For the last handful of votes, we have had some extremely close battles, which isn’t exactly a surprise at this tier of the system. There are a lot of solid but unspectacular prospects in this range, either too young to be fully bought into or close to the majors but with low ceilings. It makes sense that people couple make arguments for a number of different players. But now it seems we may have reached the end of a tier, because the latest vote was a clear blowout. Josh Winckowski had been very close to getting the nod in each of the last few rounds, and he finally broke through this time around, taking the 14 spot on our community rankings after grabbing a whopping 56 percent of the vote.
Winckowski is yet another player on this list who did not start his career in the Red Sox organization, joining Jeter Downs (No. 7), and Connor Seabold (No. 12) in that respect. Instead, Winckowski was originally drafted by a division rival in the Toronto Blue Jays. They took him in the 15th round out of high school in Florida. He was committed to a junior college rather than a four-year, and decided to go right to the pros after being drafted.
Unlike some of the other names we’ve profiled on this list, it took Winckowski quite a bit of time to actually start to make a name for himself in pro ball. In fact, he spent each of his first three seasons in short-season ball, starting on the complex before moving to an advanced Rookie League and then the New York-Penn League. As a side note, this progression wouldn’t even be possible anymore with two of those leagues wiped away thanks to Rob Manfred. Anyway, those first two seasons were middling with spotty command ballooning his ERA, but he looked to breakout in 2018 in the NYPL, pitching to a 2.78 ERA with a 2.77 FIP.
Now he had to prove he could keep it going in full-season ball, heading to Low-A Lansing to to start the 2019 season. He had no troubles at all in that level. His walk rate did climb back up a bit after showing great control in that 2018 season, but his strikeout stuff was solid and hitters had a difficult time squaring up the righty, leading to a 2.32 ERA through 13 starts and an eventual midseason promotion to High-A Dunedin. There, he just continued what he’d been doing since the start of the previous season, finishing that 2019 campaign with a 3.19 ERA through 10 starts plus a relief appearance.
Of course we know what happened in 2020 with the season being cancelled at the minor-league level, but that fall is when Winckowski’s career would really start to take off. The Fall Instructs around baseball that year were fascinating, as players who hadn’t been around the team for months were back and showing how they’d developed. The Red Sox had a pop up of their own in Eduard Bazardo, who parlayed his performance into a 40-man spot. Winckowski had a similar experience, coming into Instructs with increased velocity. He didn’t get protected from the Rule 5 Draft, but he did get traded to the New York Mets in exchange for Steven Matz. He’d only be in the Mets organization for a matter of weeks, though. Boston soon acquired him as part of the package for Andrew Benintendi last spring, and he spent the 2021 season with Boston.
This was a big year for Winckowski, who was looking to show those gains at Instructs were not smoke and mirrors and he could perform even as he moved up the ladder to more advanced levels. In his age-23 season, he spent most of last season at Double-A Portland, pitching to a 4.14 ERA with a 4.02 FIP over 21 appearances (20 starts). It wasn’t a spectacular showing, especially compared to 2018 and 2019, but it was a solid stint where he held his own. Winckowski would eventually end up in Triple-A Worcester to finish out the season, making two strong starts in which he allowed three runs over 12 innings with 13 strikeouts and three walks.
We’ve had some interesting players on this list who are still a ways out but have huge ceilings. Winckowski is more on the opposite side of that coin, though. There are some skills here that are exciting to project forward. His fastball is a good pitch, thought he velocity spikes mostly come in shorter stints. But even so, he sits 91-94 during starts. Along with the fastball the righty also mixes in a good slider and a solid changeup. The mechanics are good and he can get good movement on his pitches, especially with his slider which he can throw a couple of different ways to reshape the break as well as the velocity. All in all, there’s an argument that he could be a reliever given how his fastball plays up, but the pieces are there for him to be a back-end starter, which presumably is the preferable outcome for the organization.
Winckowski, as mentioned above, could make his major-league debut as soon as this season as he was added to the 40-man roster last winter and will be starting the 2022 season at Triple-A Worcester. He’s got some competition on the depth chart, most notably in the aforementioned Seabold, but if Winckowski keeps doing what he’s been doing really since 2018, he’ll get his chance sooner than later.
Here is our list so far:
- Triston Casas, 1B
- Marcelo Mayer, SS
- Nick Yorke, 2B
- Jarren Duran, OF
- Brayan Bello, RHP
- Bryan Mata, RHP
- Jeter Downs, 2B/SS
- Blaze Jordan, 3B/1B
- Jay Groome, LHP
- Gilberto Jimenez, OF
- Wilkelman Gonzalez, RHP
- Connor Seabold, RHP
- Brandon Walter, LHP
- Josh Winckowski, RHP
Now, you can head down into the comments and vote for the number 15 prospect. As a reminder, to do this you go down below and find the comment from me corresponding with the player for whom you’d like to vote. When you find said player, just click the “rec” button, and that will count your vote. To do this, you will need to be logged in as a member of the site. If you’d like to vote for a player who is not listed, just leave a comment saying “Vote for ___ here” and I’ll rec the comment to count your vote. We encourage discussion, of course, but please don’t comment under specific players’ names. Instead, scroll to the bottom to start a new comment thread in order to keep the players at the top of the comment section. Until next time...