The St. Louis Cardinals have their shortstop of the future. Masyn Winn, a former top prospect, has exceeded expectations to start his MLB career, and the Cardinals have him under club control through the 2029 season.
While it would make sense for the Cardinals to look into extending Winn in the near future, it feels unlikely. Whenever he ends up signing that first deal, though, he’s likely in for a big payday.
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In a recent article, ESPN MLB Insider Jeff Passan included Winn as a candidate to sign one of baseball’s next megadeals, saying that he has a chance to make well over $100 million.
Winn has always been a defense-first shortstop. In 2024, he led all major league shortstops with 14 defensive runs saved (DRS) and was a finalist for a Gold Glove.
“Nobody should question Winn’s defensive bona fides. His bat will determine his financial ceiling, and Winn has plenty of time to develop,” Passan wrote.
“What’s important to remember: He plays a position that gets paid in free agency, and he’ll turn 28 just before Opening Day in 2030. If Winn is even slightly above average, that’s a $100 million player. If he’s anything more, the number could be massive.”
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Winn had a solid rookie year at the plate, slashing .267/.314/.416 in 637 plate appearances. He also showed some surprising power, slugging 15 home runs.
Cardinals shortstop Masyn WinnKatie Stratman-Imagn Images
The 23-year-old got off to a slow start to the 2025 season, but after a brief IL stint due to lower back spasms, Winn appears to have figured things out at the plate. Since returning from injury, Winn is slashing .311/.373/.578 with two homers and seven runs batted in.
With other young stars like Lars Nootbaar and Brendan Donovan set to hit free agency in 2028, Winn isn’t the only Cardinal with a potentially significant contract extension looming.
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The Cardinals don’t exactly have a history of signing players to big deals like this either. The last time they handed out a $100 million-plus deal was when they gave Paul Goldschmidt a 5-year, $130 million extension in 2019.
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