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Jacob Webb has a club option for 2027 and the Chicago Cubs won't have to think that hard about picking it up despite his late-season struggles.
Seiya Suzuki finally found the defensive brilliance to match his offensive consistency in 2026. Can the Cubs really afford to let such a well-rounded player get away?
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With a weak starting pitching market crowded with suitors, the Chicago Cubs will be forced to bet heavily on a return to form from Edward Cabrera in 2027.
Jed Hoyer and the Chicago Cubs must explore every potential avenue of addressing the pitching staff this winter, including unexpected trade possibilities.
Chicago Cubs pitching coach Tommy Hottovy is expected to return for the 2027 season, but that doesn't change what needs to happen.
The Chicago Cubs are anchored by likely NL MVP Pete Crow-Armstrong, but Jed Hoyer could use the winter to inject more youth around his cornerstone.
The Chicago Cubs have hired Steve Miller away from the Tampa Bay Rays, and he will oversee the team's international scouting department.
The Chicago Cubs are expected to extend the qualifying offer to Seiya Suzuki but that shouldn't change his free agency fate.
Michael Soroka might be a reunion candidate for the Chicago Cubs this offseason, but there remains a clear reason why they should stay away.