Jason Cipolla grew up in Queens, New York and went on to play at the legendary high school Christ the King. Some notable basketball alumni from Christ the King include Speedy Claxton, Lamar Odom, Tina Charles, Sue Bird and of course, Louie McCroskey.
In his senior year of high school, Cipolla was part of a Christ the King team that eventually sent seven players to Division I. Cipolla wasn't one of them as his academic work wasn't up to standards and he attended Tallahassee Community College, playing two seasons before transferring to Syracuse. At TCC, Cipolla averaged 24 points, seven rebounds and five ssists per game.
As a Syracuse Orange, Cipolla would average 7.7 points and two rebounds per game in his first season. With a nagging heal injury in his penultimate campaign, Cipolla would lose his starting job, only to start every game in Syracuse's run to the National Championship game in his final season. As a senior, Cipolla upped his assist total twofold from the previous year and almost doubled his scoring and rebounding averages for 13.2 point per game and 3.5 rebounds per game.
Cipolla's claim to fame remains his illustrious shot in the 1996 Sweet Sixteen against Georgia. With 2.4 seconds left on the clock and Syracuse trailing by two, John Wallace lobbed an inbounds pass from half-court to Cipolla along the far baseline. Cipolla rose coolly from just inside the three point line and buried a jumper to send the game into overtime. John Wallace went on to hit the game-winning three to send Syracuse to the Elite 8 and the team carried its momentum all the way to the National Championship game before falling to Kentucky.