Winston began his football career in college, playing for the Florida State Seminoles at Florida State University. He had a successful college career, leading the Seminoles to a national championship in 2013 and winning the Heisman Trophy in the same year. Winston was selected as the first overall pick in the 2015 NFL Draft by the Tampa Bay Buccaneers, where he played for five seasons before joining the New Orleans Saints in 2020. He signed with the Cleveland Browns in 2021 as a backup quarterback.