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Writer's pictureJovan Popovic

Meet One of Toronto’s Most Underrated Prospects: Josh Winckowski

In-depth prospect evaluation, as well as an actual Q&A with Winckowski himself!


Written by: Jovan Popovic

Edited by: Noah Britt


Who is he?


Meet Josh Winckowski, a 21 year old right handed starter. Winckowski was drafted by Toronto in the 15th round of the 2016 MLB draft as an 18 year old out of high school. Chances are that even if you are a hardcore Blue Jays fanatic, you might not of heard of him. If you look at the top 30 prospects list, he won’t be there. If you look into past drafts, you likely won’t find him without some help. However, there is a reason for this article, and it is to show off possibly the most underrated prospect in the organization.


Winckowski spent last season between class A Lansing, and advanced A Dunedin, succeeding greatly at both levels, despite a rocky past. His age 18 and 19 seasons in rookie league were rather unimpressive, and poor to say the least, but Winckowski managed to redirect his career going into the 2018 season. He impressively pitched to a 2.78 ERA for low A Vancouver, followed by a 2.32 ERA in class A in 2019, as well as a 3.19 ERA after his third promotion to advanced A. After his 2019 season, Winckowski ranks as the 35th overall prospect in the organization.


Winckowski has a large 6’4 frame, and has large potential on his fastball, which is already sitting mid 90s. With some improvement of consistency of fastball control, he could quickly become an elite pitcher. Why he isn’t on any prospect lists yet, I cannot provide a good answer for. Perhaps i


t’s because he was a late round draft pick? Maybe it’s because Nate Pearson, Eric Pardinho, and recent draftee Alek Manoah are in the spotlight ahead of him. However, his name will be there sooner than later, and it shouldn’t be a surprise to anyone.


A couple months ago I reached out to Winckowski, and was fortunate enough to receive a response, agreeing to answer a few questions for me. The interview is below, with myself labelled J, and Winckowski (W) :


J: Did you ever think you’d be doing this as a career one day?


W: Ever since I was 7 or 8 I always told people I’d play baseball, so it was something I believed in for a long time. Still crazy to think it happened.


J: Did you notice yourself standing out from others? Were you always an ace on your teams, or were you just one of the guys?


W: I don’t think I stuck out an insane amount, but I definitely felt like one of the better players. It wasn’t until my senior year where I started to see me separate.


J: That’s really interesting, as you were drafted out of high school. Were you aware that you had scouts watching you, being that you didn’t feel like you stuck out until becoming a senior? Did you expect to be drafted out of high school coming into your senior year?


W: Yeah, I had a few scouts come check me out my senior year, and going into the draft, I wasn’t really sure what to expect to be honest. I was kinda playing it by ear.


J: Wow. I assume you also had college offers. Did you consider continuing on in school, or were you just positive on signing with the team? Was it an easy decision?


W: I went under the radar college wise, I only had one offer out of high school. It was the toughest decision of my life, I flip flopped a lot.


J: That’s real interesting. I’m surprised a draftee would only get one offer. I never expected that! Well, as a Jays fan, I am glad with the decision you made. What were some of the largest changes you noted once becoming a pro ball player?


W: Just the level of play and dedication, it’s no longer practice after school, it’s every day all year. Overall level of professionalism has to go up.


J: When you say all year, does the organization work with you throughout the year, or do you just work on your own during the off-season, or both?


W: It’s usually all on you. Occasionally they’ll bring you in for a camp, but it’s up to you.


J: I saw online that you are from Toledo (MI), but you were drafted out of Estero high school (FL). I know a lot of ball players move south when they begin to take baseball very seriously. Was the move a baseball move? Were you thinking far ahead like that?


W: It was 60% or so baseball related. I played against a lot of southern teams and got smoked. That when my family realized if this is what I was gonna do, we needed to move.


J: Very cool. Around the draft time, were you sure that you were going to get picked? Did you have a draft party?


W: No. I was just hanging out with my mom, and I was getting a lot of calls around the time.


J: Who do you think played the largest role in your success?


W: I think it’s hard to point to one person specifically, as it’s really a group effort of a lot of

great coaches. Since joining the Jays I’ve been blessed with two very good coaches, Tony Caceres and Jim Czajkowski. Both of them taught me different things, and helped my development a ton.


J: In 2017 (rookie league), you put up some poor numbers (5.33 ERA). A year later in 2018, you looked like an elite prospect, pitching to a 2.78 ERA (low A). What was the biggest adjustment you make to take that jump?


W: This is a question I’ve asked myself. Bluefield (Rookie league team) was a weird year for me. Felt like I wasn’t myself and almost all of my pitches got away from me that summer. I came home that offseason and did a lot of reflecting. A part of it was telling myself I never wanna pitch that bad again. I hated that feeling of being awful start after start. Mix that in with refining some things and tuning in my approach to starts and you see the difference in the next couple years where I look like an actual pitcher. I think it was a confidence thing as well, I definitely lost it in rookie ball, and was fortunate enough to regain that in Vancouver.


Winckowski’s story is an extremely interesting one. He felt he never stood out overly until his senior year, yet he was drafted out of high school. Despite getting drafted, he only received one college offer. Some of these things are completely unexpected until you go through it yourself. These answers were very different than expected, and are really eye opening. The other major point from the interview could be that the major change in success from 2017 to 2018 was credited to mental changes, not so much mechanical, or physical. Each athlete has their own story, and this one is yet another interesting example of that.


Going forward, Winckowski is a name to watch for. He is likely to start the year in advanced A Dunedin, and will likely complete his age 22 season in AA New Hampshire, or AAA Buffalo if he keeps up his current level of production. Winckowski is likely only a few adjustments from shooting up in the system, and you could expect him in the top 30 prospects like by the deadline. He might just be one of the major players in the future rotation of the Blue Jays, alongside Pearson, Borucki, and others.



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