How does Cardinals' contender status complicate May’s future?

The Cardinals entered 2026 focused on the future. Through 74 games, they’ve complicated those plans.

Holding the first National League Wild Card spot and playing meaningful baseball into late June, the Cardinals face a challenge that few expected when the season began: deciding how aggressively to pursue long-term value while remaining in the middle of a postseason race.

No player embodies that dilemma more than Dustin May.

Among the potential trade candidates on the Cardinals’ roster, May has emerged as arguably the most valuable one they possess.

May, who signed with the Cardinals as a free agent this offseason, is in the midst of a career season on the mound, posting a 3.75 ERA across his first 14 starts. While he got off to a rocky start, posting the worst ERA (15.95) by a Cardinal in the first two starts with the club since Alan Benes' 17.18 ERA in 1995, May has been excellent since then. Over his last 12 starts, May ranks Top 10 among all qualified starting pitchers in ERA (2.54), FIP (2.68), and innings (74 1/3), providing St. Louis with top-of-the-rotation production during this stretch.

The rest of baseball is surely taking notice, and if May keeps pitching like this when the Aug. 3 Trade Deadline comes around, there’ll be plenty of contenders looking to add May to their rotation. But what if the Cardinals still find themselves in the thick of the postseason race?

On one hand, St. Louis would be wise to stay the course and continue accumulating young talent, even when it hurts. On the other hand, subtracting May would be a significant blow to its postseason hopes. The better May pitches, and the better the Cardinals play, the harder this choice becomes.

The challenge for Chaim Bloom, St. Louis' president of baseball operations, is determining whether the prospect return outweighs the value of keeping one of the club’s most effective starters for what could become a legitimate postseason push.

The Cardinals have other avenues to recoup value. If May continues to pitch at this level, he could be a candidate for a qualifying offer after the season, potentially netting St. Louis valuable Draft-pick compensation if he departs in free agency. There’s even the possibility that May’s strong first half opens the door to extension discussions, giving St. Louis an arm to build around moving forward.

Since his early-season hiccups, May has been far and away the Cardinals’ best starter this season. Outside of Michael McGreevy, no one in their rotation has an ERA below 4.00 during that stretch. After posting a career-worst 4.96 ERA in 2025, May has experienced quite the turnaround.

May’s regained velocity and improved command have helped him limit baserunners this season and minimize the damage from opposing batters. The improvements May has made this season have put his fastball run value (12) among the best in baseball, according to Baseball Savant.

On top of that, May has yet to miss a start, and he is fast approaching his career highs of 23 starts and 132 1/3 innings pitched. He’s the Cardinals' most effective and consistent starter this season, and he’s been the lone arm in their rotation they can consistently rely on for length.

If St. Louis parts ways with May, the club will likely be looking at a substantial return to build its talent base for the future. But at what cost to its current state of affairs? That decision is far more difficult if St. Louis remains in the race.

There’s no guarantee that the Cardinals can keep their heads above water if they lose the most dynamic arm on their staff, but a trade would clear room for a young starter like Hunter Dobbins or No. 6 prospect Quinn Mathews to have a runway in the rotation. Dobbins has already flashed his upside with St. Louis this season (3.63 ERA in four appearances, including two starts), and Mathews seems to be knocking on the door of an MLB debut as he hones his command and continues to miss bats with his exciting repertoire.

The Cardinals signed May to stabilize their rotation and give them a valuable trade chip at the Deadline. There is still time until St. Louis needs to make a decision, but May’s production and the club’s record have turned what felt like a straightforward plan into quite the dilemma.