The Chicago Cubs went out and got their man. Finally. The signing of third baseman Alex Bregman, announced on Saturday night in the heat of a historically awesome Bears-Packers playoff game, was equal parts shocking and tremendously well-received.
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In the Bregman deal, the Cubs signed off on a 5-year, $175 million contract which, in and of itself, is pretty surprising given the team’s recent spending trajectory. Especially surprising was the fact that the Ricketts family ownership agreed on a contract using deferred money, something which they had steadfastly refused to do in the past (including in their failed bid to sign Bregman last offseason).
By all accounts, Chicago was uncharacteristically aggressive in getting the three-time All-Star on board, reportedly swooping in from the back of the “interested” line, behind the Boston Red Sox and Arizona Diamondbacks, to get their man.
Why the Cubs were “all in” on Bregman
Aug 12, 2025; Houston, Texas, USA; Boston Red Sox third baseman Alex Bregman (2) runs to first base on a single during the ninth inning against the Houston Astros at Daikin Park. Mandatory Credit: Troy Taormina-Imagn Images
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Part of that, of course, is due to the fact that Bregman is a really good, multi-faceted player. An elite contact hitter who averages 28 home runs per 162 games, he matches the career offensive stats of outgoing right fielder Kyle Tucker and will fill the lineup hole created by his departure. He’s also a top-notch defender at third, with a Gold Glove award in 2024 to prove it.
However, a big motivating factor in the Cubs going “all in” on Bregman (and bucking standard business operating procedure to do so), may lie in what the team sees in their immediate future.
Chicago is facing an absolute tidal wave of departures after the 2026 season as multiple contracts are set to expire. Barring extensions signed during the season or activated options, here are the players headed toward free agency:
Ian Happ
Seiya Suzuki
Nico Hoerner
Matthew Boyd
Jameson Taillon
Shota Imanaga
Carson Kelly
Colin Rea
Caleb Thielbar
Hoby Milner
Jacon Webb
Hunter Harvey
Tyler Austin
The mass exodus of talent after 2026
Nov 13, 2023; Chicago, Illinois, USA;
Chicago Cubs president of baseball operations Jed Hoyer speaks before introducing Craig Counsell as new Cubs manager during a press conference in Chicago. Mandatory Credit: Kamil Krzaczynski-USA TODAY Sports
That’s thirteen players– half of their 2026 projected 26-man roster. Any way you look at it, this represents a huge degree of uncertainty as the veteran core of the team may be gone after next season. The loss of Hoerner, Happ, Suzuki, Boyd, and Taillon will hit especially hard as they make up a good part of the team’s heart-and-soul nucleus.
Fears of that kind of loss are probably what compelled the Cubs to get very un-Cubs-like in going after Bregman.
The 10-year MLB veteran is known for his leadership qualities and character, doused in praise by both teammates and coaching during his time with the Houston Astros as well as his one-year 2025 run with the Red Sox. One couldn’t find better cornerstone leadership for a soft rebuild.
The Cubs, realistically, may lose all thirteen of their free agent-bound veterans. Even in a best case scenario, they stand to lose at least ten of the thirteen.
That’s why securing Bregman was approached with such urgency. Nobody in the deep end of this year’s free agent talent pool provides the intangibles that Bregman does.
The impending mass exodus after 2026 is also also likely why the Cubs were okay with spending so freely.
Laying the foundation for a new Cubs team
May 10, 2025; Kansas City, Missouri, USA; Boston Red Sox third baseman Alex Bregman (2) throws to first base in the fourth inning against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Peter Aiken-Imagn Images
With the potential departures, about $130 million could also be coming off the books. Signing a proven asset to what amounts to a $30 million-per-season deal (after deferrals) is not so mind-boggling when one looks at the Cubs’ big picture.
After the coming season, the core of the team will skew young– and cheap– with Pete Crow-Armstrong, Michael Busch, Cade Horton, Matt Shaw, Daniel Palencia, Moises Ballesteros, Miguel Amaya, and possibly top pitching prospect Jaxon Wiggins earning at or near league minimum. Even veteran holdovers Justin Steele, Javier Assad, and now Edward Cabrera or on relative cheapo deals.
Chicago will have a huge opportunity to reshape their major league roster after next season– and lots of money with which to do it. But they need a sound, steady foundation laid before that.
Alex Bregman stands to be a key part of that foundation. And the Cubs were willing to spend handsomely to make that happen.
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