Alex Bregman chose to bet on himself.
Rather than opting in to his contract for the next two seasons with the Boston Red Sox, Bregman opted out and became a free agent.
Now, he gets to try to outdo the deal he negotiated last offseason, which was for three years and $120 million but a lot of deferred money.
ESPN's Kiley McDaniel projects Bregman will beat that mark with a five-year contract worth $160 million.
McDaniel doesn't predict a team outcome, but that's money that the Red Sox could afford, or someone like the Detroit Tigers.
"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 writes. "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."
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Bregman did battle injury a bit in 2025, but he was his standard consistent self when on the field.
He'll turn 32 years old in March, alluded to by McDaniel above, which might be the only major concern.
Otherwise, Bregman is a proven regular season and playoff performer who still gets the job done at the hot corner, too. That's going to earn him plenty of money.
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