4 fateful Cubs decisions that are looming very large as the 2026 season winds down

Regardless of how the Chicago Cubs' 2026 season ends, there's going to be a need for some reflection from Jed Hoyer in terms of the gap that remains between the Cubs and Milwaukee Brewers.

The Brewers once again ran away with the National League Central crown this season, and for the Cubs, it's been a feeling of if not now, when?

Here is where Jed Hoyer and the Cubs went wrong this season

The Cubs were aggressive during the offseason. They traded their top prospect in Owen Caissie for Edward Cabrera, and also signed Alex Bregman to a five-year deal worth $175 million. The Cubs took bold steps to win a division title in 2026, and in that sense, it has been a failure. There are clear reasons why.

Signing Phil Maton and Hunter Harvey

The recent struggles of Jacob Webb has once again exposed the reality that the Cubs don't like to spend top dollar for an established closer. Here's the problem with that, they are spending a total of $20.5 million on Phil Maton and Hunter Harvey over the next two years. While Maton's spiral this season would have been hard to predict, gambling on Harvey to stay healthy was never going to play to the Cubs' favor.

Trading for Edward Cabrera

It was easy to be talked into the idea of the Cubs trading for Edward Cabrera last offseason. He was an unfinished product with the Miami Marlins, but flashed signs of becoming a top-of-the-rotation starting pitcher. That hasn't been the case since his arrival to the Cubs. The Cubs needed to add a top-of-the-rotation arm last offseason, and they bowed out of the bidding for Dylan Cease once it reached $200 million. It's a lot of money, but Cease was the better gamble, even if it meant the Cubs stepping out of the financial comfort zone.

Re-signing Caleb Thielbar

Caleb Thielbar was a success story for the Cubs last season, but it felt like they were playing with house money. Instead, the Cubs tried the experiment again this season, and it hasn't worked. The Cubs coughed up $4.5 million to bring back Thielbar, and he entered Wednesday with an ERA of 5.00. Again, combined with the money spent on Maton and Harvey, the way Hoyer turned over the bullpen from last year has proven to be a failure.

Avoiding established closers

Emilio Pagan, Luke Weaver, Devin Williams, and Pete Fairbanks were among the established closers the Cubs had interest in last offseason. For one reason or another, the Cubs fell out of the bidding. In most cases, it was due to the the bidding extending beyond Hoyer's comfort level for spending on the bullpen. There needs to be an exception to every rule and if this season has proved one thing, it's time for the Cubs to make this exception.

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