Cubs Make Bold Moves for Postseason Push Ahead of 2025

CHICAGO, Ill. — The Chicago Cubs are taking significant steps toward a postseason return in 2025 after years of underwhelming performance. The team has missed the playoffs in five of the last six seasons and has not secured a playoff victory since their loss in the National League Championship Series to the Los Angeles Dodgers in 2017.

After posting identical 83-win seasons over the last two years, the Cubs have adopted a more aggressive approach to roster improvement. In a significant move, they traded with the Houston Astros for outfielder Kyle Tucker, a deal that required the Cubs to part ways with top infield prospect Christopher Morel, All-Star third baseman Patrick Wisdom, and promising young pitcher Cade Horton.

This acquisition signals the Cubs’ intent to enhance their offensive lineup. Tucker is expected to provide a much-needed anchor, especially with his impressive track record, which includes a career slash line of .280/.362/.527 since 2021, as opposed to the performance of departing players. While he is slated to become a free agent after the 2025 season, the Cubs are likely considering a contract extension following their investment.

Historically, teams that acquire notable players on the cusp of free agency often opt to extend their contracts. Recent examples include Fernando Tatis Jr., Manny Machado, and Freddie Freeman, all of whom signed significant extensions shortly after being traded. However, not all such endeavors yield success, with the New York Yankees’ struggles to retain Carlos Correa after trading for him last season serving as a cautionary tale.

Tucker’s potential contract demands could set a new benchmark for the Cubs. While Juan Soto‘s exceptional $765 million deal is an outlier, Tucker’s performance positions him for a substantial contract in a landscape where big-market teams, including the Los Angeles Dodgers and New York Yankees, may drive competition for his services. His value is underscored by a fWAR of 19.1 since 2021, trailing Soto’s 24.6, despite missing a significant portion of last season due to injury.

Should Tucker remain healthy and continue to perform as expected, projections suggest that he could command a contract surpassing $400 million when he reaches free agency. This would mark a significant departure from the Cubs’ history, as their highest contract to date was Jason Heyward’s $184 million deal prior to the 2016 season.

The Cubs face a substantial decision regarding Tucker, particularly given their recent history of hesitance concerning long-term contracts. Currently, only two players on the roster have guaranteed contracts beyond the 2026 season, creating questions about how willing the organization will be to extend such a significant offer.

Additionally, the Cubs are rumored to be interested in free agent Alex Bregman, which could complicate their financial strategy moving forward. Attempting to bring Bregman into the fold on a lucrative contract may influence their capacity to negotiate with Tucker.

Cubs fans have expressed a mixture of optimism and skepticism regarding the negotiations. One fan commented, “If Tucker has a breakout year, can the Cubs afford to let him walk?” Another remarked that the team has historically refrained from making bold financial commitments, citing the implications of a potential salary cap after the expiration of the current collective bargaining agreement in 2026.

As the Cubs continue to develop their roster leading into a critical season, their decisions regarding Tucker and potential acquisitions will play a pivotal role in shaping the franchise’s future.