Ray was a Lieutenant Colonel in U.S. Army Intelligence. In 1943, as U.S. forces concentrated in Cincinnati prior to attempting to cross the Ohio River, Ray had Cincinnatus Driver brought to him for questioning. Driver had been exchanged from Covington, Kentucky earlier and was connected with the black underground there. Driver was reluctant to reveal what he knew until he was assured that any uprising would involve both the blacks and whites of the city. While irregular, Ray agreed after Luther Bliss, who was present, vouched for Driver.