A native of Islip Terrace, New York, Calabrese played quarterback at East Islip High School, where he broke the school records for career passing yards and touchdowns, set by former NFL MVP and Calabrese's mentor Boomer Esiason.
After starting the first two games in 2009 as a sophomore, he was benched for Brett Hodges and spent the remainder of the season as a reserve quarterback.
[2] He suffered a serious knee injury as a junior in a game against Marshall and sat out his senior season.
[3] As a redshirt senior, he split time at both quarterback and wide receiver while taking on more of a mentor role.
However, the NFL quickly shot down the idea due to not wanting teams to stock up on players by referring to them as coaches.