The Boston Red Sox were recently accused by MLB insider Ken Rosenthal of playing chicken with free agent infielder Alex Bregman.
The third baseman's market is small — just Boston and the Detroit Tigers are rumored contenders as of this writing — but the Sox are reluctant to meet his demands. The five to seven years Bregman seeks is too far out of Boston's (minuscule) comfort zone, and it seems determined to wait out his market so he lessens the length of his desired contract.
The Red Sox's waiting game may already be coming back to bite them as another potential suitor enters the race to sign Bregman. His agent, Scott Boras, has had "casual discussions" with the Cubs about signing a short-term deal in Chicago if his market falls through.
Bruce Levine of 670 The Score reported that a potential fallback deal with the Cubs could be a three-year arrangement with opt-outs after the first two seasons. There has been no smoke about a similar contract structure being made available to the Red Sox, but based on their reluctance to sign long-term deals, Bregman's potential backup contract with the Cubs sounds like their ideal union.
Alex Bregman could turn to Cubs for short-term deal if Red Sox won't meet his contract demands
Alex Bregman could reportedly be a fit for the Cubs if he shifts his focus to a shorter-term deal.#MLBNHotStove pic.twitter.com/B3eEm09kZh
— MLB Network (@MLBNetwork) January 15, 2025
In his Jan. 10 piece about Boston holding out on Bregman, Rosenthal pointed out that it has won the long game before. The Red Sox refused to sign J. D. Martinez in 2018 until spring training began and he reduced his asking price from $200 million to $110 million. But that was before they stopped spending money on free agents, traded away their best player and a future Hall of Famer and forfeited their reputation as a big-market team. The Red Sox are not the marquee destination they were seven years ago, and it's no one's fault but their own, just as it will be if they whiff on Bregman.
A right-handed bat is one of the last things the Red Sox need to balance their lineup this offseason. Bregman, a well-established leader with a history of success at Fenway Park, is the best remaining option for Boston on both sides of the ball. The Red Sox have plenty of payroll flexibility to sign him for whatever amount he wants but continue to stand in their own way of success.