Most of our information about Anthony comes from runaway ads placed by James Madison’s father in 1786 and 1787, and from letters exchanged by Madison and his father at the time. By examining these sources, we can piece together the story of Anthony’s attempted escapes.
Anthony at Montpelier
Anthony was born ca. 1769, based on his age as listed in the 1786 advertisement. Two enslaved males named Anthony were listed in the personal property tax records of Madison’s father, James Madison Sr., in each of the years from 1782 to 1786 (the only years when enslaved people were listed by name). One was likely the man sometimes known as “Old” Anthony, and the other may have been the teenaged Anthony who made his escape later in 1786. Possibly the younger Anthony was a son, nephew, or other relative of the older Anthony.
Anthony may have had opportunities to travel on his own, prior to his escape, if he was the person that James Madison referred to in this January 1786 letter, written from Richmond to his brother Ambrose, who lived near Montpelier:
“If any fresh butter has been procured or should be on hand & Anthony can bring it, I shall be glad of it…”
Ambrose jotted on the cover of the letter:
“There is a Pott of Butter weighg abt. 12 lb. for Anthony if he can carry it.”
Anthony’s delivery of butter was the subject of this exchange between James Madison and his brother Ambrose. James was away in Richmond, serving in the Virginia House of Delegates. Courtesy of The New York Public Library.
Perhaps trips like delivering butter to Richmond built Anthony’s confidence in his ability to travel alone, and gave him time to imagine a life of independence. As a young man without a wife and children, Anthony may have been more willing to take risks than if he had already started a family of his own. Billey Gardner, the son of “Old” Anthony (and possibly Anthony’s brother or cousin), achieved freedom in Philadelphia. Could the younger Anthony find freedom as well?
The First Escape
The details of Anthony’s initial escape come from a newspaper advertisement placed by James Madison Sr., five months after the fact. Anthony left Montpelier on June 14, 1786. The ad described Anthony as
“a Mulatto Slave, named ANTHONY, about 17 years old, low, but well made, has very light hair and grey eyes; he carried with him a Great Coat, made of white plains with a small red Cape; a jacket of red plains, and another of white linen, each without sleeves; an Oznaburg coat, two pair of breeches, and a pair of striped overalls, felt hat, shoes, and metal buckles; he has been used to house business, and as a waiting servant. TEN DOLLARS Reward will be given, if he be secured so that I get him again, or the above, if brought home to me. N.B. It is probable he has procured a Pass, or a Certificate of his Freedom; and has changed his name and cloaths.”
Each sentence of this ad gives insight into Anthony’s life. His physical description – light skin, light-colored hair, gray eyes – suggests that Anthony had multiracial ancestry. Anthony had worked as a domestic servant at Montpelier and had waited at table, which required a very specific set of skills. Working in the house, Anthony was probably better dressed than if he had worked in the fields. He had two sets of clothes – two coats, two sleeveless jackets or vests, two pair of breeches – as well as overalls, a hat, and buckled shoes. Most of his clothing, however, was made of plains or oznaburg, cheap imported fabrics often purchased by plantation owners to outfit the people they enslaved. If Anthony was able to earn a little money on the side, by hunting or raising chickens on his own time, he may have purchased accessories like his hat or a handkerchief for himself.
Madison Sr. suspected that Anthony would attempt to disguise his identity, by changing his clothes, using an alias, presenting false freedom papers, or carrying a forged pass (similar to the authentic pass Benjamin McDaniel carried while on Montpelier business). Madison Sr. was correct.
Madison’s father asked him to put this ad in a Richmond newspaper. Madison, who was again in Richmond serving in the House of Delegates, replied to his father on November 1, 1786, “I shall execute your instructions as to the advertisements.” The ad ran at least three times in November 1786, advertising a reward of $10 for apprehending Anthony, or $20 for returning him to Montpelier.
Anthony was on his own for just over a year, from June 14, 1786 until June 26, 1787, when he was captured in Hanover, Virginia. As Madison Sr. had suspected, Anthony had been passing as a free man, using the alias Robert or Bob Jones. He was captured wearing “a blue cloth coat, which was too large for him, spotted waistcoat and linen overalls,” which shows that he had also attempted to conceal his identity by buying or trading for new clothes. Anthony said that he had been to the West Indies, Philadelphia, and Charlestown (probably Charleston, South Carolina), as well as the Virginia port cities of Norfolk and Portsmouth. He was working as a hired servant in Hanover, Virginia, when captured.
