Wynne, who was the No. 1 overall selection of the New York Red Bulls in the 2006 MLS SuperDraft, was known for his blazing speed and imposing physique. He won an MLS Cup with the Colorado Rapids in 2011 and logged more than 2,000 minutes in seven consecutive seasons and nine overall. He is currently one of just 37 players to appear in 300 MLS matches.
Wynne was part of the US Under-20 team that went to the Round of 16 in the 2005 FIFA World Youth Championship. He would go on to start all three matches for the US at the 2008 Olympics, as USA finished third in the group. He registered five caps with the US men's national team, most notably starting a World Cup qualifier in Costa Rica ahead of the 2010 World Cup.