Cubs and Yankees reflect on championship windows after recent playoff seasons
Yahoo Sports • 1 min read • Latest: Oct 23, 2026, 6:30 PM
Last updated Oct 23, 2026

As the World Series begins, a retrospective on the championship aspirations of the Cubs and Yankees highlights how fleeting success can be. The Cubs, who last won the Series in 2016, have made the playoffs five times since with mixed results. The Yankees, despite consistent playoff appearances, have yet to secure a title in recent years. The article discusses how both franchises face uncertain futures, with aging rosters and missed opportunities casting doubt on their playoff strategies. Both teams must navigate their next steps carefully as the continues to shift in Major League Baseball.
- •Cubs last won the World Series in 2016, making playoffs five times since
- •Yankees have had no losing seasons, yet lack recent titles
- •World Series begins with top-seeded teams competing
- •Cubs and Yankees confront aging rosters and missed chances
- 6:30 PMYahoo Sports — How open is that championship window?
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