Whitehead was born in Greenwood, Mississippi to Teveeta Whitehead and Frank Ellis.[1] Whitehead attended Amanda Elzy High School where he played cornerback and quarterback with the Panthers football team. After a productive season in 2009 as quarterback saw Whitehead earn District 3 (4A) Player of the Year, he went on to play his junior and senior seasons as a cornerback. Whitehead's defensive performances earned him numerous regional, state and All-American honors from ESPN.com, Rivals.com and Scout.com.[1] He was rated a four-star recruit by 247Sports and Rivals.com.[2][3] By his senior season, Whitehead held a 3.71 GPA.[4] Whitehead received offers from Tennessee, Mississippi, Mississippi State and Auburn.[2]
After going undrafted in the 2015 NFL draft, Whitehead signed with the San Francisco 49ers on May 5, 2015.[8] On September 5, 2015, he was released by the 49ers during final team cuts.[9] Whitehead was signed to the 49ers' practice squad the following day.[10]
Baltimore Ravens
On December 23, 2015, the Baltimore Ravens signed Whitehead off the 49ers' practice squad.[11] He was inactive for the last two games of the season. On April 19, 2016, Whitehead was re-signed by the Ravens.[12] He was released by the Ravens on May 13, 2016.[13]
Green Bay Packers
Whitehead was signed by the Green Bay Packers on May 18, 2016.[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.[15][16] On October 24, 2016, he was promoted from the practice squad to the active roster.[17] Whitehead made his NFL debut against the Atlanta Falcons in Week 8. On November 7, 2016, he was released by the Packers and was re-signed back to the practice squad.[18][19] He signed a futures contract with the Packers on January 24, 2017.[20]
On September 2, 2017, Whitehead was waived by the Packers and was signed to the practice squad the next day.[21][22] He was promoted to the active roster on October 21, 2017.[23]
Whitehead was re-signed on March 14, 2018.[24] In Week 9 against the New England Patriots, Whitehead was ejected after slapping center David Andrews in the face mask. He was then released by the Packers on November 6, 2018.[25]
Cleveland Browns
On November 7, 2018, Whitehead was claimed off waivers by the Cleveland Browns.[26] On September 29, 2019, he had his first NFL career interception and forced fumble in a game against the Ravens.[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.[28] Whitehead later apologized for the messages.[29]
After his final NFL season, Whitehead began a career in finances including jobs in payroll and financial management. From 2020 to 2021, Whitehead attended Syracuse University, graduating with a Master's Degree in accounting. Since 2022, he has worked as a senior staff accountant for Vertical Communication based in Atlanta, Georgia.[30]