Charles E. Nicholson’s reputation as a yacht designer was undoubtedly enhanced by the fabulous racing performance of his 1912 Marconi rigged 5-Meter yacht ISTIRIA and his 1913 Class-A schooner MARGHERITA. The schooner won five first prizes out of six races in her first season, and according to Nicholson’s son John, was “probably the fastest yacht ever built by my father in his long career.” The publicity attending these fast yachts, combined with the fine reputation of the firm of Camper and Nicholsons, of which C.E. Nicholson was the chairman, influenced Sir Thomas Lipton to choose Nicholson as designer for his fourth attempt to win the Cup in 1914. A naval architect as well as a builder, Nicholson had a great deal in common with N.G. Herreshoff, his principal rival. In SHAMROCK IV, he designed a hull for the racing conditions he expected. The result was a boat that the designer himself dubbed ”the ugly duckling.” The race, postponed because of the outbreak of the First World War, was held in 1920 with Nicholson on hand as the tuning took place off New York. Although SHAMROCK IV won the first two races, creating a serious threat to RESOLUTE, she lost the next three. In the first J-Class race in 1930, Nicholson designed SHAMROCK V for the Newport campaign. Her pleasing hull form did not help her performance against ENTERPRISE. In 1934 with ENDEAVOUR, Nicholson, recognizing the shortcomings of SHAMROCK V’s rig, designed an innovative, efficient rig in collaboration with engineer/crew member Frank Murdoch. ENDEAVOUR’s loss was no fault of her design. This challenger was fast, and Yachting Magazine stated, “The only man to make no mistakes was ENDEAVOUR’s designer, Charles Nicholson.” Nicholson’s reputation as a leading designer was enhanced by the fact that he never blamed anyone for the failure to win. His final Cup effort, ENDEAVOUR II of 1937, was the largest racing cutter ever built by Camper and Nicholsons. Although ENDEAVOUR II put up a good fight, she was no match for the tank-tested RANGER. Nicholson’s four challenger designs, which were both innovative and brilliant, have made a significant contribution to the America’s Cup.