No matter how the 2026 season finishes, Jed Hoyer is going to have a long look in the mirror. The Cubs are still staring at the same gap to the Milwaukee Brewers, and once again the division has gone the Brewers’ way.
That leaves Chicago in a familiar spot: close enough to feel the pressure, not close enough to celebrate. The Cubs came into the offseason acting like a team ready to push through that wall. Instead, the moves that were supposed to move the needle have become part of the problem.
The front office swung big by trading Owen Caissie for Edward Cabrera and then handing Alex Bregman a five-year, $175 million deal. Those were the kinds of aggressive decisions that signal urgency.
They were also made with the clear aim of chasing a division title in 2026. That goal has not been met, and the reasons are starting to stand out.
One of the biggest issues has been the bullpen approach. The Cubs have committed a total of $20.5 million to Phil Maton and Hunter Harvey over the next two years, and that investment has not given them the kind of reliable late-game presence they wanted.
Maton’s collapse this season may have been hard to foresee, but banking on Harvey to stay healthy was always a risky bet. The recent struggles of Jacob Webb have only made that reality louder.
The same theme showed up again when the Cubs brought back Caleb Thielbar. Last season, Thielbar worked as a nice value play.
This year, the return has gone the other way. Chicago paid $4.5 million to run it back, and Thielbar entered Wednesday with a 5.00 ERA.
Put that together with Maton and Harvey, and the bullpen reset Hoyer tried to engineer has fallen flat.
The rotation gamble hasn’t paid off either. Cabrera arrived with the kind of upside that can tempt a front office into believing it found a breakout starter.
He was still unfinished with the Miami Marlins, but there were signs he could grow into a top-of-the-rotation arm. The Cubs needed exactly that kind of pitcher last offseason, especially after bowing out of the Dylan Cease chase once the price climbed to $200 million.
Cease was the more expensive path, but the safer one too, even if it meant stretching beyond the Cubs’ usual financial comfort zone.
That’s really the thread running through all of this. Emilio Pagan, Luke Weaver, Devin Williams, and Pete Fairbanks were all names the Cubs had interest in last offseason as established closers, but for one reason or another they ended up out of reach. In most cases, the bidding climbed past Hoyer’s preferred spending range for the bullpen.
At some point, that has to change. If this season has shown anything, it’s that the Cubs may need to break their own rule.
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Shaws flexibility gives the Cubs options, but it also puts him in the middle of a tougher conversation about value. He could be in line to compete for a starting outfield job, or he could become the kind of trade piece that helps Chicago chase the elite starting pitching it still needs, even though no specific deal has been lined up. [Read more 🡒]