The Chicago Cubs came into this past offseason knowing that they needed to shore up their bullpen, and Jed Hoyer was willing to swing big to do it. In late January, the team acquired veteran righty Ryan Pressly from the Houston Astros, giving up relief prospect Juan Bello and agreeing to take on $8.5 million of the $14 million Pressly would be owed for the 2025 season — hardly an insignificant cost, considering the budget that owner Tom Ricketts had president Jed Hoyer operating under.
It's safe to say that this isn't what Chicago had in mind. Flash forward to late May: Pressly's ERA stands at an unsightly 5.71, the result of a disastrous eight-run outing against the San Francisco Giants that was so ugly Craig Counsell hasn't let him anywhere near the ninth inning since. It's easy to point to that one (very, very) bad night as an outlier; Pressly has allowed just three earned runs across his other 18 appearances, after all. But there are plenty of other warning signs suggesting that the 36-year-old isn't the high-leverage arm the Cubs thought they were getting — and that's a huge deal, considering what the team gave up to acquire him.
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Cubs' bet on Ryan Pressly looks costly in hindsight
Ricketts has made it very clear that, despite sitting on a gold mine on the North Side of Chicago, his Cubs are never going to spend in the same stratosphere as the Los Angeles Dodgers, New York Mets or New York Yankees. That put meaningful restrictions on the Cubs' offseason; every dollar Hoyer spent counted, and committing even $8.5 million to Pressly meant those $8.5 million couldn't be used elsewhere.
Chicago decided that Pressly was worth it, that he was the piece that would finally stabilize a bullpen that's been far too in flux in recent years. Instead, he's fallen flat, and it's much more than just one bad outing: Pressly's whiff and K rates have cratered this season, and his walk rate his spiked. He's not throwing as hard, and he's not missing nearly as many bats — you know, the things you're looking for from your highest-leverage arms.
The Cubs have made due without Pressly in the closer's role, largely thanks to the efforts of Porter Hodge (now on the IL), Brad Keller and Danny Palencia. But even if Craig Counsell can in fact cobble together an above-average bullpen with spare parts Chicago finds lying around, it still won't erase the opportunity cost the Pressly deal incurred, and just how much it hurts that one of the team's most meaningful offseason investments hasn't been nearly what they'd hoped.