Redwine began his football career playing college football for the University of Miami. During his time with the Miami Hurricanes, he showcased his abilities as a hard-hitting safety with a knack for making big plays. In 2019, Redwine was selected by the Cleveland Browns in the fourth round of the NFL Draft. He spent two seasons with the Browns before being waived in 2021. Shortly after, he was picked up by the Dallas Cowboys.