While most are not predicting the St. Louis Cardinals will not be a playoff-caliber team in 2026, the upcoming season is full of compelling storylines including many players who have the most to gain (or lose). There are several players who have a lot on the line in 2026.
The St. Louis Cardinals with the most obvious high stakes for the 2026 season are Nolan Gorman and Jordan Walker. Both were given a lot of “runway” (there’s that word again) last season, but neither impressed with their results. I won’t say that it’s necessarily a last chance for either Gorman and/or Walker, but it would be hard to imagine the team moving forward with them if the 2026 results resemble what they didn’t accomplish in 2025.
JJ Wetherholt looks primed to possibly make the opening day roster for the St. Louis Cardinals in 2026 barring a performance problem in Spring Training. I view JJ as only having something to gain by establishing himself as a part of the future St. Louis Cardinals core. Even if he performs below the potential rookie of the year level some are predicting, I think he’ll be allowed to have time to make the adjustments needed to be a centerpiece for the Cardinals for the foreseeable.
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I think the one Cardinal who stands the most to gain financially is Dustin May. If he bounces back from his injuries and becomes a solid mid-rotation starter again, he’ll be a valuable free agent if he declines the mutual option after the season with the Cardinals. Depending on how the St. Louis season goes, he could also be a prime trade deadline candidate for a contender if the Cardinals aren’t.
Masyn Winn could be viewed as a player that stands a lot to gain in 2026. For the first time in a year or two, Masyn is expected to start the season healthy. If he adds more offensive pop to his gold glove defense, he has the opportunity to be considered for a valuable long-term extension if he doesn’t seek more wealth in the free agent market a few years from now.
Alec Burleson is another player that could gain elevated status on the roster if he backs up his Silver Slugger performance of 2025. He signed a one-year $3.3 million dollar deal with the Cardinals for 2026 to avoid arbitration and is set to become a free agent after the 2028 season. The 2026 season could lead to several outcomes for Alec. He could be a trade deadline target, an extension possibility for the Cardinals or cash in on a nice free agent deal a few years from now if his bat continues to improve.
Matthew Liberatore has the chance to establish himself as a top of the rotation starter if he takes his game to the next level during the upcoming season. Riley O’Brien could develop into one of the NL’s top closers with a great 2026 although the mild calf strain he’s experienced already during Spring Training isn’t a great start. I could go on and on as the St. Louis Cardinals 2026 season is nothing if not a fertile field for opportunities. Who on the St. Louis Cardinals roster do you think has the most to gain or lose in 2026? The possibilities are nearly endless.