The Chicago Cubs are expected to face significant decisions in the upcoming offseason, with Kyle Tucker’s future at the forefront as he approaches free agency in 2026-27. Tucker, widely regarded as one of Major League Baseball’s elite players, will be a focal point in the Cubs’ strategy during this period, which also includes several other important players nearing free agency.
Alongside Tucker, players such as Ian Happ, Seiya Suzuki, Nico Hoerner, Jameson Taillon, and Matt Boyd are also set to reach free agency, presenting a challenge for the Cubs as they work to maintain a competitive roster.
Key Cubs Players at Risk of Leaving After 2026-27 Season
MLB insider Ken Rosenthal highlighted the stakes involved for the Cubs, noting the significant portion of the team’s performance these players represent.
“The potential members of the free-agent class of 2026-27 are left fielder Ian Happ, designated hitter Seiya Suzuki, second baseman Nico Hoerner, right-hander Jameson Taillon and left-hander Matt Boyd. That group, combined with Tucker, accounted for 37 percent of the team’s fWAR entering Tuesday. And while the Cubs might retain some of those players, they are unlikely to keep all of them, Tucker in particular,”
Rosenthal wrote.
Given the collective impact of these athletes, losing Tucker would be the most damaging blow for Chicago. However, the departure of other key players like Seiya Suzuki and Ian Happ would also deal a significant setback to the team’s competitive outlook.
Financial Implications and the Cubs’ Decision-Making Ahead
The financial commitments required to retain Tucker could shape the Cubs’ overall offseason plans. With estimates ranging from $500 million to $600 million for a potential contract, the Cubs face a difficult choice about allocating their budget. The team must weigh whether investing heavily in Tucker alone is the best path forward or if spreading resources among multiple key players offers a stronger strategy.
Although Tucker has only been with the Cubs for a single season, his performance has proved the value he brings. Meanwhile, recognized talents such as Happ and Suzuki remain highly sought after across Major League Baseball, increasing the urgency for the Cubs to act thoughtfully in free agency negotiations.
The Cubs’ management appears cautious, as committing to a massive deal without a clear, aggressive plan could be unwise. This uncertainty about their intentions adds to the tension surrounding Kyle Tucker’s potential extension with the team.
What Lies Ahead for the Cubs and Kyle Tucker
The decisions made during this upcoming free agency period will likely define the Cubs’ trajectory for years to come. Retaining even some of the players nearing free agency could preserve a competitive core, but losing Tucker would represent a major setback for the franchise. The financial and strategic balance the Cubs strike will be essential in determining if they remain contenders or enter a rebuilding phase.
With free agency looming, Chicago fans and analysts alike will be watching closely to see how the team addresses these critical roster questions and whether an agreement with Kyle Tucker is ultimately reached.