Life Story: Deborah Squash

Life Story: Deborah Squash

This text and image was provided courtesy of the New-York Historical Society and adapted by ReadWorks.

"Artist's rendering of Deborah Squash." Slavery in New York Curriculum Guide (New York: New-York Historical Society, 2005).

Deborah Squash spent her childhood enslaved on the plantation of Mount Vernon in Virginia. She
was one of about three hundred people enslaved 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.

When Deborah was born, Virginia was still a colony of England. Then, in 1775, the American
Revolution began. It started because people living in the American colonies of England wanted
independence from the English government. The outbreak of the American Revolution opened up
new possibilities for the enslaved people in the colonies. Some hoped that the new country would
stand by its principles that "all men are created equal." They 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 promised freedom to any person enslaved by an American patriot who escaped their
enslaver and joined the British forces. When the British Army and Navy moved through Virginia,
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 River. Once it got close to Mount Vernon, 16-year-old Deborah ran away from
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 Life Story: Deborah Squash

the plantation that had been her home all her life and boarded the ship. Sixteen other enslaved
people from Mount Vernon ran with her. Their enslaver, George Washington, was the commander of
the colonies' army that was fighting against Britain. Later, once the colonies gained independence
from England, he would become the first president of the United States of America.

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 Black people 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 people. 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 and made her way to New York City. New York City was 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. Over 3,000 self-emancipated Black people lived there, hoping the
British would confirm their freedom.

Eventually, the British conceded defeat. Both sides signed the Treaty of Paris, the agreement that
ended the Revolutionary War. At that point, the future of Deborah, Henry, and their self-emancipated
neighbors looked grim. In the Treaty of Paris, the Americans demanded that the British return all
escaped enslaved people to their former enslavers. 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 death, at the
hands of their angry former enslavers. 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
enslavers for every formerly enslaved person evacuated by the British. General Washington
reluctantly agreed.

Under Sir Carleton's orders, the entire emancipated Black population of New York was interviewed.
The goal was 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. They would never be
enslaved again. Deborah Squash and her husband were both cleared. They boarded a boat for Port
Roseway, Nova Scotia on April 27, 1783. The very next day, Washington wrote a letter to the
administrator in charge of this effort in New York. Washington asked him to privately imprison any
enslaved people who had worked for Washington and his family. Luckily for Deborah, she was
already far beyond his grasp.

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 Life Story: Deborah Squash - Comprehension Questions

Name: ___________________________________ Date: _______________

1. How did Deborah Squash spend her childhood?

A. self-emancipated with her family in New York City

B. enslaved on George and Martha Washington's Mount Vernon plantation
C. enslaved by the British soldiers during the American Revolution
D. self-emancipated close by the Potomac River

2. What caused enslaved people to join the British forces during the American
Revolution?

A. Lord Dunmore, the governor of the Virginia Colony, promised freedom to any person
enslaved by an American patriot who escaped their enslaver and joined the British
forces.
B. Enslaved people deeply believed in the British cause and wanted to support their fight
against the American revolutionaries.
C. The British Army helped local colonial governments create new constitutions that
supported the emancipation of enslaved people.
D. Enslaved people joined the British forces as a way to escape during the war on ships
to London.

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 Life Story: Deborah Squash - Comprehension Questions

3. Read the following sentences from the text.

"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
Black people 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 people. Historians estimate that
nearly 50 percent of the enslaved people who escaped to British lines died before the
end of the war."

What conclusion can you draw from this evidence?

A. Deborah and her fellow runaways were much safer in the British army than on the
plantations they escaped from.
B. The British forces had a detailed plan to make sure the thousands of free Black
people who joined them would be protected from the harsh elements of war.
C. Even though Deborah and her fellow runaways escaped the plantations, helping the
British forces did not guarantee their safety or survival.
D. Many of the runaway enslaved people joined the British forces right before the
Revolutionary War ended.

4. The British lost the Revolutionary War to the Americans. After this loss, why might
Deborah and other self-emancipated people have been worried about their future?

A. In the Treaty of Paris, the Americans demanded that the British return all escaped
enslaved people to their former enslavers.
B. Sir Guy Carleton, the British administrator, agreed with all of the demands set out in
the Treaty of Paris.
C. The Americans were preparing for another war with the British, and Deborah and
other self-emancipated people were planning to fight in it.
D. The Americans seized all British ships and discovered where many enslaved people
were hiding.

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 Life Story: Deborah Squash - Comprehension Questions

5. What is the main idea of this text?

A. Deborah Squash, who grew up as an enslaved person on George Washington's

plantation, lived in Virginia for most of her life and joined the American army to fight for
the colonies.
B. Deborah Squash, who grew up as an enslaved person on George Washington's
plantation, was one of many Black people who achieved their freedom by joining the
British forces during the American Revolution, despite many hardships.
C. Deborah Squash, who grew up as an enslaved person on George Washington's
plantation, boarded a boat to Nova Scotia in 1783 to start a new life as a self-
emancipated person.
D. Deborah Squash, who grew up as an enslaved person on George Washington's
plantation, stayed in Mount Vernon all of her life because the conditions in the British
Army were terrible.

6. Read the following sentences from the text.

"Eventually, the British conceded defeat. Both sides signed the Treaty of Paris, the
agreement that ended the Revolutionary War."

As used in this excerpt, what does the word "conceded" most closely mean?

A. fought against
B. gained
C. admitted
D. depended on

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 Life Story: Deborah Squash - Comprehension Questions

7. Choose the answer that best completes the sentence below.

General Washington tried to imprison enslaved people like Deborah Squash who had
escaped his plantation by writing a letter to the British administrator. _______,
Deborah and Henry Squash had already left New York for Nova Scotia and would
never be enslaved again.

A. Most importantly
B. However
C. First
D. For instance

8. What was Sir Guy Carleton's response to the American order demanding that the
British return all escaped enslaved people to their former enslavers?

9. Explain the final step the emancipated Black people of New York had to go through to
try to secure their freedom. Use evidence from the text to support your answer.

10. At the end of the American Revolution, the future of formerly-enslaved people in
New York who had fought for the British was unclear. How did the American and
British response regarding the freedom of these people differ? Use evidence from
the text to support your answer.

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