The Chicago Cubs are finally acting like a big-market team again-and that’s not just lip service this time.
After a frustrating 2025 offseason that saw the Cubs miss out on key targets and balk at financial flexibility, they’ve come into 2026 with a different mindset. The big headline? They landed Alex Bregman, and they did it by changing a long-standing organizational stance: they embraced deferred money.
Let’s rewind for a moment. Last offseason, the Cubs made a run at Bregman, offering him a four-year, $115 million deal.
Not bad on paper, but it lacked the structure and flexibility that top-tier free agents are looking for these days. Bregman turned it down, as did he a longer-term offer from the Tigers, and ultimately signed a three-year deal with Boston that included a high AAV, deferred money, and-most importantly-an opt-out after the first year.
That kind of structure gave Bregman financial security and control over his future, something players and agents value highly in today’s market.
The Cubs, at the time, weren’t willing to go there. Ownership had been firmly against offering deferred money, even for someone like Shohei Ohtani.
But after a disappointing postseason exit at the hands of the Brewers in the NLDS, something changed. Whether it was the sting of falling short or the realization that the market had evolved, the Cubs front office-led by President of Baseball Operations Jed Hoyer-finally got the green light to operate differently.
And Hoyer didn’t waste the opportunity.
This winter, the Cubs circled back to Bregman and got the deal done. During Bregman’s introductory press conference, Hoyer acknowledged the shift in strategy, saying, “You're always thinking about evolving as an organization and thinking about things different.
We had a lot of fruitful conversations about that. It led to this deal.”
The result: Bregman signed a five-year, $175 million contract with the Cubs. But here’s where the financial creativity comes in-$70 million of that total is deferred, scheduled to be paid out from 2034 through 2041. That structure allowed the Cubs to keep the average annual value at a manageable $35 million while still offering Bregman the kind of overall value and flexibility he wanted.
Here’s how Bregman’s salary breaks down over the next five seasons:
- 2026: $20 million
- 2027: $20 million
- 2028: $25 million
- 2029: $25 million
- 2030: $15 million
And the deferred money? It’s spread out over eight years starting in 2034:
- $15 million deferred in both 2026 and 2029 (paid in $1.875M annual installments)
- $10 million deferred in both 2027 and 2028 (paid in $1.25M annual installments)
- $20 million deferred in 2030 (paid in $2.5M annual installments)
This is the kind of deal we’ve seen other big-market teams execute for years. The Dodgers, Mets, Phillies-this is how they stay competitive while navigating the luxury tax and long-term payroll commitments. For the Cubs, this isn’t just a smart baseball move-it’s a philosophical shift.
And it might not be the last move they make before Opening Day.
With Cody Bellinger no longer in the picture, the Cubs have reportedly turned their attention to other potential additions. One name that’s surfaced is Miguel Andújar, the former Yankees third baseman and corner outfielder, who could provide bench depth.
But the more intriguing name is Zac Gallen. The Cubs have been linked to the free-agent starter since last summer, and he remains a viable option to bolster a rotation that could use another high-end arm.
The Cubs’ offseason isn’t just about Bregman-it’s about momentum. It’s about finally leveraging their market size, financial strength, and baseball operations braintrust to build a roster that can contend not just in April, but deep into October.
For Cubs fans, this feels different. It feels like the front office is no longer tiptoeing around the edges of contention. They’re pushing chips in, making bold moves, and showing a willingness to adapt in a rapidly evolving free-agent landscape.
And with spring training just around the corner, the message is clear: the Cubs are going for it.