Recruiting Roundup: Winters Grady


Despite missing time this summer with an injury, 2025 prospect Winters Grady has led a busy recruitment, fielding offers and interest on a national scale. Grady, a 6-foot-7 Swiss Army knife, plays for Lake Oswego High School (OR) and is expected to have a breakout sophomore season.


Grady is full of realistic upside and has already shown more than just glimpses of a highly-valuable skill set: he’s able to stretch the defense with his ability to knock down jumpers from NBA three-point range; Grady also has a strong athletic build that helps him drive to the rim with vengeance, as well as punish weaker opponents in the paint; Grady plays with pace, and can beat the opposition with his elite footwork and functional athleticism. As he continues to evolve into a true three-level scorer, his recruitment is bound to increase substantially as more programs begin to take notice.


This week, Grady spent time with Pro Insight’s Jake Lieberman to chat about the latest with his recruitment.


For the next installment of “Recruiting Roundup,” we present class of 2025 prospect Winters Grady, from Lake Oswego, Oregon:


Pro Insight: What are you hoping to show NCAA coaches, scouts and evaluators from here on out?


Winters Grady: These next couple years I'm going to be showing them the dog in me, especially with missing this whole last summer due to injury. I feel like I kind of have a chip on my shoulder, and I’m going after everything and everyone. Then I definitely want to show them that aggressive side in me with attacking the rim hard, going to dunk on someone, playing hard in the post, rebounding, getting blocks, all that stuff. Last but not least I want to prove myself on the defensive end to not only coaches but just to everyone, that I can guard 1-5.


PI: Which programs would you say are currently prioritizing you the most or expressing the most interest?


WG: I don't wanna say someone is prioritizing me most, because if i’m being honest I don’t feel like anyone is prioritizing me right now. No coaches have been calling me on a consistent basis trying to get to know me or anything. We can talk about schools that have been recruiting me longest but that’s different, when the dust settles I will probably end up somewhere that has been recruiting me for a good amount of time and where I feel wanted.


PI: Where have you visited thus far? Do you have any future visits planned?


WG: I've only been on one unofficial so far and that was at Oregon. I do not currently have anything planned and for the most part getting ready for this next season.

PI: Did you have any dream schools growing up?


WG: Growing up I always loved Kentucky and Coach Calipari. That has always been my dream school. I’m yet to actually hear from them but that’s definitely one of my goals. PI: If you could team up with any high school player in the country when you guys get to college, who would you pick?


WG: Definitely my guy JJ Mandaquit. I love playing with him. He’s a great facilitator, gets the offense running, and will always find the open man. PI: How do you project your role at the next level?


WG: I would like to have a decent role going into my freshman year, but at the end of the day I just want to develop, take my time, and figure out the game. Then when the time is right I want to declare for the draft.


PI: How’s your timeline looking?


WG: I would like to narrow down towards the start of my junior year. I am yet to go on too many visits and do not have many strong connections with coaches, so that could vary.


PI: What's your pre-game pump-up song/artist?


WG: Always Youngboy, Nardo Wick, and sometimes Rod Wave.

PI: Which player in the NBA or college would you compare your game to?


WG: I would compare myself to a Tyler Herro-type. At times some compare me to a Luka. Then I also hear Gradey Dick a lot. Basically anyone who gets buckets.


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