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Boston Red Sox
Why not revisit the club that just brought in Sonny Gray? The Cardinals and Boston Red Sox are frequent trade partners, and Willson Contreras could make a lot of sense for them in a deal.
Tristian Casas is expected to return to their lineup in 2026, but after missing the 2025 season with a significant leg injury, they may want to bank on more dependable production at first base. With a flurry of left-handed bats already in their lineup between Casas, Roman Anthony, Jarren Duran, Wilyer Abreu, Masataka Yoshida, and Marcelo Mayer, adding a big right-handed bat like Contreras could be a big win for their offense.
The Red Sox seem very open to the idea of moving one of their outfielders to fortify their starting rotation even further this offseason. If they decide to move Duran, Abreu, or even Yoshida or Casas to get that pitching, that would further open up spots in their lineup for a bat. The type of arm they could acquire, especially if Duran or Abreu is involved, could make their rotation a major strength, and Contreras would be able to replace the lost offensive production.
For Contreras, Boston would represent an awesome landing spot for him. While he came to St. Louis to succeed Yadier Molina behind the plate, play for a historic organization, and consistently compete in October, the Cardinals have let him down big time since signing him here. Boston would present him with the kind of situation I think he thought he was going to have in St. Louis - playing meaningful baseball in front of an awesome fan base.
Contreras is a competitive guy, so I'd imagine he would thrive in the Red Sox-Yankees rivalry and love the idea of going head-to-head with the Blue Jays, Orioles, and Rays as well on his way to trying to return to the World Series. And on top of all of the talent Boston has right now, they still have a strong farm system that can afford to acquire Contreras and continue to supplement their core for the future.