When the Chicago Cubs pulled off a major trade with the Houston Astros last offseason, acquiring outfielder Kyle Tucker in exchange for Isaac Paredes, Hayden Wesneski, and prospect Cam Smith, most analysts viewed it as a short-term move.
The four-time All-Star was entering his final year of team control before free agency, and Chicago’s history of conservative spending made a long-term extension seem improbable.
Tucker’s time with the Cubs proved impactful. In 136 games during the 2025 season, he hit .266 with 22 home runs, 73 RBI, and earned another Silver Slugger award, helping push the team into the playoffs and contention.
As the offseason continues to unfold, however, Tucker’s expected massive bidding war for a contract potentially exceeding $400 million has not fully developed, leaving his market unusually subdued as the new year approaches.
ESPN analyst Paul Hembekides recently highlighted this slowdown, suggesting that major-market teams, which includes the Cubs, should explore opportunities if certain conditions align. He didn’t mention Chicago by name, but the Cubs are a big market team.
Hembekides noted the lack of momentum in negotiations and proposed that Tucker might consider a shorter-term agreement to secure high pay now while preserving the option to re-enter free agency soon.
One idea he floated was a two-year contract totaling $104 million, with an average annual value of $52 million and a player option after the first season, positioning Tucker among the game’s highest-paid players by yearly salary if a lengthy deal proves elusive.
Another concept involved a four-year pact worth $172 million, carrying a $43 million average annual value and including a player option following the second year.
With Tucker having elevated the Cubs to serious playoff contenders in 2025, pursuing him again under these flexible terms could align well with the team’s goals.
Factors like injury history or shifting team priorities might explain why no club has committed to viewing Tucker as worthy of a $400 million commitment yet, or the process could simply be evolving gradually.
The relative silence surrounding Tucker’s negotiations has sparked speculation that Chicago might re-emerge as a viable option through an unconventional structure. Such a development remains far from certain, particularly given the significant financial commitment required from ownership, even if limited to the near term.
Still, under the appropriate market conditions, a continued partnership between Tucker and the Cubs cannot be completely dismissed.
As the winter progresses into January, the dynamics for one of baseball’s premier talents could shift further, keeping hope alive for an unforeseen return to Wrigley Field.
