He played college football at Auburn, and was signed by the San Francisco 49ers as an undrafted free agent in 2015.

[1] Whitehead attended Amanda Elzy High School where he played cornerback and quarterback with the Panthers football team.

Whitehead's defensive performances earned him numerous regional, state and All-American honors from ESPN.com, Rivals.com and Scout.com.

[14] On September 3, 2016, he was released by the Packers during final team cuts and was signed to the practice squad the next day.

[24] In Week 9 against the New England Patriots, Whitehead was ejected after slapping center David Andrews in the face mask.

[27] Whitehead was waived on November 4, 2019 after posting "several threatening and racist messages for people who criticized him" following the team's loss to the Denver Broncos, a game in which he missed a number of crucial tackles.

[29] After his final NFL season, Whitehead began a career in finances including jobs in payroll and financial management.