Ragsdale saw limited action in his freshman season at Virginia , where he was a member of one of the top teams in the nation this past spring. He attended North Port High School in Florida where he was named All-Area shortstop after batting .427 with 20 RBIs his senior season. He was also named First-Team All-Florida by Rawlings in 2012 for his performance.
As a junior, Ragsdale posted a .358 batting average with 19 RBIs. Ragsdale is also the cousin of Philadelphia Eagles wide receiver DeSean Jackson. He is a native of North Port, Florida.