3 offseason decisions that could end up costing the Cubs in the 2025 playoffs

The Chicago Cubs almost certainly will be playing games in October, and that will mark a return to the playoffs for the first time since 2020. The Cubs once appeared to be one of the best teams in Major League Baseball, but as the end of the regular season approaches, they seem to be walking into the playoffs backward.

Over the last two months, the power that lifted the Cubs' offense during the first two months of the season has disappeared. Kyle Tucker has been in-and-out of the Cubs' lineup, Pete Crow-Armstrong has looked lost, and Seiya Suzuki has been a non-factor as the team's designated hitter. Add in some Daniel Palencia regression at the backend of the bullpen, and it's hard to view the Cubs as a legitimate World Series' contender.

It's even possible that the Cubs don't even make it out of the National League Wild Card round. The reasons for the potential shortcoming can be tied back to decisions made in the offseason.

1. Expecting Ryan Pressly to be the answer as the team's closer

To Jed Hoyer's credit, each offseason, he does manage to find some diamonds in the rough when it comes to the construction of the bullpen. Brad Keller and Caleb Thielbar have been excellent examples of that this season. However, when it comes to the big swing, finding a closer, Hoyer has swung-and-missed far too many times.

Trading for Ryan Pressly was Hoyer's latest whiff. Pressly was awful before being released by the Cubs after the traded deadline. With Daniel Palencia's availability suddenly in question, the Cubs have a question mark at closer. Not ideal timing with the playoffs approaching.

2. Jed Hoyer's construction of the bench

One area that Jed Hoyer has failed at year-over-year is constructing a bench that is capable of finding success. The Cubs entered the season with a bench that consisted of Vidal Brujan, Jon Berti, and Justin Turner. There were far too many question marks about that collection of misfits to suggest the Cubs were serious about contending. With the core of the Cubs' offense struggling, the lack of sufficient bench options is exposing Hoyer once again.

3. Avoiding the addition of a top-of-the-rotation starting pitcher

The stated goal of the Cubs entering last offseason was to add a top-of-the-rotation starting pitcher. They lucked into the signing of Matthew Boyd, who has had an All-Star campaign during his first year in Chicago, but regression seems to be lingering in the background of his second-half outings. For a Cubs' rotation that has been without Justin Steele for most of the season, it feels like that reality could be exposed if they advance past the National League Wild Card round.

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