Dolly Shoe Boots (c. 1784-c. 1861) traveled The Trail of Tears as chattel property in 1838 and became a freed, landholding woman by her life's end. Dolly, also known as Congeeloh to her Cherokee kin, seems to be a woman of many names in historical records; her most common one was simply "Doll" (also spelled "Daull"). Doll lived a complex existence with her Afro-Cherokee family at a time when Black and Cherokee unions, especially those between a freeperson and an enslaved person, were disapproved of. Doll was simultaneously enslaved by and married to a relatively well-known Cherokee warrior named John Shoe Boots. Tiya Miles, a scholar of Black and Indigenous histories, recounts Doll and her family’s story in Ties that Bind: The Story of an Afro-Cherokee Family in Slavery and Freedom. Miles' extensive archival and recovery work reveals that much of the information about Doll’s life is limited to records from the Cherokee Nation archive and court documents from Missouri and Arkansas state courts.
Doll's life is preserved in Cherokee records mainly due to her historical and controversial union with Captain John Shoe Boots—one of the Cherokee and Shawnee warriors who, after taking complaints of white settlement on Indigenous lands into their own hands, raided Morgan Station in 1793 in what would become known as "the last Indian raid in Kentucky." Doll was purchased or captured (like Shoe Boots' first wife, a white woman named Clarinda who he captured during the raid) by Shoe Boots in South Carolina. This encounter was likely around 1800 since Doll is reported to have been about sixteen years old when she arrived in Cherokee county (present-day Georgia) with Shoe Boots. Since Shoe Boots was already married to Clarinda when Doll arrived, Doll was likely purchased as a domestic servant to Shoe Boots' first wife. In 1804, after Clarinda’s family pressured Cherokee agent Return Meigs to track and return their daughter, Clarinda left Cherokee county for Kentucky and did not return—much against Shoe Boots' wishes.
Relying on Ties that Bind, the Payne Papers, and Moravian journals, Wikitree Entries, a genealogy website, states that Doll and Shoe Boots married in Cherokee county in 1805, only one year after Clarinda left and about three to five years after Doll first arrived as a young girl. Considering that 19th century Cherokee marriage customs did not rely on written documentation, there is likely no marriage certificate available for Doll and John Shoe Boots' union. As scholars rightfully raise concerns about consent and concubinage when discussing marriage between owners and bondspeople, Doll and Shoe Boots’ marriage proves particularly complicated. Despite being the legal property of Shoe Boots, Doll engendered an Afro-Indigenous family whose story has now become symbolic of the growing antiblack sentiment that shaped Black and Indigenous relations in 19th century Cherokee society.
The Shoe Boots family line began with a daughter born on an unreported date in 1806. Shoe Boots bestowed the child the Cherokee name of Kahuga. They went on to have four more children named John, Polly, and twins, William and Lewis. Since Cherokeeness was defined by matrilineal descent, as a Black woman Doll was disqualified for citizenship and sovereignty in Cherokee county, as were her children. Up until 1824, Doll's Afro-Cherokee children were legally enslaved—though there is no evidence that Shoe Boots used them as slave labor as he did his other property. Nevertheless, Shoe Boots was aware that, by law and custom, his Afro-Cherokee children were enslaved. He therefore initiated a petition seeking their full citizenship in the Cherokee nation.
In 1824, despite the growing opposition to Afro-Cherokee unions among Cherokee leaders in the 1800s, Shoe Boots made an urgent plea for the freedom of his and Doll’s first three children, Kahuga, John, and Polly. Shoe Boots’ plea to the Cherokee Council, many of whom were his close acquaintances, states, "Knowing what property I may have, is to be divided amongst the Best of my friends, how can I think of them having bone of my bone and flesh of my flesh to be called their property?" On November 18th, 1824, The National Council approved Shoe Boots' request to emancipate and grant citizenship to his three children under the stipulation that he "cease begetting any more Children by his said slave woman." Ignoring the last stipulation, Doll and Shoe Boots bore twins about two years later.
On November 11th, 1824, three weeks after receiving Shoe Boots' petition, the Cherokee General Council passed an act outlawing marriage between "negro slaves and Indians, or whites," thus publicly making clear their disapproval of unions that cross racial and freedom lines. This change in legal rights of all African Americans after one individual gained freedom echoes earlier restrictions, like the response to the Elizabeth Key case in 17th Century Virginia
Despite the legal changes that made Doll and Shoe Boots' union unlawful, Doll would claim her marriage to the Cherokee warrior as the basis for her right to land in Arkansas. Privy to the 1850 Act of Congress that guaranteed "bounty land" to the widows of United States military officers, Doll applied for land in 1852, arguing that she was married to Shoe Boots' "according to the then existing Laws and Customs of the Cherokee Nation" and that her husband's leadership in the Creek War qualified her for the government proffered land. Though the Arkansas state would grant Doll a warrant for forty acres of land, she reapplied for land in the state of Missouri when congress passed an act allowing all U.S. military veterans 160 acres of land. When Doll's application was delayed by Missouri courts for a lack of proper marriage documentation, her Cherokee allies Pigeon Halfbreed, Stand Watie, and Wilson Loowaga attested that Dolly and Shoe Boots indeed lived as husband and wife before his death in 1829. The U.S. government therefore awarded Doll the 160 acres due to her a veteran’s widow in 1855.
In 1860, Doll, now a freewoman and a landowner, was listed as an 80-year-old housekeeper in a census of freed persons living in The Five Civilized Tribes. Since Shoe Boots did not petition for her freedom in 1824, Doll was legally freed in 1849 (on account of her age) upon the death of her second owner, Savannah Ridge; Doll was reportedly around 70 years old. During the Civil War, Doll died far away from her home in Honey Creek (present-day Southwest City, Missouri). Instead, she passed away aged about 81-years-old in the Choctaw Nation on the Kiamichi River in Oklahoma. Her Afro-Cherokee children continued to struggle for citizenship and sovereignty after her death. Her son William was twice denied citizenship into the Cherokee nation when he applied in 1887 and her son Lewis, who was sold into slavery in the 1830s, was never recovered and was presumably still enslaved upon her death.
Native Americans Project Wikitree.
Miles, Tiya. Ties that Bind: The Story of an Afro-Cherokee Family in Slavery and Freedom. Berkeley. University of California Press, 2015.