For Alex Bregman, this winter has been a case of déjà vu all over again.
The third baseman has been seeking a new contract since he opted out of the final two years and $80 million of his deal with the Red Sox, hoping to land the long-term contract that evaded him a year ago.
Last winter, Bregman pivoted from a long-term ask to a shorter-term deal with a high average annual value, ultimately signing a three-year, $120 million deal with the Red Sox on Feb. 15. That deal, which included $60 million in deferrals and a pair of opt-outs, allowed Bregman to test free agency again this offseason, though a long-term deal hasn’t presented itself to date.
If that trend continues, could Bregman shift his focus to a similar short-term, high-AAV deal for a second straight year?
“Does he want the security of more years, or is the AAV what’s important to him?” one source asked. “He might find a long-term deal, but it won’t pay him [the AAV] he got last year.”
Bregman hit 18 home runs with 62 RBIs and an .821 OPS in 114 games during his first year in Boston, missing seven weeks in the middle of the season with a right quad strain. His numbers prior to the injury (11 homers, 35 RBIs, .938 OPS in 51 games) were superior to those after he returned (seven homers, 27 RBIs, .724 OPS in 63 games), but a healthy Bregman remains among the top offensive players at his position.
Bregman will turn 32 during the opening week of the 2026 season, so it remains to be seen how many years a club — the Red Sox or otherwise — will be comfortable giving him, but after receiving a qualifying offer a year ago, he doesn’t have to deal with that potential impediment of Draft-pick compensation in free agency this winter.
The Blue Jays and Diamondbacks have been perceived within the industry as the two biggest threats to a Red Sox reunion, though Toronto’s recent signing of Japanese infielder Kazuma Okamoto likely takes the Jays out of the mix.
That leaves Arizona as a major player in the Bregman sweepstakes, though that could change if the Diamondbacks take Ketel Marte off the trade market. While a number of teams continue to monitor Bregman’s market, multiple Major League executives believe the three-time All-Star will ultimately return to Boston.
“He was a perfect fit in Boston, both on and off the field,” an American League executive said. “They know him, and he knows them. As always, it’s probably going to come down to money.”
A recent ESPN report suggested that the Red Sox “have signaled a willingness” to give Bregman a big deal in the range of the six-year, $171.5 million offer the Tigers made the third baseman a year ago.
Boston loved the leadership role Bregman provided during his first season with the Red Sox — one which can’t be overlooked given the number of young players on the club, including Roman Anthony, Ceddanne Rafaela and Marcelo Mayer. And while Mayer is capable of playing third base if Bregman signs elsewhere, it would be just as easy to move the 23-year-old to second base, slotting Bregman back at the hot corner. Another option for the Red Sox would be to sign Bo Bichette to play second base, pushing Mayer to third.
The Cubs have also been interested in Bregman since last offseason, though sources believe Chicago is unlikely to be the highest bidder when all is said and done. Another AL executive won’t count out the Cubs, however, saying he sees Boston and Chicago as “the biggest players” for Bregman.
“He’s viewed as the ‘championship’ piece,” the executive said.
The Mets have been focused on adding an outfielder — Cody Bellinger and Kyle Tucker are the primary targets — but could enter the mix for Bregman if they’re unable to land either of them. Brett Baty is currently atop the depth chart at third base, but Bregman would be an upgrade at the position and help make up for the loss of Pete Alonso in the lineup.
If Bregman pivots from a long-term deal once again, could that bring other teams into the picture? The Tigers, who took a run at Bregman last winter, have retained interest in him, though they haven’t shown any indication that they would be willing to make the type of offer they did last year.
Detroit has a big decision to make in the coming year, with back-to-back AL Cy Young Award winner Tarik Skubal headed for free agency after the 2026 season. The Tigers could opt to tighten their belts, saving money in an attempt to re-sign Skubal next year or, if they believe they are destined to lose Skubal as a free agent, they could go all-in with a big move — such as signing Bregman — in an attempt to win this year.
