The cynical side of me is kind of still annoyed that the Chicago Cubs dumped Cody Bellinger last offseason and didn’t use the money saved by off loading his contract to fully go all-in with one year of Kyle Tucker. They tried, pursuing Alex Bregman, but ended up empty handed after he signed with the Boston Red Sox. Heading into the 2026 season Jed Hoyer got his man in free agency and during Bregman’s introductory press conference Hoyer confirmed how the Cubs finally changed their strategy this offseason.

It would have been great if ownership would have been more opened minded on their approach heading into 2025, but better late than never I guess. As a reminder, the Cubs offered Bregman a four-year, $115 million contract last February. The third baseman turned that deal down along with a longer term contract from the Detroit Tigers and instead signed a three-year agreement with the Boston Red Sox.

Bregman’s $40 million AAV was certainly surprising to see when the contract was first reported, but that deal with the Red Sox included a big chunk of deferred money and maybe more importantly it gave him the chance to opt out after year one.

The Cubs wanted absolutely no part in offering Bregman deferred money a year ago, a strategy that ownership was firmly against for any top free agent. I mean, the Cubs didn’t even consider deferrals for Shohei Ohtani.

Cubs Jed Hoyer said he had manny, many emails and text with owner Tom Ricketts about money availability for Alex Bregman. Cubs will not defer money any longer on contract offers. The team is still paying Jason Heyward and Jon Lester on deferred deals.

— Bruce Levine (@MLBBruceLevine) February 13, 2025

Maybe it was the embarrassment of losing to the Brewers in the NLDS, but the Cubs did change their mind on deferred money and for as much hate as Hoyer has received since he took over in 2020, at least he convinced the Cubs to act like a big-market team again.

Hoyer openly discussed how he was able to approach Scott Boras with a much more attractive offer for Bregman this offseason after speaking to Cubs ownership that allowed deferred money to be included in the final agreement.

Jed Hoyer addressed the team being resistant to deferrals in the past: "You're always thinking about evolving as an organization and thinking about things different. We had a lot of fuitful conversations about that. It led to this deal.”

— Jesse Rogers (@JesseRogersESPN) January 15, 2026

Alex Bregman Contract Details

On the surface, Bregman is signed to a five-year, $175 million contract. That comes out to an average annual value of $35 million. However, because the Cubs included deferrals, $70 million of the $175 million will be paid out from 2034-41, here’s how much Bregman will be paid during the next five years.

Alex Bregman Cubs’ Salary 2026-30
2026: $20 million
2027: $20 million
2028: $25 million
2029: $25 million
2030: $15 million

Here’s a breakdown via Mike Mayer on how the deferred money will be paid out by the Cubs to Bregman.

Total Deferred Money $70 million
$15 million deferred in 2026 and 2029
$10 million deferred in 2027 and 2028
$20 million deferred in 2030

Deferred money is paid each July 31, 2034-41:
2026 and 2029 in installments of $1.875 million
2027 and 2028 in installments of $1.25 million
2030 in installments of $2.5 million

So, it’s good to see the Cubs flexing their financial muscles, something that has kind of felt lacking in previous years. The hope is that the Cubs don’t shy away from offering deferrals to get free agents in the future because that’s just a part of the game now and all the major markets are doing it. Avoiding the strategy only puts the Cubs at a disadvantage.

And what’s even better is that they may be looking to add more to the roster before the regular season begins.

On Saturdays Inside the clubhouse ,Jed Hoyer and Crane Kenney said the Cubs will be doing more work on adding to this 2026 club. No mention of luxury tax the entire weekend of Cubs Con.

— Bruce Levine (@MLBBruceLevine) January 19, 2026

In the past few days the Cubs have appeared in couple more free agent rumors. Cody Bellinger is off the table, but former Yankees’ third baseman and corner outfielder Miguel Andujar is reportedly on the Cubs radar as a potential bench piece for the 2026 roster. Yet, the bigger rumor surrounds free agent starting pitcher Zac Gallen, who has been a target since the summer and is still viewed as a potential addition to the Cubs’ starting rotation.

We’ll see what the Cubs do next, but it finally feels like they are using all their resources to build out a true contender heading into the regular season.