[2] 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.

In the sixth game of the season against the New York Giants, he set a franchise record for a wide receiver with four rushing attempts.

In Week 6 against the Green Bay Packers, Whitehead caught a career-long 35-yard reception from quarterback Dak Prescott,[9] as well as a season-long 26 yard run.

He shared the returner role with Beasley and running back Lance Dunbar, especially in critical situations, when better ball security was required.

On July 24, 2017, it was revealed that Whitehead was facing misdemeanor petty larceny charges stemming from an arrest in June having stolen $25 of goods from a Wawa convenience store in Prince William County, Virginia and skipped court summons.

[16] On August 16, 2017, it was revealed that Whitehead would undergo surgery for a fractured foot he suffered in practice, with an estimated recovery time of four to six weeks.

He was on the injured list during the Blue Bombers' playoff run, but was part of the 107th Grey Cup championship team.

[24] On October 4, 2021, the Lions announced that Whitehead would undergo surgery after breaking his hand in during a Week 9 loss to the Winnipeg Blue Bombers.

At the time of the injury Whitehead was second in the league in receiving yards with 665, trailing only Kenny Lawler.

He finished with 60 receptions for 932 yards and four touchdowns in just 12 games played as he was named a CFL All-Star for the first time in his career.

[35] Whitehead said that he refused to write a check for $10,000, as the perpetrator had initially demanded, but agreed to pay an undisclosed amount of money after making sure Blitz was okay.