Suffering through the first week of this four-month long offseason, the Chicago Cubs organization, got a stern lesson. Our feelings of jubilation, fist bumps, and blue towel-waving earlier this month swiftly transformed into longing for next year. Compound that with the cocktail of jealousy, despair and schadenfreude of watching the Dodgers sweep the Brewers in the NLCS, and you’ve got the start of one of the most uncomfortable offseasons in recent memory.
Craig Counsell and his Cubs aren’t the only eliminated squad back at the drawing board, figuring out a fresh blueprint for further playoff success. The San Diego Padres, the club Chicago ousted in the Wild Card round, are suddenly in need of a new skipper, as Mike Shildt abruptly announced his retirement this past week. Early speculation suggests that Cubs bench coach Ryan Flaherty could be a candidate, which would be a tough loss for the North Siders. That Craig Counsell has assembled such a formidable and even enviable staff, though, bodes well.
For the team to reach similar or greater heights in 2026, certain things must change on the field. They need a beefier, bolstered bullpen, capable of setting down opposing bats faster than a bleacher bum wolfs down helmet nachos. Enter, perhaps, Yankees free-agent hurler Devin Williams, once a standout for Counsell in Milwaukee. Williams, a former lockdown closer, is coming off his worst season by far, turning in a 4.79 ERA in Yankee pinstripes, but a reunion with his old skipper and a match with the Cubs’ solid pitching infrastructure could fix him.
Kevin Alcántara, “The Jaguar,” is one of the most intriguing prospects in the Cubs organization, and though sprinkled into the lineup sparingly toward the end of the season, he’s yet to show off his true potential. Though he played through it all season, Alcántara underwent surgery for a sports hernia that figures to alter his offseason regimen.
While the hot stove fires up, Jed Hoyer and the North Siders’ brass have much to do in maintaining the organization’s favorable position within the National League. That’s a big responsibility—staying at or near the top once you get there is difficult, and the Cubs have yet to show they can keep pace with the Brewers—but that’s the cost of high expectations. They have a tough needle to thread in the winter ahead; Hoyer is well aware of that. This time, at least, they have a foundation of success on which next season can build. rather than a hole out of which they must dig.