Gracie, a shallow centerboard sloop, was modelled by A. Polhemus of Nyack, NY and designed by Abraham A. Schank. It was launched in 1868. Originally 6-'3" in overall length, it was lengthened in 1869 by two feet, and again in 1874 to 72'9". In 1879 it was completely rebuilt by David Carll to 80' overall length. Howard Chapelle notes in his book The History of American Sailing Ships, "She had a double headsail rig, with her forestay coming to the gammoning." It barely lost to Mischief in the contested 1881 trials to defend the fourth America's Cup. The owners, Joseph P. Earle and Charles R. Flint, publicly challenged the decision. Robert Carrick writes in The Pictoral History of the America's Cup Races, "The disgruntled owners of Gracie, which was eliminated in the selection trials, sailed her over the Cup course behind Mischief and Atalanta and beat their time in both races." It lost as well to Puritan in the selection trials for the fifth America's Cup in 1885. According to the July 1886 issue of Outing magazine, Gracie's first owner was Mr. William Voorhis, followed by Wm. Krebs, John R. Waller, and the owner in July 1886, Joseph P. Earls.for the first time in UK waters after more than 65 years. Endeavour won both regattas after close racing between the yachts.