Deborah Lewis was born about 1730 in Yarmouth, the daughter of John and Thankful Lewis. She came to the Island of Martha’s Vineyard with her parents when she was about 3 years old.
In the 1730s, the settler population of the Island was less than 1,200 people, and had only recently surpassed the Vineyard’s Wampanoag population (roughly 800 at the time). Holmes Hole (Vineyard Haven) consisted of only five widespread houses — there was no village to speak of. The Lewis family evidently lived upon a shore lot in Chickemmoo (today’s Lambert’s Cove), likely on the edge of Tashmoo.
By the time she entered her thirties in the 1760s, Deborah remained single and living in Tisbury. Her parents were still residing in the town, but Deborah was evidently lodging with her good friend, Anna Luce. Anna was the daughter of Edgartown yeoman Henry Luce (known as “Long Henry” to distinguish him from his part-Wampanoag half-brother “Black Henry” Luce; both were sons of Tisbury blacksmith “White-Eyed Henry” Luce). Anna was about 10 years younger than Deborah.
In 1764, Anna made a curious announcement. She had “found herself to be with Child,” reported the Massachusetts Gazette newspaper, “and has Swore [Deborah] to be the Father of it.”
Deborah then made her own announcement. “‘Til a few Days since,’ reported the Boston Post-Boy, Deborah “constantly appeared in the Female Dress, and was always supposed to be one of the Sex, suddenly threw off that Garb, and assumed the Habit of a Man.” They were married two weeks later. “The Father instead of his former Name was Married by that of Deborah Francis Lewis,” added the Boston Evening-Post. All subsequent records refer to him as “Francis Lewis.”
Lewis was certainly not the only transgender islander in Vineyard history. There was William West, a Chilmark schoolteacher in 1860, who grew up as a girl named Rebecca until the age of 15 before openly transitioning. And there was his brother, Luther West, president of the New England Stove Co., and listed in the 1888 book “Twenty Thousand Rich New Englanders,” who grew up as Mary until he, too, transitioned in his teenage years. (Luther later sat on the Camp Meeting Association board of directors in Oak Bluffs.) And there was Edgartown summer resident Mary Swasey, who while home from college, publicly declared, “I’m a man. I shall be 21 soon, and I want to live like a man.” As David Swasey, he would go on to become a nationally recognized portrait painter. All three of these men married, but none had children.
Francis and Ann Lewis, however, would go on to have five children, and the couple have many descendants still living today on the Island. Upon his death at the age of 93 in 1823, newspapers up and down the East Coast reported, “Died. In Tisbury, (Ms.) Mr. Francis Lewis, 93 – 32 of which years he dressed as a woman, and was supposed to be such. After that, he took his proper apparel as a man, and passed the remainder of his life in the marriage state, and has left numerous descendants. The family has always deserved and received the respect of those who knew it.”