1 high end, 1 rational Red Sox trade piece Cardinals could target for Brendan Donovan

The St. Louis Cardinals have made two significant trades this offseason, both of which have come with the Boston Red Sox. Right-handed pitcher Sonny Gray and first baseman Willson Contreras are now playing in the American League East, and Chaim Bloom is still hard at work finding the best possible deals for other trade assets, including his most valuable chip, Brendan Donovan.

Well, according to Ken Rosenthal and Will Sammon of The Athletic, Donovan is also a player that the Red Sox are interested in, and sources familiar with St. Louis and Boston's conversations say that they discussed Donovan this offseason. How likely is a deal? That remains to be seen, but honestly, I recently ranked Boston as one of the three best suitors for Donvoan, so I could totally see it happening.

Why did I see Boston as such a strong fit? Well, they have a need for Donovan, and the kind of assets they could offer the Cardinals in return for him fit exactly what they are looking for: high-upside starting pitching.

Now, when I look at Boston's prospects, there is one clear name that sticks out to me that would be a home run move for the Cardinals, a high-end prospect who I doubt the Red Sox would be eager to move. And then there's a second pitching prospect, one who also has a ton of upside, that I believe is a more rational target in a Donovan deal.

1 high end trade piece the Cardinals could target from Boston in a Brendan Donovan trade: Payton Tolle

The top prospect in the Red Sox' system right now, left-hander Payton Tolle is one of the best pitching prospects in all of baseball, and I have a hard time believing they'd move Tolle for Donovan, or really any player this offseason.

Tolle stands at six-feet-six-inches tall on the mound and boasts one of the best fastballs in minor league baseball. He's set to begin the year in Triple-A for Boston, and could very well be in their rotation at some point this next season. He has three average offerings to pair with his fastball, and scouts really love the potential he boasts long-term and his ability to improve those pitches to pair with his nasty fastball.

Chaim Bloom should do everything in his power to try to pry Tolle away from Boston, but I just don't see it happening. But there is a pitching prospect they have that still has high upside, but feels far more realistic.

1 realistic trade piece the Cardinals could target from Boston in a Brendan Donovan trade: Kyson Witherspoon

Drafted by Boston with the 15th overall pick in the 2025 MLB Draft, the Red Sox were elated to have Witherspoon fall to their selection, and he is currently their fourth-ranked prospect in their farm system.

Witherspoon has a plus fastball and cutter that he pairs with an above-average slider and average control. He has middle-of-the-rotation upside with potentially a bit more in the tank as well if he can continue to enhance his offspeed stuff, and considering how good the Cardinals have been at developing changeups, he may be a good fit for them.

Witherspoon is also expected to be big league ready soon, with an MLB debut in the cards late in 2026 if all goes right, or far more likely in early 2027. That should be music to the Cardinals' ears.

If St. Louis swings a Donovan deal with Boston, I'd cross my fingers for Tolle, but definitely be expecting Witherspoon to be the headliner in a deal. Witherspoon was one of the five pitching prospects around the league I identified as targets for St. Louis this past weekend.