Last season, the St. Louis Cardinals experimented with the leadoff spot but, regardless of the hitter, the team could not find the best fit for the number one slot in the lineup. In 2025, Cardinals’ leadoff hitters combined for a .234 batting average, hitting 15 homers, and scored 91 runs while driving in 59. Each of those stats are in the bottom-10 of baseball. Further showing the organization’s shift from “Whitey Ball” and the traditional top-of-the-lineup hitter, the Cardinals received a total of four stolen bases from their pace setter, the fewest in the majors.
During the season, St. Louis had three players bat leadoff at least 10 times. Lars Nootbaar led the team with 95 games atop the order, with Brendan Donovan starting 53, and Masyn Winn hit first in 10 games. All three have qualities to do so, with Noot showing a knack for drawing walks, Donovan putting the ball in play, and Winn having the athleticism and aura of a leadoff man. The end results were mediocre for the trio, with only Donovan rating as an average hitter out of the spot, Nootbaar was the only one to total a stolen base, and Winn put up a .174 on-base percentage. All of their stats out of the one-hole were below their season totals by measure of wRC+. Rather than use this as a “who should leadoff”, I wanted to take a look at how Masyn Winn would fit in that spot, or if he is best suited elsewhere in the order. My faith in Winn as the next (current?) face of the Cardinals and as a top-10 shortstop in baseball made me want to see how the Cardinals could build the lineup around him.
Masyn Winn could be successful in multiple spots in the order
Coming off his first Gold Glove award and snub of the Platinum Glove (shoutout fan voting), Winn is garnering some national attention for his defense and flash. Flashback to Justin Turner saying Winn’s throwing arm is not impressive and he should just throw it softer, the Cardinals shortstop made a total of three errors in his stellar season at short. The 23-year-old always profiled as a good defender who could stick at the position, but he was also projected to provide more value with his bat than with his glove. Winn showed that potential during his short stay in the minor leagues, with a career .440 slugging percentage and 37 homers with 92 stolen bases in the lower levels.
Winn has played 316 games in the majors and appeared in 325 among the St. Louis affiliates. The numbers show two different types of hitters. In the minors, Winn had a .271/.350/.440 slash line with a 303:155 K:BB ratio over 1,499 plate appearances. Since being promoted, the shortstop has 1,311 plate appearances and a .252/.304/.376 slash with 26 homers and 22 stolen bases. The minor league Winn had the electric profile of a yearly 20-20 player, especially after his 18-17 season in Memphis the year after stealing 43 bags. I was excited for his debut and long-term future as the Cardinals’ shortstop and leadoff hitter for the next eight years.
During those two seasons in the minors, Winn spent most of his time hitting atop the order, but also saw plenty of at-bats out of the two spot. Winn had an .859 OPS or better each season and smacked a total of 19 homers in 524 at-bats hitting first. In his major league debut season, manager Oli Marmol opted to hit Winn ninth to ease his way into the bigs. The shortstop was overpowered in his first 137 plate appearances, hitting .172 for a 29 wRC+ in 37 games. In 2024, Winn was the starting shortstop all year and was plopped back into his familiar leadoff spot for the majority of his rookie year. While he had an above-average offensive season, he had a .692 OPS hitting first, but just a .290 on-base percentage in 440 at-bats, striking out 84 times and walking just 26. In his 147 at-bats at other spots in the order, Winn had a .327 batting average and a 24:15 strikeout-to-walk rate.
2025 put that experiment on hold and Winn spent 250 at-bats hitting second last season. From the two-hole, he hit .268 with a .736 OPS. His other 241 at-bats were spread at every spot in the order except for seventh and eighth, with most of his small-sample success coming out of the six spot. To finally get into the exercise of the article, I had to look at my expectations with the current lineup. I believe there is a greater than 50% chance that Donovan gets traded this season and Nootbaar starts the season on the injured list. That means both options who spent most of the year at leadoff may be unavailable to begin the year. I also wonder where Victor Scott II will bat, with the speed of a prototypical leadoff man but lacking the on-base prowess of last year’s players.
So, where should Winn bat? I think he has to get first crack at the leadoff spot again. Last season, he was hindered by a back issue, as well as playing through a meniscus injury before undergoing surgery at the end of the year. Winn will be entering his third full season in the majors and has shown a consistent approach at the plate, but one that could be improving as he matures as a hitter. He has not struck out more than 19% of the time and has drawn walks at a near league-average rate, while hopefully growing into the 20-homer potential. Winn has only attempted a total of 33 stolen bases in 316 games, so that is a number I want to see him match this season. In a season where development is key, seeing if Winn could become a dynamic five-tool threat at the start of a game could be a huge piece for the Cardinals’ future.
The only other spot I could see him filling is that two-hole if Victor Scott gets his shot at the top of the lineup. Winn has proved to be a tough hitter in a two-strike count, so that allows him to be patient at the plate while Scott has the green light to run at first. Until VSII can show a better approach at the plate or an increased ability to bunt for a hit, I think he is best in the nine-hole to hopefully turn the lineup over.
If either of Donovan or Nootbaar remains, the lineup becomes a question again. How the Cardinals approach the offseason will obviously do a lot to set their starting nine, but I expect Spring Training to be used to try out plenty of different lineups heading into the 2026 season.