Cardinals Legend Praises Masyn Winn Ahead of Crucial 2026 Season

The St. Louis Cardinals are entering a crucial 2026 season. They tore down their roster by getting rid of several veterans via trade and are finally clearing the way for younger players to receive runway.

St. Louis went 78-84 last year and missed the playoffs, but finally decided to initiate their first true rebuild in decades. There is a lot to look forward to with their younger players.

It is important to note that nothing is set in stone with their lineup, and they haven't decided who their leadoff hitter is going to be. Shortstop Masyn Winn is a candidate, and Cardinals Hall of Famer Matt Holliday gave him a ringing endorsement.

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Masyn Winn would be perfect leadoff hitter

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

"I think Masyn Winn has all the attributes of a good leadoff hitter," Holliday said.

"I don't see any better option at this point than Masyn Winn if he likes to hit leadoff and if he's comfortable hitting leadoff, I think that helps."

Winn has hit leadoff before for St. Louis. He was in that role for most of the 2024 season. But with Brendan Donovan gone and Lars Nootbaar likely on the injured list to start the season, Winn makes the most sense.

He has the necessary contact hitting skills to leadoff and also has the speed to generate offense on the basepaths, so with Nootbaar out and Donovan gone, Winn seems to be the most sensible option for the leadoff spot.

He won a Gold Glove last year for his elite defense, but he is still a solid hitter. He hit .253/.310/.363 with nine home runs and 51 RBI last season with St. Louis. If he can recover fully from his torn meniscus, he might just be the best option to inherit the leadoff spot.

The Cardinals need stability from that spot in the lineup, and Winn makes a lot of sense. This is some high praise from Holliday as the Cardinals assess their options for their 2026 lineup and where certain players will hit.

It will be interesting to see what they decide to do, but Winn fits the profile of what they are looking for at the top of the lineup. He can hit for contact and has solid speed, which makes him the ideal candidate.

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