Inside The Cardinals

Cardinals Superstar Linked To 8-Year, $100 Million Contract Extension

Could the Cardinals sign Masyn Winn to a new contract extension?
Zach Pressnell|
Mar 30, 2025; St. Louis, Missouri, USA; St. Louis Cardinals shortstop Masyn Winn (0) takes aim at first base in a game against the Minnesota Twins at Busch Stadium. Mandatory Credit: Tim Vizer-Imagn Images
Mar 30, 2025; St. Louis, Missouri, USA; St. Louis Cardinals shortstop Masyn Winn (0) takes aim at first base in a game against the Minnesota Twins at Busch Stadium. Mandatory Credit: Tim Vizer-Imagn Images | Tim Vizer-Imagn Images

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The San Diego Padres recently inked their superstar outfielder Jackson Merrill to a nine-year, $135 million contract extension that could be worth $200 million down the road. The Boston Red Sox signed their new second baseman, Kristian Campbell, to a new contract shortly after.

The St. Louis Cardinals could be the next team to attempt to ink their stars to contract extensions.

With all this in mind, Thomas Gauvain of Redbird Rants recently suggested the Cardinals could take a page out of the Padres and Red Sox's books and sign Masyn Winn to an eight-year, $100 million contract extension this season.

"Masyn Winn would be my choice for a long-term extension," Gauvain wrote. "He's a superb defender at a premium defensive position, he has the ability to steal 25 or more bags in a year, and his offensive output last year was strong for a shortstop.

"In November, I posited an eight-year, $100 million deal for Winn. He would top out at $25 million in year eight of his deal, and an additional year with a mutual option would give him another $25 million. A deal of this size would lock Winn in as the club's cornerstone, and he would immediately become the face of the team."

Winn would be the perfect player to sign to an extension. An eight-year deal, especially with club options on the back end, would lock Winn down in St. Louis for the next decade. The 23-year-old posted a 4.9 WAR season last year, so his value is only going to increase from here. If the Cardinals don't sign him to an extension now, they could be forced to give him upwards of $200 million when he eventually lands in free agency.

More MLB: Cardinals' Controversial Offseason Decision Aging Like Fine Wine

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Zach Pressnell
ZACH PRESSNELL

Zach Pressnell has experience covering all major US sports at both the professional and collegiate levels. He’s produced content for FanSided, Blog Red Machine, The Game Haus, Bethany College Athletics and the Bethany College online newspaper, He graduated from Bethany College (WV) with a degree in Communications and Media Arts, specializing in Sports Journalism. Pressnell was also a four-year member of the baseball team where he earned himself All-PAC recognition as a pitcher (and a cool Tommy John surgery scar). Now, Pressnell specializes in NFL and MLB coverage for Sports Illustrated’s “On SI” network among others. For all business/marketing inquiries regarding "St. Louis Cardinals On SI," please reach out to Scott Neville: scott@wtfsports.org

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