In 1930, Diamond and two henchmen kidnapped Grover Parks, a truck driver, in Cairo, New York, and demanded to know where he had obtained his load of hard cider. When Parks denied carrying anything, Diamond and his men beat and tortured Parks, eventually letting him go. A few months later, Diamond was charged with the kidnapping of James Duncan. He was sent to Catskill, New York, for his first trial, but he was acquitted. However, he was convicted in a federal case on related charges and sentenced to four years in jail. In a third trial, in Troy, New York, he was acquitted.