Alex Bregman is back on the market-and this time, he’s playing for keeps.
Just a year after inking a three-year, $120 million deal with the Boston Red Sox, Bregman opted out of the contract’s remaining two years. That move, built into the original deal via an opt-out clause, signals a clear shift in what the two-time All-Star is looking for in his next chapter: long-term security and a cleaner financial structure.
Let’s break that down. The Red Sox deal included significant deferred money, spreading out payments well beyond the life of the contract.
That kind of structure can be appealing in some cases, but Bregman’s decision to walk away after just one season suggests he’s looking for something more straightforward-and more stable. He’s not chasing another short-term, high-AAV (average annual value) deal with strings attached.
He’s aiming for a long-term commitment.
According to recent reporting from ESPN’s Jeff Passan, Bregman-along with fellow free agent Cody Bellinger-is shifting away from the short-term, opt-out-heavy contracts that have defined recent offseasons for many top-tier players. Instead, both are seeking multi-year deals that offer security and staying power. In Bregman’s case, he’s reportedly targeting a six-year deal.
And honestly, that tracks. This is likely Bregman’s last big swing at free agency.
He’s 31, still a productive hitter, and a proven postseason performer. He’s not just looking for a team-he’s looking for a home.
What works in his favor? Supply and demand.
The market is thin when it comes to elite bats, and Bregman’s combination of experience, leadership, and offensive consistency makes him one of the most attractive position players available. There are teams out there that not only need a middle-of-the-order presence but are also willing to pay for one.
Right now, the Chicago Cubs and Detroit Tigers are reportedly leading the chase. The Red Sox are still in the mix, too-they’d like him back-but they may need to sweeten the pot to make that happen.
One potential edge for any team? Go longer.
Add a year or two more than the competition, and you might just land him.
That’s the key to this negotiation. Bregman isn’t just looking for the biggest number-he’s looking for the right structure. The team that’s willing to lean into that and offer a deal that stretches into the six-year range will likely have the inside track.
So whether it’s the Cubs, Tigers, Red Sox, or a team waiting in the weeds, one thing’s clear: Bregman is going to land a significant contract. The only question now is which front office steps up with the years-and the dollars-to make it happen.