The St. Louis Cardinals aren't expected to be in a position to compete for a playoff spot this year but there are several players on the roster that will play a critical role in the future of the franchise.
One of those players is shortstop Masyn Winn.
Winn is arguably the Cardinals' best returning player this season. The only All-Star St. Louis had in 2025, Brendan Donovan, was traded this offseason to the Seattle Mariners.
There's a lot of expectations on Winn, who'll enter his fourth season (third full year) in the major leagues in 2026, to take another step forward.
One former St. Louis hitter, Matt Holliday, put his hat in the ring to support Winn taking an extended role with the team this upcoming season.
"You haven't seen JJ Wetherholt against big-league pitching," Holliday said on the Foul Territory podcast. "So, I think in spring training, you watch how his at-bats are. ... As the spring goes, he'll face pitchers that are more and more dialed in and pitching (to) him more and more like they will in the regular season. So you'll have a better idea where he'll fit in the batting order. I think Masyn Winn has all the attributes of a good lead-off hitter. ... In a perfect world, (Victor Scott II) would be your lead-off hitter, in my mind, because then you can hit Winn second, put him in a position to drive in more runs. But I don't see any sort of better option at this point than Masyn Winn. If he likes to hit lead-off, comfortable hitting lead-off, I think that helps."
"I think he has all the attributes of a good leadoff hitter."
— Cardinal Territory (@CardTerritory) February 23, 2026
Matt Holliday doesn't see a better option than Masyn Winn to hit at the top of the order. pic.twitter.com/5rfQuSK0iA
Winn is coming off a Gold Glove-caliber season in 2025. He became the youngest Gold Glove-winner in franchise history at just 23-years-old. He had a .994 fielding percentage with just three errors in 501 total chances. He had 21 outs above average, which ranked in the 100th percentile of the major leagues, according to Baseball Savant.
On offense, Winn slashed .253/.310/.363 with a .673 OPS and hit 27 doubles and nine home runs with 51 RBIs in 129 games last season.
Winn has played two of the team's three spring training games so far and is 0-for-5.
If the former second-round pick and Katy, Texas, native is able to make an improvement with his bat in 2026 and his defense remains at an elite level, he'll have a legitimate argument to be one of the best two-way players in the major leagues.
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