Red Sox Pegged as Early Favorite to Sign Blue Jays’ Vladimir Guerrero Jr. Next Winter

USA Today's Bob Nightengale added to that with insight of his own, reiterating his report from January that suggested Guerrero told his friends he would "love" to play in Boston.

The Red Sox are hovering right around the luxury tax threshold as it is, but they could have roughly $47M coming off the books if Walker Buehler, Lucas Giolito, Liam Hendriks and Aroldis Chapman all hit free agency. Alex Bregman – who Boston signed to a three-year, $120 million contract last week – could opt out and give the front office another $40 million to work with.

There is a scenario in which the Red Sox build an infield of Guerrero at first base, Bregman at second base, Rafael Devers at third base and Trevor Story at shortstop – until top prospect Marcelo Mayer is ready to take over at that position. Even if Bregman leaves, top prospect Kristian Campbell could take his place at second.

Either alignment would bump Triston Casas off first base, though. Casas could become a full-time designated hitter, but that role currently belongs to Masataka Yoshida, who is under contract through the 2027 season.

Poaching Guerrero from their division rival would therefore cost more than the $400-plus million contract he gets in free agency, as Boston would either have to part ways with a promising young first baseman in Casas or eat a chunk of Yoshida's contract in a potential trade. It also remains to be seen if Red Sox ownership would be willing to pay Devers, Bregman and Guerrero simultaneously – let alone starting pitcher Garrett Crochet, who they acquired in a blockbuster trade with the Chicago White Sox in December and have yet to extend past 2026.

The Mets and Yankees provide much cleaner landing spots for Guerrero, even if those are not his preferred destinations. Both New York teams could easy see their starting first basemen – Alonso and Paul Goldschmidt – walk in free agency, opening up a spot for Guerrero without too many moving parts.

On the other hand, if Guerrero really has his sights set on Boston, it's up to the Red Sox front office to make the necessary moves to make his dreams a reality.

Guerrero hit .323 with 30 home runs, 44 doubles, 103 RBI, a .940 OPS and a 6.2 WAR in 2024. He was named an All-Star for the fourth year in a row, finishing sixth in AL MVP voting and earning a spot on the All-MLB First Team for the second time in his career.

The 25-year-old has missed a grand total of 12 games over the last five seasons.