He then attended Saint Louis University where he was part of the men's soccer team from 2002 to 2005. In March 2006, the Milwaukee Wave of the Major Indoor Soccer League selected Wynn in the MISL Draft. However, the same month, the New England Revolution selected him in the first round (11th overall) in the 2006 MLS Supplemental Draft and signed him to a developmental contract.
Wynn then attended Saint Louis University, where he participated in the men's soccer team from 2002 to 2005. In March 2006, the Milwaukee Wave of the Major Indoor Soccer League selected Wynn in their draft, but the New England Revolution chose him a month later in their supplemental draft and signed him to an agreement for development.