Even after Alex Bregman opted out of his contract, the prevailing assumption among reporters and insiders is that he'll return to the Boston Red Sox.
Bregman sought a deal in the six-to-seven year range last offseason, but couldn't find a team to meet both his length and price demands. He signed a three-year, $120 million bridge deal with Boston to test the water and it went well for both sides — Bregman embraced the city in multiple ways while serving as the veteran presence and leader the Red Sox needed to guide them back to the postseason.
The $40 million average annual value (AAV) of Bregman's deal with Boston beat out the six-year, $171.5 million that the Detroit Tigers offered him last winter, despite the certainty of a long-term deal. Bregman told Chris Cotillo of MassLive that finding a club he can call home for the rest of his career is of "very high priority" this offseason, so the Red Sox will have to be ready to cough up enough money to keep him in Boston long-term.
Bregman's contract demands haven't been revealed yet, as the offseason hasn't officially started, but it's likely that he still seeks a five or six-year deal to find his permanent home. The third baseman's counter offers to the Tigers throughout their contract negotiation process could reveal his ideal price — he and his agent, Scott Boras, asked for six years at $186 million with an opt-out after the first season or seven years at $200 million (per Evan Petzold of Detroit Free Press).
Red Sox pursuing Matt Chapman-like deal with Alex Bregman could be risky
The Red Sox may be hesitant to offer Bregman such contracts, however, partially due to their hesitance to spend on large deas. Bregman is also entering his age-32 season and only posted 114 games in 2025 due to a quad injury. After his six-week stint on the injured list, Bregman struggled to rebound offensively, and only batted .250/.341/.386 with just 17 extra-base hits in 61 games after the All-Star break.
Both Alex Speier of The Boston Globe and Tyler Milliken of WEEI suggested Matt Chapman's contract as a comparison to what Bregman could get. The third baseman signed a bridge deal with the San Francisco Giants in 2024, posted a rebound season, then signed a six-year, $151 million extension. Chapman is also a Boras client, and he signed his extension before his age-32 season. He posted a higher WAR (7.1 bWAR) than Bregman did in 2025 (3.5 bWAR) and he played in 40 more games than Bregman.
Chapman's contract carries an AAV of just over $25 million, and some may find it easy to argue that Bregman deserves the same due to the discrepancies in their performances on their respective bridge deals. It will be difficult to convince Bregman and Boras to accept such a deal due to the history that comes with Bregman's name — he's a perennial playoff contender, a three-time All-Star, a well-documented leader and winner, and a two-time World Series champion. The Red Sox also sacrificed a lot of their leverage when they traded Rafael Devers to the Giants in June, as they don't have another third baseman in their organization to take Bregman's spot if he were to sign elsewhere.
If Boston approaches Bregman with the same deal Chapman got, there's little chance he signs it based on his pedigree. Boras is known for holding out to get the absolute most money possible for his clients, and the Red Sox will need to get comfortable with overpaying for free agents. That's the only way they'll land any in this market, but they have more than enough money to do so.