Maybe the most interesting player the Cardinals drafted this year, or at least the most interesting storyline they committed themselves to, is Masyn Winn. It’s been a while since the draft, so to quickly review, in case you’re a little fuzzy on who Winn is exactly: Masyn Winn was the Cardinals’ second round selection (#54 overall), in this year’s draft. The backstory is that of a supremely gifted athlete, a high school shortstop, who suddenly threw his name into consideration as a legit two-way prospect when he hit 98 off the mound at a wood bat showcase. Winn had always been both a position player and a pitching prospect, but wasn’t really seen as a legitimate pitching possibility until he started lighting up radar guns, which is how these things generally go. (If that sounds a little like the story of Trevor Rosenthal, it is somewhat similar. Rosie was a juco shortstop who just happened to have a radar gun on him when he threw 96+ in an inning of relief. The scout took note, the Cardinals decided they liked the arm better than the bat, and the rest is history.)
To be sure, there are plenty of high school kids who have talent on both sides of the ball, and a reasonable number who are good enough at both to continue pitching and hitting through college. Until recently, though, there were very few two way prospects in the pro ranks, simply because the orthodoxy of the past forty or fifty years has been that doing both is simply too hard at the highest level. And, to be fair, it probably is, for 99% of players. Which, of course, means that hitting and pitching is too tough for 99% of the most gifted 99.9% of athletes on earth, more or less. So we’re talking about a vanishingly small class of athlete who might have a chance to do both, and the risks, both perceived and real, of attempting that developmental track are simply too great for teams to risk it, usually.
Even the college two-way players generally do not get drafted as two-way players. College ball is a great winnowing, in lots of ways, and what typically happens to a player talented enough to hit and pitch in college is that he’ll top out on one side, show potential for further growth on the other, and the decision will be made. The very few serious two-way prospects in baseball right now are all players who came out of that winnowing process with their potential still both undefined and undimmed, like the Rays’ Brendan McKay. The obvious exception here is Shohei Otani, who really does seem to be a unique player. Professional baseball teams do not, as a rule, draft high school kids as two-way players. They prefer to let college serve as the separator, giving the players time to realise their fates and the teams time to let it happen.
Enter Masyn Winn.
Winn throws a lot of our preconceptions about the two-way player dynamic into flux, and really doesn’t fit well into that box. Nearly all the two-way prospects we have floating around currently are some variant of pitcher-slash-low-value-defensive-position guy. First base is a popular spot. Designated hitter just as much. The outfield seems doable. There are a few reasons for this bias; one, pitchers tend to be some of the tallest players in the game, and guys above a certain height tend to be relegated to corner outfield or first base duty, two, it seems slightly more common for these guys to be left-handed, which limits their positional possibilities, and three, if you’re working your arm as hard as pitchers do, you don’t really want to be throwing much on the other days.
So what do we have with Winn? We have an undersized but hyper athletic middle infielder who also throws 98 righthanded. Like I said, he really kind of doesn’t fit the profile that well. Then again, the fact he doesn’t fit the profile is what makes him so unique, so exciting, and ultimately so intriguing that you would spend a high draft pick and an overslot bonus on a kid who has never even played against college competition as either of the things you’re hoping he can be.
All of which leads to the thing I’m really most interested in with Masyn Winn, which is a relatively simple question: how does all of this work? Now, to be clear, I say it’s a simple question, and I stand by that. The answer, on the other hand, seems to be fairly complicated.
Of course, the most likely answer to the question of how this all works is: it doesn’t. That’s the base assumption with any prospect, even very high level ones. Really good prospects still don’t turn into anything a huge proportion of the time, and in the case of Masyn Winn we can take that a step further. Or maybe even two steps. If we assume that every prospect outside the Kris Bryant types fail more often than they succeed, we can then posit that Masyn Winn could a) fail completely, b) succeed as a pitcher but fail as a position player, or c) succeed as a hitter but fail as a pitcher, and any of those outcomes makes the rest of this column null and void, since all of those outcomes come with mechanical simplicity. If he fails at both, he washes out. If he fails on either side of the ball, he just becomes a regular prospect, to maybe someday be a regular player, but not a unique and strange player worth writing a feature on.
Okay, now with that out of the way, let’s just pretend that Winn does not, in fact, fail in any of those ways, because those are all boring. Let’s assume that he succeeds, at least for awhile, so that we can consider just what it would look like to try and utilise a player with his skillset.
So here’s the thing, right off the bat: I don’t see any possibility of a player managing to be a starting pitcher and an everyday position player at very many positions. There is a certain amount of wear and tear involved with pitching, and in particular starting pitching. Now, there is an argument to be made about how much easier relief work really is, given the greater number of appearances, short notice warm ups, extra pitches thrown getting ready, etc., but even with all that it’s still pretty well established that working the arm to the level of fatigue involved with starting is the greater injury risk. The structure surrounding the one day of starting helps with the workload, but throwing 90-110 pitches at very close to max effort (probably closer than is ideal, if we’re being honest about the modern game), takes an enormous toll on the arm, even if a player is otherwise uncompromised mechanically or physically.
