The Chicago Cubs and St. Louis Cardinals have long stood as bitter NL Central rivals, their history marked by intense competition and mutual disdain. Yet as the MLB trade deadline approaches on Aug. 3, baseball’s business side may override old animosities, creating the possibility of an unlikely deal centered on Cardinals right-hander Dustin May.
Chris Landers of FanSided has pitched the idea of a May-to-Cubs move, as Chicago is entering the deadline with a potent offense but a rotation heavily compromised by injuries.
Edward Cabrera, Ben Brown, and Justin Steele are on the injured list, while Cade Horton is sidelined for the season. Behind Shota Imanaga and Matthew Boyd, the Cubs need multiple reinforcements if they hope to challenge the Milwaukee Brewers and Los Angeles Dodgers in October. While the front office will almost certainly explore higher-profile arms, May represents a potentially strong secondary addition.
May carries a 4.59 ERA this season, but his underlying numbers tell a more encouraging story, with a 3.96 xERA pointing to better results ahead. He still shows flashes of the stuff that once made him a highly regarded prospect, and the Cubs’ elite infield defense could help him unlock more of that potential over the final two months. As a pending free agent, he is available as a short-term rental rather than a long-term commitment.
Landers suggests a package built around high-upside pitching prospect Jostin Florentino could get a deal done. The 21-year-old has not fully taken the step forward expected after a strong 2025, yet his strikeout rate remains elite—over 40 percent in his most recent High-A starts.
For the Cardinals, who have slipped after a surprising first half and appear unlikely to contend this year, acquiring a live young arm fits the long-term vision under their current regime. It would allow them to convert a soon-to-be free agent into future value without sacrificing a cornerstone piece.
From Chicago’s perspective, president of baseball operations Jed Hoyer has historically avoided the steepest prices at the deadline. Acquiring May would not require emptying the farm system and would leave capital available for additional moves.
The pitcher could stabilize the rotation through the regular season and even serve in a playoff role, whether as a starter in Games 3 or 4 or as a high-leverage reliever whose fastball plays up in shorter outings.
Landers notes that such a calculated, depth-oriented addition feels consistent with Hoyer’s past approach, even if previous deadline acquisitions have sometimes fallen short of expectations.
On the St. Louis side, the recent skid has clarified the team’s standing. Selling May for a prospect with upside aligns with efforts to build for 2027 and beyond.
While a hotter market might yield a larger return elsewhere, May’s recent inconsistency and free-agent status make the proposed package reasonable value. Both clubs, in Landers’ view, would have reason to say yes.
A Cubs-Cardinals trade remains a long shot given the rivalry, but the mutual benefits outlined by Landers make it an intriguing deadline scenario worth watching. If completed, it would stand as a rare moment of pragmatic cooperation between two of the National League’s most historic adversaries.
