Cubs Enter Offseason Facing Pitching, Roster Questions

The Cubs face a major offseason challenge after finishing 14 games behind the Brewers, and an early 2027 ranking placed Chicago 17th amid questions about how it will replace departing starters and outfielders. Milwaukee’s success—built on pitching depth and the ability to replace traded aces—has sharpened criticism of Chicago’s reliance on fewer high-impact moves; the Cubs allowed more home runs and had a weaker bullpen than the Brewers. Chicago’s infield appears comparatively stable, but catcher is uncertain: prospect Owen Ayers could join Miguel Amaya in place of free-agent Carson Kelly. The Cubs’ decision to pass on Dylan Cease and bet on Edward Cabrera also drew scrutiny after Cabrera was limited by injuries while Cease had a standout season, prompting calls for the team to be more willing to pursue long-term deals for top pitchers.