Cubs' Ryan Pressly trade looks way too much like one of Jed Hoyer's biggest blunders

After several days of waiting, the Chicago Cubs finally found some much-needed bullpen help on Sunday evening, convincing Houston Astros righty Ryan Pressly to waive his no-trade clause and agree to a deal sending him to the North Side in exchange for Minor League righty Juan Bello.

This was arguably the biggest need left for Jed Hoyer to fill this offseason. Chicago's bullpen was bumpy last season, and the team's high-leverage hierarchy was set to feature Nate Pearson, Julian Merryweather and not a whole lot else. The Cubs were reportedly in on star lefty Tanner Scott, but once the Los Angeles Dodgers (surprise, surprise) won that bidding war, there weren't many options remaining with the sort of pedigree that Pressly brings to the table. On the surface, this makes all the sense in the world.

That doesn't mean there aren't some reasons for Cubs fans to feel a little nervous, though. For starters, Pressly just turned 36, and while he was an integral part of Houston's golden age, he's began to show signs of age of late — punctuated by a 2024 campaign in which he missed fewer bats than ever and posted the highest WHIP of any 162-game season in his career. And as if that weren't enough, the last time Chicago turned to Houston for a new closer, things didn't work out so well.

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Ryan Pressly trade may have Cubs fans remembering Hector Neris disaster

Cubs fans, we apologize in advance for invoking Neris' name. One of the best relievers in the league in 2023, Chicago signed him to a one-year, $9 million deal back in February to be an important part of its late-inning formula. Unfortunately, everything went pear-shaped: Neris got knocked around over the first half of 2024, posting a 3.89 ERA with several ninth-inning meltdowns before the Cubs eventually cut their losses and released him in August.

Neris and Pressly aren't the same pitcher; they have very different repertoires, for starters. But Neris was an aging righty with a solid track record that masked signs of regression, regression that arrived in force with a new team. All of which ... well, sounds a lot like Pressly, who by the end of the 2024 season had pitched himself down Houston's pecking order. In his one postseason appearance, he was the goat of the Astros' season-ending loss to the Detroit Tigers in Game 2 of the AL Wild Card Series, giving up three runs on two hits in a walk in just 0.2 innings of work.

Maybe the Cubs have identified something that they think they can fix in Pressly's game, and he undoubtedly brings late- and big-game experience to the table that Chicago otherwise lacked. This feels like paying for a name brand that's a little past its sell-by date, though: Pressly's velo and contact metrics are all trending in the wrong direction, and those trends don't usually reverse at his age. Hoyer may have just made the same mistake twice, and it might cost the Cubs late in games in 2025.