Wynn was drafted by the Cleveland Browns in the 6th round (183rd overall) in 2000. Wynn proceeded to play for the Browns in 2000, seeing action in 7 games. including one start - a 48-0 loss to the Jacksonville Jaguars. With the Browns, Wynn went 22 for 54 (40.7%) passing, for 167 yards, no touchdowns, one interception, and a passer rating of 41.2.
Following the 2000 season, September 3, 2001, Wynn was traded to the Minnesota Vikings, along with RB Travis Prentice, in exchange for draft picks in the 2002 and 2003 NFL drafts. Wynn was a third string backup to Daunte Culpepper and Todd Bouman in the 2001 and 2002 seasons and played in the last three games of the 2001 season, starting two of them. This was due to season-ending injuries to both Culpepper and Bouman.
After his 2002 stint with the Minnesota Vikings, Wynn made his way north to Canada to play for the BC Lions, completing 67 of 99 passes for 894 yards, 6 touchdowns, and one interception. He also rushed for 2 touchdowns and 145 yards on 36 attempts.