Now he faces another arduous task, guiding the underperforming U.S. Olympic sailing team as its new executive director. One of America’s most accomplished sailors, Cayard now faces another arduous task: guiding the underperforming U.S. Olympic Sailing Team as its new executive director. Cayard takes over just four months before the rescheduled Tokyo Games, but says a turnaround is going to take much longer. The United States has won the most Olympic sailing medals in history, 60, but the well-funded British have quickly pulled within two and lead the Americans in gold medals, 28 to 19. The previous head of U.S. Olympic Sailing, Malcolm Page — who won two gold medals for Australia — was forced out in September 2019.