5 Cardinals worthy of an extension into the club's next competitive window

SS Masyn Winn

Redbird Rants site editor Josh Jacobs and I have been calling for an extension for Masyn Winn for almost two years now. The Gold Glove shortstop has proven himself worthy of a payday, and he could be just the player the Cardinals need to guide them to their next World Series trophy.

Winn will turn 24 just a few days before Opening Day 2026, so age is certainly on his side. He has yet to hit his true peak, but we've certainly gotten a taste of what he's capable of doing. The speedy defender posted a 104 OPS+ as a rookie in 2024 and followed that up with one of the best single-season defensive seasons by a shortstop in Cardinals history in 2025. if he's able to put it all together and swipe some more bags in 2026, the Cardinals may have an MVP candidate on their hands in short order.

Masyn has a career slash line of .252/.304/.376 for a 91 OPS+. His numbers were far better in the first half of 2025 before a nagging knee injury sapped his offensive production. Now that he's gone under the knife, there's hope that he can regain his physical form. Winn's defense won't be a worry, but he needs to prove that he can hit at the major-league level and use his burning speed on the base paths to get to the next level of stardom.

Winn has every chance to lock down the leadoff spot in next year's lineup. Playing shortstop and hitting leadoff is a potent combination for any player, and it's a clear jumping-off point for the young Winn.

An extension for Masyn Winn at this point will have to be around seven years to make it worthwhile. That would make him a free agent at the age of 30, still a decent point to enter the open market. Outfielder Tyler Soderstrom, who is a far better hitter than Winn is up to this point in their careers but lacks Winn's defensive abilities, received a seven-year, $86 million extension last week. That's a wonderful starting point when evaluating a potential extension for Winn, who is at the same point in his career when it comes to service time.

Giving Masyn Winn an extension now will send a clear message to fans that he's the organization's cornerstone player for the future. It will give fans an immediate favorite Cardinal to take the leadership torch, and it will allow Winn to take over as the face of the franchise, something he's more than capable of doing.