Winger prepped at Olympia High School and was a five time letterman in baseball. He was coached by Randy O’Neal who gave seven years of service to the Detroit Tigers. He was named to the Rawlings/Perfect Game All-America Third team in ’09,’10 and a Second Team member in ’08. Winger was a Preseason Baseball Factory/Under Armour All-American in ’10. Named All-Metro First Team and All-Central Florida Second Team in ’10.