A native of Denver, he attended Thomas Jefferson High School, where he played for the football team and was teammates with Daniel Graham[1] Woolfolk recorded 171 tackles and 19 interceptions in high school.
[4] He earned third-team All-Big 12 honors in 2000 and 2001 and was also a member of the Oklahoma team that won the national championship in 2000.
[1] Woolfolk was selected by the Tennessee Titans in the first round, with the 28th overall pick, of the 2003 NFL draft.
He played in 13 games, starting seven, for the Titans during the 2005 season, accumulating 42 solo tackles, 13 assisted tackles, one interception, seven pass breakups, one forced fumble and one fumble recovery.
[6] In 2021, The New York Times named Woolfolk the biggest draft bust ever chosen with the 28th overall pick.