WILLIAM FERNANDEZ HARDIN “This Unpleasant Business” Slavery, Law, and the Pleasants Family in Post- Revolutionary Virginia n 1799, the Virginia Court of Appeals decided the case of Pleasants v. Pleasants .1 John Marshall, future Chief Justice of the U.S. Supreme ICourt, persuaded the court to free more than 400 slaves according to the will of their deceased former master. It was the largest judicial manumission in American history, and yet it has received limited attention. 2 The case is often overlooked, it seems, because the facts are unique and the decision itself was not cited extensively. 3 In addition, the reasoning supporting the decision is extremely technical and complex, making it difficult to decipher. Judges and lawyers of late eighteenth-century Virginia did not, it must be observed, esteem brevity or clarity. The historical value of the Pleasants case, however, comes into view when it and the family dispute that drove the case are placed in a historical context. Presented in this manner, the Pleasants dispute demonstrates how the legal relationship between manumission and the law shaped the lives of Virginians at a pivotal period in the formation of American slavery. In 1790, Virginia was home to more slaves and slaveholders than any other state in the nation, and it would continue to be so through the 1860 census. After the Revolution, slaveholders in Virginia for the first time faced well-organ - ized politically savvy opponents who denied the legitimacy of slavery along moral, religious, and legal lines. Always a small minority of the white popu - lation, nonetheless, antislavery activists compelled slaveholders to justify their slaveholding in religion, morality, and law. Reconstructing the William Fernandez Hardin, J.D., Ph.D., is a history teacher at Montgomery Bell Academy in Nashville, Tennessee. VIRGINIA MAGAZINE OF HISTORY AND BIOGRAPHY VOL. 125 • NO. 3 212 • Virginia Magazine Pleasants dispute provides a fresh insight into how lesser-known slavehold - ers in the post-Revolutionary period responded to the challenge of antislav - ery along these lines. In the dispute, larger forces—the law, antislavery, religion—helped to shape and define a generational debate over slavery at a critical moment in a critical place in the history of emancipations. That debate, spanning a number of years, forced the court to consider the nature of manumission and how it would function in the common law. The court would decide if manumission was the restoration of a natural right to freedom or the ultimate largesse, the gift of a benevolent slaveowner to a grateful slave. THE DISPUTE BEGAN WITH the will of John Pleasants III, a wealthy slavehold - ing Quaker. His plantation, Curles Neck, sat on a marshy peninsula along the James River fifteen or so miles downriver from Richmond. The estate, it was said, abounded in “riches, negroes and grandeur.” 4 On a summer evening in 1771, John Pleasants collapsed in his hallway and died soon after. 5 Like many Virginia planters of the time, his wealth was in his slaves. Numbering 212, they were valued at £10,000; the total value of his estate, slaves included, was tabulated at £12,000. 6 Earlier that year, he had revised his will with the assistance of his eldest son, Robert—a committed abolition - ist, political activist, and religious elder in the Society of Friends (known as the Quakers). 7 After retiring from commerce, the elder Pleasants took an increasingly active role in the Society just as it was attempting to rid itself of slaveholding members. Father and son, in accordance with Quaker antislav - ery imperatives, drafted a will they hoped would free the slaves. There was one major problem: private manumission (the act of freeing of a slave) was illegal in colonial Virginia. Freedom would have to wait until the law changed. According to John Pleasants’s will, elderly slaves of his household—Joe Cooper, old Suckey, Fanny, old Robin, Carpenter Will, old Nat, old Cesar, and Aggy—were set at liberty to live with any of his children they chose and enjoy the “benefit of their [own] labour.” But the trustees of the estate were empowered to revoke their liberty. Freedom was often conditional under the will and contingent, in some cases, on continued economic productivity. Charles White and his sons, for example, were permitted to ply Virginia’s Hardin— ”This Unpleasant Business” • 213 waterways as a batteauxmen as long as White “proved honest” by remitting two-thirds of his earnings to the estate. 8 Other people were retained as quasi- servants under unique terms. 