Let's hope Jed Hoyer has done his fair share of lateral dumbbell raises.

The Chicago Cubs' lead executive came into the winter with plenty of weight on his shoulders. The organization faced an ugly end to a 2026 season that was shrouded in high expectations. While their offense crumbled in the end with only one run scored during their swift two-game Wild Card series, it was their pitching that started to sink the ship well before that.

Yes, injuries to both the bullpen and rotation played a critical role. But the Cubs simply didn't execute on the mound, which is exactly why they were left searching for answers midway through the season. They made two aggressive trades for veteran arms in Kevin Gausman and Clay Holmes. Nevertheless, neither had enough time to get truly comfortable, and they are now both sifting through offers on the free agent market.

Indeed, Hoyer is tasked with revamping his starting rotation this offseason. Holmes and Gausman join Shota Imanaga, Matthew Boyd, David Peterson, and Colin Rea as free agents. Javier Assad, Cade Horton, and Ben Brown are the only controlled arms with meaningful starting experience left in the mix.

Decent options? You could say that, but there is no ignoring that both Horton and Brown are true wild cards at the moment. The former is working his way back from Tommy John Surgery, while a recent update on the latter is far from encouraging.

What's the Latest on Ben Brown?

According to The Athletic's Sahadev Sharma, Ben Brown's health remains up in the air as the offseason is kicked into full swing.

While addressing the Cubs' free agency plans, Sharma referred to Brown as the "biggest question mark." The 27-year-old still isn't throwing and could end up needing surgery. The news comes after Brown was shut down midway through the season due to a neck injury. It was the same issue that forced him to miss time in 2024.

The fact that it was a recurring issue for Brown already raised red flags. But now it's been over four months and Brown seemingly still hasn't advanced in his recovery. It's very troublesome news for a Cubs team that already has so many obvious holes to fill in the pitching department.

Brown finally broke onto the scene early in 2026. The addition of a sinker seemed to unlock something new for Brown, who was pairing it with his typical mid-to-high 90s fastball and devastating curveball. While he was still hit hard at times, this was far less of a problem over his 20 appearances, which included eight starts. Overall, Brown has an impressive 1.85 ERA in 68.0 innings of action.

Brown has experience both in the bullpen and as a starter, but the hope has always been that he could turn into a third or fourth guy in a rotation. He finally showed signs of taking that step this season, which was undeniably exciting with the future of Chicago's rotation so up in the air. However, whether they will ever truly have an opportunity to capitalize on that remains to be seen. And, knowing that, they will have to be even more aggressive in their pursuit of long-term starters this offseason.

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