Dick graduated from the University of Florida in 1961. He also has an additional BA from Chapman College in 1973 and the equivalent of an MA from the Industrial College of Armed Forces in 1981.
Whittington served in various management positions with the United States Air Force, both in the cockpit and Logistics. As Deputy Chief of Staff-Logistics, he supervised logistics operations at 15 stateside and off-shore locations which included various duties from vehicle and aircraft maintenance, contracts, supply line engineering, transportation and finance for 38,000 personnel. After leaving the service, he became Director of Quality Assurance and Configuration Management (Hardware, Software, Firmware, and Courseware) for CAE-Link Corporation; a 6000-employee aircraft simulator manufacturer and government aircrew-training contractor. Lead quality representative on all contract proposals. He was responsible for TQM training and ISO 9000 documentation preparation and certification efforts.