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2021-22 Dirty Flirty: Prospect #5


These are my top 40 prospects in The Cardinals organization, aside from the players that I’ve already covered in The Dirty Annexes. This little ditty here is the preface to all of the post in our Dirty series. So, if you’ve read this once then you don’t need to read it again!

A warning to those looking for Lars Nootbaar, Scott Hurst, Junior Fernandez, Johan Oviedo, Jake Woodford, Edmundo Sosa, and anyone aside from Angel Rondon that has already made a major league debut: That’s not really my bailiwick, as I’m sure you’ve heard enough about those guys from more qualified outlets already. Most of those guys have exhausted their prospect status, anyway.

A reminder that this is an exercise in futility, ranking prospects. It’s a landscape that is ever-changing and developing. We are almost always talking about kids that are just starting to understand both themselves and their bodies, while learning the most difficult and nuanced sport in the land. You never know when someone is going to start doing 200 pushups per day on their way to postseason glory.

I ask for your thoughts and feedback. I ask that you have fun. I ask that you remember that I’m a moron. Most importantly, I ask that you take all of the prospect rankings from every outlet in the spirit of what they are: a snapshot of that moment, with a bent towards understanding what might come.


#5: SS/RHP Masyn Winn

20 Years Old on Opening Day

Drafted in the 2nd round of the 2020 draft

Peoria and Palm Beach

There is not a more exciting prospect in the entire system than Masyn Winn. He is electric. He is dynamic. He is (insert any word that conveys both excitement and energy). I do not watch every minor league game of every other organization every night like I do the Cardinals, but I am not sure that I saw a more electrifying prospect in all of the minors during the 2021 season.

Winn is a sight to behold. As Baseball America reported in THIS PIECE, there was not a shortstop at ANY LEVEL OF BASEBALL – ANY FREAKING LEVEL – that had the cannon at short in 2021 that Winn has. It is a cannon from the hole. It is a cannon coming in. It is a cannon off the cut-off. He throws the ball so fast from the shortstop position that the cameraperson can have trouble tracking it, often guessing where it is. Sometimes he throws it so damn hard that you cannot even see the ball on the feed. It is WILD. It is Rafael Furcal, but more fun. In the gif below, you'll notice that the cameraperson is trying to cheat a little with their camera work to not get beat by that cannon.

Speaking of fun, the way that Winn plays short in general is a lot of fun. During the brief write-up on Evan Mendoza in the “25 & Up” portion of The Dirty Annexes, I mentioned that Mendoza is probably the best defensive shortstop in the organization at this moment. The reason that I feel this way is because of the mature and professional consistency that Mendoza brings to such a tough position. I also mentioned that it wasn’t a knock on either Winn or Delvin Pérez. This next part isn’t meant to be a knock towards Pérez, either, but the only thing that is stopping Winn from being the best shortstop on the farm is the consistency that comes with minor league reps. He’s as dynamic of a defensive shortstop as I have ever watched for his age. He just has to keep working on that consistency.

If Winn were to reach 95% of his defensive abilities at short, he’d be better than both Delvin and Mendoza at 100% of their capabilities. That’s just how talented he is capable of being. To put that fancy claim into perspective, Delvin Pérez at 100% of his defensive capabilities is probably a Top Five-to-Ten defensive shortstops at the major league level. If I were asked to hedge my bets right now, I’d say that Winn might even be better right now that Pérez is. Even if Pérez does get a slight edge, think about how impressive that small difference is. If Delvin could have been just a little bit more consistent down the stretch he would have separated himself more than the talent gap currently is between the two.

Winn’s skills in the field are almost matched by his skills and feel on the basepaths. On more than one occasion, I’ve seen Winn tag up from first on a flyball to right field that is obviously going to be caught. His instincts for this are uncanny, and the studying that goes into understand the opposing outfielders to make sure that he can get away with it speaks to his dedication.

While at Palm Beach, we were also lucky enough to see Winn score from second on a sac fly to the center fielder. This play is preposterous. I don’t fully comprehend it. It's the first gif in this post because of how impressive it is. Winn is one of the three fastest – if not THE fastest – players in the organization. It does not take him much time to get up to speed, either. I am caught in the moment when I say this (please keep that in mind), but Winn lives at something near Magneuris Sierra’s 2nd gear. It is not just speed around the bases, either. His feel around the bases and his extra gear allow him to do showstopping things on rather mundane plays like what the tweet belows shows and describes.

Winn uses his keen and advanced baseball IQ to both steal bases and steal them efficiently. Winn stole thirty-two bases in thirty-seven attempts during the 2021 season. Both numbers were organization highs. Stealing 86.5% of bases at any level is one hell of an accomplishment. That he was that successful in that many attempts are the true sign of how aware, quick, and fast Winn is.

We are about 680 words into this, and we have talked about all of these things that Winn can do to beat a team, yet we haven’t talked about his bat yet. How truly gifted this kid is. Before we get there, we need to talk about the character and energy of Winn.

