#3 - Masyn Winn (Previous ranking: #2)
Dropping by one spot on my list, Masyn Winn still had a really good 2025 season, and if it wasn't for some regression with his bat down the stretch, he likely would have maintained his earlier ranking.
Before being placed on the injured list so he could have season-ending knee surgery, Winn slashed .253/.310/.363 with 10 home runs and 27 doubles, and swiping nine bases. His 91 wRC+ was a big drop off from the year prior, but like Donovan, it is hard to know how much playing through his knee issues contributed to his decline at the plate.
Even with that knee injury, Winn still posted 22 outs above average, which now ranks second in baseball among all defenders, but was first before his season ended. He's the runaway favorite for the Gold Glove award at shortstop and could even win the Platinum Gold Glove as well. His defense alone makes him a great player, ranking 41st in baseball in fWAR (3.5) this year.
Manager Oliver Marmol talks a lot about how he thinks Winn has a ton of potential at the plate, and I agree. He has power that should be able to play into the 15-20 home runs a year range, and his speed and gap power can get him into the 35-40 doubles club as well. He's also shown the ability to collect hits at a high level when he's on.
Now, it would obviously be one of the top outcomes of his career for him to do all of those things, but even if he can just tap a bit more into his batting average and power, he would increase his value quite a bit. I think he has the ability to be 10%-15% above league average at the plate, but even just being slightly above league average makes him a really, really good shortstop.
The Cardinals have to be very happy with what they have in Winn right now, and he's easily one of the three most valuable players in their organization right now. I am eager to see what he does in year three of his big league career next season.