The St. Louis Cardinals are facing a challenging and lengthy rebuilding process. In the near future, the team will likely commit fully to this rebuild, potentially making major trades to reshape their roster.
At the same time, the Cardinals might explore adding talent through free agency or securing some of their key players with significant contract extensions.
Bleacher Report’s Kerry Miller recently predicted Cardinals shortstop Masyn Winn would be one of the next players in baseball to land a contract worth over $250 million. Miller grouped Winn in a category tabbed “The ‘Shortstops Always Get Paid’ Tier” alongside CJ Abrams, Jeremy Peña, and Zach Neto.
“Of the 18 players currently on contracts of greater than $275M, six are shortstops: Bobby Witt Jr., Francisco Lindor, Trea Turner, Xander Bogaerts, Corey Seager and Mookie Betts. (Yes, Betts was a RF when he signed his $365M deal, but that just means he swaps spots with current RF Fernando Tatis Jr., who was a SS when he signed his $340M contract.)
“Of this quartet of fringe candidates for $250M, Peña would be the likeliest candidate if he wasn’t the eldest statesmen. Even so, Turner was 29 when he signed his $300M contract, while Bogaerts was already 30 when he got $280M, so never say never. Abrams is probably too much of a defensive liability to make the grade here, but after three consecutive seasons with at least 18 home runs and 31 stolen bases, a similar three-year run to free agency could net him a whole lot of money.”
Winn is still a few years away from free agency, but he’s trending in the right direction. He’d likely need to get to the open market in order to land a deal close to $250 million, but it’s still a possibility.
Given how exceptional Winn’s defense is, his offensive numbers would need to reach around an .850 OPS to justify a contract exceeding $250 million.
To avoid facing that hefty price tag after the 2029 season, the Cardinals might consider negotiating an extension sooner rather than later — and this offseason could be the ideal time to start those discussions.
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