Richard Bott attended Winchester School, and was one of the six generations of the Bott family to enjoy competing on the Cresta Run. One of them, Arden Bott, was, in 1902, responsible for modifying the skeleton toboggan by adding metal runners. One of the leading Cresta Run events is the family-named Bott Cup, launched in 1905, and won by Richard in 1948. The previous year, he also won the famous Curzon Cup. At the 1948 St. Moritz Olympics, Bott finished sixth out of 15 starters in the skeleton event.