The Chicago Cubs have long been known for taking a hardline stance when it comes to free-agent contract structures-no early opt-outs, no deferred money. That approach, while once standard, has fallen out of step with the direction the market has taken in recent years.

Players and agents today value flexibility and long-term financial planning, and deferrals have become a key part of that conversation. For a while, it felt like the Cubs were playing catch-up.

But that changed in a big way with the signing of Alex Bregman.

In what marks a major shift in organizational philosophy, the Cubs inked Bregman to a five-year, $175 million deal-with a reported $70 million of that total deferred. That’s more than 40 percent of the contract pushed into future payments, and it’s a clear signal that the front office, with ownership’s blessing, is finally willing to play ball with the modern financial strategies teams across the league have embraced.

Let’s be honest: this isn’t just about being more player-friendly. There’s a strong Competitive Balance Tax (CBT) angle here.

Without the deferrals, a straight $35 million average annual value (AAV) would’ve put the Cubs right at the doorstep of the first CBT threshold, which sits at $244 million. And Chicago, like many teams, likes to leave itself a little breathing room-typically $5-10 million-for in-season additions.

By deferring a significant chunk of Bregman’s salary, the Cubs give themselves that cushion, keeping their options open for July while still landing a marquee name.

Right now, the Cubs rank eighth in MLB payroll and sixth in the National League, according to Spotrac. That’s a notable jump, and it reflects just how aggressive this offseason has been for Jed Hoyer and his front office.

First came the complete bullpen overhaul. Then came the trade for Edward Cabrera, a young, controllable arm with upside.

And now, the Bregman deal-arguably the biggest free-agent splash the team has made in years.

What’s especially striking is how different this pursuit looked compared to last winter. A year ago, the Cubs made a run at Bregman but came up short.

This time, they didn’t just stay in the race-they won it. Not only did they outbid the presumed frontrunner, the Boston Red Sox, but they did so with a contract that reflected real urgency and intent.

Chicago’s offer of $175 million over five years topped Boston’s reported $160 million, and that extra push made all the difference.

It’s a move that feels long overdue. Bregman brings elite defense at third base, postseason experience, and a bat that still profiles as one of the best at his position when healthy.

He fits the Cubs’ timeline, their needs, and their clubhouse culture. And now, with Bregman in the fold, the Cabrera trade bolstering the rotation, and a revamped bullpen, the Cubs are positioned to make a serious run in 2026.

There’s still work to do. Rumors continue to swirl about potential cost-cutting moves-Nico Hoerner’s name has come up-but for now, the Cubs have made a statement.

They’re not just spending. They’re adapting.

And in today’s MLB landscape, that might be the biggest win of all.