Wynn started his college career playing for the Minnesota Golden Gophers of the University of Minnesota, but he transferred to play quarterback for the Southwest Texas State Bobcats of Southwest Texas State University, now known as Texas State University, between 1998 and 1999. In these two years, Wynn piled up 3,497 yards passing, good for sixth on Southwest Texas State's record books. In 1998, Wynn threw for 1,851 yards and 10 touchdowns. In 1999, Wynn was selected to the All-Southland Conference second team after throwing for 1646 yards and 14 touchdowns for the Bobcats.
Wynn was drafted by the Cleveland Browns in the sixth round (183rd overall) in 2000. He was the fifth quarterback picked in that draft, although chosen before New England drafted Tom Brady. Wynn played for the Browns in 2000, seeing action in seven games, including one start – a 48–0 loss to the Jacksonville Jaguars. With the Browns, Wynn completed 22 of 54 (40.7%) passes for 167 yards, no touchdowns, one interception, and a passer rating of 41.2.
In the summer of 2001, Wynn was sent to NFL Europe to develop his skills. He started for the Amsterdam Admirals, throwing 14 touchdowns and 2,039 yards.
On September 2, 2001, Wynn, along with running back Travis Prentice, was traded to the Minnesota Vikings in exchange for draft picks in the 2002 and 2003 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 because of season-ending injuries to both Culpepper and Bouman. In the Vikings’ next-to-last regular-season game against the Green Bay Packers on December 30, 2001, Wynn threw the only touchdown pass of his NFL career, a 47-yard strike to tight end Byron Chamberlain.
After failing to move beyond third string with the 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.