Breaking Down What Cardinals, Masyn Winn Extension Could Look Like

The St. Louis Cardinals are clearly building towards the future.

St. Louis has done a good job flipping veterans for pitching this offseason and the club will enter the 2026 season with a very young roster in hand. One thing the club has done throughout the offseason is save cash in the long run as well by trading Sonny Gray, Willson Contreras and Nolan Arenado. Now, the club had to pay money to get the deals done, but it did save cash in the long run. Which is a positive.

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St. Louis has a very young roster and most of the pieces with the club are cost-controlled beyond the 2026 season. With the Cardinals saving cash in the long run and clearly looking ahead towards the future, one avenue that should be considered is handing out a few long-term extensions to players they view as core pieces moving forward. Early extensions increase the short-term cost, but save money in the long run if the team hits on the deal. For example, look at Ronald Acuña Jr. of the Atlanta Braves. When healthy, he's someone who has a legit claim at being the top overall player in baseball. He's an MVP and a five-time All-Star and is just 28 years old.

The Cardinals should be looking at early extensions

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

Acuña signed an eight-year, $100 million deal with the Braves that also has club options in 2027 and 2028 at $17 million per season. He's worth much more than that to the Braves, but Atlanta took care of business early. The Cardinals should follow a similar strategy, specifically when it comes to shortstop Masyn Winn.

Winn is just 23 years old and has been in the big leagues over the last three seasons. He had a cup of coffee in the majors in 2023 and followed up with a 4.9-WAR rookie season in 2024. In 2025, he dealt with a knee injury but still was one of the very best defensive players in baseball and won his first Gold Glove Award while also slashing .253/.310/.363 in 129 games played.

Back in May, ESPN's Jeff Passan projected various contracts around the league and noted that if Winn is "even slightly above average" before free agency, he'll be a $100 million-plus player. Right now, not expected to hit free agency until after the 2029 season so the Cardinals have four more seasons of control. He'll turn 28 years old before the 30 campaign.

Right now, Winn looks like the safest bet on the roster. If the team views him as a long-term piece an extension that essentially buys out the first few years of free agency would be wise. Acuña got his deal younger than Winn is now, so eight years may be unrealistic because it would eat pretty heavily into free agency. $100 million over eight years holds an annual value of $12.5 million.

For Winn, something along the lines of $80 million over six years. That would be an annual value of $13.3 million per year and essentially would cover the next four seasons of control, plus buy out two years of free agency. If the Cardinals want to build a sustainable winner, these are the types of deals that would help in the long run.

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