What We Know About Elijah
In 1818, James Madison leased several enslaved laborers – including Elijah – from his wife’s uncle Isaac Winston III, who lived in Culpeper. On August 18, Madison wrote to Winston to discuss whether to continue the arrangement into 1819:
“I promised to let you know within this Month whether it wd. be convenient to hire your negroes now with me for the ensuing year. It was at one time my intention to retain the whole, But the conduct of Chs. & Spotswood has been such of late as to put them out of the question. If you are willing to separate them from the others, making the proper deduction for any loss that may happen from the lameness of Elijah, I am willing to hire them at the rate of $80 each, and I will take on the same terms the fellow called I believe Big Elijah.”
Elijah was presumably younger than “Big” Elijah, and may have been his son or nephew. Despite noting Elijah’s “lameness,” Madison intended to lease him again for the next year, although he expected to pay a discounted rate if Elijah worked more slowly or was less productive. Perhaps Elijah’s condition was a temporary situation due to an injury or illness. That would explain why Madison wrote of “any loss that may happen,” as though he was uncertain how this disability would affect Elijah.
Madison made many revisions on the draft of his August 1818 letter to Isaac Winston, as he decided how to phrase his thoughts about re-hiring Elijah and other enslaved laborers. Madison inserted the phrase “that may happen” to the sentence discussing the “loss from from the lameness of Elijah,” which suggests that he was unsure whether Elijah would have a lingering disability.
Isaac Winston sent his terms for the lease agreement in November. In Madison’s December 3 reply, he grudgingly accepted the price charged for Charles and Spotswood, noting that Montpelier overseer Abraham Eddins “is disposed to retain them rather [than] look out for others.” Madison added, “The other two will remain of course on th[e] terms already settled” – the “other two” being Elijah and “Big” Elijah. 
The address flap of Madison’s December letter reads
“Capt: Isaac Winston
indicating that Elijah was sufficiently recovered by this time to be able to carry Madison’s letter to Winston in Culpeper County.
Elijah is not mentioned again in Madison’s surviving correspondence. Presumably he was at Montpelier for the year 1819. Whether Madison leased him from Winston in the following years is unknown.
Elijah and the Winstons
Isaac Winston III died in 1821. He specified in his will that his estate would loan his wife Lucy Coles Winston his plantation in Culpeper (called Zhe Hole) along with nineteen enslaved people, during the rest of her lifetime. The enslaved included “Elijah the younger,” presumably the same young man had been leased to James Madison in 1818 and 1819. At Lucy’s death, these nineteen enslaved people would be distributed among the Winstons’ adult children. “Elijah the younger” would become the property of son William Alexander Winston.
The terms of the will also allowed Lucy this option: “if it is her wish at any time hereafter she may remove [the enslaved] out this this state.” This suggests that before Isaac Winston wrote his will in 1820, family members may have been considering relocation. In 1822, the year after Isaac died, daughters Martha Winston Armistead and Dolley Winston, along with other family members, made the 700-mile move to Alabama. The widowed Lucy Winston decided to go with them. Lucy was unhappy after reaching Alabama and planned to return to her sons in Virginia, but was not able to make the trip. She died in Alabama in October 1823.
Did Elijah go with Lucy Winston to Alabama? Isaac Winston’s will permitted Lucy to “remove” Elijah from the state, so it is possible. Daughter Dolley Winston inherited “Elijah the older” when her father died, and may have taken him to Alabama as well.
If Lucy did bring the younger Elijah to Alabama, he likely stayed there only for a year or so. After Lucy’s death, her son William Alexander Winston became Elijah’s new enslaver. Elijah presumably moved back to the Zhe Hole plantation, which William also inherited upon his mother’s death.
Despite a bout of “lameness,” Elijah’s story is filled with movement: back and forth between Culpeper and Montpelier, and possibly from Virginia to Alabama and back. When James Madison and Isaac Winston negotiated contract terms, and when Lucy Winston decided where she would prefer to spend her widowhood, their decisions had significant impacts on Elijah’s life.
Elijah’s work routine, his family and community connections, and even his view of the world – as insular as his own neighborhood or as varied as the scenery on the 700 mile path to Alabama – could change in an instant.
 James Madison to Isaac Winston, III, August 18, 1818, James Madison Papers, Library of Congress, Washington, DC, accessed February 26, 2021, MRD-S 16206, Montpelier Research Database.
 James Madison to Isaac Winston, III, December 3, 1818, MS 2 M2655 a 2, Virginia Museum of History and Culture, Richmond, Virginia, accessed February 26, 2021, MRD-S 22293, Montpelier Research Database.
 Isaac Winston, III, Will dated July 12, 1820, Culpeper County Will Book H: 367-368, Library of Virginia, Richmond, Virginia, accessed March 24, 2021, MRD-S 25025, Montpelier Research Database.
 Milly Wright, “Dolley Madison’s Winston Kin,” editorial essay for the Dolley Madison Digital Edition, accessed March 25, 2021.
Hilarie M. Hicks, MA
Senior Research Historian
Hilarie came to Montpelier in 2010 and joined the Research Department in 2011, where she provides documentary research in support of the Montpelier Foundation’s many activities. A graduate of the College of William and Mary (B.A) and the Cooperstown Graduate Program in Museum Studies (M.A.), Hilarie has a broad background of experience in research, interpretation, and administration of historic sites. She enjoys following a good paper trail, and she thanks past members of the Montpelier research staff who blazed the trail for The Naming Project.