Winters Grady

#91

SF•Prolific Prep•Class of 2025

"6”7 Bucket"

@WintersGrady_@win2ers

Attending

Michigan

6-5

185 lbs

Napa

96 Rating

#91 National#10 State#21 Position

Scout Report

At 6-5, this athletic wing brings versatility and upside that caught the attention of Michigan coaches despite flying under the radar compared to his more heralded teammates.

Background

Hailing from Napa, CA, Winters Grady made the move to Prolific Prep to elevate his game alongside some of the nation's elite prospects. At the prestigious program, he shared the court with future stars like Darryn Peterson (#2 in 2025, committed to Kansas), Caleb Holt (#4 in 2026, committed to Alabama), and Bruce Branch III (#6 in 2026, also committed to Michigan). Despite being ranked #91 nationally in the 2025 recruiting class, Grady's development trajectory and potential made him an attractive target for Michigan.

Playing Style

Grady possesses the prototypical size and athleticism coveted in today's positionless basketball landscape. As a small forward, he brings length and versatility on both ends of the floor, with the ability to guard multiple positions and contribute in various facets. His time at Prolific Prep playing alongside elite-level talent has accelerated his development and basketball IQ. While still refining his skill set, Grady shows flashes of being a complete wing player who can impact winning through energy, hustle plays, and timely contributions rather than overwhelming individual statistics.

Recruitment

Now enrolled at Michigan, Grady joins a program that clearly saw something special in his potential beyond his national ranking. His connection to Bruce Branch III, who also committed to the Wolverines, suggests the coaching staff values the chemistry and experience these Prolific Prep teammates bring. At the college level, Grady projects as a developmental piece who could emerge as a key contributor with continued growth and seasoning in Michigan's system.

Updated Feb 17, 2026 · Analysis by PrepRadar Scouting Team