Deborah Squash spent her childhood enslaved on the plantation of Mount Vernon in Virginia. She was one of about three hundred enslaved people held or overseen by George and Martha Washington. There are no records of her early life, so it is impossible to know whether she worked in the fields of the Washingtons’ plantations or in one of the homes on their property. But it is certain that Deborah worked hard, because George Washington believed that all people, male and female, enslaved and free, should work as hard and as long as their strength would allow.
The outbreak of the American Revolution opened up new possibilities for the enslaved people who lived and worked in the English colonies. Some hoped that the new country would stand by its principles that “all men are created equal” and pushed for their local governments to abolish slavery. Others took advantage of the chaos of the war to run away and start new lives. Still others took advantage of the offer made by Lord Dunmore, the governor of the Virginia Colony, in 1775. Dunmore’s proclamation promised freedom to any person enslaved by a patriot who escaped their owner and joined the British forces. Other British war leaders issued similar decrees as the war dragged on. When the British Army and Navy moved through the colony, thousands of enslaved people joined their ranks, hoping to earn their freedom.
Deborah was one of these hopefuls. In April of 1781, a British ship called the Savage was plundering its way up the Potomac when it arrived within a quarter mile of Mount Vernon. The 16-year-old Deborah ran away from the plantation that had been her home all her life and boarded the ship. Sixteen other enslaved people from Mount Vernon ran with her. Lund Washington, George Washington’s cousin and the man who oversaw the management of Mount Vernon while George was away fighting the war, was furious, and decided to pursue the captives. He boarded the British ship, offering supplies in exchange for the return of the enslaved people. The ship captain happily took the provisions, but declined to return the runaways.
News of Lund’s actions traveled fast in the Continental Army, where many people were horrified that a member of Washington’s own family had given supplies to the enemy. General Lafayette wrote to George Washington to demand something be done about it. Washington wrote his cousin a very stern letter, calling his actions “exceedingly ill-judged.”
Following this daring escape, Deborah and her fellow runaways were free from Mount Vernon, but they were by no means safe. They joined the thousands of free Blacks who followed the British Army. The British were happy to encourage escaping enslaved people, but had no means to support them. Cold, starvation, and disease took a terrible toll on the self-emancipated. Historians estimate that nearly 50 percent of the enslaved people who escaped to British lines died before the end of the war.
Deborah survived all of these hardships, including a case of smallpox, and made her way to New York City, the headquarters of the British armed forces during the war. At some point, she married Henry Squash, another enslaved young man who was hoping to gain his freedom by helping the British. By 1783, they were living in New York City, where over 3,000 self-emancipated Blacks hoped the British would confirm their freedom.
Deborah joined the thousands of free Blacks who followed the British Army. The British were happy to encourage escaping enslaved people, but had no means to support them.
When the British conceded defeat at the Battle of Yorktown, the future of Deborah, Henry, and all their self-emancipated neighbors looked grim. In the Treaty of Paris, the agreement that ended the Revolutionary War, the Americans demanded that the British return all escaped slaves to their rightful owners. But Sir Guy Carleton, the British administrator in charge of evacuating the British Army and loyalists from the colonies, refused to carry out this order. He feared that the self-emancipated people would face a life of punishment, or even execution, at the hands of their angry former masters. He thought that would be a very poor outcome for people who had risked everything to help the British cause. Instead, he offered to compensate American slaveowners for every formerly enslaved person evacuated by the British. General Washington reluctantly agreed. This resulted in the creation of the famous Book of Negroes, in which Carleton’s clerks recorded information about every enslaved person who boarded a British navy ship. But there is no evidence that the British ever actually paid the money they promised American slaveowners.
Under Sir Carleton’s orders, the entire emancipated Black population of New York was interviewed to determine who had served the British cause faithfully. Those deemed worthy were given official certificates of freedom and safe passage out of the colonies so they would never be enslaved again. Deborah Squash and her husband were both cleared, and boarded a boat for Port Roseway, Nova Scotia on April 27, 1783. The very next day Washington wrote to the commissioner of embarkation at New York, asking him to privately imprison any enslaved people who belonged to Washington and his family. Luckily for Deborah, she was already far beyond his grasp.