Spying in the American Revolution: How a Virginia Slave helped Colonists win victory at Yorktown in 1781

James Armistead Lafayette, a Virginia slave who risked his life spying for the Colonists, helped win the American Revolution at the Battle of Yorktown in 1781.

General George Washington served a portion of the French and Indian War as a spy and put his experience to work in the American Revolution. He settled spy rings into places where British soldiers gathered: coffeehouses, taverns and tea shops, then shipped their messages to him by complicated routes through Long Island and by whale boat to Connecticut.

Washington knew it unlikely the inexperienced, under-trained and out-numbered Colonists’ could pose a serious threat to the greatest fighting force on the planet without a bit of intelligence. America had no navy to stand up to the strongest fleet prowling the Atlantic and the European waters. Seemingly no contest.To even the odds would require out-witting the British, using American ingenuity, and a strong desire for freedom.

Initially on April 18,1775, the Massachusetts Colonists were out-numbered at Lexington 700 British to 77 Colonial militia. Eight defenders died and nine were wounded. The following day the Minutemen, 2,000 strong with 1,500 militia streamed into Concord and the results were different–250 British died to 90 Colonists. The sound of the “shot heard around the world” reached London on May 28. (1)

Suddenly King George realized he had a full revolt, more serious than Bostonians dumping English tea into the harbor five years earlier. Shutting down the harbor with British ships posted outside wouldn’t do the trick. Neighboring port of Braintree gathered supplies and shipped them overland. So King George gathered his generals, encased them with their Red-clad soldiers onboard masses of British men-of-war, then launched them across the Atlantic. He felt confident that a foray or two would be sufficient to quel the rumpus and return the Colonists to obedience.

Washington accepts command of Colonists’

After being named Commander-in-Chief George Washington in June 1775, Washington hadn’t reached Boston when the Battle of Bunker Hill concluded on the 17th. In confounding results, the British took territory in the encounter, even though their casualties exceeded the Colonists’ losses. The British lost over 110 officers, overall 226 killed and 828 wounded, while the Americans’ losses included 140 killed and 450 injured. British General Clinton said: “A few more victories (like this) could have put an end to British dominance of America.” (2)

Such a situation faced General Washington when he accepted command. As he assessed his generals and assembled the men in favorable positions, he also began to assemble a spy network, attempting to out-fox the British and take full advantage of the American’s innate knowledge of their countryside. He instructed his generals to “leave no stone unturned, nor do not stick to expense” in gathering intelligence, and urged that those employed for intelligence purposes be those “upon whose firmness and fidelity we have safely rely.” He delegated significant field responsbility to trusted officers, including Alexander Hamilton, who was deeply involved with intelligence operations, including developing reports received in secret writing and investigating a suspected double agent. (3)

Washington made known his desire for information and worked with those who could develop codes for Colonist spies to use in translating messages, ciphers to complicate translation, and code brakers. The Continental Congress created a Secret Committee (later to become Foreign Affairs in 1777) to help obtain information in 1775. It helped gather intelligence about secret Loalist ammunition stores and seized them. James Lovell, a teacher arrested by the British after the Battle of Bunker Hill on charges of spying, was exchanged for a British prisioner and elected to Congress. He became Congress’s expert on codes and ciphers and gained the title “father of American cryptanalysis.” (4)

Anna Strong (dramatization), mother of 10 and tavern owner, who gathered news from British troops in her tavern.

Anna Smith Strong: Spy in Petticoats

Raised in the house her great-great grandfather built in Setauket, Long Island, Anna Smith Strong knew the land and the people that surrounded her. She had strong motivation to defeat the British. They’d captured her husband who joined the minutemen early in the war and sent him to the notorious prison ship in New York Harbor.

This patriotic housewife and tavern owner, joined Washington’s brigade hanging her “clothesline codes” –petticoat and handkerchiefs to signify the location of a ship drop off point for a message destined for Washington. (5)

She belonged to the Culper Spy Ring, many of the participants were people she’d known from childhood, which helped defray concerns of being betrayed. Their codes were a combination of letters and words. Code letters were taken from Entick’s Dictionary. But Major Benjamin Tallmadge, the network’s leader, took several hundred words from people and places and assigned each a number from 1 to 763. Attack was 38 and George Washington, 711. Once a week one of Washington’s spies rode to New York City to dig up information from the troops stationed there. Returning to Long Island, he would hide the message in a wooden box buried on a farm owned by Anna’s friend, Abraham Woodhull, across the bay from Anna. She would await word from another, the whaleboat capatain, Caleb Brewster. He’d slip past the British ships and hide in one of the island’s coves. (6) .