Did Anthony actually travel as widely as he said he did? James Madison was doubtful, writing to his father:
“It does not appear to me probable that all the circumstances mentioned by Anthony with regard to his rambles can be true. Besides other objections which occur, there seems to have been scarcely time for all the trips which he pretends to have made.”
If Anthony had gone to Norfolk or Portsmouth and had hired on to a ship’s crew, it is not impossible that he could have been to other ports from Philadelphia to Charleston and the West Indies in a year’s time. It may be significant, however, that Anthony was captured in Hanover, less than 70 miles from Montpelier. Does this mean that he actually never left the state? Or does it mean that Anthony could easily take on another identity when he was far from Montpelier, but was ultimately recognized when he returned to more familiar surroundings?
Wherever Anthony was during that year, his experience of freedom was probably tinged with the constant fear of being discovered, and the anxiety of inventing and perhaps changing his cover stories. Yet as stressful as the year may have been, Anthony was only too ready to seize his freedom again. On June 27, 1787, when his captors stopped overnight in Louisa on the way back to Montpelier, Anthony escaped a second time – barely a day after his apprehension.
The Search Begins Again
According to a newspaper advertisement initially placed on August 16, 1787, James Madison Sr. had heard that Anthony headed to Fredericksburg and obtained a pass under the new alias of Billy Willis, on his way to Alexandria and Philadelphia.
James Madison Sr. did not refer to Anthony by name in this advertisement, but as “the mulatto lad I advertised … last November as run-away.” Madison Sr. gave the ominous warning that “if he is taken and is not well secured with irons he very probably will make his escape again,” and increased the reward to $30 if Anthony was brought back to Montpelier.
While Anthony was thought to be making his way to Philadelphia, James Madison was already there, attending the Constitutional Convention. Madison attempted to get information about Anthony from two other young men with possible ties to him. John was Madison’s enslaved manservant who had traveled with Madison to Philadelphia. Billey Gardner, whom Madison had formerly enslaved before selling him into short-term servitude, now lived in Philadelphia. Madison likely suspected that if Anthony reached Philadelphia, he would approach John or Billey Gardner for assistance.
Madison learned nothing. “The enquiries which I have at different times made of Billey concerning Anthony satisfy me that he either knows, or will tell nothing of the matter,” Madison reported to his father on July 28, 1787. “I have not communicated to John the suspicions entertained of him,” Madison continued, possibly implying that his father, or Madison himself, believed that John was not telling the truth about Anthony.
The Fugitive Slave Debate
On August 28 and August 29, 1787, the delegates to the Constitutional Convention discussed what would become known as the Fugitive Slave Clause. Was Madison thinking about Anthony as he took these notes during the Convention proceedings on August 28?
“Mr. BUTLER and Mr. PINKNEY moved ‘to require fugitive slaves and servants to be delivered up like criminals.’
Mr. WILSON. This would oblige the Executive of the State to do it at the public expence.
Mr. SHERMAN saw no more propriety in the public seizing and surrendering a slave or servant, than a horse.”
While South Carolinians Pierce Butler and Charles Pinckney supported the return of enslaved people who escaped, it was two northern delegates — James Wilson from Pennsylvania, and Roger Sherman from Connecticut — who objected. Their objections, however, were based on a concern that it was improper for the government to intervene in a property issue, rather than a concern that it was morally wrong for the government to uphold slavery.
Pierce Butler withdrew his proposal that day, only to reintroduce it the next day in a slightly different form:
“If any person bound to service or labor in any of the U. States shall escape into another State, he or she shall not be discharged from such service or labor, in consequence of any regulations subsisting in the State to which they escape, but shall be delivered up to the person justly claiming their service or labor.”
Madison’s notes suggest there was no further debate; the motion passed unanimously. Presumably Madison was in agreement that this should be Anthony’s fate if recaptured outside Virginia.
Madison remained in Philadelphia until after the Constitution was signed on September 17, 1787. No further information about Anthony came to light during Madison’s stay there.
One Year Later
Anthony was not mentioned in any surviving Madison correspondence for over a year. Then, in July 1788, Madison apparently made a brief stop in Philadelphia on his way to the Confederation Congress in New York. He wrote to his father on July 27 that “my stay there [being] so short … prevented my taking any steps with regard to Anthony.” Presumably Madison Sr. had suggested a new strategy to get information about Anthony, because Madison added, “Perhaps some other opportunity may offer for making the trial you suggested. I think however there is little ground to count on much success in the case.” Madison updated his father from New York on August 18, writing simply, “I have had no opportunity of doing any thing as to Anthony, since my last [letter].”
