After returning home from the Olympics to Whistler, the picturesque ski town and resort he then called home, he enjoyed his newfound celebrity for a while, even sharing a joint backstage with Keith Richards at a Rolling Stones concert in Denver. But disappointed by his gold medal having failed to deliver on its promises, he quit competitive snowboarding in 1999. Deprived of the discipline, he turned inward. He became a recluse, living in a camper by a lake.Mr. Rebagliati says the Olympic gold medal he won in Nagano, Japan, has been a source of misfortune. Now, with the legalization of cannabis in Canada, he’s hoping his fortunes are about to change.CreditAlana Paterson for The New York TimesHe bought and sold real estate, initially investing some of his snowboarding winnings, and he hoped to build a luxury hotel. But he went into debt when the property market crashed after the terror attacks of Sept. 11, 2001, and he was forced to eke out a living as a builder. His first marriage ended in divorce.Things became so bad, he recalled, that he turned the number nine upside down on the address sign of his gate to keep the “repo man” away. “There were times when I didn’t have money to buy food,” he said. “I didn’t even have two pennies to buy weed.”For a one-time Olympic golden boy, it was a precipitous fall.Born in a Vancouver suburb he characterized as having “big houses and progressive politics” to a geologist father and an accountant mother, Mr. Rebagliati became a skiing prodigy before he was 10 and he was being groomed for the Canadian national ski team. But he discovered snowboarding at 15, around the same time he tried marijuana for the first time, and was immediately drawn to the sport’s baggy pants and freewheeling, iconoclastic spirit.Snowboarding, which was born in Vermont and California in the late 1970s, was slow to catch on. Mr. Rebagliati recalled that at ski areas in California, snowboarders were often banned and ski patrols would call the police to complain that riders were trespassing.When he was unable to find a snowboard in a ski shop in British Columbia while he was in high school, Mr. Rebagliati built a makeshift snowboard from plywood, cutting off the toes of his ski boots and using the inner tube of a bike as a strap to hold his feet in place. He and his friends would train by sneaking into ski resorts in the Vancouver area before ski season began and hiking up the mountains.