An All American Swimmer in high school, he received a swimming scholarship to attend college. After graduation from the University of Alabama in 1974, he entered Naval Aviation flight training and flew the F-4 Phantom and A-4 Skyhawk aircraft for the Marines. Upon release from active duty, he entered the airline industry and flew 25 years for an international airline, obtaining the rank of Captain. He has flown over 23,000 accident free hours and transported over one million people safely to their destinations.
In 1990, he was recalled to active duty in the Air National Guard where he flew the F-16 Falcon. He flew 52 missions with Operation Desert Storm and was awarded with the Distinguished Flying Cross for heroism in combat. He retired from the Guard after 20 years, obtaining the rank of Lieutenant Colonel. Today, Whiteside is one of only a few military aviators to possess both Senior Command Air Force wings and aircraft carrier qualified Naval Aviator wings. He retired from the airline industry in 2003.