Many reporters and analysts predict that the Boston Red Sox will reunite with free agent third baseman Alex Bregman after his 2025 season with the club. Not only are his years of experience well-suited to a young Boston team, he’s the best third baseman available on the free agent market, and the Red Sox need to go for elite options while their contending window is wide open.
Since Bregman is the best free agent third baseman available this offseason, his market could be extra competitive. The Detroit Tigers could jump into the fray after losing out on the veteran last season, and recent comments about Bregman from their ace, Tarik Skubal, could cause them to ramp up their chase.
“He’s a great player,” Skubal said of Bregman 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.”
Skubal will be a free agent after the 2026 season, barring an unforeseen contract extension. If signing Bregman gives Detroit an advantage to help keep the two-time Cy Young Award winner around, it just might pull the trigger. The same argument could be made for the Red Sox to bring Skubal to Boston.
Not only do the Red Sox need Bregman after trading their homegrown third baseman to the Giants in 2025, he could incentivize Skubal to sign an extension in the event he's traded to them. Boston has been linked to Skubal in trade rumors, and it has more than enough top prospects and big leaguers to send to Detroit to make a deal.
Red Sox reuniting with Alex Bregman could make Tarik Skubal more likely to want to play with Boston
If the Sox do trade for Skubal — which is easier said than done, given his status as the best pitcher in the American League in the last two seasons — having Bregman under contract long-term could convince him to sign an extension. Having Roman Anthony and Garrett Crochet locked down for the next few years certainly won't hurt, either.
Even if the Red Sox don't pull off a trade for Skubal, he'll be a free agent the following winter. Only the biggest market teams will be in on the ace, as he has the potential to become the highest-paid pitcher of all time. Having Bregman locked down could motivate him to sign with the Sox.
Boston still hasn't proven that it's committed to signing top-tier free agents. It didn't sign Bregman until he was desperate, in February of 2025, and only managed to keep hold of him for a year until he hit the open market again. The Red Sox have also not proven their willingness to compete with other big market teams for elite free agents, like Juan Soto, and Skubal's contract is sure to be in the $300-400 million range.
Other non-financial factors could also impact the 2026-27 offseason. The collective bargaining agreement between MLB and the MLB Players Association is set to expire after the 2026 campaign, and many experts are forecasting a lockout that could shorten the 2027 season. Front offices could be hesitant to commit to megadeals if there's a chance they won't get the full value out of them.
The Red Sox need Bregman back, and re-signing him could come with the added bonus of top-tier free agents wanting to join him. The hope that Bregman might lure Skubal to Boston is delusional, but that doesn't make it impossible.