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As O'Connor climbed the corporate ladder at Sears, he became the head of marketing for sporting goods in Canada and handled the company's relationships with major sports figures. These included Ted Williams and Sir Edmund Hillary, who became the first man to summit Mount Everest in 1953. O'Connor and Hillary met while O'Connor was on a camping trip in Ottawa in 1973 and struck up a friendship. Later that year, Hillary invited O'Connor and several other Sears executives to visit Nepal and consider charitable contributions for the Sherpa people who helped him climb Everest. O'Connor suffered from altitude sickness on the trip, but agreed to establish the Sir Edmund Hillary Foundation of Canada when he returned to Toronto.