Cantalupo worked in his father Anthony Cantalupo's realty business "Cantalupo Realty", it was here that he became acquainted with many of his fathers friends and associates who were members of the New York mob. Boss Joseph Colombo used the offices of Cantalupo realty as his headquarters for a time, and there he would meet with his criminal associates to discuss business until law enforcement surveillance and harassment forced him to find another headquarter. Cantalupo also became personal notary to "chairman of the board" Carlo Gambino.
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