Chief baseball officer Craig Breslow is in the middle of his second offseason in charge of the Boston Red Sox. He's been more aggressive with this crop of available players, highlighted by the acquisition of two starting pitchers. Ace Garrett Crochet came over in a trade with the Chicago White Sox for four prospects, including two of the Red Sox' top ten minor leaguers. Right-hander Walker Buehler came aboard on a one-year deal as well.
Breslow is still actively working on trying to improve the roster, particularly an offense that can use more pop. The free agent market features three star hitters in first baseman Pete Alonso, third baseman Alex Bregman and outfielder Anthony Santander. There are other starting and depth options as well, 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's close with Buehler off the field.
As tempting as signing Bregman would be, that transaction might ruffle some feathers. It would likely cause current third baseman Rafael Devers to first base, something he would do but would prefer not to right now. Alonso wouldn't fit the timetable that the Red Sox are trying to stick to, but the man also known as “Vladdy” would. Furthermore, he'd be an upgrade on current first baseman Triston Casas. Bregman might 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, wouldn't it?
Would Vladimir Guerrero Jr. be a better fit with Red Sox?
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Devers has been the heart and soul of the Red Sox the last few seasons. Especially after the departure of Xander Bogaerts in free agency two years ago. He has become one of the clubhouse's key leaders 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 hit that the position would take might offset a good amount of the offensive benefits.
This isn't saying that Bregman would not be a good fit. Guerrero Jr. would just be better. Boston already has a deep Latino contingent (Devers, starting pitcher Brayan Bello and utility man Ceddanne Rafaela come to mind), and Vladdy would be coming to a park that he already knows well. His time with the Blue Jays has prepared him for what the pressure cooker of Beantown could be like. He's already an established star that has taken plenty of criticism. Those experiences should prepare him for what he would face as a home resident of Fenway Park.
Whether it's Bregman now, Guerrero Jr. next offseason, both of them, or neither, the Red Sox still need to improve. Finding good hitters to take advantage of Fenway can be tough. It's a park that has challenged plenty of the majors' best and beaten them. That's why waiting for Vladdy to hit the market next offseason (or even during the season) might be the right choice for Breslow and Boston. For a team looking to find its way back to October glory, waiting just a little bit longer for the right fit to come through the door would be worth the wait.
