He graduated in the class of 2011 from Gardner Edgerton High School in Gardner, Kansas. Starling was an All-State selection in three different sports at Gardner-Edgerton. He earned first team Top 11 picks as a quarterback in all classifications in Kansas two years in a row. He was rated as high as the No. 6 quarterback in the class of 2011 and No. 112 in the nation for high school football recruits and was also touted as the No. 1 ranked baseball recruit in the nation.
Starling started at quarterback for Gardner-Edgerton's football team, and was considered one of the top quarterback prospects in the nation. Starling accepted a scholarship to play both football and baseball for the Nebraska Cornhuskers, but later turned it down to join the Royals.
Starling was also a member of Kansas's high school All-State team in basketball.
As a baseball outfielder, Starling was selected by the Kansas City Royals with the 5th overall selection in the 2011 Major League Baseball Draft. He had widely been considered to be the most athletic prospect in the draft. Starling received a $7.5 million signing bonus, the second largest in draft history. Starling's bonus was also the largest ever for a high school player and his contract also represented the most guaranteed money ever given to a high school player. On July 18 he sustained a grade 2 strained spleen against the Springfield cardinals in Double-A.
Starling was one of three Royals prospects cited for underage drinking at a random alcohol checkpoint following a college football game between Arizona State and Southern California in Tempe, Arizona.