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That was reported during the World Series Alex Bregman planned to opt out of the final two years of the three-year contract he signed with the Boston Red Sox prior to last season. Just a few days later, he made it official.
As a reminder, after Bregman first became a free agent after the 2024 season, he sought long-term contracts with several clubs. The Detroit Tigers offered him six years, $171.5 million, and a chance to reunite with his former Astros manager, AJ Hinch. He turned down that $28.6 million per year offer.
The Houston Astros, hoping to keep their nine-year veteran in the fold, offered six years and $156 million. Of course, Bregman also rejected that.
When the music stopped, the third baseman opted to go with a short-term deal with a high average annual value (AAV). He landed in the Back Bay on a three-year, $120 million deal. But there were all kinds 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, giving the player security and options. His agent, Scott Boras, was happy to have these two bats at his disposal when I talked to 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 the Detroit or Houston bids. And now, with his opt-out, Bregman will still receive $20 million from Boston, spread from 2035 to 2046 – call it an annuity.
Boras was quick to point out that this decision marks Bregman as an unrestricted free agent for the first time. Last year, Houston made him a qualifying offer, which meant an acquiring team had to pay with a draft pick and international bonus money, potentially limiting his market and marketability. (The Red Sox gave up the 54th pick in the draft and $500,000.) But because a player can only receive a qualifying offer once in his career, the Red Sox have no recourse and Bregman is in complete control.
By all accounts, Bregman had a great season in Boston, which was unfortunately curtailed by a quad injury that forced him to miss 43 games between May and July. He still posted 3.5 bWAR (which was his lowest mark in 2021) and slashed .273/.360/.462, with 18 home runs and 28 doubles. But just as important, if not more so, was what he brought to the clubhouse and dugout. He provided a veteran presence and voice of experience for the young Red Sox players. There are countless stories of him dissecting pitchers and pitches and providing guidance after each at-bat.
Alex Bregman leaves the field after suffering a quad injury during a game against the Baltimore Orioles on May 23, 2025. (Photo by Brian Fluharty/Getty Images)
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When asked what makes Bregman so special, Boras said he is one of the most unique players in history, acting as a manager in the dugout. The agent said his knowledge is that of a player in his 40s, not his early 30s. He then compared Bregman, ostensibly because of his acumen and will to win, to Pete Rose. He claimed that the diminutive third baseman has a knack for baseball and is driven by what he can give to his teammates. While this may sound like the self-serving words of a sales rep trying to land another nine-figure deal for his client, here’s what Boston’s chief baseball officer and former big league pitcher Craig Breslow said: had to say:
“At the same time, I won’t miss an opportunity to talk about his contributions on the field, in the clubhouse, to the coaching staff, to the front office. From every conversation we’ve had, I think I’ve learned something about how his impact and influence have rubbed off on his teammates.”
The Athletics Jim Bowden predicts that Bregman will receive a new six-year contract worth $182 million (about $30 million per season). CBS Sports’ RJ Anderson aims higherby $192 million over the same number of years. Bregman may hold on to that elusive $200 million figure he was looking for last winter. And because he has shown a willingness to defer, there is a very good chance that he can get that amount while pushing some of it into the future (another annuity).
There are a lot of teams that could use Bregman’s bat (career .272/.365/.481), his glove (Gold Glover in 2024), and his brain (for all the reasons explained above). Will Detroit go back on last year’s offer? Will the Cubs go so far as to become uncomfortable after (eventually) losing Kyle Tucker? Will the Red Sox decide that this is simply too valuable as a player to lose? Only time (and with Boras it can take a long time) will tell.
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