Why the Red Sox must pass on Alex Bregman for Vladimir Guerrero Jr. in 2025 free agency.

Chief Baseball Officer Craig Breslow is in the midst of his second offseason from the Boston Red Sox. He was more aggressive with this number of players available, highlighted by the acquisition of two starting pitchers. Ace Garrett Crochet was traded to the Chicago White Sox for four perspectives, including two of the Red Sox’s top ten minor leaguers. Right-hander Walker Buehler also signed a one-year deal.

Breslow is still actively working on trying to improve the roster, especially an offense that could use more pop. The free agent market has three star hitters in first baseman Pete Alonso, the third baseman Alec Bregman and outfielder Anthony Santander. There are other starting options and depth, and Boston could improve in those areas. Bregman in particular has been the subject of many rumors linking him to the Red Sox, as he is close with Buehler off the field.

As tempting as signing Bregman would be, that transaction could ruffle feathers. That would likely move current third baseman Rafael Devers to first base, something he would do but doesn’t want to now. Alonso wouldn’t fit the schedule the Red Sox are trying to stick to, but man also known as “Vladdi” bi. Furthermore, he would be an upgrade on current first baseman Triston Casas. Bregman may not be an upgrade on Devers. So in reality, it would make more sense for Boston to wait for the current Toronto Blue Jay to hit free agency, right?

Devers was the heart and the soul of the Red Sox the last few seasons. Especially after Xander Bogaerts left in free agency two years ago. He became one of the key leaders of the club house and is a player that many peers look up to. Moving him to first base to accommodate Bregman wouldn’t be a bad idea, and it would upgrade first base offensively. However, the defensive punch that the position could make up for a good portion of the offensive advantages.

This is not to say that Bregman wouldn’t be good. Guerrero Jr. would simply be better. Boston already has a deep Latino contingent (I remember Devers, starting pitcher Brian Bello and utility man Ceddanna Rafael), and Vladdi would come to a park he already knows well. His time with the Blue Jays prepared him for what a pressure cooker Beantown could be. He is already an established star who has received a lot of criticism. Those experiences should prepare him for what he would face as a resident of Fenway Park.

Whether it’s Bregman now, Guerrero Jr. next offseason, both, or neither, Red Sok still needs to improve. Finding good hitters to exploit Fenway can be difficult. It is a park that has challenged many of the best players and defeated them. That’s why waiting for Vladdi to hit the market next offseason (or even during the season) could be the right choice for Breslov and Boston. For a team looking to find a way back to October glory, it would be worth waiting just a little longer for the right example to walk through the door.