2026 looms as a pivotal season for the Chicago Cubs. A wave of key players are set to hit free agency while facing a new collective bargaining agreement that could reshape the financial landscape. Despite this, the team has already shown a willingness to spend big by locking in Alex Bregman, Pete Crow-Armstrong, and Nico Hoerner, on top of Dansby Swanson,who is locked up through the 2029 season.
For Cubs fans, it’s encouraging to see Jed Hoyer getting the green light from the Ricketts Family to commit $175 million to Bregman, $115 million to Crow-Armstrong, and $141 million to Hoerner, bringing their total spending since the end of last off-season up to $488 million. That said, many might be wondering “how are they doing this?”
Chicago Cubs post-2026 payday window could be driving recent contracts handed out
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 they are unlikely to get long term contracts.
Money coming off #Cubs books at the end of this season (luxury tax):
Imanaga: $22.025M
Happ: $20.3M
Suzuki: $17M
Taillon: $17M
Boyd: $14.5M
Rea: $6.5M*
Harvey: $6M
Kelly: $5.75M
Thielbar: $4.5M
Milner: $3.75M
Carlson: $2M
Conforto: $2M
Webb: $1.5M*
Austin: $1.5MTotal:…
— Michael Cerami (@Michael_Cerami) March 28, 2026
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.
Chicago Cubs: Alex Bregman points out major change in Cubs business mindset
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