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 teams in the world to compete in the event. 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