3 Jed Hoyer moves that quietly wrecked the Cubs' playoff run

If the Chicago Cubs' playoff run proved one thing, it's that there were several Jed Hoyer decisions that came back to bite the team when it mattered the most. Above all else, that was the reason why it felt rushed when the Cubs announced that Hoyer had signed a multi-year extension the week of the MLB trade deadline. The goal of the 2025 season hadn't been accomplished yet, while the team did outperform their projections, it felt like Hoyer was the center of the Cubs' failures in October.

In fact, there are several moves that are directly tied to what wrecked the Cubs' playoff run. Not that it would have changed Hoyer's fate, as making the playoffs seemed to be the ultimatum that was set at the start of the season, but keeping these receipts is needed to see if the Cubs' President of Baseball Operations will ever learn from his mistakes.

2025 was a polarizing season for Jed Hoyer and some mistakes were made

Trading for Michael Soroka at the MLB trade deadline

Many have been quick to point out that there were no controllable starting pitchers moved at the deadline as a way to defend what Hoyer did at the deadline. That is certainly true, but it feels like a hindsight way of moving the goalposts. The Cubs needed a starting pitcher with playoff experience for THIS SEASON, so it feels lazy to give Hoyer a pass because names such as Joe Ryan, MacKenzie Gore, Sandy Alcantara, and Edward Cabrera weren't moved. Shane Bieber was moved at the trade deadline and had a 3.57 ERA in 7 starts with the Toronto Blue Jays.

Trading for Ryan Pressly to solve their need for a closer

For two consecutive years, Jed Hoyer targeted a Houston Astros' relief pitcher who had signs of regression littered across their final season with the Astros. Pressly was the latest example of that, and it should be the last time. There will be plenty of turnover in the Cubs' bullpen this offseason, and Hoyer shouldn't overthink it: don't target an aging veteran who is in need of fixing.

Not addressing the need for a third baseman

Matt Shaw had flashed signs of being the long-term option for the Cubs at third base, but the playoffs proved that the team may have been a season too early in handing him the job. Something they may have been aware of when they were targeting Alex Bregman at the end of the offseason. They turned down the Red Sox, who tried to get the Cubs involved in the Rafael Devers trade, and already came away from the deadline with a utility player in Willi Castro. Shaw's lifeless offensive approach in the playoffs certainly exposed that the Cubs needed an experienced third baseman in a season where they pushed their chips to the middle of the table.