Cubs Linked To Cy Young World Series Standout As Free Agency Rumors Swirl

The 2025 MLB season is over for all but two of the league's 30 teams.

Therefore, while there's a lot of interest surrounding whether the Toronto Blue Jays can take down the Los Angeles Dodgers in this year's World Series, the fan bases of many teams are more interested in how their roster is going to improve this winter, hopefully so that they can be watching their team in the World Series this time next year.

The Chicago Cubs have many offseason decisions to make that will ultimately mold the franchise's chances of making a deep run in the 2026 postseason. Among these are whether to try and re-sign star outfielder Kyle Tucker (and how much they're willing to spend to bring him back) and which of their numerous free agent relievers they're going to pursue.

What's more, Chicago could be active in trying to bolster their starting rotation, as their current starting staff has several question marks. There are a couple of compelling free agent starting pitchers available in this year's free agency market. But the one that might be the best fit for the Cubs is still playing games.

Chicago Cubs president of baseball operations Jed Hoyer speaks on July 3, 2025 — Kamil Krzaczynski-Imagn Images

Insider Links Cubs to Blue Jays Pitcher Shane Bieber

In an October 22 article, MLB.com insider Mark Feinsand listed the Cubs as one of three potential fits for Blue Jays pitcher Shane Bieber.

Bieber is a fascinating free agency target for Chicago. Just a few years ago, Bieber was one of the premier pitchers in the entire sport, which is proven by his being a two-time MLB All-Star, the 2020 AL Cy Young Award winner, and the recipient of a Triple Crown in 2020, which is when a pitcher leads the league in Wins, ERA, and Strikeouts.

MORE: Why Cubs’ Michael Busch Was Robbed Of NL Silver Slugger Finalist Nomination

The 31-year-old Bieber then suffered a torn UCL in his throwing elbow in April 2024, which kept him sidelined for over a year. The Cleveland Guardians traded him to the Blue Jays before the 2025 trade deadline (before Bieber made his return from injury). He made his 2025 season debut on August 22 and has been solid ever since, posting a 4-2 record and a 3.57 ERA in seven regular-season starts.

Shane Bieber, Dirty 86mph Slider. 😨 pic.twitter.com/YRg3od92sQ
— Rob Friedman (@PitchingNinja) October 21, 2025

Bieber has been decent in three starts this postseason. However, a great World Series performance against the Dodgers would work wonders for his free agency stock and could convince the Cubs that he's worth a contract once he becomes available later this winter.

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