5. Masyn Winn
I'm so high on Victor Scott as a player that I almost had him above Masyn Winn on my list, but Winn's track record at Triple-A which Scott does not have yet slots him in at number five on my rankings.
While Winn didn't impress beyond some flashes in his brief Major League debut, he's still someone that the Cardinals, and baseball in general, are very excited about. Winn has the strongest arm we have ever seen at the shortstop position, and if he can continue to develop his entire arsenal defensively at shortstop, he also has Gold Glove upside at the position.
While he's not in the same class as Scott when it comes to base stealing, he's a plus runner himself and someone who is going to swipe a long of bags at the big league level. What is going to make or break Winn's ceiling as a player is how his bat develops.
Winn himself has acknowledged that he tends to start his career slow at every level he has been promoted to, which showed true at both Triple-A and St. Louis in 2023. After a scorching hot Spring Training, Winn struggled out of the gate in Memphis, posting a .608 OPS in the month of April. Things slowly progressed through May and June before Winn took off in July and August with 1.177 OPS and .941 OPS respectively.
While Winn struggled at the plate in St. Louis in 2023, getting his feet wet has allowed him to enter this offseason knowing what it's like to hit at that level, and can now work at translating his top-end bat to ball skills and sneaky power to be an above-average hitter eventually. The expectation is that Winn will be below-league average at the plate in 2024, but if he's proven anything in his career thus far, it's that he tends to outperform what people think he can be at the plate.
The Cardinals have lacked a shortstop with Winn's upside for decades, and he has a chance to cement himself as the franchise's shortstop in 2024 for a long time.