Raymond was one of the seven Porrello brothers who immigrated to the United States from Licata, Sicily. The Porrello's operated together with the Lonardo brothers with whom a bloody gang war would later be fought for control of the Cleveland rackets. On December 5, 1928, Joseph Porrello, leader of the Porrello crime family, invited high level American Mafiosi from across the country to a meeting at the Statler Hotel in Cleveland to declare him the official Mafia boss of Cleveland. Raymond became Joseph's underboss, a position he would hold within the crime family for just over a year.