Wynn attended De La Salle Institute in Chicago and gained honors as an All-Midwest selection by Tom Lemming's Prep Football Report and All-State second-team choice by the Chicago Tribune.

He was team captain; recording 50 tackles with three interceptions and five fumble recoveries as an outside linebacker and rushed for 500 yards with nine touchdowns as a fullback in his senior season.

Wynn lettered four years in basketball, averaging 12 points 11 rebounds per game while serving as team captain as a senior.

Wynn played in ten games in 1994, starting the first six at right outside linebacker and four others, including the Fiesta Bowl against the University of Colorado, at left defensive end.

Wynn recorded 47 tackles with one sack, four stops for losses, forced two fumbles and recovered another.

In 1996, Wynn played left defensive end as a senior, making 61 tackles with nine sacks, six stops for losses, recovered two fumbles and deflected one pass.

In the 2001 season, Wynn ranked sixth on the Jacksonville Jaguars with 75 tackles and tied for fifth with five sacks, both career highs.

He was voted as team captain by his teammates, and Wynn posted 30 tackles and two sacks for the season.

He appeared in 12 games for the Saints that season including one start, recording 13 tackles and 3.5 sacks.