The Boston Red Sox made their first big move of the winter last week by acquiring Chicago White Sox ace Garrett Crochet via trade. Doing so also prevented the New York Yankees from landing the southpaw. Could they beat out the Bombers again for free-agent slugger Anthony Santander?

Now that outfielder Juan Soto has signed with the New York Mets, the Yankees are looking for ways to replace him in their lineup. The Bombers have reportedly shown interest in Santander. They’re quite familiar with the 30-year-old switch-hitter, as he’s spent the last eight years in the American League East with the Baltimore Orioles.

Santander had a career season in 2024. He was named an All-Star for the first time and won his first Silver Slugger Award after hitting 44 home runs with 102 RBI and 91 runs scored with a .814 OPS. A return to Baltimore doesn’t seem likely after the Orioles signed outfielder Tyler O’Neill to a three-year deal.

Could he bypass the Bronx and land in Beantown? FanSided’s Michael Brakebill is predicting that will happen. “Boston still needs another starter to complete an elite rotation, but they also need an outfielder. Switch-hitting Anthony Santander feels perfect for hitting balls over the Green Monster or wrapping them around the pesky pole,” Brakebill wrote. “He blasted 44 homers in 2024 and given his price range and Baltimore signing O’Neill, Santander will find a new home this winter.”

Spotrac is projecting a five-year, $89 million contract for Santander. But now that teams who lost out on Soto are getting involved, his next deal could reach nine figures. Bleacher Report’s Kerry Miller is predicting Santander will sign a $100 million guarantee.