After two ugly losses ended their 2026 run, the Cubs are headed into an offseason that figures to keep Jed Hoyer busy from the jump. There are big calls coming on a long list of important players, and the winter could get messy fast.
But the biggest item on Chicago’s to-do list may not be the one fans are staring at first. ESPN’s Jesse Rogers says the Cubs’ main priority is not sorting out the outfield market around Seiya Suzuki and Ian Happ. It’s fixing the pitching staff.
“The Cubs need to rebuild their pitching staff, and that includes both their rotation and bullpen,” Rogers writes. “The good news is they can concentrate on that part of their team because they have enough position players to fill the void left by Happ and Suzuki, who are both likely to leave the team via free agency.”
That’s the pivot here: as painful as it would be to lose two popular stars, the Cubs appear better positioned to cover those bats than they are to patch together a staff that was a liability in 2026. Kevin Alcantara, Matt Shaw, and others give the organization some depth on the position-player side, which could let Chicago direct its energy toward the mound instead.
And the mound is where the problems stack up. Shota Imanaga, Kevin Gausman, Clay Holmes, and plenty of others are set to reach free agency after the 2026 season, leaving the Cubs staring at major turnover. At minimum, they need to fill three rotation spots, and maybe more depending on how they feel about Justin Steele and Cade Horton.
That leaves Chicago with a wide-open market to attack. Tarik Skubal, Michael King, Robbie Ray, Nick Pivetta, Casey Mize, Freddy Peralta, Tyler Mahle, Foster Griffin, Dustin May, Zac Gallen, Merrill Kelly, Sonny Gray, and others are all names that could be in play. Trade options such as Hunter Brown, Joe Ryan, and Sandy Alcantara are also out there.
So while the outfield losses would sting, the bigger reality is simpler: the Cubs have to rebuild the pitching side first. Rotation help and bullpen help aren’t luxuries this winter. They’re necessities.
In Other News...
Cubs May Regret How Much Jed Hoyer Paid For A Short-Term Push
The Cubs pushed hard at the deadline, and the cost of that urgency is already easy to see in the shape of the deal Jed Hoyer made. Chicago brought in Kevin Gausman and Ryan Zeferjahn to bolster the pitching staff, parting with a batch of prospects that included Brett Bateman, Ty Southisene, Moises Ballesteros and Mason McGwire in the process. It was the kind of move that can look bold in July and much tougher to judge once the season has had time to breathe.
Gausman gave the Cubs nine starts and finished with a 4.83 ERA before getting hurt late in the year, while Zeferjahn showed enough to keep some intrigue with a 4.50 ERA over 18 innings. The harder part for Chicago is looking back at what went out the door: Bateman has performed well with the Blue Jays, while Ballesteros has struggled since landing with the Angels. Those mixed returns only sharpen the question of whether the Cubs paid too much for a short-term push. [Read more 🡒]
Craig Counsell Is Safe But Cubs Changes May Be Coming Behind Him
Craig Counsells first three seasons in Chicago have been productive enough to keep the Cubs in the postseason mix, but not quite enough to quiet the larger questions around a club that expected more. The manager is still viewed as secure in his seat, even as the organization looks ahead to what comes next under a new front office regime.
Ryan Flahertys name is one to watch in that process, with the bench coach potentially in line for managerial chances elsewhere. Tommy Hottovys status is another point of interest, since the Cubs are also weighing ways to sharpen pitching development, and any staff turnover behind Counsell could become one of the first signs of how aggressively the club plans to adjust around him. [Read more 🡒]
Pete Crow-Armstrong Had A Brutal Take On Cubs Wild Card Exit
The Cubs Wild Card trip to San Diego ended with a familiar postseason problem, as the offense never really found a footing and the Padres completed the sweep. Pete Crow-Armstrong was at the center of that frustration, going 0-for-7 with four strikeouts and one walk, a line that underscored how little Chicago was able to sustain at the plate in the series.
Crow-Armstrong did not soften the evaluation afterward, acknowledging that he did not give the Cubs enough and saying he needs to be better in the games that matter most. For a young player who figures to remain a big part of Chicagos future, the blunt self-assessment only adds to the sting of a short October that ended before it ever had a chance to settle in. [Read more 🡒]