Also setting out for Philadelphia in the fall of 1790 was the adolescent slave Christopher Sheels, who would eventually replace Billy Lee as Washington’s body servant. A third-generation Mount Vernon slave, the fifteen-year-old Sheels was separated from his mother, Alice, a spinner, and his grandmother Doll, a cook. The mulatto slave Austin, separated from his wife at Mount Vernon, arrived in Philadelphia by stagecoach along with Hercules. Martha also brought along her two dower slaves, Moll and the teenage Ona Judge, for her personal entourage. As the person who dressed Martha’s hair and laid out her clothes, Ona Judge held a special place in the presidential household.

In early April 1791 Attorney General Edmund Randolph delivered a startling piece of news to the Washingtons. Under the 1780 Pennsylvania statute, any adult slaves resident in the state for six consecutive months were automatically free. Three of Randolph’s own slaves had served notice that they planned to claim their freedom. Bizarrely, the attorney general of the United States urged the president and first lady to evade this local law. Coaching them how to do so, he noted that once slaves were taken out of Pennsylvania and then brought back, the clock was reset, and another six months needed to elapse before they could demand their freedom. At first Washington imagined, wrongly, that federal officials in the capital were exempt from the law. Still, he fretted to Tobias Lear that people in “the practice of enticing slaves” might not make such fine distinctions.31 With paternalistic certitude, he doubted that, even if any of his slaves opted for freedom, they would be “benefitted by the change, yet the idea of freedom might be too great a temptation for them to resist.”32 Washington was especially alarmed about this prospect, since all of his slaves in Philadelphia, except Hercules and Paris, were dower slaves, meaning that Washington would have to reimburse the Custis estate if they fled his household.

Not taking any chances, Washington decided to shuttle his slaves back to Mount Vernon for brief stays before their six-month time limits expired. As minors, Christopher Sheels, Richmond, and Ona Judge were all debarred from seeking their freedom. To keep the adult slaves in bondage, Washington resorted to various ruses so they would not know why they were being sent home temporarily. As he said bluntly, “I wish to have it accomplished under pretext that may deceive both them [i.e., the slaves] and the public.”33 This was a rare instance of George Washington scheming, and Martha Washington and Tobias Lear connived right along with him. In April Martha sent Austin back to Mount Vernon under the pretext of honoring a promise that he could return periodically to see his wife. In writing to Fanny about the visit, Martha showed how coolly she could lie, saying that Austin’s stay at Mount Vernon “will be short, indeed. I could but illy spare him at this time, but to fulfill my promise to his wife.”34 That spring, when Martha took a short excursion to Trenton, she deliberately took two slaves across state lines. In a similarly duplicitous vein, Washington advised her to return to Mount Vernon in May, then summon Hercules home to cook for her. So top secret were these machinations that Washington advised Tobias Lear, “I request that these sentiments and this advice may be known to none but yourself & Mrs. Washington.”35

Such devious tactics ran counter to Washington’s professed abhorrence of slavery, not to mention his storied honesty. Even more startling was the acquiescence of Tobias Lear, the young idealist who had balked at working for Washington because the latter owned slaves. In the midst of corresponding with Washington over foiling the Pennsylvania law, Lear suddenly remembered that he and Washington were supposed to be long-term opponents of slavery, and he wrote guiltily to the president: “You will permit me now, Sir . . . to declare that no consideration should induce me to take these steps to prolong the slavery of a human being had I not the fullest confidence that they will, at some future period, be liberated and the strongest conviction that their situation with you is far preferable to what they would probably obtain in a state of freedom.”36 This strange declaration shows that Washington had already told a few confidants of his intention to free his slaves someday, while saying that, in the interim, the slaves were somehow better off than if they were emancipated.

Washington and Lear wondered whether the slaves knew of the Pennsylvania law that lay behind these subterfuges. They were especially curious about Hercules, who had been told he would be sent by stagecoach to Mount Vernon in June. Since he would arrive a little ahead of the president, Tobias Lear informed him that “being at home before [Washington’s] arrival, he will have it in his power to see his friends.”37 When somebody in the presidential household evidently tipped off Hercules to the true reason for his return, he was outraged, but not for the obvious reason. As Lear wrote privately to Washington, Hercules “was mortified to the last degree to think that a suspicion could be entertained of his fidelity or attachment to you. And so much did the poor fellow’s feelings appear to be touched that it left no doubt of his sincerity.”38 As we shall see, Hercules was an extremely shrewd man who knew how to feign loyalty and play his master to perfection. To reaffirm her faith in Hercules, Martha Washington told him that he could stay in Philadelphia past the six-month expiration point before returning to Virginia. Hercules took her up on the offer, stayed past the deadline, then dutifully returned to Mount Vernon. Perhaps to make the return more tolerable, Tobias Lear bought Hercules two new shirts for the trip.

All this collusion occurred against a backdrop of unusual turmoil on the slavery issue. Even as Washington and Lear conspired to keep slaves in bondage, Lafayette rose in the National Assembly and demanded the extension of full civil rights to free blacks in the French colonies. In August 1791, inspired by the French Revolution, slaves in the French colony of St. Domingue (later Haiti) began a bloody rebellion that raged for a dozen years. Many slave owners fled to American seaboard cities, where they stoked dread among American masters that their slaves, too, would stage a bloody insurrection. In 1792 the House of Commons in London enacted its first ban on the slave trade, further fueling fears among slave owners that abolitionism might spread.

Faced with such ferment, Washington struggled to find a stand on slavery that reconciled his economic interests with his private principles. As president, he insisted that the British compensate Americans for slaves spirited away during the Revolution. Politically, his weakest backing lay in the southern states, which were alarmed by Hamilton’s financial system, and this disaffection made it difficult, if not impossible, for him to take a courageous public stand against slavery. All the while he remained the symbol of American liberty, so that abolitionists yearned to claim his aegis for their cause. One antislavery society was named “The Washington Society for the Relief of Free Negroes, and Others, Unlawfully Held in Bondage.”39 The same George and Martha Washington who circumvented the Pennsylvania law also donated money in May 1792 to a slave who approached them with a list of “respectable” people assisting him to obtain his freedom.40 The same George Washington reacted with dismay when the South Carolina legislature refused to renew a two-year ban, enacted in 1791, on importing slaves. The president, of course, had been pleased two years earlier when Congress buried the Quaker proposal for banning the slave trade.