The first 2025 player to commit to Michigan, Winters Grady can provide a scoring boost for the Wolverines next season and beyond. Here’s a deep dive into how he could fit in Dusty May’s rotation:
Three talented 2025 recruits are joining Michigan’s roster next season — five-star in-state guard Trey McKenney, four-star forward Oscar Goodman and four-star guard Winters Grady.
We’ve already done deep dives on what Michigan fans can expect from McKenney , who was recently named a McDonald’s All-American , and Goodman, who is practicing with the team after graduating early in New Zealand.
With a month left of the high school season, let’s check in on Grady, Dusty May’s first 2025 commit , and project where he could fit into Michigan’s rotation over the next few seasons.
Recruiting and high school details
On the 247Sports composite , Grady is rated No. 83 overall, the No. 19 small forward and No. 9 player from California. He had about a dozen offers and took visits to Oregon, Oklahoma, Colorado, Iowa and New Mexico before signing with Michigan.
Grady is a key player for Prolific Prep. Playing alongside 2025 No. 3 recruit and Kansas commit Darryn Peterson, Prolific Prep boasts a 24-5 record , including two wins over Utah Prep, led by No. 1 recruit A.J. Dybantsa.
Breaking down Grady’s game
Grady likes to push the ball in transition and can knock down deep threes within the flow of the half-court offense. One of the main ball-handlers for Prolific Prep, he plays well next to Peterson, finding him while also getting shots of his own.
Grady is not afraid to challenge players one-on-one, knocking down threes by using a few decisive dribbles. He can also create his own looks in the mid-range. Watching highlights, it appears he shoots better off the dribble rather than in a catch-and-shoot role, which speaks to his shot creation.
He can finish at the rim in transition, but shooting from deep seems to be a default for him. Looking at his jump-shot, he’s got consistent form and a nice follow-through — I just want him to develop a higher release point to make his jumper harder to contest.
His court vision is excellent, as he does a great job finding cutters and delivering a pass that only the cutter can get to set them up for an easy bucket. Grady is really good going down-hill off a dribble hand-off; he doesn’t have that burst to get to the rim off a pick-and-roll, but he’s crafty enough to finish from 10-15 feet out. He does jump-pass too often in the half-court, but he delivers accurate passes more often than not.
In terms of the shooting ability, he reminds me of Fletcher Loyer. In terms of the shot creation, he may remind Michigan fans of Muhammad Ali Abdur-Rahkman with his craftiness, although he can’t get to the rim nearly as well as MAAR did.
Where Grady could fit in Michigan’s rotation this season and beyond
As is often the case with freshman guards, Grady’s playing time next season will depend on how well he can defend. The shot making is there, and he likely won’t be in a lead-ball handler role with Tre Donaldson possibly returning and all the 2024 players — Justin Pippen, L.J. Cason, Phat Phat Brooks — ahead of him being guards.
Could I see him playing a Sam Walters role, with 5-10 minutes a game and more minutes than that if he makes some three-pointers? Sure, but he’s going to have to defend quicker Big Ten guards to stay on the floor, which may be a tall task right off the bat.
In Michigan’s ball screen-heavy offense, I could see Grady thriving down-hill and knocking down some threes off the dribble. If he can learn to turn that corner and get to the rim, his ceiling as a scorer raises immensely.
Beyond his freshman season, Grady can develop into a lead guard and play well alongside McKenney. The shooting prowess of that duo could give Michigan one of the most feared backcourts in 2026-27 once they establish some chemistry.