Born in Winnipeg, Rupert Whitehead learned to skate on a rink in a yard on Kingsway Ave. His exposure to figure skating came when he saw skaters doing “all kinds of crazy things” on a sheet of outdoor ice at the Winnipeg Lawn Tennis Club. They told him it was “fancy skating” and he soon joined the newly formed Winnipeg Skating Club. Whitehead participated in the club’s first skating carnival in the early 1920s. He began to skate competitively and won the under-14 boys championship in 1924. During the next few seasons, he won the boys, junior and intermediate titles and passed the Canadian Figure Skating Association bronze test. In 1932, Whitehead won the Canadian Junior Championship in Toronto. During the 1930s he also won several Winnipeg Winter Club championships and passed the CFSA silver and gold tests.
Whitehead was invited to appear in carnivals in Chicago, Minneapolis, Montreal and Regina and in Edmonton where he spent the 1938 and 1939 seasons as the Glenora Skating Club professional. In 1940, he served as the Winnipeg Winter Club pro. After the Winter Club was sold to the Royal Canadian Naval Reserve, Whitehead formed the Ice Club of Greater Winnipeg, which he ran until 1950. In addition to teaching the sport, he produced carnivals that filled the Winnipeg Amphitheatre and showcased Manitoba’s young figure skaters. His troupe also performed throughout Manitoba and he assisted rural communities with the organization of their carnivals. In 1996, following a reunion organized by his former students, Whitehead started skating again on a weekly basis and continued to do so into his nineties. In recognition to his contributions to the sport, the man whose autobiography was titled Unstoppable Energy, Unshakable Faith, was invited to perform at the 2001 CFSA championships in Winnipeg.
b. April 16, 1910