Thus, my first assumption: if a player is going to be a starting pitcher, he cannot play in the field the rest of the time. First base might be the one exception, simply because of the lack of throwing, but even there I feel like the starting pitcher needs more rest between starts than he’s going to get if he’s in the field. A DH/first base/corner outfield part time role would seem to be the maximum one could expect.
Which is, of course, an instant monkey wrench as things pertain to Masyn Winn. Winn’s position is shortstop, and a big part of his appeal is the fact he has the superlative athleticism to make a legitimate go of it up the middle. He’s a plus or better runner, has range and explosiveness on the infield, and just generally looks like a possible impact defender even at such a premium position. (He’s shorter, but has Brendan Ryan-like twitchy athleticism up the middle, to give an idea of the type of defender he could be.) So if one were to develop Winn as a starter, it would seem to me you would have to sacrifice his ability to play those premium positions long term to protect his arm.
So maybe we don’t make him a starter. What if we make him a reliever? Could he play short or some other premium position (center field?), every day if he were only relieving? Again, I have concerns there. If you’re expecting him to play in the field every day, you would be seriously limited in terms of how you might be willing to use him on the mound, even in a relief capacity. If Winn were a five day a week starter, how often could he work as a pitcher? And if he threw an inning or got five outs one night, could he be back in the field throwing and moving around the next day? Or would you have to give him a day off to, again, protect his arm. (And legs, for that matter.) Relievers can work back to back days, of course, or even three in a row, but they’re not playing full games as middle infielders in between. The physical toll would seem prohibitive.
The other issue here is that if even if you’re willing to take steps to protect Winn’s arm and give him days off after he pitches, that puts a real strain on the rest of the team. Is he really a starting shortstop if he has to have two days off a week because he pitched the night before? Do you have to then invest in a starting-quality player to complement him? Is there a starting-quality shortstop who wants to play three days a week? It’s complicated.
To me, all of this suggests that the smartest way forward in trying to use Masyn Winn (and to be clear here, I’m hypothetically framing all this as if he’s making it to the majors and is really exciting as both a pitcher and hitter, but a lot of these questions apply to the process of trying to develop him in the minors as well), will be to limit and balance his workload on both sides of the ball, in an attempt to juice as much impact as possible from him without burning him out entirely. He is a uniquely gifted player, in that he could be an impact talent as both a premium position player and a pitcher, and to give up either of those things in service of trying to maximise one or the other might be the easier path — and maybe the one you end up taking regardless through necessity or happenstance — would be to give up on a potential dynamo unlike just about anything else in the game.
So what do we do? Well, if we are really going to try and turn Masyn Winn into a swiss army knife player, we probably need to first eliminate most of our reliance on him. That may sound paradoxical, but I promise it isn’t. If you really need him to fill any specific hole, it makes it far less likely you can deploy him as flexibly as you would want to make an impact in every situation. Needs are limitations just as much as they are opportunities.
The solution, to my mind, is to have Masyn Winn start at exactly zero positions, and instead make him a super utility player who can be your primary backup at a few. He’s already a shortstop, and has the talent to not only stay there, but potentially excel defensively there. As I said before, I don’t think you can actually start him there, but he could be your primary backup at short. If your shortstop needs, say, one day a week off, that would seem to be entirely doable. Winn is currently a 65-70 grade runner, more than enough to handle center field in terms of speed. So maybe he’s your primary backup in center as well. The question, of course, would be how good a center fielder he would be, given he probably wouldn’t get a lot of practice there, but you have to hope his athleticism can help him be average, even if he’s not out there enough to really lock in great reads.
So that’s, say, two starts a week, at two premium positions. Now, given Winn has the arm and range to play short, he can almost certainly handle third and second base as well, barring some odd throwing issue due to positioning or something. Now, I don’t think you can count on him to be your primary backup at both of those spots as well; if you’re trying to build in an average of one day a week off for every position (I said average, not exactly one day every week), then requiring four days a week from Winn might be tough. So maybe your primary guy at those spots is a Brad Miller type, the offensive-minded utility guy who plays three or four positions, none of them all that well, but gives you the bat to make up for any defensive shortcomings on his days to start. We could also call him a Jedd Gyorko type, but Gyorko was probably too good for most teams to use in such a luxurious manner. Still, Winn might be your favourite guy at third base, maybe, but he gets one out of every two off day starts there.
If he has the speed to play center, he could certainly hold down an outfield corner. Again, will he be good? Tough to say. But he has the talent to be good, so let’s give it a try. As with the infield spots, I don’t think you make Winn the primary backup in the corners; maybe you’ve got a Lane Thomas type or an Allen Craig you want to make the number one guy. If you want a current Cardinals’ system example, who I’m really thinking of is Justin Williams or maybe Juan Yepez, neither of whom are any great shakes in the outfield, but have significant offensive upside. By the time we’re talking about Masyn Winn in the big leagues it may very well not be either of those specific guys, but that’s the kind of player I mean. Your fourth outfielder is your primary pinch hitter and source of pop off the bench, while your fifth outfielder is also secretly your primary backup center fielder and shortstop and plays one day a week at either second or third base.
