Cubs trade package for Cardinals' Dustin May would be an MLB trade deadline shocker

The Chicago Cubs and St. Louis Cardinals famously don't like each other very much. But baseball is, first and foremost, a business — especially this time of year, when contenders are desperate to add any piece that can fortify a postseason run.

The Cubs find themselves in just such a position ahead of the Aug. 3 trade deadline, with a red-hot offense but a pitching staff that's been decimated by injuries. If Chicago is going to finally get past the Milwaukee Brewers and Los Angeles Dodgers in October, they're going to need to add at least one impact arm. And while they'll certainly pursue sexier options, one of the best values on the market might require dealing with their hated rival down I-55.

What a Cubs trade for Dustin May would cost

The Cardinals are in a bit of a free fall at the moment, looking more like the team we thought we'd see at the start of the season than the one that took the NL by surprise in the season's first half. This team remains ahead of schedule, and they can take another step toward real contention in 2027 by selling at the deadline — starting with righty Dustin May, who's flashed some awfully enticing upside at points this season and will be free agent come the winter.

Cubs fans undoubtedly hope the team will set its sights higher than a pitcher with a 4.59 ERA, but May looks much better under the hood (3.96 xERA) and still has plenty of the potential that made him a top prospect several years ago. Plus, with Edward Cabrera, Ben Brown and Justin Steele all on the IL and Cade Horton done for the year, Chicago can't afford to add just one starter. They'll need multiple reinforcements behind Shota Imanaga and Matthew Boyd, and May could serve as a very nice secondary piece with the potential to take off behind the Cubs' elite infield defense.

Of course, St. Louis won't love the idea of giving him to a division rival, so Chicago will have to pay more than you might expect for two months of an 87 ERA+. Florentino hasn't taken the step forward the Cubs expected after his 2025 breakout, but the strikeout stuff remains — he's fanned over 40 percent of batters faced in his last five High-A starts — and he's still just 21 years old. The Cardinals get another live arm to try and develop into a mid-rotation starter, while Jed Hoyer gives his team a far stabler foundation heading toward October.

Would the Cubs make this trade?

Again, the Cubs would no doubt love to add a frontline option like Tarik Skubal, Joe Ryan or even Reid Detmers. But Hoyer has always been loath to pay those sorts of prices at the deadline, and that still wouldn't obviate the need for more depth considering all the injury risk in Chicago's rotation right now. May could be invaluable in helping get the Cubs to the postseason in better shape, and you wouldn't feel terrible about him starting Game 3 or 4 of a playoff series if need be. Plus, his electric fastball arsenal would play up well in a bullpen role.

This feels like a very Hoyer move, akin to the ill-fated acquisition of Michael Soroka at last year's deadline. May won't break the bank, even if Chicago has to pay a Cardinals tax, and there's still upside to be unlocked here. The Cubs have the prospect capital to land him with plenty left over to make other moves, and a certain point, this core deserves a front office that will push all of its chips in.

Verdict: Yes

Would the Cardinals make this trade?

The Cardinals have made Bloom's life a little easier with this recent swoon. St. Louis clearly isn't good enough to make a real run at a pennant, and now they can sell at the deadline and still take plenty of postiives away from what was a real step forward in 2026. May is about to test free agency, and even if the Cardinals might want him back, he doesn't have the sort of ceiling that should prevent you from trying to shop him for future value.

Florentino is in keeping with the sorts of high-upside arms that Bloom targeted in various trades this past winter, a big arm that St. Louis' new pitching development team could have a lot of fun with. It's possible that a seller's market yields a stronger return elsewhere, but May also hasn't been pitching well of late and comes with risks of his own. This feels like fair value for a player that doesn't really factor into St. Louis' team-building plans.

Verdict: Yes

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