A Wonder From Winnipeg: The Rupert Whitehead Story

Photo courtesy City Of Toronto Archives

The son of Edward and Julia (Davis) Whitehead, Rupert Whitehead was born on April 16, 1910 in Winnipeg, Manitoba. Rupert and his four siblings, Eleanor, Katherine, John, and Virginia, were largely raised by a British nurse. The Whitehead children attended elementary school in Winnipeg but their mother pulled them all out of school for a time when the family suffered through a year of whooping cough, chicken pox and the mumps. The family relocated briefly to Prince Rupert and Victoria, British Columbia before returning to Winnipeg.

Rupert received his first pair of skates at Christmas when he was in grade five. "It was a mild winter," he recalled in his memoir "Unstoppable Energy, Unshakable Faith", the primary source material for much of this blog. "Our front walk was covered with ice. So I went to the front steps and laced them on. My father was behind me urging me, 'Don't do it. Don't do it, Rupert. You have to learn to skate.' But I wasn't listening. I got them laced on and started off. I skated all the way to the boulevard, turned around and skated back. I can still see the white marks from the blades. That is how I learned to skate."

Rupert took to skating in the flooded backyard of a family friend's home on Kingsway and on the flooded courts of the Winnipeg Lawn Tennis Club. Encouraged by the 'fancy skaters' who practiced on the frozen tennis courts, he joined the Winnipeg Skating Club and took lessons at rinks on Smith Street and Portage Avenue. He recalled, "It was great. We would skate for two hours, have food and milk and then walk home under the stars. Because there were few street lights we learned about Orion, the Big Dipper and the Little Dipper. Those were happy times."

Rupert entered several of the Winnipeg Skating Club's competitions, winning the championship for boys under fourteen in 1924 and later, the club's intermediate and junior competitions. In one event, he narrowly defeated a young man named Elswood Bole who later played an important role in Winnipeg's city administration. He also performed in the club's first carnival in the early twenties. He recalled, "One act took the form of a three-ring circus. For reasons unknown I was the last skater to leave the ice. I realized there would be no skating action while the rings were removed so I stepped into a ring and began to practice my sit spin. Each time I tried, I ended up sitting on the ice. Then I managed about a half a revolution and then two and then I was spinning and managed to stand up instead of sitting down. Suddenly there was deafening applause. For a second I was frightened. Mr. Dick Bingham, the carnival producer, stopped me. 'That was great, Rupert, do it again tomorrow night.'

Aidrie Main and Rupert Whitehead. Photo courtesy City Of Toronto Archives.

After graduating high school at the age of sixteen, Rupert tried his hand at banking. A series of bad investments and failed business ventures left him in serious debt at a very young age. It was during this period that the Winnipeg Skating Club became the Winnipeg Winter Club, and while the financial industry struggled through The Great Depression, he borrowed from Peter to pay Paul. He took solace in ice dancing with a group of eight friends at the club. He recalled, "One day we found ourselves welcoming a new member. Her name was Aidrie Main and [she] hailed from Montreal. She and I became good friends. Her energy seemed to watch mine... Aidrie suggested we both try to pass the '2nd test' as it was known in those days. We practiced diligently for several weeks and succeeded. At the end of the skating season, she returned to Montreal."

In 1930, Rupert's father fell ill and passed away. Shortly thereafter, his uncle - a millionaire from California - passed away leaving Rupert and a cousin in England the bulk of his fortune. As 'the new man of the house', Rupert settled into his role with reluctance. Though his substantial windfall could have solved his money woes, through failed business venture after failed business venture, the money was lost and young Rupert developed what would be a long term, very public drinking problem. Fortunately, it was one he eventually overcame.

Photo courtesy City Of Toronto Archives

Through it all, Rupert got up at six or seven in the mornings and practiced at the Winnipeg Winter Club in hopes of passing his gold figure test. During this period, he competed thrice at the Canadian Championships, winning the bronze medal in the junior men's event in 1931, the Canadian junior men's title in 1932 and the bronze medal in the senior men's competitions in both 1933 and 1934 behind Bud Wilson and Guy Owen. He recalled that at one event, "The present holder, Montgomery (Bud) Wilson said he would not come to Winnipeg unless there was competition. So, you know who became the competitor! I volunteered and skated against him. Of course, he got very high marks and I got very low marks. But I got marks for being a good sport. Also, it gave me a chance to try for the gold [figure test] because there would be enough judges in Winnipeg. By George, if I didn't win my gold medal in figures, very difficult figures, and a very difficult long free skating program!"

