In 1941, Wanderone and friend Jimmy Castras arrived in southern Illinois—a major hustling center on a fast track to televised tournament play—and settled in Du Quoin, Illinois, where he continued hustling. Eventually, he met Evelyn Inez Graff; they married two months to the day later, on May 7, 1941. Following their wedding, the Wanderones settled in Dowell, Illinois. In 1942, the couple moved to Norfolk, Virginia. Norfolk had become a key mustering point for American soldiers, as well as a shipbuilding center. The growing population led to an enormous interest in gambling; Wanderone, in partnership with fellow hustler Lassiter, quickly recognized the financial possibilities. Following World War II, however, the action soon "dried up", and the Wanderones returned to Little Egypt, Illinois. Throughout the 1950s, Wanderone was in semi-retirement, making only occasional hustling trips to New York City.