Cowden attended Lebanon High School in Virginia where he was one of the state's top multi-sport athletes,[1] playing football as a quarterback, baseball as an outfielder, basketball as a point guard and track and field.
[2] He was a three-year starter in football and compiled an overall record of 30–6, leading them to the Region C, Division 2 championship in 1994 where they lost 34–33, in what was considered one of the greatest games in Southwest Virginia history.
[3] As a senior in 1999, he recorded a total of 59 tackles, placing third on the team, and was the holder for kicks, throwing in that position a 29-yard touchdown on a fake field goal.
[10] After Jon Robinson was fired as general manager of the Titans in December 2022, Cowden was named interim replacement.
[12] On January 13, 2025, the Giants let Cowden out of his contract to join the New England Patriots as a front office advisor.