whitehead was born in manassas, virginia on june 2, 1992. he attended george c. round elementary and osbourn high school where he played wide receiver and cornerback on the football team, while being named all-conference as a senior. whitehead moved on to dean college in franklin, massachusetts, where he played wide receiver and return specialist, receiving all-american and all-conference honors. in 2013, he transferred to florida atlantic university and registered 284 all-purpose yards. as a senior, whitehead was the team's slot receiver, registering 76 receptions, which led the conference, for 706 yards and six touchdowns, 21 carries for 210 yards and two touchdowns, and a 24.7-yard average on kickoff returns. he had a 73-yard punt return for a touchdown in his last college game against old dominion university