9 The vast majority of Pleasants’s slaves were, however, distributed by lots. Samuel Pleasants of Philadelphia, Robert’s brother, was assigned one-third. Jonathan Pleasants (Robert’s half-brother) and Robert himself each received the remaining thirds. All the slaves were bequeathed according to the following condition: “all of [the slaves] as I shall die possessed with shall be free if they choose it when they arrive to the age of thirty years, and the laws of the land will admit them to be set free with - out their being transported out of the country. I say all my slaves now born or hereafter to be born, whilst their mothers are in the service of me or my heirs, to be free at the age of thirty years as above mentioned, to be adjudged of by my trustees their age.” 10 The antislavery imperatives of the Quakers dovetailed in this case with Robert’s responsibility as executor of his father’s will. 11 That responsibility was doubled when his half-brother Jonathan died and left a similar, but more expansive, provision in his 1777 will. 12 But little could be done until manu - mission became legal. In 1782, the General Assembly, responding to Quaker petitions and political lobbying, did so. 13 Some in the Pleasants family immediately freed their bondsmen—most did not. 14 Robert Pleasants spent the next two decades trying to convince a lot of his kin to emancipate his father’s former slaves. The duty to emancipate was a straightforward issue for Robert Pleasants. By accepting custody of the slaves, family members had implicitly endorsed the beneficent purposes of the freedom provision. Slaveholding family members were, in this view, more like custodial guardians rather than slaveowners. 15 This line of reasoning appealed most strongly to heirs who inherited slaves directly under the will. But it found little traction among heirs who received title to slaves from secondary sources. For example, Jonathan Pleasants, Robert’s half-brother who died in 1776, stipulated that his one-third share of the slaves (received under the will of John Pleasants III) were to be divided among his own heirs under the same freedom provi - sion. And it is this group of subsidiary, often former Quaker, slaveholders that were the most resistant to emancipation and most active in responding to calls of emancipation with proslavery formulations. 214 • Virginia Magazine Robert’s half-sister Mary “Molly” Pleasants is a good example. As a young girl she inherited approximately fifty slaves under her late brother Jonathan’s will. Her parents had died and Robert Pleasants was tasked with her upbringing. Fearing that she might fall prey to “some designing fellow,” he sent her to Philadelphia to live under the watchful care of her Quaker rel - atives. She soon met Charles Logan, the very sort of fellow Pleasants hoped she would avoid. 16 He was the high-born, low-achieving grandson of the esteemed colonial statesman, James Logan. 17 Molly’s fifty or so slaves, along with the land she inherited in Virginia, undoubtedly helped attract Logan’s attention. However, under pressure from Quaker family members and friends, the couple signed a written promise to free the slaves. 18 They, how - ever, reneged on that promise and moved to Virginia and Molly’s sizeable inheritance. Both were subsequently expelled by the Quakers for their con - duct. 19 Robert Pleasants demanded that they fulfill their promise to emanci - pate. 20 When they refused, he consulted Edmund Randolph, one of Virginia’s most respected lawyers, who concluded that the promise could not be legally enforced. Because the deed of emancipation was signed just moments before the wedding ceremony, the law supposed a groom in Logan’s position to be under “particular influences” that were deleterious to sound judgment. Nuptial bliss forestalled by a request to sign the deed, Randolph explained, may have put Logan under sufficient mental duress to negate his legal consent to the manumission. 21 Randolph also concluded that Logan did not possess the right to free Molly’s slaves because the marriage had not yet taken place when the promise was made. 22 Lastly, the promise would fail because Molly was “under age” and lacked the legal capacity to emancipate the slaves or to consent to their manumission. 23 It was a matter like the transfer of any other valuable property under common law. A slave’s humanity, according to Randolph, lacked relevance in a purely legal consid - eration of the matter. Pleasants was not dissuaded, however, but he was troubled. Logan, he suspected, was selling slaves out of state and was wait - ing for a “suitable opportunity” to sell many more. 24 Pleasants therefore enlisted the aid of the Pennsylvania Abolition Society (PAS) to assist in the matter. 25 The PAS had previously assisted Pleasants in several other freedom cases, and he hoped its members could persuade Logan. 26 Hardin— ”This Unpleasant Business” • 215 Mentor and former law partner of John Marshall (1755 –1835), Edmund Ran- dolph (1753 –1813) represented the slaveholding defendants in the Pleasants case. He had returned to his Richmond law practice after resigning as George Washington’s (1732 –1799) secretary of state.