In 1955 and 1956 he was runner-up behind his fellow countryman Hayes Alan Jenkins . He also landed behind Jenkins at the 1956 Olympic Games and won the silver medal. At the 1955 World Cup, he was the first figure skater to show a triple salchow . After a scandal at the US championships in 1956, he quit competitive sports and signed a two-year contract at the Ice Capades figure skating show, which brought him a hundred thousand dollars.
In the 1950s, he had a relationship with Tab Hunter who also helped him fund his amateur career . Robertson was not infrequently featured on television, for example on the Ed Sullivan Show in 1957.