Madison’s final letter on the subject of Anthony’s disappearance hints at the personal dynamics between Anthony, Billey Gardner, and John. Madison wrote to his father on September 6, 1788:
“I have not yet been able to determine whether Anthony is still in Philada. I am inclined to believe he is not. Indeed some circumstances wd almost tempt me to think he never has been there. On this supposition John must have practised a gross deception on us. He could have no motive for this unless it were a spite to Billey, which I fancy he entertained. But the deception could hardly promise a gratification that would prompt it.”
This suggests that John had previously told Madison that Anthony was in Philadelphia, perhaps being aided or sheltered by Gardner. Madison could only assume that John’s motivation was to create trouble for Gardner with this story. Another possibility, however, is that John himself was aiding Anthony simply by misdirecting the Madisons’ search. By focusing their attention on the Philadelphia area, John may have made it easier for Anthony to slip away to a different location.
The Trail Goes Cold
Anthony was never discussed again in Madison’s correspondence with his father. John, who was suffering from consumption, appears to have died in New York in late 1788 or early 1789, without revealing anything he may have known about Anthony’s whereabouts. Billey Gardner either knew nothing, or refused to share what he knew.
The paper trail for Anthony runs out here. Perhaps Anthony died while enduring dangerous conditions to remain concealed in out-of-the-way locations. Perhaps Anthony adopted a new identity, blending into a large city or joining the crew of a ship, while still looking over his shoulder for those who would pursue him.
And perhaps, by asserting himself to be a free man, Anthony actually lived out the rest of his life in freedom.
 “Twenty Dollars Reward.,” Virginia Gazette (Richmond, VA), November 22, 1786, accessed June 28, 2021, MRD-S 42360, Montpelier Research Database.
 Personal Property Tax Records for James Madison, Sr., 1782-1786, Orange County, Virginia, Tax Records, Library of Virginia, Richmond, Virginia, accessed June 28, 2021, MRD-S 43968, Montpelier Research Database.
 James Madison to Ambrose Madison, January 21, 1786, Ford Collection, New York Public Library, New York, New York, accessed June 28, 2021, MRD-S 39304, Montpelier Research Database.
 “Twenty Dollars Reward.,” Virginia Gazette (Richmond, Virginia), November 22, 1786, accessed June 29, 2021, MRD-S 42360, Montpelier Research Database.
 James Madison to James Madison Sr., November 1, 1786, James Madison Papers, Library of Congress, Washington, DC, accessed June 29, 2021, MRD-S 10084, Montpelier Research Database
 All the details about Anthony’s aliases, clothing changes, and whereabouts come from the ad placed by James Madison Sr. after Anthony escaped for the second time. See: [”The mulatto lad I advertised”], Virginia Herald (Fredericksburg, Virginia), September 6, 1787, 4, accessed June 29, 2021, MRD-S 45435, Montpelier Research Database.
 James Madison to James Madison Sr., July 28, 1787, James Madison Papers, Library of Congress, Washington, DC, accessed June 29, 2021, MRD-S 10780, Montpelier Research Database.
 [”The mulatto lad I advertised”], Virginia Herald (Fredericksburg, Virginia), September 6, 1787, 4, accessed June 30, 2021, MRD-S 45435, Montpelier Research Database.
 James Madison to James Madison Sr., July 28, 1787, James Madison Papers, Library of Congress, Washington, DC, accessed June 30, 2021, MRD-S 10780, Montpelier Research Database.
 James Madison, Notes on the Debates in the Federal Convention, The Avalon Project, https://avalon.law.yale.edu/18th_century/debates_828.asp, accessed June 30, 2021.
 James Madison, Notes on the Debates in the Federal Convention, The Avalon Project, https://avalon.law.yale.edu/18th_century/debates_829.asp, accessed June 30, 2021.
 James Madison to James Madison Sr., July 27, 1788, James Madison Papers, Library of Congress, Washington, DC, accessed June 30, 2021, MRD-S 21358, Montpelier Research Database.
 James Madison to James Madison Sr., August 18, 1788, James Madison Papers, Library of Congress, Washington, DC, accessed June 30, 2021, MRD-S 21372, Montpelier Research Database.
 James Madison to James Madison Sr., September 6, 1788, James Madison Papers, Library of Congress, Washington, DC, accessed June 30, 2021, MRD-S 21380, 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.