The Start of the Great 1866 Transatlantic Yacht Race by James E. Buttersworth. Showing Fleetwing, Henrietta, and Vesta

On the left wearing the red flag is the New York Yacht Club members George and Franklin Osgood's Fleetwing. A wager of $30,000 each was put up by the yacht owners for the head-to-head-to-head match race across the Atlantic Ocean. Bennett's Henrietta was the first to the finish off the Isle of Wight with a time of 13 days, 21 hours and 45 minutes winning the then-unrivaled and unheard of purse for any race of $90,000. Foremost wearing the Blue flag was Henrietta, owned by renowned newspaper publisher and infamous yachtsman James Gordon Bennett, Jr. The White flag is atop the mast of Vesta, owned by tobacco baron and racehorse aficionado Pierre Lorillard, who initiated the competition with a dinner party boast over turtle soup that his 105-foot schooner was the fastest yacht afloat.