Winstead originally signed with the San Francisco 49ers as an undrafted free agent following the 2023 NFL Draft. He also spent time with the New York Jets.
Winstead spent time in the UFL, first with the Dallas Renegades. He appeared in 17 games for Dallas over two seasons, with 43 receptions for 482 yards and two touchdowns.
In 2026, Winstead played for the UFL's Louisville Kings. He played in eight regular season games, finishing with 29 receptions for 474 yards and three touchdowns. He also played in two postseason games, pulling in seven receptions for 88 yards and one touchdown.
Winstead played one season (2022) of college football at East Carolina where he had 88 receptions for 1,085 yards and six touchdowns, while earning All-American Athletic Conference Honorable Mention honors. Winstead began his college career at Toledo.
