The San Francisco Giants, a team with a gaping hole at second base and in dire need of making a major offseason splash appeared to be the favorite to acquire St. Louis Cardinals second baseman Brendan Donovan. Well, the Luis Arraez signing to play second base throws a monkey wrench in that idea and forces the Cardinals to pivot elsewhere.
The Giants being out of the running allows a team like the Boston Red Sox, a familiar trade partner, to swoop in and acquire Donovan, knowing that the Cardinals have lost some leverage. Here's what a trade could look like.
A mock trade that sends Brendan Donovan to the Red Sox after Cardinals lose leverage
The Cardinals not having the Giants in the running means it's the Red Sox and maybe one or two other teams that seriously need a second baseman. The lack of options for the Cardinals to turn to makes it so that the Red Sox can get him for a package that might not blow the Cardinals away.
This would be classified as that. The Red Sox would acquire Donovan and his two years of club control and part with three pitchers, only one of which would be very painful. Payton Tolle, a top 30 prospect according to MLB Pipeline, has a ton of upside, and he could very well be a rotation lynchpin in St. Louis for the next decade. As for Kyle Harrison and Juan Valera, they're different kinds of dart throws.
Why the Red Sox would accept this trade
It hurts to part with Tolle, but do the Red Sox seriously need him? I mean, look at their rotation depth without Tolle.
Red Sox Rotation Depth | Name |
|---|---|
SP1 | Garrett Crochet |
SP2 | Ranger Suarez |
SP3 | Sonny Gray |
SP4 | Brayan Bello |
SP5 | Johan Oviedo |
SP6 | Patrick Sandoval |
SP7 | Kutter Crawford |
SP8 | Connelly Early |
SP9 | David Sandlin |
The Red Sox have arguably the most starting pitching depth in the league, even without Tolle and Harrison, and even without Tolle, Connelly Early is a high end, MLB-ready left-handed pitching prospect for them to be excited about.
No, this absurd depth doesn't mean the Red Sox should just give Tolle away, but Donovan would be a major upgrade and fit what the team is reportedly looking for. According to Alex Speier of the Boston Globe ($), the Red Sox are prioritizing defense with on-base ability over power. Donovan only hit 10 home runs in 2025 and has never hit more than 14 in a single season, but he has a career .361 on-base percentage and has consistently been a high-end defender at the keystone.
Adding another left-handed hitter might be less-than-ideal, but Donovan checks every other box. After whiffing on impactful position player free agents like Pete Alonso, Alex Bregman and Bo Bichette, it's on Craig Breslow to be aggressive in the trade market. Parting with three starters they really don't need all that much to fill a glaring hole feels like an obvious move to make.
Why the Cardinals would accept this trade
In an ideal world, the Cardinals would acquire Tolle and a better second piece from a team like the Red Sox, but they're running out of options. Sure, the Cardinals could hold onto Donovan, but doing so has more cons than pros.
- Donovan could suffer an injury
- Donovan could have a down year
- The longer Donovan stays in St. Louis, the closer he is to hitting free agency
Something could happen that could negatively impact Donovan's trade value, and even if he has another strong year, Donovan will be several months closer to free agency at the deadline than he is now. It feels like now is the best chance for Chaim Bloom to sell high, and it's not as if they'd be getting fleeced in this deal.
The Cardinals need starting pitching for 2026 and beyond, and Tolle, a big-league-ready arm who can contribute in 2026 and beyond, is a fit. He might be the best prospect the Cardinals can realistically get.
In addition, it's not as if Harrison and Valera are valueless. Harrison was just a key piece in the Rafael Devers trade that sent the slugger to San Francisco last June, and not too long ago, he was one of the best left-handed pitching prospects in the sport. Perhaps without pressure of pitching for a contender and with a rotation spot in his grasp, Harrison can tap into his potential. Valera is a 19-year-old in High-A who can hit the upper 90s with his fastball and has the stuff to rise up prospect rankings sooner than later.
The best time to trade Donovan is now, and this trade addresses the Cardinals' biggest need.
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