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
Whitehead was signed as an undrafted free agent by the Dallas Cowboys after the 2015 NFL Draft. He made the team as one of the players that was looked upon to replace the departed Dwayne Harrisspecial teams production. Although wide receiver Cole Beasley was the assigned punt returner early in the season, because he provided better ball security, Whitehead was given opportunities until earning the returner role for the final six games. He only averaged 5.8 yards per attempt as a punt returner, but showed glimpses as a kickoff returner, like his 79-yard kickoff return against the Philadelphia Eagles or his key 46-yard kickoff return against the Washington Redskins to set up the game-winning field goal with 14 seconds left. Whitehead was used on offense with special runs designed for him. 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. He finished the 2015 season with 10 rushes for 107 yards and six receptions for 16 yards.
2016 season
In the preseason opener, which was the first NFL game in Los Angeles since 1994, against the Los Angeles Rams at the Los Angeles Memorial Coliseum, Whitehead returned the opening kickoff 101 yards for a touchdown. In addition, he had one catch for six yards and one rushing attempt for 11 yards. In Week 6 against the Green Bay Packers, Whitehead caught a career-long 35-yard reception from quarterback Dak Prescott, as well as a season-long 26 yard run. Whitehead experienced problems during the season, like his critical fumble during a run against the Minnesota Vikings. The next week after being late to team meetings on the Saturday before the trip to New York, he was subsequently left home, fined and de-activated against the New York Giants. Whitehead remained more effective as a runner out of the backfield than at wide receiver, and was inconsistent as a return specialist. He shared the returner role with Beasley and running backLance Dunbar, especially in critical situations, when better ball security was required. He had a total of three fumbles, losing two.
2017 season
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 Wawaconvenience store in Prince William County, Virginia and skipped court summons. Later that day after the team's first training camp practice, he was released by the Cowboys. The charges were dropped and he was cleared by the police when it was determined the next day that the charges were based on mistaken identity.
New York Jets
On July 26, 2017, Whitehead was claimed off waivers by the New York Jets. 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 waived/injured on September 2, 2017 and was placed on injured reserve. He was released by the team on September 11, 2017. He was re-signed to the Jets' practice squad on November 24, 2017. He was promoted to the active roster on December 30, 2017. On August 26, 2018, Whitehead was waived/injured by the Jets and was placed on injured reserve. He was released on August 31, 2018.
Winnipeg Blue Bombers
Whitehead signed with the Winnipeg Blue Bombers of the Canadian Football League on May 9, 2019. He had a breakout performance in Week 3 of the 2019 regular season, catching 7 passes for 155 yards with two touchdowns. Whitehead finished the year with 52 catches for 521 yards and two touchdowns, one rushing touchdown, and one kickoff return for a score.
Personal life
Whitehead was given the nickname "Lucky" by his cousin. In July 2017, Whitehead posted on Instagram that his dog, Blitz, was stolen and held for ransom. The following day, Whitehead posted on Snapchat, confirming that Blitz was safely returned to him. 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.
