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Cubs Face Urgent Deadline Decisions as Key Players Approach Free Agency

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Chicago Cubs Kyle Tucker Baseball

CHICAGO, IL — The Chicago Cubs are feeling an urgent need to make roster improvements ahead of the trade deadline, especially given the potential free agency of key players. Right fielder Kyle Tucker could leave after this season, and the Cubs risk losing five other significant players after 2026.

This group, which includes Ian Happ, Seiya Suzuki, Nico Hoerner, Jameson Taillon, and Matt Boyd, combined for 37 percent of the team’s fWAR as of Tuesday. While the Cubs may try to keep some of these players, retaining all of them seems unlikely.

The Cubs face extra pressure due to the emergence of center fielder Pete Crow-Armstrong, giving the 2026 roster a promising look even if Tucker departs. However, ownership appears concerned about a shrinking competitive window, particularly with a potential work stoppage looming in 2027.

After losing left-hander Justin Steele to season-ending elbow surgery and righty Javier Assad to a strained oblique, the Cubs’ biggest need is a starting pitcher capable of handling postseason action—a commodity expected to be scarce at the deadline.

The Cubs are reportedly looking into Miami Marlins pitchers Sandy Alcantara and Edward Cabrera. Alcantara, who is under contract for the next two seasons at $17 million per year, would demand a significant payroll increase. Cabrera, at $1.95 million with three years of arbitration left, represents a better financial fit but may require a heavier prospect cost.

As the trade market develops, the Cubs are keeping their options open, considering various other starters like Arizona’s Zac Gallen and Baltimore’s Zach Eflin. However, time is of the essence, especially with their lead in the NL Central narrowing to just 2.5 games over the St. Louis Cardinals and Milwaukee Brewers.

Cubs owner Tom Ricketts has enforced a tighter payroll following 2024. This situation complicates the Cubs’ ability to build a competitive roster, particularly around star players like Tucker and Crow-Armstrong.

The Cubs’ offensive performance has been strong, ranking second in the majors for runs per game, only behind the Los Angeles Dodgers. Tucker, along with the resurgence of Cody Bellinger, has had a transformative effect on the lineup.

However, the Cubs must find a way to keep Tucker long-term, ideally pairing him with Crow-Armstrong, both of whom are at prime ages for productivity. Despite the challenges, adding Tucker and other prospects is critical for the Cubs’ aim of a World Series title in the next two seasons.

As the trade deadline approaches, Cubs’ president of baseball operations, Jed Hoyer, is under pressure to make impactful decisions. With the postseason on the horizon and the risk of losing key players, the urgency is palpable.