The 2026 season for the St. Louis Cardinals might not be a playoff contender, but it’s shaping up to be a pivotal year for several players whose careers hang in the balance. This is the season where legacies are made—or broken. With so much at stake, let’s dive into the players who have the most to gain or lose in the coming months.
And this is the part most people miss: while the team’s overall success may be uncertain, individual storylines are anything but boring. Take Nolan Gorman and Jordan Walker, for instance. Both were given ample opportunities last season, but neither delivered results that inspired confidence. While it might not be their last chance, another underwhelming performance in 2026 could make it difficult for the Cardinals to justify keeping them in the long-term plans. But here’s where it gets controversial—do the Cardinals owe it to these young talents to give them more time, or is it time to cut ties and focus on newer prospects?
On the flip side, JJ Wetherholt is a name to watch. Barring any Spring Training setbacks, he’s poised to crack the opening day roster. Even if he doesn’t live up to the lofty Rookie of the Year predictions, his potential as a cornerstone of the Cardinals’ future seems secure. But how quickly can he adapt to the big leagues? That’s the million-dollar question.
Speaking of money, Dustin May could be the player with the most to gain financially. If he rebounds from his injuries and solidifies himself as a mid-rotation starter, he could become a hot commodity in free agency—or a prime trade deadline target if the Cardinals aren’t in contention. But what if his injuries linger? The risk is as high as the reward.
Masyn Winn is another player with a lot on the line. After battling injuries, he’s expected to start the season healthy for the first time in years. If he can pair his Gold Glove defense with a more consistent bat, he could secure a long-term extension. But in today’s game, where offense reigns supreme, can he do enough to stand out?
Alec Burleson is in a unique position after his Silver Slugger performance in 2025. With a one-year, $3.3 million deal to avoid arbitration, 2026 could be a make-or-break year for him. Will he become a trade chip, a long-term Cardinal, or a future free agent cashing in on his potential? The possibilities are endless.
And let’s not forget Matthew Liberatore and Riley O’Brien. Liberatore has the talent to become a top-of-the-rotation starter, but can he take that next step? O’Brien, despite a recent calf strain, could emerge as one of the NL’s top closers—if he stays healthy. But injuries have a way of derailing even the brightest prospects.
The 2026 Cardinals season is a fertile ground for opportunities, but it’s also a high-wire act for many players. Who do you think has the most to gain or lose? And more importantly, do you think the Cardinals are handling these players’ futures the right way? Let’s hear your thoughts in the comments—this is one debate that’s sure to spark some fiery opinions.
