Whitehead played at the 2014 McDonald's All-American Boys Game, the 2014 Jordan Brand Classic, and many other prestigious tournaments in high school.

[1] Whitehead was named preseason Big East Rookie of the Year and made the All-Rookie Team as a freshman.

[1] At the conclusion of the 2015–16 regular season, Whitehead was unanimously selected to the All-Big East first team.

[2] He also received the Haggerty Award, given to the New York area's top men's Division I basketball player.

In March 2016, Whitehead declared for the NBA draft, forgoing his final two years of college eligibility.

[6] On January 6, 2017, Whitehead recorded his first career double-double with 10 points and 10 rebounds in 116–108 loss to the Cleveland Cavaliers.

[8] On April 8, 2017, with one block against the Chicago Bulls, Whitehead tied an all-time team record by a guard in a single-season with 36, set by Darwin Cook during the 1980–81 season.

[9] On November 27, 2017, Whitehead tied his career high with 24 points while shooting 10 of 16 from the field in a 117–103 loss to the Houston Rockets.

[10] During the 2017–18 season, he was assigned multiple times to the Long Island Nets of the NBA G League.