The Red Sox and Cardinals can’t seem to stay out of each other’s orbit this offseason. First it was Sonny Gray.
Then Willson Contreras. And now, just days before Christmas, the two clubs are back in talks-this time with Brendan Donovan in the spotlight.
It’s become clear that Boston’s front office has a blueprint this winter: raise the floor, stabilize the roster, and bring in players who offer versatility and consistency. They’re not swinging for the fences with splashy, headline-grabbing moves. Instead, they’re targeting guys who bring structure-players who can plug multiple holes and bring a sense of calm to a roster that’s seen its share of turbulence in recent years.
That’s where Donovan comes in.
According to league sources, the Red Sox and Cardinals have discussed a potential trade centered around the 2023 All-Star. Donovan’s appeal is obvious.
He can play second base, slide into the outfield, and give you quality at-bats no matter where he’s penciled in. That kind of flexibility is gold for a team like Boston, which still hasn’t locked down its middle infield and could use a player who can wear multiple hats without sacrificing performance.
But Donovan isn’t just a utility guy. He’s a high-contact hitter with excellent plate discipline and several years of team control ahead of him.
That combination makes him a much pricier asset than Gray or Contreras-and that’s why the talks are ongoing rather than done. The Red Sox love the fit, but the cost?
That’s the big question. Are they willing to part with the kind of young talent it would take to pry Donovan loose?
From the Cardinals’ perspective, moving Donovan would be a clear signal that they’re not just tweaking around the edges-they’re committing to a real rebuild. Trading Gray and Contreras already hinted at a shift, but Donovan is a homegrown, controllable piece.
If he’s on the move, the message is unmistakable: St. Louis is tearing it down to build it back up.
The recent Contreras deal already showed how far the Cardinals are willing to go. On December 21, ESPN’s Jeff Passan reported that the veteran catcher was traded to Boston in exchange for pitchers Hunter Dobbins, Yoaner Fajardo, and Blake Aita. The Red Sox are also taking on $33.5 million of Contreras’ remaining contract-a significant financial commitment that underlines how serious they are about reshaping this team.
Contreras brings a veteran presence behind the plate and a bat that still has plenty of pop. He’s not a perfect player, but he fits the mold Boston’s been targeting: experienced, steady, and capable of helping right away. Add in the earlier acquisition of Sonny Gray, and the Red Sox have already made two notable additions from the Cardinals’ roster.
Meanwhile, St. Louis is clearly leaning into a reset.
They’re offloading contracts, stockpiling arms, and signaling a shift toward youth and long-term planning. That’s not always an easy sell for a fan base used to competing every year, but the moves they’ve made suggest this isn’t just a soft reboot-it’s a real pivot.
And while the Red Sox were once rumored to be in on Ketel Marte, USA Today’s Bob Nightengale recently reported that Boston has closed the book on that pursuit. That only reinforces the idea that they’re not chasing stars-they’re building a roster with balance, depth, and flexibility.
So, what’s next? If the Red Sox do manage to land Brendan Donovan, it would be another calculated step in a winter that’s been more about precision than flash. And if the Cardinals move him, it’ll mark a turning point in how they’re choosing to reshape their future.
Same teams. Same winter. But the stakes just keep getting higher.