Early Life and Work Outside of The Chicago Outfit
Calabrese was born the son of James and Sophie Calabrese, growing up near the intersection of Grand and Ogden Avenues on Chicago's Near West Side. As a boy, Calabrese worked at a newsstand at the corner of Grand Avenue and State Street, in downtown Chicago, where some of his brothers had worked as well. Calabrese graduated from Steinmetz High School in Chicago.
Calabrese served in Vietnam in the United States Navy from 1965 until 1967, working as a radioman and having top-secret clearance on the USS Bainbridge. Calabrese also had worked as an ironworker on the John Hancock Center construction project in Chicago, as a Teamster working for trade show contractor United Exposition at Chicago's McCormick Place and as a Cook County security officer at the courthouse in Maywood, Illinois from 1977 until 1989.
In the 1970s, Calabrese and two partners operated a restaurant and lounge in Hoffman Estates, Illinois for a couple of years, and also worked for a private detective agency.
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