Middleton was also a member of the Tampa Bay Buccaneers, Jacksonville Jaguars and San Diego Chargers.

Middleton attended Marist High School where he totaled 148 tackles, 10 interceptions, six pass deflections, two kickoff returns for touchdowns, and two blocked punts.

He was named First-team All-county and All-region honors in 2003 after helping his squad to a 14-1 record and state championship.

As a junior in 2007 he started at right cornerback in all 11 games and totaled 53 tackles, including three for-loss, three interceptions, and nine pass deflections.

In 2006 Middleton won starting job at right cornerback and helped Furman to an 8-4 campaign that included a third straight playoff appearance.