The Boston Red Sox have stopped dishing out massive free agent deals in the last half decade or so. Some of that has been due to money tied up in long-term extensions for homegrown stars, while John Henry's divided focus has left him more reticent to spend at the levels he did in the past.
But the Red Sox aren't exactly a small-market team, and in addition to the mountain of cash the Rafael Devers trade freed up, they're shedding a good deal of money from the books, which should give them plenty of room to throw their weight around this offseason.
One MLB insider believes that will lead Boston to chase first baseman Pete Alonso. Like Alex Bregman, Alonso was left out in the cold last winter, forced to return to the New York Mets on a pillow contract. Also like Bregman, he's coming off a stronger 2025 campaign than how he performed in 2024, and will no longer have the weight of the qualifying offer on his market.
Alonso won't come cheap. Even more than Bregman, he's motivated to land a big payday after he rejected the Mets' five-year, $158 million extension offer back in 2023. In order to avoid further egg on his face, he'll need to top that mark this winter, and is said to be seeking at least a seven-year deal.
MLB insider Mark Feinsand's logic for the Red Sox's pursuit of Pete Alonso will leave you scratching your head
The money coming off Boston's books thanks to Devers leaving town and Bregman's contract expiring (among other players) is why Mark Feinsand believes the Red Sox will pursue Alonso and ultimately could be the team to lavish him with the contract he so desperately seeks.
Alonso is one of the league's most prolific power hitters, and would fit the middle of the order thumper Craig Breslow claims to desire.
It would seem that an Alonso signing would mean the end of Bregman in Boston, meaning the shell game would finally be coming to an end with Breslow essentially exchanging Devers for Bregman and then swapping Bregman for Alonso.
And while Alonso is a very good player, the logic doesn't really hold water. Of the three, Alonso is the biggest bopper, but he's also the worst overall player.
Bregman won fans over by playing stellar defense while providing balanced production at the plate. Devers' glove had clearly become a problem, but Alonso's fielding prowess is equally bad at an easier position. Devers also might not have 50+ homer power, but his 30+ homer pop, combined with stellar contact and on-base skills, make him a more well-rounded and flat-out better hitter than Alonso.
Alonso could still make sense for Boston, but he would need to be in addition to Bregman or a similarly talented player. If not, Boston will have just burned through two talented players in order to land a good but inferior option, all while saving exactly zero money in the process.