From Pritchard, Alabama, Winston was named 1st-team All-State during his senior season after leading Vigor High School to the 5A state championship game. He was ranked as the 51st-best DE in the country by Scout.com, and the 50th best weakside DE in the nation by 247Sports. He committed to the University of Arkansas for college ball.
Winston enjoyed a solid career as a Razorback. He started 12 games as a sophomore, logging 26 tackles (2 for a loss). He was elected team captain by his teammates during his junior season, and continued to post solid numbers throughout his collegiate career.
As an undrafted free agent in 2016, Winston received a tryout from the Tampa Bay Buccaneers. Now, in 2018, Winston will continue to chase his NFL dreams with The Spring League.