Chicago Cubs: Alex Bregman points out major change in Cubs business mindset

Chicago Cubs ownership had been blasted prior to this offseason for being too conservative, too unwilling to spend like the major market team they are. Those criticisms have been quieted this year.

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Over the offseason, the Cubs restocked a depleted bullpen with four free agent relievers, signed free agent three-time All-Star third baseman Alex Bregman, and extended center fielder Pete Crow-Armstrong on a six-year-deal. After Opening Day, they then extended second baseman Nico Hoerner on another six-year deal. They even flipped on their informal policy against deferred money by using some of that down-the-road cash in the Bregman and Hoerner deals.

Per Patrick Mooney of The Athletic:

“Within one fiscal quarter, the Chicago Cubs guaranteed $431 million to three players [Bregman, PCA, Hoerner] in deals that will cover 17 total seasons.”

Throw in the bullpen acquisitions, minor league contract deals, and a couple of position players, and we’re talking about a half-billion dollars invested into the team this year by the Ricketts family. It’s not Dodgers-level spending, but this isn’t something done unless ownership is really serious about winning.

Bregman speaks on Cubs investment

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“They see the potential of this team being a winner for a sustainable period of time,” Bregman told reporters Saturday at Wrigley Field. “When you have a team like that, you want to invest in it.”

The soon-to-be 32-year-old Bregman was acquired as a cornerstone of the Cubs immediate future and now he has company in that regard with Crow-Armstrong and Hoerner.

Including shortstop Dansby Swanson and first baseman Michael Busch, who are both under contract through the 2029 season, the Cubs are guaranteed to be featuring the same five of eight position players for at least the next four season. And that number becomes six of eight if you include catcher Miguel Amaya, who is also under contract through the 2029 season.

That’s the kind of security most teams would kill for. The Cubs, specifically, believe in the team they’re fielding to such a degree that they were willing to go all-in, monetarily (at least as all-in as the Cubs would realistically go).

Daring in the face of uncertainty

Chicago’s offseason daring wasn’t just limited to spending, though. Trading their top prospect Owen Caissie (along with two other prospects) for three years of pitcher Edward Cabrera also screams of confidence that they can not only compete for a championship right now, but also win one (or more).

“It’s hard to try and re-create something good every year with a bunch of new pieces,” Swanson told media. “That’s in any business. So when you have good things going, you try and find ways to keep them and also improve at the same time. Continuity is huge.”

The Cubs are still facing a lot of uncertainty this offseason, however. Core elements of the team such as Ian Happ, Seiya Suzuki, Carson Kelly, Matthew Boyd, Jameson Taillon, and Shota Imanaga could all be gone next season via free agency. The bullpen could also find itself nearly as depleted at the end of 2026 as it was at the end of 2025.

For now, though, the Cubs have locked in much of the foundation for the future. Whether they’re actually serious about winning should stop being a question.

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