[4] He was selected as All-County, All-South Jersey and All-State during his senior year in 2003–04 while playing for Woodbury High School.

His high school football coach was former Pittsburgh Steelers linebacker Zack Valentine, who won Super Bowl XIV as a member of the famous "Steel Curtain" defense.

Pressley’s collegiate statistics were not outstanding, but his hard work ethic and willingness to sacrifice his body landed him on an NFL roster after going undrafted in 2009.

On November 22, Pressley made his NFL regular season debut for the Buccaneers in a 38–7 loss to the New Orleans Saints.

Cincinnati then re-signed him, and on December 10 was promoted to their roster after cornerback Rico Murray sustained an ankle injury.