What We Know About Webster
Webster was born on September 18, 1781. His mother was Eliza, and he had four older sisters: Dianna, Joanna, Demas, and Pendar. James Madison Sr. enslaved the entire family, and their names appear on his personal property tax records for 1782 (the first of the five years in which enslaved people were listed by name as individuals.)
After Madison Sr.’s eldest daughter Nelly Conway Madison married Isaac Hite on January 2, 1783, her father gave her 15 of the people he enslaved, including Webster, his mother, and his four sisters. It was common for wealthy enslavers to give enslaved people to a son or daughter at their marriage. By transferring “personal property” to the Hites, Madison Sr. likely intended to provide unpaid labor that would allow the young couple to build their own wealth at Belle Grove, their Shenandoah Valley plantation. A deed of transfer was formally recorded in 1785, stating that the transfer was “in consideration of an intermarriage which hath taken place between Isaac Hite, Jr. of the County of Frederick and my daughter Nelly Madison, now Nelly Hite.” 
Madison Sr. later confirmed this gift of 15 enslaved people in his will, writing, “I do also confirm to my daughter Nelly Hite the following slaves, to wit; Jerry, Jemmy, Sally, Milley Eliza and her children Joanna, Dianna, Demars, Pender and Webster, also Truelove and her children, Peggy, Priscilla, Henry and Katey and their increase since the first day of March 1783 and for the future.” This suggests that Madison Sr. sent Webster’s family and the other nine enslaved people to Belle Grove on or about March 1, 1783.
Madison Sr. may have also transferred to the Hites some records or information regarding the enslaved people he gave to them. Although there are no surviving logs of birth and death dates in James Madison Sr.’s papers (see Where Have All the Papers Gone?), Isaac Hite recorded the birth dates of Webster, his mother and sisters, and the other nine people he received, in his commonplace book. Webster is also referred to as “Webber” and “Billy Webster” in the commonplace book, but it is clear that each of these name variations refers to the same person. His birth date is always listed as September 18, 1781, and his mother’s name is listed as Eliza (alternately spelled Lysa or Lisa).
Webster was under two years old when he was taken to Belle Grove with his mother and sisters. Since we don’t know Webster’s father’s name, we can’t tell whether his father also went to Belle Grove, if he remained at Montpelier, or if he was enslaved at another Orange county plantation. Webster may have had aunts, uncles, grandparents, or cousins at Montpelier who would never see him again. While Nelly and Isaac Hite’s union was undoubtedly a joyful event for the Madison family, for the enslaved community, it was a time when family ties were torn asunder.
James Madison Sr.’s will confirmed the names of the enslaved people he gave to his adult children during his lifetime (as of the writing of the will in 1787). This section includes the names of Eliza, Webster, and her other children, all of whom were given to Nelly Madison Hite, as well as the names of the enslaved people Madison Sr. gave to his sons Ambrose and William. (Enslaved people given to his sons James Jr. and Francis appear on a previous page.) Madison Sr. concluded this section by bequeathing comparable shares of his estate to any of his younger children who did not receive slaves during his lifetime. Courtesy of James Madison Papers, Library of Congress.
 Personal Property Tax Records for James Madison, Sr., 1782-1786, Orange County, Virginia, Tax Records, Library of Virginia, Richmond, Virginia, accessed September 2, 2020, MRD-S 43968, Montpelier Research Database.
 James Madison Sr. to Isaac Hite Jr., Deed of gift for slaves, August 25, 1785, William H. English Collection (Hite-Bowman Papers), Indiana Historical Society, Indianapolis, Indiana, accessed September 2, 2020, MRD-S 42048.
 James Madison Sr., Will dated September 17, 1787, James Madison Papers, Library of Congress, Washington, DC, accessed September 2, 2020, MRD-S 20954, Montpelier Research Database.
 Hite Family Commonplace Book, 1776-1859, Hite Family Papers, Vol. I, MS IH637535a-40, Virginia Historical Society, Richmond, Virginia, accessed September 2, 2020, MRD-S 44306, Montpelier Research Database.
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.