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Cubs Enter Offseason Facing Pitching, Roster Questions

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Cubs Enter Offseason Facing Pitching, Roster Questions

11 sourcesUpdated Nov 1, 20261 min read

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Cubs Enter Offseason Facing Pitching, Roster Questions — © IJR

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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.

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Astros Reportedly Favor Brewers’ Kleine for GM

The Houston Astros have identified Milwaukee Brewers assistant general manager Matt Kleine as their leading candidate to replace Dana Brown, though no deal has been finalized. Kleine’s nearly two decades in Milwaukee, where he worked on roster construction and helped build a competitive team without a top-tier payroll, fits owner Jim Crane’s stated interest in that model.

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Wisconsin Family's World Series Sausage Race Goes Viral

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Last updatedNov 1, 2026

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Broke Chicago Sun-Times · Oct 30, 10:00 AM ETLeft within the hour11 sources +2d on

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Brewers fans celebrated their team’s World Series Game 3 win, while an Onalaska family’s homemade version of the baseball sausage race drew laughs and went viral on TikTok.

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Imai Reportedly Opts Into Astros’ $18 Million Option

Tatsuya Imai will remain with the Houston Astros in 2027, declining his contract’s opt-out after a difficult first MLB season. He posted a 4.93 ERA in 76⅔ innings and will have another chance to opt out after 2027.

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