Alex Bregman was one of the Big Four position players left on the MLB free agent board, and now he’s found a new home. The savvy veteran is headed to the North Side of Chicago in what registers as surprising news that leaves his former club with a massive void.
The Chicago Cubs shelled out $175 million to land Bregman late on Saturday night, a move that cements a new pillar in their organization. On the flipside, the Boston Red Sox have let a key cog slip through their grasp.
Here’s a closer look at the deal and its ramifications for both clubs.
The deal:
Alex Bregman agrees to a five-year, $175-million deal with the Chicago Cubs.
The runners up:
The Boston Red Sox are the team that’s seemingly left at the altar here. All off-season, it seemed as though the club would keep Bregman in the fold after what was a successful 2025 campaign for both sides.
Reports indicate the Red Sox were outbid for the third baseman, a fact that’s somewhat confusing given that chief baseball officer Craig Breslow traded third baseman Rafael Devers and his north-of-$200-million contract last season.
It felt at the time that the club was choosing Bregman over Devers and that was supported by the fact that the club was willing to quickly move Devers off third base to make room for his new teammate. That contributed to an uncomfortable scenario for the homegrown Red Sox star, and, in hindsight, Boston’s handling of the situation warrants questioning.
The player:
Bregman initially signed a three-year, $120-million deal with the Red Sox last February that featured an opt-out that he utilized after the 2025 season to re-enter free agency. Add the $40 million he made last year to his new deal with the Cubs, and the Scott Boras client will have made $215 million over six years.
It’s a hefty total for a player whose OPS over the past six seasons stands at .799.
Bregman turns 32 in March and while it’s likely true that his best years are behind him, he’s still a well-rounded player who can contribute in many ways and produce three-to-four wins above replacement per season.
He’s an excellent contact hitter who rarely strikes out, a combination that consistently makes him a tough at-bat for opposing pitchers. There might not be a better “pest” in MLB and Bregman comes with pop in his bat, too, having averaged 23 home runs over the past four seasons.
Additionally, Bregman’s defence has remained steady with his outs above average ranking in the 83rd percentile, per Baseball Savant.
The fit:
Perhaps Bregman’s greatest strength is his leadership. I covered the 2025 American League Wild Card Series in the Bronx, and it was glaringly evident how much Bregman’s Red Sox teammates revered him. They seemed to mention the veteran and his calming presence in almost every interview.
Bregman owns a reputation for being among the best clubhouse guys in the league, and that’s not hyperbole. He’s built that with the help of extensive exposure to the grandest spotlight.
A second overall pick by Houston in the 2015 MLB Draft, Bregman debuted in the big leagues the following season and was an integral contributor for the dynastic Astros, a club that was chock full of impact players. For context, the two-time World Series champ has played in 102 post-season games, which ranks ninth all time. During that span, he’s hit 19 homers and posted a .791 OPS.
Such wealth of experience should instantly benefit the Cubs, whose one-year experiment with Kyle Tucker didn’t work out as planned. The outfielder was good, not great, during his time in Chicago, and the Cubs do not appear likely to retain Tucker as the free-agent outfielder’s market appears limited to the Toronto Blue Jays, New York Mets and Los Angeles Dodgers, according to reports.
Bregman slides into that Top Dog spot at Wrigley and his presence should help deepen a roster that already features six-WAR players Pete Crow-Armstrong and Nico Hoerner. The Cubs also acquired promising starter Edward Cabrera, as well as several relievers earlier in the off-season.
The market:
MLB Trade Rumors predicted a six-year, $160-million deal for Bregman. He received less term, but bested that forecast in total value.
The next domino:
The obvious answer here is Bo Bichette. Tucker and Cody Bellinger round out the now Big 3 of remaining position player free agents, yet because they’re outfielders, their markets won’t be affected by the Bregman signing.
Bichette, however, figures to become the focus of clubs looking for an infielder who can provide major offensive impact. The Red Sox are a clear fit and it will be interesting to see how they react to losing Bregman.
The Philadelphia Phillies have also expressed serious interest in Bichette in recent days and have a reported meeting lined up with the infielder on Monday.
Stay tuned.
