Alex Bregman gets congratulations after hitting a home run. His contributions to the team happened as much on the field as in the dugout. (Photo By Winslow Townson/Getty Images)
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During the World Series it was reported that Alex Bregman intended to opt out of the last two years of the three-year deal he signed with the Boston Red Sox prior to last season. He made it official just a few days later.
As a reminder, after becoming a free agent for the first time following the 2024 season, Bregman sought a long-term contract with various clubs. The Detroit Tigers offered him six years, $171.5 million, and a chance to be reunited with his former Astros manager, A.J. Hinch. He turned down that $28.6 million/year offer.
The Houston Astros, hoping to keep their nine-year veteran in the fold, offered six years and $156 million. Bregman, obviously, turned that one down as well.
When the music stopped, the third baseman elected to go with a short-term, high average annual value (AAV) deal. He landed in the Back Bay, on a three-year, $120 million deal. But there were all sorts of bells and whistles. While the AAV was $40 million, Bregman agreed to defer $20 million per season. The deal also included opt-outs after the first and second years, thus providing the player with security and optionality. His agent, Scott Boras, was gleeful about having these two cudgels available to him when I spoke with him about Bregman’s situation.
When MLB calculated the actual terms, it had a present value of three years, $90 million. But, even at the lower valuation, the contract had a higher AAV than either of the offers from Detroit or Houston. And now, with his opt-out, Bregman will still be receiving $20 million from Boston spread out from 2035 to 2046 – call it an annuity.
Boras was quick to point out that with this decision, Bregman is an unrestricted free agent for the first time. Last year, Houston made him a Qualifying Offer, which meant that an acquiring team had to pay with a draft pick and international bonus pool money, thus potentially limiting his market and marketability. (The Red Sox gave up the 54th pick in the draft and $500,000.) But because a player may only be given a Qualifying Offer once in his career, the Red Sox have no recourse, and Bregman has total control.
By all accounts, Bregman had a great season in Boston, which was unfortunately limited by a quad injury that forced him to miss 43 games between May and July. He still accrued 3.5 bWAR (which was his lowest showing 2021), and slashed .273/.360/.462, with 18 home runs and 28 doubles. But equally if not more important, was what he brought to the clubhouse and the dugout. He provided a veteran presence and the voice of experience to the young Red Sox players. Stories are legion of him dissecting pitchers and pitches and providing guidance after each at-bat.
Alex Bregman leaves the field after suffering a quad injury in a game against the Baltimore Orioles on May 23, 2025. (Photo by Brian Fluharty/Getty Images)
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When asked to describe what makes Bregman so special, Boras said that he is one of the most unique players in history, who acts as a manager in the dugout. The agent said his knowledge is that of a player in his forties, not his early thirties. He then, ostensibly for his acumen and will to win, compared Bregman to Pete Rose. He claimed that the diminutive third baseman has a spark for baseball and is driven by what he can give to his teammates. While those may sound like the self-serving words of a representative trying to secure another nine-figure deal for his client, here is what Boston’s chief baseball officer and former big league pitcher, Craig Breslow, had to say:
“At the same time, I will not miss an opportunity to talk about his contributions on the field, in the clubhouse, to the coaching staff, to the front office. Every conversation we’ve had, I think I’ve learned something about how his impact and influence have rubbed off on his teammates.”
The Athletic’s Jim Bowden predicts that Bregman will get a new six-year deal, worth $182 million (approximately $30 million per season). CBS Sports’ RJ Anderson aims higher, with $192 million over the same number of years. It may be the case that Bregman holds out for that elusive $200 million number he was seeking last winter. And because he has shown a willingness to entertain deferments, there is a very good chance that he could get that figure, while pushing a bunch of it into the future (yet another annuity).
There are many teams that could use Bregman’s bat (career .272/.365/.481), his glove (Gold Glover in 2024), and his brain (for all of the reasons set forth above). Will Detroit jump back in and up their offer from last year? Will the Cubs pony up to the point of being uncomfortable after they (ultimately) lose out on Kyle Tucker? Will the Red Sox decide that this is as player simply too valuable to lose? Only time (and, with Boras, it might be a LONG time) will tell.