth $15M over 3 yrs plus $3.5M “transfer buyout”

Confirmation: good!

Three years: what?

Indeed, Heyman’s three-year report was different from all the other reports, and it seems likely Heyman just made a typo, because according to ESPN:

Theo Epstein and the Chicago Cubs have agreed to a five-year, nearly $20 million deal for him to join the team, sources told ESPN The Magazine's Buster Olney Wednesday.

Everybody else is saying five years. Theo Epstein’s new contract with the Chicago Cubs will be worth $15 million over five years, with an additional $3.5 million conclusion bonus. I’m not exactly sure what “conclusion bonus” means and I don’t think I’ve heard that term before, but does it really matter? It’s a bonus. It’s money. It’s money that Theo Epstein will receive from the Cubs.

It would appear that one of the only remaining hurdles between now and everything being official is the matter of compensation, given that the Cubs are hiring Epstein while Epstein was still under contract with the Red Sox. For this, we go back to the Heyman well:

there is a bit of discussion whether #cubs send cash or minor leaguers to #redsox for theo. so far boston prefers the $.

Maybe that seems underwhelming to you. The Red Sox aren't going to be getting anyone from off of the Cubs' major league roster. But Ozzie Guillen set the precedent, as the White Sox received two middling prospects from the Marlins in return, and the Red Sox were never going to get a top-of-the-line talent for a departing GM. They'll get C-level talent, or they'll get cash, and cash is pretty neat. You can use cash to do just about anything!

It’s just a matter of time, now. Ben Cherington is considered the heavy favorite to assume Epstein’s position in Boston.

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