Champion skipper Walter Windeyer showed the European yachting community just how seaworthy a Great Lake captain could be when he won the prestigious Gold Cup in 1959. The son of a sailing enthusiast, Windeyer spent his childhood summers on the waters surrounding Toronto's Ward's Island. He started sailing at age ten and won his first major race, the Douglas Cup, aboard a 14-foot dinghy before he turned 20. In the late 1920s, Windeyer collected three consecutive Wilton Morse Trophies and, in 1932, he was skipper of Invader II that competed in Canada's Cup Challenge. In 1936, he was a member of the Canadian team that won the Currie Cup in the 14-foot International Dinghy class at Lowestoft, England. In the 1950s, dragon class boats, the smallest international class vessels that can be categorized as yachts, began to gain popularity in Canadian competition. In 1954, the O'Keefe Brewing Company donated a trophy to be awarded annually to the champion dragon of the Great Lakes. Windeyer quickly took an interest dragon racing and, in 1958, sailed Corte to victory in the O'Keefe Trophy race. Part of his prize included a trip to Europe the following year to compete in the Dragon Gold Cup, emblematic of the Dragon World Championships. Windeyer, however, didn't think that the Corte could measure up to the speed of the sophisticated European vessels, so he entered a syndicate with the O'Keefe firm and his longtime sailing friend Ian Armour to buy the Danish-built Tip, a vessel which had won the Gold Cup in 1957 with Danish skipper Ole Berntsen. With crewmen Ken Bradfield and Sicotte Hamilton, Windeyer skipped Tip to victory in the fifth and final race of the 1959 Gold Cup. Beating out 41 of the world's finest crafts, Windeyer and his crew were the first non-Europeans to win the coveted Cup. After another victory in the O'Keefe Trophy race, Windeyer sailed overseas once more in 1960 to defend his Gold Cup title at Holland's Royal Netherlands Yacht club. Just before the start of the fourth race, however, he was struck with a mild heart attack. Ignoring doctor's orders, the devoted captain sailed anyway, finishing eighth out of 40 competitors. He went to the hospital directly afterward, and was too sick to participate in the fifth and final race. Unfortunately, Windeyer's illness also prevented him from competing in the Olympics, as he was scheduled to do directly after the Gold Cup events. A replacement crew was sent instead, and it finished fifth. Windeyer bounced back in 1961 to claim the Duke of Edinburgh Trophy, a prestigious North American prize. He also claimed his third O'Keefe Trophy, but this time he was given permanent possession of the prize in honour of his historic achievement. Other significant victories included the Royal Canadian Yacht Club Founder's Trophy and the Toronto Telegram Trophy for dragons. Unfortunately, his sailing career, as well as his life, was cut short in 1964 by a second heart attack. An active member of Toronto's yachting community, Windeyer served on the Royal Canadian Yacht Club's sailing committee for several years, was fleet captain in 1960, and vice commodore from 1961 to 1964. He was widely respected both for his brilliant skills as a seaman and his noble conduct as a gentleman.