Whittington attended Oakland Mills High School in Columbia, Maryland where he was a four-year letterwinner playing for the basketball team.

[10] Whittington failed to appear in any games for the Hoyas in the 2013–14 season due to a torn ACL suffered during the summer, as he was dismissed from the team on November 30, 2013.

[9] He subsequently transferred to Rutgers University,[11] only to go back on his commitment by not enrolling for the spring semester with no comment given on his decision not to join the school.

[18][19][20] On November 2, 2015, Whittington was acquired by the Sioux Falls Skyforce of the NBA Development League as an affiliate player of the Heat.

[28] In the 2016 off-season, Whittington decided against participating in Summer League activities and instead went home to Maryland to work out with his local counterparts.

[30] He made his debut for the Kings in their season opener on October 8, 2016, but struggled to make an impact offensively in 24 minutes due to foul trouble.

[32][33] In the Kings' fourth game of the season on October 20, Whittington scored a season-high 22 points in a 92–78 win over the New Zealand Breakers.

On September 20, 2018, Whittington signed a one-year deal with Hapoel Gilboa Galil of the Israeli Premier League.

[40] On April 15, 2019, Whittington recorded a career-high 29 points, shooting 10-of-17 from the field, along with 14 rebounds, 5 assists and 2 blocks in a 96–93 win over Ironi Nahariya.

[44] On June 30, 2021, Whittington signed with Russian team Lokomotiv Kuban of the VTB United League.

[46] On November 8, 2022, Whittington signed with Hapoel Be'er Sheva of the Israeli Basketball Premier League.

[53] He is the son of the late Gregory and Jana Lisa Whittington, and has an older sister, Hana, and a younger brother, Cortez.