Wescott grew up in Aurora, Colorado, attending Smoky Hill High School where he was a four-year starter and three-time All State on the boys’ soccer team.
That fall, he signed with the Wichita Wings of the National Professional Soccer League (NPSL).
On February 7, 1996, D.C. United selected Wescott in the 14th round (140th overall) in the 1996 MLS Inaugural Player Draft.
On July 23, 2003, the St. Louis Steamers of the Major Indoor Soccer League selected Wescott in the eighth round of the Expansion Draft.
In 2004, he spent one season as the head coach of the St. Louis Strikers in the fourth division Premier Development League.