It came as no surprise to reporters and fans when Alex Bregman opted out of the second two seasons of his three-year, $120 million deal with the Boston Red Sox. The third baseman coveted a long-term deal in free agency last winter, and when none of the teams in his market met his price, Bregman signed a high-average annual value bridge deal with Boston.

After reinforcing his reputation as a leader in the young Red Sox clubhouse and guiding the team back to the postseason for the first time since 2021, Bregman again seeks a long-term deal. The veteran told Chris Cotillo of MassLive that finding a team he can play with for the rest of his career is a “very high priority” this offseason.

Joel Reuter of Bleacher Report predicts his priorities will be met. In their free agent contract predictions piece from October 16, Reuter imagines that Bregman will land a five-year, $175 million contract. Reuter did not specify which team would give him said contract, but most insiders and reporters agree that a reunion with Boston is the most likely outcome of Bregman’s free agency.

Reuter’s proposed contract for Bregman looks strikingly similar to the deal he rejected from the Tigers last season. Detroit offered him six years and $170 million, but Bregman preferred to play in Boston on a higher AAV deal.

Bleacher Report’s proposed contract for Alex Bregman should be an easy ‘yes’ for the Red Sox

If Bregman and his agent Scott Boras approach the Red Sox with contract demands in the range of Bleacher Report’s estimate, it should be an easy sell for them. Not only is Bregman’s swing well suited to Fenway Park, he’s embraced Boston and quickly become a fan-favorite.

A five-year, $175 million deal would carry an AAV of $35 million, which is only $5 million less than Bregman made in 2025, when he played just 114 games due to a quad injury. Some fans may be hesitant to pay Bregman that kind of money because of his recent injury and age, but it’s in Boston’s best interest to bring him back.

After the Rafael Devers trade, the Red Sox don’t have another experienced third baseman in their system to take Bregman’s place if he walks in free agency. Bregman also brought leadership and over a hundred games of postseason experience to the Red Sox as one of the only trusted veterans on the roster. Trevor Story also has the opportunity to opt out of his contract, and if both he and Bregman leave, so does nearly all of the veteran leadership and the entire left side of the infield.

This year’s class of free agent third basemen is also rather underwhelming, and Bregman is the best available option. Eugenio Suárez, Yoán Moncada, Paul De Jong and Luís Urías are also among the options, but none meet the Sox’s needs as well as Bregman does.

The Devers trade has put all of his remaining contract money back in the Red Sox’s pockets, and they must spend it on Bregman and another free agent power bat. The other options at third base are underwhelming and not as well-rounded as Bregman, and he aligns well with the team’s goal to consistently return to the playoffs to compete for a World Series.