The Chicago Cubs did very little at the MLB trade deadline, a tale as old as time. Days after receiving a contract extension, team president Jed Hoyer sat on his hands as premium assets changed hands across the league. Nobody should be more upset about the Cubs' inactivity than Craig Counsell.
Chicago entered Thursday with a 63-45, a game behind the Milwaukee Brewers in the NL Central. That is the second-best record in MLB, which should've been all the incentive necessary for the Cubs to push their chips in. Want more incentive? Kyle Tucker is a free agent at season's end and his return is far from guaranteed. This might be Chicago's best chance to scale the mountain for a long time.
Hoyer didn't do nothing. He acquired Willi Castro from the Minnesota Twins. That's an upgrade at third base, although it's fair to wonder if it's enough of an upgrade to be worth stymieing the development of top prospect Matt Shaw. The Cubs also DFA'd Ryan Pressly to make room for new acquired reliever Taylor Rogers.
The Cubs DFA'd Ryan Pressly as a corresponding roster move for Taylor Rogers, who was acquired from the Pirates for High-A outfielder Ivan Brethowr.
— Patrick Mooney (@PJ_Mooney) July 31, 2025
That is simply not good enough for a team in the Cubs' position. Counsell ought to be seething.
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Cubs' lackluster trade deadline leaves them vulnerable in NL standings
The Cubs are going to make the playoffs and potentially go deep into October, but fans can't help but feel uncertain after such a quiet deadline. Other contenders in the National League were active. The Phillies acquired Jhoan Durán and Harrrison Bader. The Mets overhauled their bullpen with several big trades. The Padres dealt half their farm system away for several star upgrades because A.J. Preller is a certified sicko. And the Cubs did next to nothing.
Castro and Rogers are positive additions, don't get me wrong, but axing Pressly in the middle of a reasonably positive stretch and replacing the upstart Shaw with a serviceable veteran in Castro does not move the needle nearly enough. Not when other teams around them in the standings are cranking the needle as high as possible, with a purpose.
Craig Counsell left the Brewers for this?
Counsell left a perennially competitive Brewers team for more resources in Chicago — a bigger pond to play in. Milwaukee has often undermined its success with cheap deadline moves and a lack of aggressiveness in free agency. That roster is built more for the regular season than the postseason. It is what it is.
But the Brewers are, after all this time, still very competitive. Counsell has the Cubs moving in the right direction in his second campaign as manager, but Hoyer looks similarly reticent to go all-in. Milwaukee never makes a trade like the one Chicago made for Kyle Tucker last winter, but their unwillingness to stack big moves on top of that — and risk ending Tucker's tenure with a dud after just one season — is what makes this Cubs front office under Hoyer so frustrating. No team with Chicago's finances and market power should play it so safe.
Chicago's rotation desperately needed another top-shelf arm behind Matthew Boyd and Shōta Imanaga, but nope. The bullpen could've used a bit more juice than Rogers, but yeah, nope. Even the Castro trade feels like a letdown after Eugenio Suárez went to Seattle and Ryan McMahon went to New York. The Cubs could've done so much more, but missed the boat.