[1] Winfrey was rated a three-star prospect, but was not heavily recruited after failing to qualify academically to play NCAA Division I football.

[4] Winfrey was rated the best junior college prospect in the nation by 247Sports.com and committed to transfer to Oklahoma over offers from Alabama, Baylor, LSU, and Texas.

He was named second-team All-Big 12 Conference by the league's coaches after recording 19 tackles, six for loss, and three pass breakups.

[12] On July 19, 2023, Winfrey was waived by the Browns, after being investigated for threatening and pulling a gun on a woman in Cleveland.

[15] On October 3, 2024, Winfrey was signed by the Birmingham Stallions of the United Football League (UFL).