 Coming out of Stephenville High School led by head coach Art Briles, Stewart was the Texas high school football player of the year and was recruited by virtually every major program in the country, ultimately signing with the University of Tennessee, which had also signed highly regarded quarterback Peyton Manning as part of the same recruiting class.He was inducted into the 2008 Texas High School Football Hall of Fame induction class.Stewart played in 11 of 12 games at quarterback for the Volunteers as a true freshman in 1994, but Manning started the final eight games of the season while exhibiting the skills that would make him a perennial All-American and, eventually, All-Pro quarterback.