Ragone attended St. Ignatius High School and was a student and a letterman in football and basketball. In football, as a senior quarterback, he was an All-State first team honoree and led his team to the State Semi-Final game, losing 20–19 against Canton McKinley. Also as a senior, he was a starter on the basketball team that went on to be the State Runner-Up.
In the fall of 2009, Ragone was inducted into the Saint Ignatius Athletic Hall of Fame.
During his college career at the University of Louisville, he went 27-11 as a starter, including an 11-1 mark in 2001. Ragone finished his collegiate career as Louisville's second all-time leading passer. He was a three-time All-American Honorable Mention and three-time Conference USA Offensive Player of the Year.