Brewster would send word to Anna which cove he’d hidden his boat and Anna would put her black petticoat on the line, followed by a number of handerchiefs signifying which cove he boat could be found. They’d established a map with numbers for each of the coves. Then Woodhull would wait for darkness to sneak across the fields to Brewster’s boat to deliver the message. Brewster rowed over to Connecticut and gave the message to the spymaster, who took it directly to Washington.

Enoch Crosby, Continental soldier who played the role of a cobbler, roaming across the Hudson Valley for six years 1776-1781 gathering news from the British to assist General Washington.

Crosby: Long serving spy in Revolution

Enoch Crosby became a hero to General Washington for his unassuming manner and the material he could obtain from British soldiers and Loyalists. He played along when Loyalists invited him to a meeting in New York. Crosby reported what he learned to Patriot John Jay (future Chief Justice of the U.S. Supreme Court), who recruited him among the first counterintelligence operatives. He began his work early in the Revolution, around 1776, and became one of the longest serving spies. Many British sympathizers were unmasked due to his efforts. (7)

Dr. James Jay creates “sympathetic stain”

The Secret Committee made good use of the talents of Dr. James Jay, brother of the future Chief Justice of the Supreme Court. Living in London, he used the technology available to him to create a “sympathetic stain” that could make a message appear invisible until a certain chemical was applied to the paper. A physician living in London, Dr, Jay had been knighted by George III, and used the stain to report military information from London to Washington. Silas Deane, serving as a diplomat in Paris, used a heat-developing invisible ink–a compound of cobalt chlorive, giycerine and water. Later Deane switched to Jay’s method because it required specific chemical applications one at the time of writing and a second to develop the message. (8)

Armistead’s Intelligence turns Yorktown

Yorktown became the final battle of the Revolution with the assistance of a Virginian slave assigned to General Marquis de Lafayette, commander of the French forces and a key ally of Washington. Lafayette and the entire American force suffered at the hands of British General Cornwallis–better equipt and more numerous army.

James Armistead on orders from Lafayette posed as a runaway slave and infiltrated British forces in General Arnold’s camp. His knowledge of the terrain, proved helpful to the British to obtain their trust, then he became a double agent when they ask Armistead to spy on the American forces. He obtained information on the British position for Lafayette, then carried back inaccurate information to the British. At the end of summer 1781 Armistead sent a note to Lafayette that outlined Cornwallis’s move from Portsmouth to Yorktown and the expected arrival of 10,000 British troops. This knowledge gave Washington forewarning. He, Lafayette and French General Comte de Rochambeau set up a blockade by land and sea around Yorktown peninsula. Simultaneously code master James Lovell determined the encryption method that British commanders used to communicate. A translated message from Lord Cornwallis in Yorktown to General Henry Clinton in New York told Washington how desperate Corwallis was and enabled him to time his attack. Then warning that a British relief expedition approaching Yorktown was blocked by a French fleet offshore. The blockade and the bombardment of the British position convinced them to surrender.

Armistead returned to slavery in 1783 after the war. Slave soldiers were granted freedom as part of their agreement upon joining. But spy slaves were not given freedom. When General Lafayette, heard about this, he sent a letter to the Virginia legislature, indicating Armistead’s service and the need to grant him freedom. Virginia’s political leadership agreed and agreed to a pension of $40 annually for his service. He purchased 40 acres south of New Kent, Virginia, married, raised a family, and lived to be 82. (9)

(1) https://www.history.com/topics/american-revolution/battles-of-lexington-and-concord

(2) His words mimic Pyrrhus of Epirus of the Battle of Heraclea: “one more such victory and our cause is lost.”

(3) https://en.wikipedia.org/wiki/Intelligence_in_the_American_Revolutionary_War

(4) https: //en.wikipedia.org/wiki/Intelligence_in_the_American_Revolutionary_War

(5) https://beyondword.com/blogs/beyond-words-blog/anna-smith-strong-spy-in-petticoats Ryan Ann Hunter, “Excerpt from In Disguise”

(6) Ibid

(7) http://www.hvmag.com/Hudson-Valley-Magazine/June-2014/How-a-Shoemaker-Turned-Into-a-Spy https://www.history.com/news/5-patriot-spies-of-the-american-revolution

(8) “Intelligence in the American Revolution”

(9) https://www.history.com/news/battle-of-yorktown-slave-spy-james-armistead Access date June 7, 2019 Publisher A & E Television Networks Last updated February 5, 2019