Welcome to the annual Over The Monster One Big Question season preview series. Over the next 40(ish) days, we will be running through every player on the Boston Red Sox 40-man roster and identifying a key question for them pertaining to the coming season. We will go through the roster in alphabetical order. For the most part, these will run Monday through Friday every week running up to the week before Opening Day, at least as things are scheduled right now. Obviously, the lockout may change the timing of the season, and it also means we will likely see more additions of new faces. If need be, we will add some weekend posts to fit any and all additions to the 40-man before Opening Day. You can catch up with every post by following this link. With that, today we cover Josh Winckowski.
The Question: Can Josh Winckowski miss more bats?
In 50 years, assuming humanity still exists and lives in a society where they can still care about relatively silly things like baseball, we’ll look back at this era of MLB as one that was littered with more strikeouts than before. Perhaps it will keep increasing and we’re only at the start of this trend, but that seems hard to believe. It’s a three true outcomes kind of game, for better or for worse. That doesn’t mean, to be fair, that a pitcher has to miss bats at a high rate to be successful. There is still room for command/control guys to succeed, but their ceilings are lower now, and it’s a lot easier than ever before for them to fail. Josh Winckowski, one of the better pitching prospects in the Red Sox system, isn’t exactly a command/control pitcher, and his stuff has improved in the last couple of years, but to increase his ceiling he could really use the harnessing of that stuff into more missed bats.
Winckowski wasn’t always seen as the kind of pitcher who could even be considered a top prospect in an organization, originally entering pro ball as a 15th round pick with the Blue Jays. After a couple of slow seasons to start his professional career, the righty broke out in 2018 and 2019, improving that strikeout rate we’ll be talking about and getting up to High-A by the end of that season. Of course, as we know the 2020 season was cancelled for minor-league players, and he ended up being one of the big pop ups for that fall. Winckowski reported to Toronto’s Fall Instructs with a fairly significant velocity boost, putting him on other teams’ radars. He’d end up getting traded twice in that offseason, first to the Mets for Steven Matz before ultimately being flipped to the Red Sox as part of the three-team Andrew Benintendi trade.
While Franchy Cordero was the player who would get the first chance to make an impression on Red Sox fans in that deal, it was Winckowski who was generally considered the best get of that initial package, with plenty of excitement around that uptick in velocity. Boston placed the righty at Double-A Portland to start his first season in the organization, and he ended up making it to Triple-A Worcester for a small cup of coffee at the end of the year. All in all, his 2021 was... fine. He didn’t really jump off the page in any way, but in Double-A he pitched to a 4.14 ERA with a 20.5 percent strikeout rate and a seven percent walk rate.
If I’m being honest — and why wouldn’t I? — this ended up being one of the hardest questions to come up with because, well, Winckowski is basically fine at everything but not great at anything. Sum of the parts kinds of prospects are not necessarily bad, but it’s a tighter rope to walk when there’s not a carrying tool. For a pitcher, that tightrope often comes when there’s a lack of a true putaway pitch. This, to me, is what Winckowski is lacking most and why he may end up as more of a long reliever than a consistently trusted member of a rotation. His strikeout rate was fine last season, but it’s likely to come down against more advanced hitters without key adjustments, and it’s also a bit of a let down after the uptick in stuff reported following the 2020 season.
And so the conversation around an improved strikeout rate so probably start with that fastball, which is the source of excitement around that fall pop-up performance. He can now sit in the 94-96 range, and he has approached triple digits in shorter stints in the Arizona Fall League. That kind of velocity can work at the highest level, and he does sometimes switch it up and take a little velocity off for more two-seam movement. However, his command isn’t great and it doesn’t miss as many bats as it should. While he does a good job throwing it for strikes, he sometimes does that by catching too much of the plate and not getting it up high enough. At that velocity, he should be able to get plenty of whiffs above the zone, and commanding the pitch on the edges more consistently is the next step to take.
He also needs to take another step with his secondaries as well. Winckowski, along with the fastball, offers a slider and a changeup. The changeup is more of a fringe-average pitch at this point, and while crazier things have happened than that turning into a true out-pitch, that offering’ development is mostly about becoming consistent enough to give him a true three-pitch repertoire. It is, for what it’s worth, on the path to getting to that level.
The slider, however, is a pitch that would probably need to emerge as the true strikeout pitch. Getting back to this era of baseball, there is nothing more tried and true than a pitcher generating whiffs with a big fastball up in the zone paired with a slider that can get bad swings on pitches out of the zone. For Winckowski, everything is there for that kind of repertoire, it just hasn’t gotten there yet. Most reports for his slider have been good, and the couple of times I saw him it looked fine, but it just didn’t manifest in above-average strikeout rates last season for whatever reason.
To me, this all comes down to the fastball and shoring up the command there. He needs to get more consistency with his secondaries as well, but they look on track to be good enough for at least a long reliever who can make spot starts at the major-league level. If he wants to be a clear major-league starter for a long time, even in the back end, he needs to take a step forward in some area. Strikeouts seem the most likely, because the stuff and arsenal is there. Winckowski is on the door step of the majors and should make his debut this year. And in the short-term, he should be fine as a reliever. But in thinking about his long-term development, I’d like to see more missed bats before I really pencil him in as a true future starter.