Alex Bregman has decided to bet on himself.
Instead of opting in to remain under contract with the Boston Red Sox for the next two seasons, Bregman chose to opt out and enter free agency. That move gives him the opportunity to top the three-year, $120 million deal—with significant deferred money—that he secured last offseason.
According to ESPN’s Kiley McDaniel, Bregman is projected to surpass that figure and land a five-year deal worth around $160 million. McDaniel didn’t specify which team might sign him, but noted that clubs like the Red Sox or the Detroit Tigers have the financial flexibility to make such an offer.
“Age is a massive factor in the math teams do to set the years and price they’re willing to pay to sign free agents, so five years is probably where things land if Bregman ends up getting a longer-term deal to his liking,” McDaniel wrote. “I think teams with real interest would be fine with a roughly $30 million AAV at a four- or five-year term. My best guess is that negotiations will end up just above that because Bregman is the most consistent option (at least 14% above league average as a hitter every year of his career) of the hitters behind Kyle Tucker, with real age, defensive or consistency questions hindering the other hitters in contention for this kind of payday.”
Despite battling some injuries in 2025, Bregman remained his usual steady self when healthy. He turns 32 in March, which could be the only real concern for teams, but his track record—both in the regular season and postseason—combined with his continued strong play at third base, should make him one of the more sought-after free agents this winter.