The St. Louis Cardinals are preparing for a major transition at season’s end, with John Mozeliak stepping down and Chaim Bloom set to take over. But the front office shift isn’t the only sign of a new era in St. Louis.
This season, the Cardinals have fully embraced a youth movement, with rising star shortstop Masyn Winn emerging as its centerpiece.
According to ESPN’s Jeff Passan, who projected the next wave of $100 million free agents, Winn could headline the 2028-29 class. His elite defense alone makes him a long-term Gold Glove contender, but what truly raises his value is his age and upside at the plate.
Though he started the season slowly, Winn has bounced back and was batting .268 with three home runs and two stolen bases as of Tuesday. If he continues to tap into his speed and adds more power, he could become a consistent 20-20 threat.
Winn will be just 28 heading into the 2030 season—right as he enters his prime. If his offensive game continues to grow, his future contract could easily exceed $100 million.
The Cardinals might consider locking him up now, securing their shortstop of the future before his market value soars.
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