Many reporters and insiders around MLB foresee a reunion between free agent third baseman Alex Bregman and the Boston Red Sox for the 2026 season and beyond. After one season, it's clear the veteran is an ideal fit in Boston. He's also the best all-around third baseman on the free agent market, and the Red Sox need his skillset after trading Rafael Devers in June.
Multiple teams have been tabbed as a good fit for Bregman, and his market could be bigger than last year's since teams saw his impact in Boston. The Detroit Tigers were one of the finalists for his services last winter — Bregman even said he believed he would sign there until his contract with the Sox was confirmed — and they could resume their pursuit this winter.
If Detroit has any interest in keeping Tarik Skubal beyond the 2026 season, signing Bregman could help. The two-time American League Cy Young Award winner sang Bregman's praises to Chris Cotillo of MassLive.
“He’s a great player,” Skubal said at the November 13 MLB Awards. “I’d love to play with him, obviously. Hopefully, we can do it again (pursue him) this year. I know he’s a free agent again. I’d love to be teammates with him. He’s a great player and he’d bring a lot to our club, for sure.”
Tarik Skubal's hopes to play with 2025 Red Sox Alex Bregman could pull free agent to Detroit
Skubal's endorsement could be devastating for the Red Sox's pursuit of a reunion with Bregman. Not only could the Tigers be even more aggressive in Bregman's market than they were last winter, but Bregman could be more interested in signing with them after finding out what Skubal thinks of him.
Detroit could have a chip on its shoulder after Bregman opted to sign with Boston instead last winter. The Tigers offered him a six-year, $171.5 million deal, but the third baseman accepted a more flexible deal with a higher average annual value from the Red Sox. The Tigers could try even harder to sign him this go-round, or avoid him entirely to prevent dipping into their already way-too-small Skubal extension fund.
Boston and Detroit are at similar points in their contending windows. The Red Sox have an ace and Cy Young contender of their own in Garrett Crochet, their top prospects have reached the majors and, rumor has it, they finally could be willing to spend big to win. The Tigers have an ace, their top prospects are expected to break into MLB within the next year, but they're not big spenders and Skubal isn't under contract long-term, unlike Crochet. After Skubal leaves (and most believe he will), the Sox will be in a better place.
Even with Skubal's praise, the Red Sox still have just as good a chance, if not better, at signing Bregman. Money matters, though, and Boston knows that after beating Detroit for Bregman once. The Sox should do everything they can to reunite with their 2025 third baseman because Skubal's endorsement could be hard to beat.