Chicago Cubs post-2026 payday window driving recent contracts

As things currently stand, right now the Cubs are scheduled to have $124.325 million come off the books at seasons end, according to a deep dive of the finances by Michael Cerami at BleacherNation. Of the 14 players potentially becoming free agents , five are making more than $10 million and two more than $20 million. Additionally, all of Shota Imanaga, Ian Happ, Seiya Suzuki, Jameson Taillon, and Matthew Boyd are over 30 years old, meaning t hey are unlikely to get long term contracts.

In other words, the Cubs aren’t just spending to spend, they’re strategically extending their competitive window. By committing big money now, they’re locking in cornerstone talent before that financial flexibility opens up, positioning themselves to supplement the new future core even further once contracts from Imanaga, Happ, Suzuki, Taillon, Boyd, and others roll off.

Furthermore, no matter how the next collective bargaining agreement shakes out, the Cubs are positioned to have significant financial flexibility next winter. Even if a new CBA introduces stricter payroll thresholds or spending penalties, this kind of built-in breathing room ensures the Cubs can remain aggressive, whether that means pursuing top free agents or trading for more talent.