It's looking more and more like Yankees will see Red Sox suffer in Alex Bregman chase

It's been a quiet offseason for the New York Yankees, but it's been a weird one for the Boston Red Sox. The Yankees' timeless nemesis went into the winter with some clear goals, with adding another front-line starter and acquiring a big-time slugger to join Alex Bregman at the top of the shopping list.

They haven't accomplished any of those goals. They went out and acquired Sonny Gray, who seethes pinstripe hatred, but to call the 36-year-old, coming off a 4.28 ERA campaign, a top-of-the-rotation starter is a stretch.

Boston also traded for Willson Contreras in what was a lopsided deal in their favor. Contreras is no doubt a good hitter, but with a single-season high of 24 homers in his career, he misses the mark as far as adding a true power source.

These moves, both coming via trade, are telling. Gray is in the final year of his deal with a mutual option for 2027. Contreras is signed through 2027 with a club option for 2028. These are short-term commitments, and in both cases, the St. Louis Cardinals kicked in some financial assistance.

That seems to be the Red Sox modus operandi this offseason. Short-term, moderate expenditures that preserve future flexibility seem to tickle their fancy. That's the opposite of what Bregman is seeking.

A top Alex Bregman suitor bowing out might benefit the Yankees and harm the Red Sox

According to Detroit Tigers insider Evan Petzold, Detroit isn't involved in the Bregman chase. That is somewhat surprising, as Detroit was the only club to step up to the plate with a long-term offer for Bregman last winter, though he ultimately asked for more money, leading to them balking and setting the scene for him to take the pillow contract with the Red Sox.

On the surface, one less horse in the race should help the Red Sox in their quest to retain Bregman's services, but in actuality, it only hurts their case.

Bregman will be more motivated than ever to get the security he desires, meaning if a team that isn't an ideal fit in his mind offers him something close, a la the Tigers last offseason, he won't hesitate to take it.

Going into his age-32 season, Bregman realizes that time isn't on his side. If he reads the market incorrectly again, he'll find himself in an even worse bargaining position next winter. On top of that, the cracks have started to show.

While Bregman's numbers were better in 2025 than they were in 2024, he missed nearly two months with a right quad strain. He was off to a scorching start, slashing .299/.385/.553 through 51 games before hitting the IL on May 23, but when he returned on July 11, he hit just .250/.338/.386 in the 63 games he played to close out the year.

Other teams like the Arizona Diamondbacks are lurking, as are the Chicago Cubs and Toronto Blue Jays, according to reports. All it takes is for one of them to get desperate (or aggressive) enough to give Bregman a long-term offer, and even if it's not quite what he wants, there's a good chance he jumps rather than betting on himself again in 2026.

For the Yankees, that means, despite a flurry of moves, a weaker Red Sox club to worry about in 2026.