Free agent third baseman Alex Bregman will certainly go down as one of the best players of his generation.
The former Houston Astros and Boston Red Sox infielder is a two-time World Series champion, collecting three All-Star appearances, and was the MVP runner-up in 2019.
Bregman departed the Astros last offseason for a new start. He signed with the Boston Red Sox on a contract worth three years and $120 million that included opt-outs after each season.
$20 million of his annual salary, however, was deferred. This meant that of the $40 million in AAV that Bregman was signed for, he only made half in the 2025 season. Starting in 2035, he will receive $2 million in annual payments over the course of the following ten years.
Weirdly, Bregman has secured a salary for himself in his post-baseball career. This move by him and agent Scott Boras now sets him up for 2026 and beyond.
Long-term contract
Bregman opted out of his deal with Boston in an effort to obtain a long-term contract. He was seeking this caliber of deal last offseason but was unsuccessful.
The veteran third baseman seems willing to take less on a year-by-year basis to make this happen. Chances are, this will be the last big contract of his baseball tenure.
With his future already set, Bregman can now be a little more selective with the club he signs with. Knowing his passion for the game, he will want to head to a team with a chance to compete.
Plan Bregman
If Bregman lands with a contending team on a long-term contract, he will officially have accomplished his goal.
However, if his market doesn’t pop as expected, and he is forced to take another short-term deal, I would consider his opt-out from Boston to be a mistake.
Returning on a short deal with anything less than $40 million in AAV would be a loss. At that point, the veteran would have been better off staying in Boston for another season.
Time will tell if he made the right choice. As it stands, Bregman is still in control of his destiny. I expect this to shake out in favor of the star third baseman.
Matt Watson Media 
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