All offseason, the expectation around the league was that Alex Bregman and the Boston Red Sox would eventually find a way to stick together. A long-term deal felt almost inevitable. Bregman had thrived in Boston, the fit was there, and the Red Sox had the resources to make it happen.
But then the Chicago Cubs stepped in-and changed the script.
Jed Hoyer and the Cubs front office didn’t just make a strong offer; they gave Bregman exactly what he was looking for. A five-year, $175 million contract with full no-trade protection-something Boston reportedly wasn’t willing to include. That detail turned out to be a dealbreaker, and just like that, one of the game’s premier infielders was headed to Wrigleyville.
Red Sox CEO Sam Kennedy addressed the media over the weekend in Florida, and when asked about Bregman’s departure, he didn’t mince words: “If Alex Bregman wanted to be here, ultimately, he’d be here.”
That’s a strong statement, but it also sidesteps the reality of modern free agency. Players want security, both financially and in terms of stability.
Bregman earned that leverage. And the Cubs were willing to meet him where Boston wouldn’t.
For Cubs fans, this is a refreshing twist. They’ve seen their front office hold firm on contract terms in the past-sometimes to their frustration. But this time, Chicago was the team that pushed the chips in and walked away with a player they’ve had their eye on for years.
Bregman Delivered in Boston-and Cashed In
Let’s not forget what Bregman did in a Red Sox uniform. He came out of the gate last season red-hot, arguably playing the best baseball of his career before a quad injury sidelined him in May. He missed nearly two months, but when he returned, he picked up right where he left off.
Even with the time missed, he posted a 3.5 bWAR, a 128 OPS+, and racked up 46 extra-base hits. That’s not just solid production-it’s the kind of season that puts you in a strong negotiating position heading into free agency. And Bregman knew it.
Kennedy acknowledged as much: “We’re so grateful to Alex Bregman and what he meant to us. But look, in the end, when you have choices the way he did, you work really hard to be in a position to become a free agent and perform at that level. He chose a different path, and we wish him well.”
The Red Sox will get a chance to see Bregman again when the Cubs visit Fenway from September 25-27. That series already had some intrigue-it might carry even more weight now, depending on where both teams are in the standings.
Pressure Mounting in Boston, Optimism Rising in Chicago
There’s no sugarcoating it: losing Bregman just months after trading away Rafael Devers has left Red Sox leadership in a tough spot. The fan base is restless, and the team didn’t make a major offensive splash to offset those losses. For a franchise with Boston’s pedigree, that’s a hard sell.
Meanwhile, out in Mesa, things are feeling a lot different. Bregman’s arrival has injected fresh energy into a Cubs team that’s already thinking big. The front office made a statement with this signing: they believe this group is ready to contend, and they’re not afraid to spend to make it happen.
Bregman gives the Cubs a proven postseason performer, a steady glove, and a right-handed bat that can anchor the heart of the lineup. If he stays healthy, this move could be a game-changer-not just for the Cubs’ offense, but for their clubhouse culture, too.
The Red Sox may have stuck to their principles. The Cubs?
They got their guy. Time will tell who made the right call.
But for now, the North Side of Chicago is buzzing-and Boston is left wondering what could’ve been.