October never even started for the Chicago Cubs, Boston Red Sox and Houston Astros. With a trio of wild-card sweeps Wednesday, they became the first teams to make exits in the 2026 MLB playoffs -- on the last day of September. So, what's next for Chicago, Boston and Houston -- and all of the other teams that won't be celebrating a World Series parade this fall?
For every eliminated contender this October, ESPN MLB experts list its key free agents and biggest offseason questions and also make their predictions for the long, cold winter ahead. The Cubs need to rebuild their pitching staff, as Kevin Gausman, Ian Happ, Seiya Suzuki and Shota Imanaga are key free agents likely to leave. Pitching is the key to their offseason, whether it comes from within or from outside the organization.
The Red Sox's biggest priority could be replacing Sonny Gray in the rotation, as he has hinted at retirement. A healthy Garrett Crochet will help fill that void, but adding pitching depth looks necessary after trading away so many arms. The shortstop and second base positions will probably be resolved in 2027 with top prospect Franklin Arias and Curtis Mead.
Source: ESPN MLB · Summarized by HeadlinesBriefing