Yukitaka Osaki, a Japanese expatriate whose life reflected Connecticut’s motto, “He who transplants sustains,” came to the United States with his elder brother Yukio in 1888 after their family supported the Japanese emperor against the shogunate and the brothers found it prudent to go abroad for political reasons. Yukio eventually returned to Japan, where he entered national politics and helped facilitate the gift of the famous Japanese cherry trees to Washington, DC, while Yukitaka remained in the United States to study drama and was at the Oberlin Academy in 1895. By 1897 he was working on William Gillette’s houseboat the Holy Terror, and he continued as a cabin boy when Gillette built the Aunt Polly in 1899. Osaki and Gillette remained close companions for the next several decades, and Osaki served in many roles, including valet, secretary, and castle factotum. After his official retirement in 1919, when Gillette moved into the castle, Osaki moved into a tranquil cottage Gillette built for him, and he continued to visit Gillette each evening while also running errands for the castle and driving guests in his cart. He became a popular member of the Hadlyme community and a close friend of the Hamilton sisters, Alice, Edith, and Margaret, who lived across the street. In 1941, Japan’s bombing of Pearl Harbor devastated Osaki, and community members, fearing he would be sent to an internment camp, took steps to support him. He was cleared by the FBI and allowed to remain in his home, and after his death on September 29, 1942, a service was held at the Hamiltons’ home and he was interred at Cove Cemetery in Hadlyme. The cottage itself was originally only about two-thirds of its present length, with a small living room, a bedroom that fit only a cot, a galley kitchen, and a bathroom upstairs, while downstairs Osaki kept his donkey and mule. He maintained elaborate gardens and planted the wisteria around the castle that still survives. Ownership of the house passed from Gillette to Osaki to the Hamiltons to their caretaker Purvis, who enlarged it to its current size for himself and his wife. Except for a brief use as a canoe rental building, it has stood empty since Purvis’s death in 1971.