Winston finished his college career at Michigan State University before joining the Washington Wizards. He also played for the Erie Bayhawks and the Capital City Go-Go of the G League before joining FC Bayern Munich, where he made his EuroLeague debut in the 2022-23 season, averaging 11.0 points and 3.4 assists in 29 games. He helped Bayern win the German Cup title in 2023. Winston has also played for Tofas Bursa of Turkiye.
Winston is set to make his BKT EuroCup debut with Jerusalem next season, sharing backcourt duties with the competition’s reigning MVP Jared Harper.