Kevin Winston Jr. attended DeMatha Catholic High School in Hyattsville, Maryland where he played high school football. As a senior in 2021, he was named the All-Met Defensive Player of the Year by the Washington Post after recording 50 tackles, three interceptions and a fumble recovery for a touchdown. Winston was a four star recruit who had several Division One offers and finally committed to Penn State.
As a true freshman in 2022, Winston Jr. played in 12 games and had 16 tackles in a reserve role. As a sophomore in 2023, he started 13 games and tallied 61 tackles and an interception. After the season, Winston was awarded All-Big Ten honorable mention.
Winston Jr. only played in three games in 2024 before he suffered a partially torn ACL and missed the rest of the season. After the season, Winston announced he was entering the NFL draft and should be ready by March to join football activities.