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Come Fan with UsWednesday, June 24, 2026

Cubs, Theo Epstein ‘close’ to an extension

Tuesday’s Say Hey, Baseball includes an impending agreement, the Orioles’ switch to cake and the top 175 players under 25.

Chicago Cubs v Los Angeles Angels of Anaheim
Chicago Cubs v Los Angeles Angels of Anaheim
Photo by Sean M. Haffey/Getty Images

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Barring some unforeseen disaster, the Cubs and Theo Epstein are going to agree to an extension. We knew this to be the case even before a report came in saying the two sides have made progress and are “close,” but this most recent update serves as a reminder: Theo isn’t going anywhere. He’s built this Cubs’ team that very well might be the World Series favorite despite their being, you know, a Cubs team. He might not stick around forever -- he has already left one organization he had reshaped when a new opportunity came up -- but he won’t be leaving Chicago anytime soon.

The plan as of February was to make Epstein the highest-paid executive in the game, and if Cubs’ owner Tom Ricketts was saying as much publicly then it’s likely what’s being said privately, too. When Epstein took over the Cubs following the 2011 season, the team had a bloated payroll and few prospects worth noticing. They had finished in fifth place in the Central the two previous seasons, and would finish in fifth the next three as well as Theo and Co. reshaped the roster and the farm system one deal and signing at a time. After winning 97 games in 2015, the Cubs added Jason Heyward, John Lackey and Ben Zobrist, so it’s no wonder people are starting to believe they can actually win it all.

Whether the Cubs actually do or not, though, Epstein has put them in a position to succeed -- a better position than they’ve been in over the last 100-plus years, even -- and deserves to stick around for a chance to go all the way with this team.

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