Michigan basketball's offseason has begun with its first significant roster move. Freshman guard Winters Grady intends to enter the transfer portal, as confirmed by a source to the Detroit Free Press.

This decision comes after a challenging debut season for the 6-foot-6 shooting guard, who was limited to just nine appearances in 2025-26 due to a persistent foot injury. The issue, stemming from a broken fifth metatarsal suffered in high school, significantly hampered his ability to carve out a role.

On the court, Grady showed flashes of his potential as a shooter, averaging 2.9 points in limited minutes. However, he found himself deep on a crowded wing depth chart behind veterans like Nimari Burnett and Roddy Gayle Jr., as well as fellow freshman Trey McKenney.

While the impending departures of Burnett and Gayle could have opened a path for more playing time, the Wolverines' recent recruitment of five-star guard Brandon McCoy and the expected return of McKenney meant Grady still faced a steep climb for minutes in Ann Arbor.

As he looks for a fresh start, one potential destination to watch is Oregon State. The Beavers are now led by former Michigan assistant Justin Joyner, and the program is located just over an hour from Grady's hometown of Tualatin, Oregon, making it a natural fit for the young guard seeking a new opportunity.

Grady is expected to apply for a medical redshirt for his injury-shortened season. His departure signals the beginning of what is likely to be an active roster reshuffling period for the Wolverines in the coming weeks.