So here’s kind of what we have: roughly four starts a week for Winn, one at short, one in center, one in either outfield corner, and one at either second or third base. He could obviously pinch hit other days, and maybe you use the DH going forward to get him a few extra at-bats, but four starts a week is probably more than enough, because we haven’t gotten to the other side of the ball yet.
This is where things really start to get interesting to me, because I happen to think Winn is an incredibly talented pitcher, but if you really want him to do both it’s hard to see him functioning in a fireman role the way you might like one of your most talented relievers to. If you’re trying to have him play the field three to four times a week, I feel like his appearances have to be somewhat structured, rather than entirely based on need. You can use him when you need him, of course, but probably only something like twice a week, maybe a third day every couple weeks, if you’re trying to avoid burning him out physically. He has a brilliant fastball and a very good curve already, and he’s shown decent feel for a changeup. In other words, he really has a starter’s toolkit, so could probably step into that multi-inning role, which for me would fit better than a true fireman. I could see a guy getting four to six outs twice a week and still playing three or four days in the field more easily than I can envision three or four super high stress plate appearances three times a week still being compatible with position play. If you’re willing to pull the trigger on Winn multiple times a week pitching, he has to have recovery time, and that limits his ability to play the field.
So maybe you don’t schedule the days Winn is going to pitch, but you limit him to two outings a week most weeks, and you try to get multiple innings from him if you can, rather than leaning on him for two or three outs in a close eighth inning. He gets the last out of the fifth inning, throws the sixth, and get the first out of the seventh before you go to a lefty, then the next day he’s limited to DH or pinch-hitting duty. Maybe if he’s already playing the field and the game is not close one way or the other he throws the eighth and ninth, not exactly a mop up reliever, but use his innings strategically to give the other on-call guys the night off, if that makes sense.
I think the ideal way to try and balance the playing time of Winn or a player like him would be something like three starts a week in the field, one at short, one in center, one at third base, three innings of defensive replacement play in center or right field, one or two pinch hit appearances as needed. Maybe he’s at DH the first part of that game where he takes over late for your Allen Craig type. All told you’re talking about ~20 plate appearances a week on average, or roughly 450 PAs at the end of the season, assuming health. On the pitching side, he makes two appearances a week, occasionally a third if you really need him, and throws something like three or four innings each week. Over the course of a season, maybe that’s 80-90 innings, which sounds like a lot, but they’re a little more carefully managed than what a lot of other relievers are getting. No back to backs unless it’s an emergency, no up and down endless warmups waiting for a situation that may not arrive. You get him around two-thirds of a season’s worth of plate appearances, and half a good starting pitcher’s workload, and it’s possible you could have a serious impact player contributing on both sides. Maybe that innings total is a little too aggressive, and you end up backing it down to 60-70. That’s still potentially a very strong relief season, even if the innings are a little less leveraged than might be ideal for a guy whose talent is so notable.
Now, does this sound complicated? Yes. Yes, it does. And that’s sort of the point of this column. I really like Masyn Winn the player, and I find the gamble the Cardinals took in drafting him to be one of the more interesting, and exciting, storylines in recent memory. The idea of having a player with so much talent, and so much flexibility, is hard not to fall for. But on the other hand, deploying a player in such a way as to try and benefit from all his tools and skills could, in this case, be very complicated and difficult. Ordinarily, we think that if a player is good, then any questions about his playing time will work themselves out. It seems, though, that it might actually be possible for a player to be talented enough in so many different ways that things boomerang, and it becomes complicated again.
The Cardinals have set themselves a challenge in drafting Masyn Winn. As I said, I wrote this column with the hypothetical understanding that he makes it to the big leagues and turns out to be awesome at all the things you want him to do. But pretty much all of this applies to the developmental process as well. How do you make sure a player gets enough backfield work to try and improve his changeup when he also needs to be taking extra batting practice because he’s pulling off the slider down and away lately? The game of baseball has become so high skilled that specialisation is an almost unavoidable side effect. So where does that leave a player like Winn, whose chief attraction is the fact he could be a jack of all trades for you? The modern roster cries out for this kind of flexibility, and if a player really could fill the role of multi-inning reliever, backup shortstop, center fielder, and corner utility guy, that would be an absolutely incredible boon to a team. But think of just how much effort would go into getting that guy the playing time he needs to improve, and then figuring out how best to deploy his talents if he does, in fact, make it.
It definitely wouldn’t be simple. And maybe things worth having often aren’t simple, but the path of least resistance is always going to be a temptation when the alternative requires 3500 words to break down. Well, okay, maybe not requires, exactly. But you know what I mean.