James Lee was only 10 years old when his father Cornelius was lost at sea. Commodore of the Seawanhaka Yacht Club on Long Island, 34-year-old Cornelius was an heir to his grandfather’s fortune in New York City. He worked little, traveled extensively, surrounded himself and his family with servants, and spent his days buying and racing pleasure yachts. He joined a friend on a six-month cruise to Jamaica and the West Indies, but they never made it; shortly after their departure, the Great Blizzard of 1888 struck the East Coast, wrecking some 200 ships, and Cornelius and his comrades were never heard from again.
The family — widow Mattie and their three young children — came to Martha’s Vineyard that summer to grieve. Over the next few years, Mattie’s health deteriorated, and she fell into “a nervous and melancholy condition.” She wrote her will, entrusted her children to her brother-in-law in Newport, and departed for a place she had long been infatuated with: Paris, France. She died there the next year, leaving the three children without parents: Laura, 18; James, 17; and Cornelius “Connie” Jr., 13. Under the provisions of the wills of both parents, they would inherit the family fortune when they reached 21 years of age.
At 21, James did what many young men might do upon coming into a huge inheritance: He moved full-time to Martha’s Vineyard and bought an automobile, a motorcycle, and a speedboat. But this was the turn of the 20th century, and his car is believed to be only the second on the island; his speedboat and motorcycle, each the first on the Vineyard.
James moved in with James and Mary Cleaveland in West Tisbury, the 21-year-old describing his occupation as “capitalist” to the town’s 1900 census taker. His sister Laura joined him a couple of years later, and she became a landscape painter, writer, and interior designer. Their youngest brother Connie eventually became associated with the island as well, founding the Edgartown Golf Club in 1926.
Dionis Coffin Riggs, granddaughter of the Cleavelands, described Lee as “an experimenter, trying all sorts of schemes for social betterment, new techniques in boat-building and in farm equipment.” Riggs told Linsey Lee (no relation) of the Martha’s Vineyard Museum in 1995, “The Lees boarded here with my grandparents first, and then Jim sort of took over the East Room … Jim considered this his home.”
Lee’s automobile arrived about 1903. There is some disagreement as to whether it was the first or second car on the Island owned by a year-round resident, and even as to what kind of car it was. Leonard Athearn was cited in the book “Sanderson’s to Alley’s” as stating that it was a 1902 Rambler, and that his father Horace Athearn drove it up from New York City in a trip that took nearly two weeks. Riggs claimed it was “a handsome French automobile”; she told Linsey Lee, “I was quite young, about 5 or 6, when Jim Lee who boarded with us came back from France with a car. And it was right-hand drive. And you had to crank it.”
Lee’s speedboat was a 15-foot “gliding boat,” fitted with a Franklin air-cooled motor, built by James Look of West Tisbury in about 1907. It was said to be the first speedboat on the island. (The previous year, Look had built a 23-foot swordfishing boat for Benjamin Attiquin, and a 22-foot launch for Rodolphus Manning, both of Gay Head.)
Lee also brought home the island’s first motorcycle, and later suffered a debilitating motorcycle accident in New Zealand.
Joseph Chase Allen once described James Lee as “a man whose income permitted him to enjoy life as he saw fit.” But his inheritance eventually began to dwindle. Elmer “Mike” Athearn told Linsey Lee in 2001, James “was kind of a ne’er-do-well and spent his money foolishly; he had quite a lot of money, I guess, at one time. Between bouts of running and many things, the money didn’t last very long, I guess.”
Lee began to dabble in business, describing himself as a West Tisbury “fruit grower” in 1920, and opening a gas range shop in Vineyard Haven, selling bottled gas stoves and water heaters during the late 1920s. He eventually retired to Florida, where he died in 1958 at the age of 80.