The Boston Red Sox have spent much of this offseason watching marquee free agents sign elsewhere, and while they did land All-Star lefty Ranger Suárez to bolster the rotation, the offense still feels a bat short. If Boston wants to make a real push in 2026, the upgrade may have to come via trade - and there’s a familiar front office face who could help make it happen.
The St. Louis Cardinals, now led by former Red Sox chief Chaim Bloom, could be a natural trade partner once again.
The name on the table? Brendan Donovan - a versatile All-Star who might be exactly what Boston’s lineup needs.
The Proposed Trade:
- Red Sox receive: UTIL Brendan Donovan
- Cardinals receive: LHP Payton Tolle (MLB No. 28 prospect), LHP Kyle Harrison, RHP Juan Valera
Let’s break this down.
Boston’s pitching depth is no joke. Even without Tolle and Harrison, the Red Sox have arms to spare.
Connelly Early, another left-handed prospect in the pipeline, is knocking on the big-league door and could help soften the blow of moving two young southpaws. That kind of depth gives Chief Baseball Officer Craig Breslow the flexibility to deal from a position of strength - and the need for an offensive upgrade makes Donovan a compelling target.
Now, Donovan isn’t just a plug-and-play guy - he’s a true Swiss Army knife. The 2023 All-Star can play all over the diamond, but he’d most likely take over at second base, a position that’s been a revolving door since Dustin Pedroia’s retirement. And he wouldn’t just be filling a need - he’d be elevating the position with a bat and glove that both play at a high level.
Last season, Donovan slashed .287/.353/.422 with 32 doubles, 10 homers and 64 RBIs in 118 games. That’s steady production from the left side, and while the Red Sox might prefer a right-handed bat to balance things out, Donovan brings enough to the table to make that a secondary concern. He’s a table-setter, a grinder, and the kind of player who fits Boston’s identity - gritty, smart, and versatile.
Financially, he’s a steal. At just $5.8 million for 2026 with another year of team control beyond that, Donovan offers both performance and value. That’s the kind of asset teams covet, and the kind Boston should be aggressive in pursuing - especially after missing out on free agents like Pete Alonso, Alex Bregman, and Bo Bichette.
If the Red Sox want to compete in a loaded AL East, they’ll need more than just arms. They’ll need lineup depth, defensive reliability, and a spark in the middle infield.
Brendan Donovan checks all those boxes. The cost - three promising arms - is significant, but it’s a price Boston can afford to pay.
And if they do pull the trigger, the next step is clear: don’t let Donovan get away. Lock him up before he hits free agency. Because if he brings his Gold Glove defense and All-Star bat to Fenway and keeps producing, Donovan could be a long-term solution - not just a short-term fix.