Calandra grew up in the Bensonhurst neighborhood in Brooklyn, New York. During his childhood he grew up seeing wiseguys on the street, pulling up to the curbs in their big shiny Cadillacs, loafing around social clubs wearing pricey suits and sporting hundred-dollar haircuts and manicured fingernails. Mafia members interacted with Calandra and other the kids in the neighborhood. They joked around with them and showed them there were other ways to make it through life. The wiseguys also paid Calandra and other kids to do work for them such as washing their cars, watching out for police, or running numbers.