How the Chicago Cubs can get everything this winter (while staying on budget)

The Chicago Cubs have long been hobbled by internal budget pressures that almost invariably butt heads with the desire to actually have the team succeed on the field. This has left Cubs president of baseball operations Jed Hoyer with the perpetually unenviable task of fielding premium performers who come at a bargain price.

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“We took it as a real challenge,” Hoyer told media last February as he was putting the finishing touches on the 2025 squad. “We knew we had certain constraints. How do we work within those constraints and continue to get better at the same time? Only time will tell if we were successful. But I feel good about what we accomplished this offseason, given that we had some constraints.”

All things considered, Hoyer did an outstanding job of getting the most bang for the buck provided to him. Last season was special in a lot of ways, as most everything clicked and played out to a best case scenario result. But what’s asked of the veteran exec is an unsustainable balancing act. Every team needs pleasant surprises and successful gambles, but you can’t build a consistent winner on lottery tickets and crossed fingers.

The Chicago Cubs do have the money

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However, what if the Cubs could get everything they need and want this offseason while still staying on budget and, possibly, even below the luxury tax threshold? There’s actually a path for doing just that.

It’s been estimated that Chicago could still have around $50-$60 million to spend this offseason. They’re also facing the possibility of around $115 million coming off the books after 2026, as a ton of established talent (Ian Happ, Seiya Suzuki, Nico Hoerner, Carson Kelly, Matthew Boyd, Jameson Taillon, Shota Imanaga, Colin Rea) will be eligible for free agency.

The money’s there.

In a recent appearance on the MLB Network, insider Steve Phillips talked about his take on the Cubs’ winter pursuits and how spending beyond the luxury tax threshold would make sense this coming year.

Per Phillips:

“Here’s what, in the ideal world, I’d love to see for them (Chicago Cubs),” Phillips said. “They sign either (Kyle) Schwarber or (Pete) Alonso to DH. They sign (Alex) Bregman to play third, and they go get a quality starting pitcher. They can’t do it within $50 million, but they can do it within $70 million. It would take them over the luxury tax threshold, but you’re the Chicago Cubs!

“You’re the Chicago Cubs, why can’t you be $20 million over the luxury tax threshold and actually put the finishing pieces together on your team? You know what I mean? Go out and get the starter – (Ranger) Suarez or Framber Valdez, get Bregman and then get a slugger in your lineup and really go out there and win. If they want to go to the World Series, that’s what they need to do.”

Having their cake and eating it too

However, we ARE talking about the frugal Cubs ownership, frazzled by being one year away from a possible labor dispute/lockout. But, maybe, the Cubs can have their cake AND eat it, too, staying under the threshold while finding a way to build a World Series-viable roster. It would take some shuffling around and a few uncomfortable trades, but it can be done.

If the Cubs did bend reality by acquiring Alex Bregman (ESPN contract projection: 5 years, $160 million) and Kyle Schwarber (4 years, $128 million), that would put them right at the top of their self-imposed spending limit. It would more than make up for the loss of Kyle Tucker, though, and also establish two firm building blocks ahead of a likely mass exodus of talent after next season.

For the top-of-rotation starter they need, the Cubs could bite the bullet and trade some of the top prospects they’ve been hoarding the last couple of years. With Bregman at third and Schwarber at DH, guys like Matt Shaw, Owen Caissie, and Moises Ballesteros would be expendable.

Picking up a top-tier budget-friendly starter could be done with the Cubs willing to spend their trade capital. They could target team-controlled guys like the Marlins’ Edward Cabrera, the Twins’ Joe Ryan, or the Nationals’ Mackenzie Gore (who are projected by MLB Trade Rumors to make $3.7 million, $5.8 million, $4.7 million, respectively) without too much of a strain on the payroll.

But…

Obviously, this is a very simplistic strategy to a complex problem for the Cubs. You’d also have to take into account the need to add more bullpen and bench pieces (and maybe the reality that Bergman and/or Schwarber may not want to play for the Cubs). Whatever the case, spending above the luxury tax threshold may be necessary no matter what, if the goal is to secure a team capable of a World Series run (and to stock the team for a run beyond 2026).

The question is whether Cubs ownership is willing to get so close to their internal spending cap– and maybe surpass it– in pursuit of winning. They did it in 2016 and immediately after. They haven’t been inclined to do it since.

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Source: https://www.chicitysports.com/chicago-cubs-free-agency-trade-budget-2026