Cubs Made Major Mistake This Offseason By Trading For Overpaid Relief Pitcher

The Chicago Cubs made a major mistake this winter that is costing them.

Jul 28, 2025; Milwaukee, Wisconsin, USA; Chicago Cubs manager Craig Counsell looks on during batting practice before game against the Milwaukee Brewers at American Family Field. | Benny Sieu-Imagn Images

With the Chicago Cubs continuing to play mediocre baseball, the team has gone quite flat of late.

It has not been a great stretch for the Cubs, who have seen the Milwaukee Brewers blow by them and take complete control of the National League Central. While a majority of that is because of how well they are doing, some of it has to do with Chicago taking a step back as well.

Unfortunately, their offense has been a mess of late. Their two stars aren’t performing like it at the plate anymore, with both Pete Crow-Armstrong and Kyle Tucker in extended slumps.

David Banks-Imagn Images

As the team hopes to be playing meaningful baseball in October, they will be relying on their batting order to get back to what they did in the first half of the year. Fortunately, the team does have an improved bullpen compared to recent campaigns, but they will be without one player who figured to be a staple for the unit by their own choice.

Kerry Miller of Bleacher Report recently wrote about former Cubs closer Ryan Pressly being one of the most overpaid players in baseball this season.

“At least the Astros retained one-third of this, so the Cubs only set $11 million ablaze here.”

During the offseason, Chicago was focused on improving a bullpen that, in 2024, held the team back. They were able to accomplish that for the most part with the unit being better in 2025, but that had nothing to do with the biggest splash that they made to improve.

Was Trading for Pressly a Mistake?

Jun 29, 2025; Houston, Texas, USA; Chicago Cubs pitcher Ryan Pressly (55) delivers a pitch against the Houston Astros during the seventh inning at Daikin Park. | Erik Williams-Imagn Images

After trading for Kyle Tucker from the Houston Astros, the Cubs pulled off another deal for Ryan Pressly. This was largely a cap dump of a trade by the Astros, but that turned out to be a wise decision.

Houston had to eat some of his $16 million contract, but Chicago was on the hook for the rest. With the Cubs in 2025 before being let go, Pressly totaled a 4.35 ERA and a 2-3 record. While that doesn’t scream completely awful, he seemingly fell apart at the end of July, resulting in the decision.

The 36-year-old has had a great career in the Majors, but his performance based on his contract this year was extremely poor. Chicago added a couple of new arms at the deadline to hopefully help solidify the unit, but Pressly not being what they were expecting was a significant blow this campaign.