The Windermere Cup got its start in 1987, when Windermere Real Estate founder, John Jacobi, joined up with the University of Washington to expand the annual rowing event that was part of the Seattle Yacht Club’s Opening Day of Boating Season celebration. The goal was to showcase the excellence of the UW Rowing program and the Montlake Cut as a premier rowing venue by bringing the best competition in the world to compete in the event. At the time, this was the team from the Soviet Union. That occasion marked one of the few athletic competitions for the Soviets inside the U.S. in 25 years, due to the strained relations resulting from the Cuban Missile Crisis in 1962. The Soviet Union brought both its men's and women's crews and won both races in convincing fashion. After that, the precedent was set for what has become one of the world's premier rowing events, and certainly a staple of Seattle's rowing community.