Evelyn Rogers and Rupert Whitehead

Rupert also tried his hand at fours skating for a time. He recalled, "Skating fours were very popular, usually two men and two women. Ours consisted of Betty and Peggy Holden, sisters, Philip Lee and myself. Of course, I was in charge, planned the program and was even going to design the costumes... [My mother] made us two sets of terrific costumes: a Russian four and another in black and white. The front was white, the back, all black. The division down the sides was absolutely perfect." By 1936, he'd put together a new four with Burton Kennedy, Mary Arckle and Evelyn Rogers. They achieved some popularity and were invited to carnivals as far away as Minneapolis. He was coached by Leopold Maier-Labergo during this period.

Rupert Whitehead skating with the Winnipeg Winter Club four in 1937

In 1937, Royalite, an oil company Rupert had bought stocks in, struck Texas Tea and he made a pretty penny. He was also invited to be a guest skater in the Royal Glenora Skating Club's carnival in Edmonton. He recalled, "I was standing at the middle of the ice waiting for my music to start. The spots came on. The music began. From then on, I cannot remember a thing! What I do remember is that there was an awful lot of applause... When the show was over people actually leapt over the fence onto the ice to shake my hand." Rupert's good impression led to an invitation from the club to be their head professional. He accepted, and worked long, cold days, teaching figures and ice dance and organizing competitions amongst his students with wrapped gifts as prizes.

When his contract ended, Rupert married his wife Yvonne and returned to Winnipeg to work as a professional at the Winnipeg Winter Club. His position was short lived. In the autumn of 1941, he arrived at the club to prepare for the upcoming season only to find the doors locked. He later learned that the club had been sold to the Royal Canadian Naval Reserve. Again having made another series of bad investments, his oil money was gone and he was flat broke.

Unphased, Rupert decided to start his own skating club, which he first called The Figure Skaters Of Greater Winnipeg, later the Winnipeg Ice Club. He plastered the city with posters that said 'Rupert Whitehead, Gold Medallist, Dance, Silver Medallist, Former Junior Canadian Men's Champion will teach figure skating' and started giving lessons at the Sherburn outdoor rink. His club was an instant hit and soon he was presenting carnivals at the Amphitheatre. As director of these shows, Rupert brought in some big names, including Barbara Ann Scott and Belita Jepson-Turner. He performed as well, waltzing with his wife and skating solo exhibitions. One of his favourite programs was set to "Giannina Mia" from Rudolf Friml's opera "The Firefly". He recalled the program thusly: "My number was just graceful dance movements, one jump, what is called a half a revolution or waltz jump, one spin, and then a flip jump at the very end." He closed the number by having the lights blacked out, skating out the curtain, running up to the other side of the rink and emerging when the lights came on. The audience ate it up. Rupert's shows added a touch of colour to the grey Prairies throughout much of World War II.

The Whitehead home in Westgate. Photo courtesy Cheryl Whitehead.

During the War, Rupert and Yvonne welcomed three sons, Bill, Michael and Tim. For a period, Rupert stepped away from skating to undergo training with the army reserve, but in no time he was back on the ice, putting his students through the paces with the same iron fist as his military trainers.
However, by 1950, Rupert was struggling with the lows of his alcoholism and quit skating and coaching altogether, giving his position and even his skates to 1934 Canadian Junior Champion and former fours partner Philip Lee. Unfortunately, under Lee's direction, the Winnipeg Ice Club absolved within a year. Penniless and with few prospects, Rupert turned his life around as the Executive Director of the Greater Winnipeg and Manitoba Safety Councils. He played a major role in devising and implementing defensive driving programs in the province and even for a time dabbled in real estate.

Three decades later, Rupert had somewhat of a personal epiphany. He sold his real estate holdings, cancelled all of his subscriptions to business magazines and newspapers and turned towards religion. He considered a visit to a Franciscan monastery a life-changing event. A book lended to him by one Father Oswald called "The Sermon On The Mount" greatly changed his perspective on life. In retirement, he devoted his time to curling, playing bridge, attending church and writing. He even penned four novels: "The Gold Caper", "The Top Of Water", "The Note Skater" and "The World, A Fresh Start". Unfortunately, none of these books were ever accepted by a publisher.

In April 1996, a group of Rupert's former students organized a touching reunion full of speeches where they described the impact that he had made in their lives. Soon, Rupert and his former students were on the ice every week at the River Heights Community Club and he was welcomed back to the skating world with open arms. After attending the 2000 Canadian Figure Skating Championships in Calgary, he was inducted into the Manitoba Sports Hall Of Fame in 2004. On April 16, 2010, accompanied by three of his former students, he skated two laps around the ice at the Winnipeg Winter Club to celebrate his one hundredth birthday. He passed away on October 30 of that year, having left an indelible impression on Manitoba's skating community.

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