Get to Know Future Wolverine Winters Grady
4/30/2025 10:00:00 AM | Men's Basketball
This is part two of a three-part series in which Shira Black sits down with three signees for Michigan men's basketball.
By Shira Black
When Winters Grady steps into the gym, he hears two distinct voices.
His dad, Ron Grady, is always there to motivate him, keeping Grady on track to reach the goals he has set for himself -- chief among them, playing college basketball.
And his mom, Jenni Grady, his self-proclaimed number one fan, is the steady, supportive voice in the crowd that helps him stay grounded.
Both former Oregon State basketball players, they've built the foundation that has allowed Grady to push forward in becoming the extraordinary player he is today.
Another strong pillar of support for Grady has been his former teammates before his Prolific Prep days. A Tualatin, Oregon, native, he grew up playing basketball in Oregon's AAU circuit with a close-knit group that stayed together from kindergarten through middle school. Even after going their separate ways, they reunited each summer for tournaments, chasing wins and creating lasting memories.
Oregon offered Grady more than just close ties -- being surrounded by picturesque landscapes gave him the chance to explore and spend time outdoors. One of his favorite spots back home is in Bend, filled with beautiful parks and serene views.
After two years of top-level high school play in Oregon, Grady moved to Napa, California, to play for Prolific Prep, a premier basketball academy and the former school of Nimari Burnett. The decision meant leaving behind his parents, younger brother Rocco and two French bulldogs, Dexter and Danger.
"It was a change for sure. My two biggest supporters being in a different state and so far away from me... but I feel like I've grown a lot, whether it's my game or my mindset. It's kind of been like taking a job to a certain extent -- we're traveling every weekend."
Playing for Prolific Prep gave Grady the platform to compete on a national stage, showing what he could bring to a high-level program like Michigan. He had the chance to engage more with the analytical side of the game, something he believes will serve him well in Dusty May's system.
Watching the 2024-25 Wolverines, Grady was a fan of their energy and edge.
"The new era -- I really enjoy the vibe that they have going there. It's young, it's intense, dudes are always in the gym, the coaches are always in the gym working out players, watching film, just trying to get their players better and their team to take that next step forward.
I just knew -- I went on all these official visits and then I went to Michigan, I was like yeah, that's the one."
Grady looks forward to connecting with his new teammates and coaching staff, drawn in by a U-M coaching group that values relationships just as much as results. He prides himself on constantly learning from those around him, especially his coaches.
"I'm not really a transactional kind of guy, like if I do this for you, you've got to play here, you got to do this. I like consistency in relationships and that's kind of the main thing for me. I love that I'm going to be able to build a relationship, no matter how long I'm there... and I know that I'm going to have a great relationship with every single one of the coaches when I leave."
Like his fellow incoming freshmen Trey McKenney and Oscar Goodman, Grady points to his versatility as a defining part of his game. While he's widely recognized as one of the best knockdown three-point shooters in his class, he's also efficient, crafty and an exceptional playmaker who can score in a variety of ways.
Grady brings a fiery energy to the court, but above all, he brings a winning mindset. After all, his name does start with "win." And a winner he is, going 47-0 in his two seasons with Prolific Prep and the Grind Session, the international elite prep basketball circuit. He joined the 2,000-point club in January, then dropped 21 points to lead Prolific Prep to its third straight championship.
That competitive fire runs in the family -- he credits his dad, who never turns down a challenge, for his gritty mindset. Grady plays with a chip on his shoulder, confident in his game and never missing a chance for some good-natured trash talk. Expect some of that passion at Crisler Center come fall.
He is named after his dad's best friend, who passed away from a heart attack -- a name that lives on through this relentless player ready to leave his legacy.
