Life Story: Peggy Gwynn

An Unsuccessful Bid for Freedom

This resource is adapted from the New-York Historical Society’s Slavery in New York curriculum.

Artist’s rendering of Peggy Gwynn

“Artist’s rendering of Peggy Gwynn.” Slavery in New York Curriculum Guide (New York: New-York Historical Society, 2005).

Very few images of Black people were recorded in the colonial era. The drawing that accompanies this life story is an artist’s interpretation of Peggy Gwynn based on some of the earliest available photographs of Black people from the mid-19th century. It is intended to help students understand that Peggy was a real person not fundamentally different from us.

The little we know about Peggy Gwynn’s life begins in 1775, at the outbreak of the American Revolution. Peggy was an enslaved person living on the plantation of a Mr. Crammon in Virginia. She likely worked in the production of tobacco or other cash crops.

The Patriot leaders of the Continental Congress who came together to determine the course of the war fought bitterly over what to do about the question of slavery. Some argued that it was useless for the Patriots to fight against the oppression of the English government without undoing the oppression slavery imposed on enslaved people. Others refused to endorse any independence movement if the practice of slavery was threatened.

The English colonial government saw this disagreement as a weakness, and tried to use it against the Americans. On November 7, 1775, Lord Dunmore, the British governor of the Virginia colony, issued a proclamation promising freedom to any enslaved person belonging to a rebel who escaped and joined the British cause. Dunmore hoped that losing their enslaved workers would cripple the Patriots’ ability to produce the supplies they needed to fight the war. Other British war leaders issued similar proclamations as the war dragged on.

Peggy was one of the estimated 20,000 enslaved people who took this opportunity to emancipate themselves. She made her way to New York City, which was the base of English operations during the war. She became a member of a quickly growing Black community of self-emancipated people in the city, all of whom hoped to earn their freedom by helping the British win the war. The men became soldiers or laborers in the British Army. Women like Peggy were cooks or laundresses.

Life for self-emancipated people was not easy. A quarter of New York was burned down in a fire in 1776 and the living conditions for even the wealthiest New Yorkers were dismal. The British colonial government did not have the resources to properly support the self-emancipated, so there was not always enough food, and many lived in makeshift tents in the burned-out parts of the city. There were no records kept to keep track of which self-emancipated people were supporting the British cause.

Even so, Peggy had more personal freedom than she had ever been before. She could demand payment for her work, go to a tavern with friends, dance, and listen to fiddle music. At some point during the war, Peggy met and married another self-emancipated person who was working for the British artillery.

Peggy became a member of a quickly growing Black community of self-emancipated people in the city, all of whom hoped to earn their freedom by helping the British win the war.

The British lost the war, and the Treaty of Paris required that all escaped enslaved people be returned to their original masters. But British commander Sir Guy Carleton was determined to honor the promises made to the thousands of self-emancipated Blacks. He promised to provide any self-emancipated person with papers that granted their freedom as well as transportation away from the American states. American slaveowners were furious. George Washington himself came to argue with Carleton about the situation. Carleton compromised, and said he would only free Blacks who could prove they had been in New York City before the first peace treaty was signed on November 30, 1782. This meant every self-emancipated person had to have their case reviewed by a British clerk, who would determine if they were eligible for freedom.

Peggy submitted her petition for freedom directly to Sir Carleton. She explained that she had come to New York with the King’s troops, and requested that she be allowed to leave the city with her husband, the artillery man. But she was not able to provide concrete evidence of when she arrived in the city. She and her husband simply begged that Sir Carleton help her keep her hard-earned freedom.

Peggy’s petition did not sway the British. She was returned to a life in slavery under Mr. Crammon in Virginia. Her husband sailed to freedom without her.


  • cash crop: A crop grown for sale, rather than for the use of the farmer.
  • Loyalist: A person who supported the British during the American Revolution.
  • self-emancipated: People who have freed themselves from slavery, usually by running away or purchasing their freedom.
  • smallpox: A deadly, highly contagious disease that causes a high fever and pustules. It leaves permanent scars on survivors.
  • Treaty of Paris: The official peace treaty between the United States of America and Great Britain that ended the American Revolutionary War. It was signed on September 4, 1783.

Discussion Questions

  • What does Peggy’s story teach us about slavery during the American Revolution?
  • Why was Peggy’s petition for freedom denied?
  • What does this story teach us about the British government’s attitude toward the self-emancipated people who fought for them?

Suggested Activities

  • Include Peggy Gwynn’s life story in any lesson about the American Revolution or the history of slavery in America.
  • Peggy Gwynn and Deborah Squash had very different outcomes to their bids for freedom. Ask the students to compare their life stories and discuss what differences might have led to their disparate conclusions.
  • Teach this life story together with any of the following for a lesson about how enslaved women responded to the opportunities of the American Revolution: Book of Negroes, Life Story: Elizabeth Freeman, Life Story: Deborah Squash, and Abolition and Revolution: The Poetry of Phillis Wheatley.



New-York Historical Society Curriculum Library Connections

Source Notes