The Boston Red Sox could be in real trouble. They needed clear upgrades in the lineup following the 2025 season, and only adding Willson Contreras won't make them a better team than they were last year.
Red Sox Nation still hopes for a long-term reunion with Alex Bregman, plus the addition of another marquee bat. Hope started to dwindle when Kyle Schwarber resigned with Philly, and then Pete Alonso went to a division rival in the Baltimore Orioles. At least when those two signed, not much had come out about Bregman's market, with fan interest turning fully to bringing him back.
Then, out of the blue, the Arizona Diamondbacks got involved in the Bregman sweepstakes. Reporting trickled in over a few-day span, with some insiders finding out that the Diamondbacks were willing to commit longer than the Red Sox, but others saying it was still a long shot.
Then, MLB insider Ken Rosenthal of The Athletic dropped a bomb: the Toronto Blue Jays had engaged with Bregman. While agent Scott Boras is known for leaking links to teams to force another's hand, this still comes as a major blow to the Red Sox.
The Red Sox's lack of commitment to Alex Bregman might be leading him into the arms of the rival Blue Jays
Blue Jays officials have been in recent contact with Scott Boras about Alex Bregman and are showing interest, according to @Ken_Rosenthal. pic.twitter.com/50gkiQAlEr
— Gordo (@BOSSportsGordo) December 21, 2025
Boston has already lost one of their main offseason targets, Alonso, to a division rival. Now, the reigning AL champs are courting the player who got the Red Sox over the edge and into the playoffs.
The Blue Jays have already given out a mega contract this winter when they gave Dylan Cease a seven-year, $210 million contract. Toronto has shown a willingness to spend over the last few years, and it doesn't come as a surprise that they are now checking in on a player who has never missed the playoffs.
On the other side, the Red Sox seem to be falling behind in their own division. Every other team in the AL East has made moves via free agency and trades; the Red Sox have only made trades so far. Craig Breslow promised Red Sox fans a lot this winter, and so far, he has underdelivered.
Red Sox fans were rightfully upset when Alonso ended up in Baltimore. It was a player who fit everything Breslow described when talking about their offseason needs, and then it came out that the Red Sox were lower in money and years than Baltimore. If Bregman were to stay in the AL East but be on another team, fans may riot on Jersey Street.