He chose to attend college at Michigan State,[2] and averaged 6.7 points and 5.2 assists per game in 35 games as a freshman.[3] As a sophomore, he became a full-time starter, averaging 12.6 points and 6.9 assists per game for the Spartans, and earning third-team All-Big Ten Conference honors.[4]
Prior to the start of the 2019–20 season, Winston was unanimously named a preseason All-American by the Associated Press (AP), the only player so honored.[9] On December 29, Winston missed a game against Western Michigan with a bone bruise in his knee.[10] He scored a career-high 32 points along with nine assists in a 87–69 win over Michigan on January 5, 2020.[11] Winston passed Mateen Cleaves' Big Ten record of 816 assists on January 17, in a win against Wisconsin.[12] At the close of the regular season, Winston was named to the First Team All-Big Ten by the coaches and media.[13] The remainder of the season was canceled due to the ongoing COVID-19 pandemic prior to any postseason tournaments being held.[14] The Spartans were, at the time, considered a favorite to win the NCAA tournament.[15][16] Winston averaged 18.3 points and 5.9 assists per game as a senior.[17]
On August 19, 2021, Winston signed a second two-way contract with the Wizards.[19] He appeared in 7 games for the Wizards during the 2021–2022 regular season.[20]
Winston has two younger brothers, Zachary and Khy, who played basketball at Albion College. On November 9, 2019, Zachary Winston was killed after being struck by a train, in an apparent suicide.[25] Cassius played in a game the day after his brother's death, scoring 17 points and adding 11 assists in a blowout win.[26] He received a standing ovation from the home crowd when he exited the game.
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