On April 27, 1931, Diamond was again shot and wounded, this time at the Aratoga Inn, a road house near Cairo, New York. After eating in the dining room with three companions, Diamond walked out to the front door. He was shot three times and collapsed by the door. A local resident drove Diamond to a hospital in Albany, New York, where he eventually recovered. On May 1, while Diamond was still in the hospital, New York State Troopers seized over $5,000 worth of illegal beer and alcohol from Diamond's hiding places in Cairo and at the Aratoga Inn.