|Olympic medal record|
|Competitor for United States|
|Gold||1960 Rome||coxless fours|
Wailes began sport rowing when he entered Yale University in the fall of 1954. Within two years he was part of the gold medal-winning eight-man U.S. team at the 1956 Summer Olympics in Melbourne. Wailes and his Yale teammates represented the United States in the 1956 Olympic team after defeating other collegiate teams in the eight-man Olympic trial. At the Olympic trials just Wailes and his crewmates set a world record in 5 minutes, 52 seconds.
Wailes's crews defeated Harvard four consecutive years in the Harvard-Yale Regatta. Wailes was heavyweight crew captain his senior year.
Rusty earned again Olympic Gold as part of the four-man coxless crew at the 1960 Games in Rome. That team included John Sayre and two other rowers from other colleges at the Lake Washington Rowing Club. They won the Pan American Games in 1959 and then went off to the Olympics in Rome.
John Sayre, Rusty, and his wife Lynne were a part of the original group, 'Sing-Out 65,' which became Up With People. John had been a member of the Moral Re-Armament show 'Space is so Startling' (recording year 1962). Rusty then became Dean of Men at Mackinac College, which was located on Mackinac Island site where Sing-Out had formed. Mackinac College was dedicated to training students who were 'Learning to learn, learning to live, and learning to lead.'
In 2002, Wailes, who lived in Woodinville, died of a heart attack while rowing on Lake Washington.