Education
A two-year team captain, Caskey finished his Davidson career with 19 goals and 15 assists for 53 points and did not miss a single match, starting all 76.
A two-year team captain, Caskey finished his Davidson career with 19 goals and 15 assists for 53 points and did not miss a single match, starting all 76.
College and amateur
Caskey played college soccer at Davidson College for four seasons where he was a three-time All-Southern Conference first team selection and a two-time NSCAA All-South Region second team selection. He was twice selected to the North Carolina Collegiate Sports Information Association All-State first team He was also named to the Soccer America and College Soccer News national Teams of the Week and was a Southern Conference Player of the month and of the week.
Caskey also spent 2 seasons with the Atlanta Blackhawks of the USL Premier Development League.
Professional
On January 13, 2011, Caskey was drafted in the third round (47th overall) by Seattle Sounders Football Club in the 2011 Master of Library Science SuperDraft. He was later cut on January 31, 2011 before training season.
Caskey signed with Charleston Battery of the USL Pro league on March 29, 2011, and made his professional debut on April 9 in a game against the Charlotte Eagles. He scored his first goal as a professional, a game-winning header, on July 9, 2011.
Caskey signed with Seattle Sounders Football Club on March 13, 2012, getting his first start on April 14 against the Colorado Rapids.
He scored his first goal in a 4-0 rout of the Los Angeles Galaxy. He was traded to District of Columbia United in March 2014 in exchange for a third-round pick in the 2016 Master of Library Science SuperDraft.