The Cardinals are spending the final stretch of their 2026 season doing something that matters just as much as wins in the moment: sorting out what this roster is supposed to look like when they’re ready to push again.
A few spots already feel spoken for. Jordan Walker’s breakout has changed the picture.
Alec Burleson keeps moving forward. Leo Bernal, only 22, has looked like a real starting catcher.
JJ Wetherholt is locked in through his prime. But shortstop remains one of the louder questions, and Masyn Winn sits right at the center of it.
That’s because Winn’s case is a strange one: the glove is already carrying real franchise value, while the bat has yet to match the promise. Since his rise through the minors and his major league debut as a 21-year-old, there has never been much doubt about the defense.
He moves like a natural shortstop, has the kind of arm that can bail out an inning in a hurry, and he stays in the conversation for the best defensive shortstop in baseball. The Ozzie Smith comparisons never really stop.
The problem is that modern teams don’t survive on glove work alone. Power and run production drive the market now, and Winn’s offense has not lived up to the talent he showed in the minors.
In parts of four minor league seasons, he hit .271 with a .790 OPS and 37 homers in 325 games. Since arriving in the majors late in 2023, those numbers have dropped to a .247 average, a .667 OPS and 31 homers in a little more than 100 additional games.
His strikeouts, walks and power have all moved in the wrong direction, and even his stolen base totals have fallen off sharply, from 92 in the minors to 32 in the majors.
The injuries haven’t helped. Winn has dealt with knee and leg problems, plus back and thumb pain that has surfaced at different times.
He’s still only 24, so there’s room for the wear and tear to matter less in the short term, but he has also already logged more than 125 games in each of his three seasons. That kind of mileage matters when you’re asked to play shortstop every day.
There’s still a belief that Winn can be a near-annual 20-homer, 20-steal player. But the last two seasons have looked fairly similar once you dig into the numbers.
He knows the zone, yet he hasn’t consistently punished strikes, and the swing-and-miss has crept up. Even so, the defense keeps him firmly in the conversation as a player worth building around.
That’s where the Cardinals’ long view comes in. Winn won’t reach free agency until after the 2029 season, and he’ll be just 27 then.
That gives St. Louis time, and plenty of it.
He may not be the kind of player the club should rush into a long extension for right now. A wait-and-see approach makes sense, especially if the front office wants to learn whether the bat ever catches up.
Money won’t make this a heavy lift, either. Winn is making about $780,000 a year and is heading into arbitration for the first time this offseason.
Matthew Liberatore came into arbitration this year with 2.14 years of service time, close to Winn’s 2.04 by season’s end, and ended up on a $2.8 million deal. If Winn lands in that same neighborhood, it shouldn’t change the Cardinals’ bigger financial picture very much.
A raise like that would still leave him 30th among shortstops by the 2026 payroll rankings on Spotrac. By fWAR, his 2026 season sits 18th at the position, with defense doing most of the heavy lifting - third-best overall on that side of the game - while his offensive value lands way down at 72nd.
So the Cardinals don’t need to force the issue. Winn is under team control through 2029, and with third base, the bullpen and possibly center field also needing upgrades, Chaim Bloom can afford to let shortstop breathe a little. For now, the club can keep banking on the defense and hope the offense finally catches up.
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