Red Sox Play Waiting Game with Alex Bregman Amid Free Agency Standoff

BOSTON — The Boston Red Sox appear to be playing a high-stakes game of chicken with free-agent third baseman Alex Bregman and his agent, Scott Boras, as the team weighs whether to make a significant investment in the two-time All-Star. The strategy mirrors the Red Sox’s approach seven years ago with another Boras client, J.D. Martinez, whom they signed in February 2018 after a prolonged negotiation.

Bregman, 30, is coming off a season in which his walk rate declined and his OPS+ dropped for the second consecutive year. Despite these concerns, he remains a valuable asset, boasting 99 games of postseason experience and the ability to transition from third base to second base. This flexibility could allow the Red Sox to keep Rafael Devers at third base, though the team’s interest in Bregman remains uncertain.

According to Mass Live, Red Sox manager Alex Cora and team president Sam Kennedy have advocated for signing Bregman, but some members of the baseball operations staff, including chief baseball officer Craig Breslow, are hesitant. The Red Sox have been burned by long-term contracts in recent years, including deals for Chris Sale, David Price, and Trevor Story, which have not panned out as hoped.

“I can tell you this ownership group feels urgency and hunger to improve and build upon this team to get back into the postseason,” Kennedy said in September. However, the Red Sox’s reluctance to spend big has frustrated fans, who booed ownership at recent fan events. The team’s Fenway Fest, replacing its traditional Winter Weekend, offers tickets starting at $85 for adults, including a voucher for a 2025 home game.

Bregman reportedly turned down a six-year, $156 million offer from the Houston Astros, seeking a deal that accounts for the income tax differences between Texas and other states. Boras, known for securing lucrative contracts for his clients, may push for a higher average annual value or opt-outs in any deal with the Red Sox. The Athletic’s Tim Britton predicts Bregman could land a seven-year, $189 million contract.

Meanwhile, the Red Sox have made modest moves this offseason, acquiring pitcher Garrett Crochet and signing free-agent pitchers Walker Buehler, Andrew Chafin, and Matt Moore. However, these additions have done little to quell concerns about the team’s competitiveness in a weakened American League. As the Red Sox continue to delay a decision on Bregman, the risk of another team swooping in remains a real possibility.

“If the Sox are playing a game of chicken with Boras, they had better win,” said Ken Rosenthal, senior baseball writer for The Athletic. “If their interest in Bregman is muted, they had better have a good reason.”