Alex Bregman has signed a five-year, $175 million contract with the Chicago Cubs.
The deal is considered a win for Bregman, his agent Scott Boras, and the Cubs’ infield.
The Boston Red Sox are seen as a loser in the deal after Bregman opted out of his contract with them.
Alex Bregman wasn’t the top prize on the free agent market this winter. In fact, the top three targets in USA TODAY Sports’ pre-winter rankings remain available.
But Bregman’s signing with the Chicago Cubs will have significant ripple effects throughout the game.
With Bregman set to be introduced to Chicagoland at next weekend’s Cub Convention, USA TODAY Sports breaks down the winners and losers of Bregman agreeing to a five-year, $175 million contract to call Wrigley Field home:
Winners
Alex Bregman
Nicely played. When the anvil of draft pick compensation was attached to Bregman’s back last winter, he did not find a home until spring training camps had opened, when he agreed to a three-year, $120 million contract with the Boston Red Sox. The two opt-outs in the deal ensured he’d be able to try the market again without the dreaded compensation pick accompanying him.
And even though injuries limited him to 114 games in Boston, his .821 OPS and winner’s swagger that helped the Red Sox to their first playoff berth since 2021 nicely reestablished the market for a two-time World Series champ who turns 32 the first week of the season.
Now Bregman’s two-year free agency gambit looks like this: Six years, $215 million. He received the highest annual salary in Cubs history, and the largest on the market so far this witner.
Throw in his team-friendly five-year, $100 million extension signed in Houston back in 2019 and Bregman’s career haul looks like this: 11 years, $315 million. That’ll buy a few ponies, for sure.
Scott Boras
The man always gets his revenge tour.
It certainly takes a certain mindset to be a Boras client, one where abundant patience and confidence in your ability to perform are paramount. And after a handful of winters where some of the uber agent’s finest clients have been frozen out, all are finding their happily-ever-afters.
In addition to Bregman’s two-year haul, slugger Pete Alonso’s five-year, $155 million deal with Baltimore suddenly makes his free agent haul look pretty sweet: Six years, $185 million when you consider the $30 million he hauled in during his make-good season with the Mets.
Next up: Cody Bellinger, still locked in a staring contest with the New York Yankees but likely to top $200 million wherever he lands, concluding a saga of non-tenders, short-term deals, opt-outs and trades since he first hit the market four years ago.
Bo Bichette
No, he’s not a Boras client, but the erstwhile Toronto Blue Jays infielder is probably smiling like one. While the Cubs weren’t exactly a “mystery team” in the Bregman sweepstakes, his signing there comes as a moderate surprise – and certainly amps up the pressure on the Red Sox to fill the Bregman-sized hole in their lineup.
Now, it’s just Bichette, Bellinger and slugging outfielder Kyle Tucker left on the elite hitter market and Bichette should come at a significantly lower price point than Tucker.
SEC baseball honks
While Bregman will have the highest salary on the Cubs, he doesn’t quite have the largest contract – that would belong to Dansby Swanson, who will gross $177 million over seven years.
And that’s just the latest installment in a saga of two guys with a history of one-upping the other who will now share the left side of an infield.
When Bregman and Swanson were juniors at LSU and Vanderbilt, respectively, it was Bregman who was named first-team All-SEC at shortstop. But it was Swanson’s Vandy squad that advanced to the College World Series final.
And it was Swanson who was selected No. 1 overall by the Arizona Diamondbacks – allowing the Astros to draft Bregman No. 1. Bregman was so unbothered by that, he chose No. 2 as his number.
Now, they join forces, having put away childish things long ago. And for a conference that can no longer maintain the façade of football dominance, at least there’s one place where it still matters more.
Losers
Boston Red Sox
Tough one, man. We were fairly stunned a year ago when the Red Sox broke out of several years of long winter’s naps to sign Bregman and trade for Garrett Crochet, who finished second in Cy Young Award voting. Their three-year playoff drought ended with a spirited three-game wild card series defeat to the Yankees.
That seemed like a jumping-off point – only for Bregman to bolt, reportedly for just $10 million more than the Red Sox offered.
Now, the Red Sox lineup looks way too thin once you get past the first five or so spots – especially since budding star Roman Anthony won’t have a Bregman-like companion at the top of it. Fellow minor league product Marcelo Mayer is penciled in at third, but significant questions remain about his durability, and he’s far from a finished product.
This does not sound like a club ready to go toe-to-toe with the Blue Jays, Yankees and Orioles, even with a fortified pitching staff.
Alex Bregman’s statistics
For a man who peppered Houston’s Crawford Boxes and then Fenway Park’s Green Monster to post an .846 career OPS, Wrigley Field will be a decidedly tougher hang.
In fact, Fenway ranked as the second hitter-friendliest ballpark in 2025, according to Statcast’s park factors. Wrigley? Second-to-last. The parks move to the top and bottom of the list when it comes to hitting doubles.
Suddenly, Bregman’s pull-side dominance will have to contend with Wrigley’s capricious winds. It’s well worth it for the Cubs to make that investment – but the back of Bregman’s baseball card might not be so pretty going forward.
Matt Shaw
The Cubs were somewhat Red Sox-esque in their inability to land marquee free agents and instead tout the upside of their farm system products. But Bregman’s signing shows it’s not time to wait around for the kids to grow up.
What does that mean for Shaw? He took modest steps forward on both sides of the ball as his rookie season proceeded, producing 3.1 WAR in 126 games, though with a .226 average and 98 adjusted OPS.
That doesn’t mean there’s no future for Shaw in Wrigleyville. Second baseman Nico Hoerner is a free agent after this season, and Shaw could slide there in 2027, or sooner, should the Cubs decide to deal Hoerner for, say, pitching help.
Or, it could be Shaw dangled in trade talks. Either way, it’s clear the Cubs had no patience to count on Shaw’s development proceeding in a non-linear fashion.
