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#3 - Boston Red Sox
Another deal with the Boston Red Sox?!?! According to Tim Healey of the Boston Globe, the Red Sox are among the teams that have expressed interest in acquiring Donovan's services, and we all know how much these two teams have made trades in recent years.
Since the beginning of last offseason, the Cardinals and Red Sox have made three trades (Tyler O'Neill, Steven Matz, and Sonny Gray) while agreeing in principle on a fourth deal involving Nolan Arenado. The Red Sox have also expressed interest in Willson Contreras this offseason, and Arenado could be another retread conversation for them, depending on how the offseason unfolds.
Bloom is very familiar with Boston's farm system from his time running the organization, and he obviously has relationships with the staff that remain there. If the Red Sox really want Donovan, they have the prospect capital to make the Cardinals an offer they can't refuse.
There is still a lot of uncertainty in the Red Sox's infield right now, and they clearly are interested in upgrading that unit, considering their interest in re-signing Alex Bregman or trading for Ketel Marte as well. Donovan would be the most cost-effective of the trio in terms of dollars, and may not cost as much prospect capital as Marte would in a trade.
Lefty Payton Tolle is likely off the table in any trades for Boston right now that don't involve bringing back a superstar, but they have plenty of other prospects worth bringing back to St. Louis. Right-handed pitcher Kyson Witherspoon was a name linked to the Cardinals in the 2025 MLB Draft and could be Major League-ready as soon as 2027. Righty Luis Perales has a 70-grade fastball and plus cutter, so he'd be a major upside play if the Cardinals brought him back in a deal. Lefty Connelly Early presents more of a low-upside, high-floor arm that I'd be less interested in.
Boston has so many names that could be of interest to the Cardinals, so if news drops that Donovan is going to Boston, that could very well mean the Cardinals got an awesome offer to part ways with their fan favorite.