Eskay is among the most successful male soccer players to hail from Frederick County, spending four years in the United Soccer league (USL) with the Phoenix Hearts and Arizona Cotton. Eskay played college soccer for Air Force from 1983-85 and William & Mary from 1986-87. He helped William & Mary to a conference title and NCAA Division I tournament appearance in 1987.

He was a three-time all-county and all-league player at Linganore, earning local Player of the year and All-State First Team honors in 1982. He launched FC Frederick's Academy program in 2003, and helped coach the first class to a Maryland State Cup title and No. 3 national ranking, making FC Frederick '94 the most successful boys' club team in Frederick County history.