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Come Fan with UsWednesday, June 24, 2026

Theo Epstein is going to get paid

Thursday’s Say Hey, Baseball includes Theo Epstein’s looming extension, David Freese’s poor timing on free agency and criticism of the Pablo Sandoval fat-shamers.

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Listen, we know it’s tough to catch up on everything happening in the baseball world each morning. There are all kinds of stories, rumors, game coverage and Vines of dudes getting hit in the beans every day. Trying to find all of it while on your way to work or sitting at your desk just isn’t easy. It’s okay, though, we’re going to do the heavy lifting for you each morning, and find the things you need to see from within the SB Nation baseball network, as well as from elsewhere. Please hold your applause until the end, or at least until after you subscribe to the newsletter.

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When Theo Epstein became the Cubs’ president of baseball operations, he received a contract that general managers could only dream of. Epstein joined up with Chicago on a five-year, $18 million deal, but in the four years since signing it, his salary has been eclipsed -- most notably, by his former AL East rival, Andrew Friedman, who left the Rays for the Dodgers on a five-year, $35 million deal last offseason. If you’re a Cubs fan, don’t worry: owner Tom Ricketts plans to make Epstein the highest paid executive in the game on his next contract. If you’re not a Cubs fan, well, sorry. Theo probably isn’t going anywhere just yet.

Epstein has revamped the Cubs since taking over baseball ops. He pried Jed Hoyer and Jason McLeod from the Padres -- both of whom worked under Epstein with the Red Sox -- to bolster the front office, then, over the years, improved the farm system with trades, signings and drafting until it bore the fruits that helped them earn entry into the 2015 National League Championship Series. Now that the kids are here, the Cubs have opened their wallets back up, too. After adding Jason Heyward, John Lackey and Ben Zobrist on top of all the inexpensive youth, the Cubs have a club-record $145 million payroll.

Whether Epstein becomes the man who brought championships back to both the Red Sox and the Cubs remains to be seen, but the latter’s chances have improved significantly since his arrival -- of course he deserves to be the highest-paid executive in the game. Luckily for the Cubs and their fans, their owner realizes as much.

Now, we just need to convince him to enter the press conference announcing his eventual extension like this.

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