Alex Bregman's $175M Contract Detonates Big-Market Reputations of Cubs and Red Sox

Almost a year after the Boston Red Sox outbid the Chicago Cubs to sign Alex Bregman, the tables have turned in a way that feels properly discombobulating.

For now, how Bregman became a Cub on Saturday night feels straightforward. He accepted a five-year, $175 million offer, whereas Jon Heyman of the New York Post says that Boston was in the $160 million range. If so, then he took the better offer.

Otherwise, what we'll presumably hear when Bregman is introduced by the Cubs is something along the lines of him leaving a good situation in Boston for a better one in Chicago. And you know what? He won't be wrong.

The Cubs Just Flipped Their Spending Narrative On Its Head

Remember when the book on the Cubs was that they had a ton of money to spend but just didn't?

Well, you should. Because that book was accurate right up until news of the Bregman signing dropped. We can go ahead and put some numbers to it:

2024 Revenue: $584 million, 3rd in MLB
2025 Opening Day Payroll: $190.6 million, 12th in MLB

The Ricketts family hates the narrative that they don't spend on the Cubs. But whereas Yankees owner Hal Steinbrenner at least alludes to how MLB financials are more complicated than fans understand, Tom Ricketts tried out a different line last year: "I don't think fans should spend all their time thinking about which teams have more money or how much they're spending."

That was nonsense, and the club's approach only got more infuriating as fans' hopes for a Kyle Tucker extension went for naught… yet right now, these things also feel like water under the bridge.

With Bregman aboard on a $35 million-per-year deal, the Cubs are expected to open 2026 with a $231 million payroll. It'll be the highest in their history, and it certainly feels well-timed after a 92-win season that marked a return to the playoffs. As of now, the Cubs project to be the best team in the NL Central.

Bregman is likely to contribute a .800-something OPS and good defense, and Chicago's lineup just plain looks better with him alongside Pete Crow-Armstrong, Dansby Swanson, Seiya Suzuki, Michael Busch and Ian Happ. If the Cubs fancy another top-level starter after landing Edward Cabrera, they can now shop Matt Shaw or Nico Hoerner. Even as is, any rotation that has Jameson Taillon as a No. 5 starter is a deep one.

With the Los Angeles Dodgers still lurking out west, one doesn't want to go so far as to anoint the Cubs as National League favorites. But they're firmly in the mix after pushing the envelope to where fans wanted it pushed, which pretty much puts them in "no notes" territory as their offseason winds to a close.

The Red Sox Have Some Explaining To Do

Meanwhile, in Boston, the timing of Bregman's decision could not have been more awkward.

The Red Sox held their fan fest at Fenway Park earlier on Saturday, and it was replete with notables all but begging for Bregman to come back. Craig Breslow said something. Alex Cora said something. And Roman Anthony said it best.

"I'd love to have him back. I love Breggy," the 2025 AL Rookie of the Year finalist said. "He was a huge part of my success and a lot of the young guys, not only the young guys but many guys in the clubhouse."

Well, now he's gone. And if anyone hasn't yet taken to X to see how it's playing with the Fenway Faithful, be warned: It's ugly out there.

As well it should be, frankly. Despite a quad injury that took some of the shine off his star in the latter half of 2025, Bregman still gave a playoff-bound Red Sox club a .821 OPS, 18 home runs and 3.5 rWAR. And as Anthony alluded to, he was the glue guy in the clubhouse.

The combination of those things should have convinced the Red Sox that Bregman was worth more to them than he was to any other team. They also should have been mindful that they had staked their reputation to him when they traded Rafael Devers last June—a deal that would not have happened if Bregman hadn't been there.

Bregman is a 31-year-old (32 on March 30) whose mortality has become more apparent in recent years. Boston's offer was a fair one, but an extra $15 million should have been doable. Or at least, less deferred money than the whopping $70 million in deferrals worked into his Cubs deal.

It's now the Red Sox who look cheap, in other words, and they might as well have taken the Cubs' place as the worst offender among big-market clubs. Once again, some numbers:

2024 Revenue: $574 million, 4th in MLB
2025 Opening Day Payroll: $195 million, 11th in MLB

That's a "Yikes," and here's the double whammy: Boston is set to open 2026 with an even lower payroll at $191 million.

That could change if the Red Sox pivot from Bregman to a star of equal stature. Bo Bichette will be the guy, according to Bob Nightengale of USA Today, and it isn't hard to make the case for him as the upgrade option. He's younger, more athletic, more experienced in the AL East, and historically an offensive dynamo at Fenway Park (.907 OPS) and against the Yankees (.860 OPS).

Especially with less negotiating leverage after Saturday's events, Bichette will almost certainly cost the Red Sox more than Bregman would have. And even a larger splash on Bichette might not quell the unrest the Red Sox have sown. Re-signing Bregman would have been them asking fans to trust a proven process. Signing Bichette would mean spending more money just to sell fans an unproven process.

In the parlance of our times, the Red Sox have stepped in it. That's for them to overcome, and for the Cubs to laugh at. That used to be them, and they know how much it sucks.

Stats courtesy of Baseball Reference, FanGraphs and Baseball Savant.