The St. Louis Cardinals are heading into a new chapter, with John Mozeliak stepping down and Chaim Bloom taking over, and they’re also embracing a younger roster. Leading that youth movement is Masyn Winn, a dynamic shortstop who’s catching attention across the league. ESPN’s Jeff Passan has listed him among potential \$100 million free agents in the 2028-29 offseason.
Winn’s standout defense already makes him a strong Gold Glove candidate, and that kind of skill alone can command a major contract. But what makes him even more intriguing is his age and upside at the plate. Though he had a slow start to the season, he’s bounced back, hitting .268 with three home runs and two steals as of Tuesday. If he continues to develop power and leverage his speed, he could easily become a consistent 20-20 player.
By the time the 2030 season rolls around, Winn will be just 28—right as he enters the prime of his career. If his offensive production improves, a \$100 million deal could be a conservative estimate. The Cardinals may want to secure their rising star now, before his value climbs even higher.