The Chicago Cubs achieved 92 wins this season, showing a nine-game improvement and returning to October baseball at a bustling Wrigley Field. As a wild-card entrant, however, they fell short by nine victories in the postseason to clinch the World Series.
Addressing this gap will be a key focus for Cubs president of baseball operations, Jed Hoyer, and his team in the upcoming months. With the offseason beginning following the Los Angeles Dodgers’ victory over the Toronto Blue Jays in Saturday’s thrilling Game 7, the Cubs are looking ahead.
Strengthening the pitching lineup is one way to transform a playoff team that lacked depth in trustworthy arms in October. As there are no signs the Cubs are prioritizing Kyle Tucker’s return—especially since the All-Star outfielder likely won’t agree to a short-term deal—they will likely maintain their focus on pitching.
This offseason’s free-agent pool is expected to feature pitchers such as Framber Valdez, Dylan Cease, Michael King, Zac Gallen, and Shane Bieber. The Cubs have a track record of identifying starters who excel within a game-planning method that emphasizes their strengths and utilizes Gold Glove defenders across the field.
However, the Cubs have not committed nine figures to a pitcher since signing Yu Darvish at the beginning of spring training in 2018, a contract that was ultimately traded during the pandemic. The Cubs have largely refrained from engaging the top free agents in recent years, missing out on players like Shohei Ohtani and Trea Turner, and did not participate in the bidding for Yoshinobu Yamamoto’s $325 million deal with the Dodgers or the $765 million hunt for Juan Soto.
Nonetheless, the Cubs still have the potential for significant moves. Hoyer’s decision to replace former manager David Ross with Craig Counsell from the Milwaukee Brewers took many by surprise, as did the bold trade for Tucker ahead of his free agency. Despite this, Cubs officials maintain that consistently qualifying for the playoffs is the best approach to winning a championship, indicating a cautious business model tied to ownership’s conservative strategy and ongoing collective bargaining uncertainties.
As the Cubs prepare for the 2026 season, they boast a competitive lineup that could contend for a wild card, even without any offseason trades. With the potential departure of Tucker, they will investigate options to replace his contributions, likely focusing on securing a strong left-handed batter or enhancing their third base position. Meanwhile, discussions around players like Kyle Schwarber and Alex Bregman will unfold this winter as they strategize for the next season.
