Essex attended Paul Harding High School in Fort Wayne, Indiana, and was a student and a letterman in football and basketball. Essex played in the first ever U.S. Army All-American Bowl on December 30, 2000. In football, he was a four-year letterman. In basketball, he was a member of the 2001 class 2A Indiana boys high school championship team. Essex was an All-Conference honoree as a junior.
Essex attended Northwestern University and was a letterman in football. In football, he was a three-year starter as an offensive lineman. He majored in African-American studies.