The St. Louis Cardinals are on the cusp of a significant organizational shift as longtime executive John Mozeliak prepares to step down at the end of the season, with former Red Sox executive Chaim Bloom set to take his place.
But beyond the change in leadership, a broader transformation is already underway—one defined by a commitment to youth, internal development, and a new core of rising stars. At the center of that movement is shortstop Masyn Winn, a dynamic young talent who’s quickly becoming one of the most important players in the franchise’s future plans.
Winn, who entered the 2025 season as one of the team’s most anticipated prospects, is now emerging as a cornerstone player. Despite starting the year in a slump, the 22-year-old has steadily turned things around.
As of this week, he’s hitting .268 with three home runs and two stolen bases, showing promising signs of progress both at the plate and in the field.
His speed, athleticism, and improving bat make him a threat on both sides of the ball. More importantly, his elite defense at shortstop has already drawn praise across the league, with many projecting him as a future perennial Gold Glove candidate.
ESPN’s Jeff Passan recently spotlighted Winn in a feature predicting the next wave of \$100 million free agents. He pegged Winn as a likely candidate in the 2028–29 free agency class—a projection that reflects both his current upside and long-term potential.
If his bat continues to evolve and he adds more power to his game, Winn could easily develop into a consistent 20-home-run, 20-stolen-base player. Combine that with elite defense at a premium position, and you have the makings of one of the most complete shortstops in baseball.
Another factor working in Winn’s favor is his age. By the time he hits free agency after the 2029 season, he’ll be just 28 years old—right as he enters the prime of his career.
Teams are more willing than ever to spend big on young, athletic players with upside, and Winn checks every box. His youth and growth trajectory could even push his value beyond the \$100 million mark if he continues to progress.
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For the Cardinals, the situation presents a strategic opportunity. Rather than waiting until Winn becomes one of the most sought-after free agents in the league, the front office could move early to extend him and secure their shortstop of the future at a more team-friendly rate.
Locking him in now would give St. Louis stability at one of baseball’s most important positions and send a clear message that the new era of Cardinals baseball is centered around homegrown stars with game-changing potential.
As the organization transitions both on the field and in the front office, Masyn Winn represents the kind of player every team hopes to build around—young, athletic, and only scratching the surface of what he could become.
If he continues on his current path, the Cardinals may soon find themselves with one of the best shortstops in baseball—and potentially one of the smartest long-term investments they’ve made in years.
