The Boston Red Sox won the Alex Bregman sweepstakes last offseason, but they had to give him a contract with an opt-out in it to land him. As a result, Bregman is a free agent again this winter after opting out of his deal.

Bregman should be one of the Red Sox’s top priorities this winter, but there are bound to be a few top teams in the sweepstakes to sign the star.

The Athletic’s Andy McCullough recently predicted Bregman would ditch the Red Sox and sign a deal with the Detroit Tigers this winter.

Boston Red Sox infielder Alex Bregman

“If the Tigers aren’t going to trade Tarik Skubal, then they should try to win the World Series with him,” McCullough wrote. “The market for Bregman heading into 2026 should be similar to the market for his services heading into 2025. Detroit’s infield is crowded, but you can make room for a player with Bregman’s talent.”

The Tigers need to try to win the World Series with Tarik Skubal on their roster. Going after a new deal for Skubal should be their top priority, but they also need to add talent like Bregman.

Bregman would fill a huge hole on the roster for the Tigers. He’d slot into the middle of the lineup for the Tigers, while being one of their best defenders.

It’s hard to imagine the Tigers outbidding the Red Sox by a lot, but Detroit has enough money to make it an interesting bidding war.

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