Maddox received a Bachelor of Arts from Morgan State University, summa cum laude, in 1999 where he majored in philosophy and religious studies and minored in psychology.

[5] From 2011 to 2012, he served as a law clerk for Judge Gerald Bruce Lee of the United States District Court for the Eastern District of Virginia and from 2014 to 2015, he served as a law clerk for Judge Andre M. Davis of the United States Court of Appeals for the Fourth Circuit.

[5] Maddox was named the identity theft coordinator in 2018 and deputy chief of the Major Crimes section in 2020.

President Biden nominated Maddox to the seat vacated by Judge Paul W. Grimm, who assumed senior status on December 11, 2022.

[9] During his confirmation hearing, Senator Mike Lee questioned Maddox about his past membership with both ACORN and the American Constitution Society.