New York Yankees
The New York Yankees and their fans have been trying to pry Brendan Donovan from the Cardinals for years now. John Mozeliak and the Cardinals have resisted these advances, but with Chaim Bloom at the helm now, perhaps Brian Cashman can finally get his All-Star utility man that he's been eyeing for several years now.
The Yankees have no shortage of offensive production as a team, but the bulk of that offense has been carried by Aaron Judge. Jazz Chisholm Jr. and Ben Rise have made decent contributions to the lineup, but this is an offense that goes when Aaron Judge goes.
New York isn't in desperate need of a left fielder considering Jasson Dominguez, a former top prospect, looks to be their left fielder for now. Right field certainly isn't a need with Aaron Judge out there. Jazz Chisholm Jr. is at second base for at least one more year for the Yankees, too. Ryan McMahon is also at third base, and he's not a free agent until after 2027.
The Yankees aren't as desperate as they once were for Brendan Donovan, but his production would likely be better than what Ryan McMahon provided at the hot corner, and his versatility could play anywhere. The Yankees already lean left-heavy as a lineup, so adding another lefty in Donovan could really clog up some areas. While trading Donovan to the Yankees is a possibility, I would venture to guess that they'll fill holes on the roster in other ways for 2026.
Should a deal be struck between these two historic franchises, look for the Cardinals to once again target controllable starting pitching. The Yankees have a full rotation with Max Fried, Carlos Rodon, Cam Schlittler, and Luis Gil. Could Brendan Donovan be enough to land the Yankees' top pitching prospect in Carlos Lagrange (11-8, 3.53 ERA with 168 strikeouts in 2025)? St. Louis would probably be happy with any one of Lagrange, Elmer Rodriguez, Bryce Cunningham, or Ben Hess in return.
