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It wasn't the MLB trade deadline Chicago Cubs fans were expecting, as the Cubs failed to land the top-of-the-rotation starting pitcher the team was seemingly desperately searching for. Instead, the Cubs made smaller moves--adding Michael Soroka, Andrew Kittredge, Willi Castro, and Taylor Rogers.
Specifically, adding two relief pitchers seemed to suggest that Ryan Pressly was likely going to be the odd man out in the Cubs' bullpen. The Cubs confirmed the move after the deadline on Thursday, announcing that Pressly was designated for assignment to make room for Rogers on the 40-man roster.
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
Cubs front office finally owns up to trade mistake
Specifically, it was the arrival of Kittredge that made Pressly's time with the Cubs feel all but over. Kittredge has the profile of a middle relief pitcher who thrives at missing bats. While Pressly opened the season as the Cubs' closer, struggles quickly led to his demotion. Now, with the dust settled from the trade deadline, Pressly is on his way out of the Cubs' organization.
Fittingly enough, Pressly's final outing with the Cubs was a brutal showing against the Milwaukee Brewers on Tuesday night. Pitching in back-to-back games, Pressly was tagged 4 runs on 1 hit while walking 2. The fateful pitch was a grand-slam ball he served up to Brewers' first baseman Andrew Vaughn.
Pressly's run with the Cubs ends with a 4.35 ERA, and he never quite looked comfortable in the Cubs' uniform. There were some concerns of regression when the Cubs traded for him over the offseason, but as they did with Hector Neris, they falsely thought their pitching infrastructure could squeeze out one more productive season from an aging veteran. Similarly, Neris was designated for assignment by the Cubs shortly after the trade deadline last season.
Given that the Cubs did not make a major addition to their starting rotation ahead of the deadline, bullpen stability will be something they lean on as they try to catch the Milwaukee Brewers in the National League Central.