The St. Louis Cardinals have a long and stressful rebuild on their plates. The team is likely going to lean into this rebuild in the coming months, as they could look to subtract from their roster with blockbuster trades.

The Cardinals could also add in free agency or even look to sign some of their stars to huge 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.

Masyn Winn projected to land massive contract extension

Sep 6, 2025; St. Louis, Missouri, USA; St. Louis Cardinals shortstop Masyn Winn (0) throws to first base against the San Francisco Giants at Busch Stadium. Mandatory Credit: Tim Vizer-Imagn Images / Tim Vizer-Imagn Images

“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.

With how incredible Winn’s glove is, his bat needs to be in the .850 OPS range in order to warrant a contract worth over $250 million.

The Cardinals could look to work for an extension to avoid paying this huge cost after the 2029 season. This offseason might be the perfect time for them to explore that option.