Masyn Winn is the type of kid that makes everyone else around him better. He is a kid that is enthusiastic about baseball, and he’s interested in rubbing that passion off on anyone remotely near him. He loves the sport, he has fun playing it, and he is clearly passionate about being as good at it as he can be. Winn is an entertainer in all of the right ways, and he plays with such energy and flare that it’s like watching Jim Edmonds or Harrison Bader but at short, and without all of the drama that comes with their on the field personalities (or Edmonds's off the field personality, for that matter). No, Winn is his own personality. He is infectious. He is the type of guy that will make a routine play but bring that rare energy to that play that can steer momentum and push a team beyond the mundane or struggle.

This goes double when surrounded by his friends and teammates of the same age. Jordan Walker was performing perfectly fine at the plate during his month at Peoria before Winn arrived. A 279/333/492 hitting line in sixty-six plate appearances for such a young kid at such an advanced level is beyond impressive. When Winn was promoted to Peoria one month into Walker’s tenure there, you could just see something click. His strikeout rate dropped 5-ish%, his walk rate raised a little bit, and he hit 297/348/485 to end the season in 178 plate appearances. What I really noticed is how Walker’s demeanor on the field changed. You could tell that the two of them have a lot of fun playing next to each other, and that Walker likes to try to compete with Winn’s arm. You can tell that Winn is one of the first people that he tries to pick up after he races around the bases (that could also be because Winn is usually crossing the plate and rooting loudly for his teammate). This is the type of energy boost that Winn provides for his teammates. It is an incredibly special trait.

I would be remise to not bring up Winn’s incredible work ethic and commitment to baseball. It is top of the line. His character is top of the line, his baseball IQ is top of the line, his athleticism and skill is top of the line, and he has top of the line intangibles. Remarkable.

Winn was incredible in 284 plate appearances at Low-A. He hit 262/370/388 with three homers, three triples, and fifteen doubles, while walking 14.1% of the time and striking out 21.1% of the time at a league that he was nearly two and a half years younger than on average. Keep in mind that the league that Palm Beach plays in is still one of the toughest leagues to slug the ball in, MiLB-wide. I have already gone out of my way to list all of the ways that power isn’t exactly Winn’s game, and I’ll take 21 extra base hits in 284 plate appearances there all day, errrrrrrrr day.

Before Winn was promoted to Peoria, I was quick to point out Walker and Winn were the two best prospects in the Cardinals organization. That argument could still be made, and by someone smarter than myself. I also believe that this will absolutely be the case one year from now. I just do not think Winn is there yet. This feeling all boils down to the approach that I saw as time passed in his Peoria tenure. This next part needs to be prefaced by saying that Winn was nearly three and a half years younger on average than that A+ League, and that he was one of the younger kids at that level. Regardless, Winn was really pressing while at Peoria. You will see that in his nearly 5% increase in strikeout rate and his basically 10% decrease in walk rate. Winn was getting beat a lot early on with Peoria, specifically by the high-heat/low-breaker combo. He was reasonably frustrated and often guessing, and that caused him to get more defensive in his swing. NONE OF THIS IS UNCOMMON. I would go as far as to say that this is the most likely outcome for the vast majority of teen aged/first-year prospects that were asked to take part in such a challenging assignment. You should not let his statistical struggles at Peoria taint your view of him. The offseason will do him good. He will watch the footage, collect the data, and apply the lessons that he’s learned to his 2022 season. This is an absolute fact. Winn’s hands are incredibly fast and his pitch recognition can be off the charts when he is trusting himself. And with such little movement and wasted motion in his mechanics, his base for success is at the forefront.

As most of you know, Winn was drafted as a two-way prep player, and it appeared that the Cardinals were interested in continuing to give him a chance to pitch here and there while he played short full time. It never worked out this way during the 2021 season, even though Winn stayed on a throwing program of sorts. Winn did get one inning of work, and he was as spectacular as you would expect. His fastball was mid-90’s and lively, and his slider was fuuuuuuuuuuuuuuuuuuuucking nasty. I would wager against it, but I am hopefully that Winn gets more time on the mound during the 2022 season than he did during the 2021 season.

Masyn Winn is an extremely talented baseball player with some of the purest athleticism across the board in the organization. He has work to do at the plate and some consistency to gain in the field, but he does so much in so many different facets that he will not ever need to be a 300/400/500 hitter to do tremendous amounts of damage to the opposition. Crammed full of energy, excitement, dedication, drive, passion, and every other intangible that you can laud onto him, Masyn Winn is electricity in baseball player form.

As I just take a screenshot straight from their website, I can’t begin to stress loudly enough the important role that FanGraphs plays in the statistical side of what I do with these write-ups. Please subscribe to their service BY CLICKING THIS LINK.

In addition, you all know how important and valuable @cardinalsgifs is to the pictures that fire up these articles. He’s helped with some of the gifs along the lines, too. I wouldn’t do the write-ups if it weren’t for him.

Thank For Reading!!


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