Youth and amateur

Eskay began playing organized travel soccer in 2002 when he joined the local club, FC Frederick. He was part of their development teams through 2013. Eskay played high school soccer from 2009 through 2012 at Urbana High School, where he was a four-year starter. Eskay finished his high school career ranked second in assists and fourth in points (two points for goals and one point for assists combined). While at Urbana, Eskay helped lead the Hawks to the Maryland 4A State Finals in 2010 and 2011. While in high school, Eskay was named to the Maryland ODP team and was named to the Maryland First-Team All-State selection in 2011 and 2012.^[1]

Upon graduating from Urbana, Eskay signed a National Letter of Intent to play college soccer for the William & Mary Tribe men's soccer program. During the 2012 NCAA Division I men's soccer season, Eskay made 18 appearances and earned 12 starts, scoring twice his freshman year. Eskay earned CAA Rookie of the Week honors. Eskay had a breakout season in his sophomore year, starting and playing in 19 matches, where he led the team with 8 goals, and had 5 assists, for 21 points. Notable games he earned points included two matches against the then-No. 1 teams in the nation, Creighton^[2] and North Carolina.^[3] Eskay finished the season earning Third-Team All-CAA honors. Due to injury in the spring season, Eskay had a rather quiet junior season, playing 18 matches with 12 starts, and only scoring one goal. His senior year, he returned to form earning a spot on the VaSID First-Team and earning all-CAA Second-Team honors. He led the Tribe in points (20) and goals (8) during the 2015 NCAA Division I men's soccer season.′^[4]