In April of 1876 the New York Yacht Club received a challenge from Major Charles Gifford, the Vice-Commodore of the Royal Canadian Yacht Club of Toronto, for the America's Cup, which it had held since 1871 when it was captured by the Madeleine. The New York Yacht Club gladly accepted the challenge and waived the six month waiting period that the Deed of Gift mandated. It had been five years since the last challenge and the Club wanted to spark interest in the Cup and get the challenge under way as soon as possible.
The Canadian group, headed by Major Gifford, offered the Countess of Dufferin as their challenger. Built the previous winter, the Countess of Dufferin was inspired by the well known and very successful American sloop Cora but was relatively uninterested in competition. Madeleine, on the other hand, had a prestigious reputation and had been thoroughly tested in competition at the hands of New York Yacht Club Commodore Jacob Voorhis and John S. Dickerson, a Commodore of the Brooklyn Yacht Club.
The Countess of Dufferin was no match for its seasoned opponent and fell in two lopsided races. The first, over the New York Yacht Club course of 32 miles ended with the Madeleine finishing almost eleven minutes ahead of the slower boat. A margin of greater than 27 minutes seperated the two boats in the second and deciding race around the lighthouse at Sandy Hook.
Moran's oil obviously show the Madeleine striding ahead of its competitor, but more importantly seems to depict the pomp and patriotism of the early America's Cup races that are so much a part of the matches today. Moran's unsual fascination and love for the nautical world are apparent, but unlike many of his more typical works, this oil also strongly suggests the artists's pride in America, embodied in the vehicle of the Madeleine.