How Spying Helped the U.S During the American Revolution

by Sarah Masih

George Washington used spies during the American Revolution. Yes, you hear right! Spies!

The year was 1778, the Americas were fighting against Britain for freedom. The American army was undermanned, undertrained, and undersupplied. It was crucial that America win the war. Their pride was at stake!

General Washington recruited a group of people to create an underground spy network. This underground spy network helped Washington to a huge extent and even saved his life a couple of times.

The story of Washington’s spy network is filled with all the parts of a good spy movie. Letters with invisible ink, a rare female agent who we know as Agent 355, the ghastly execution of Nathan Hale.

According to the Central Intelligence Agency: General Washington was deeply involved in intelligence operations. In fact, he was the most deeply educated until Dwight Eisenhower during World War II. It seems unreal to me, a spy network running around during a time before even my great-grandparents were born. However, it is true. A scene right out of a movie.

Brain Power

Washington’s whole career rocketed, because of his knowledge of gathering intelligence. In the beginning, he gathered information from Native Americans. He soon discovered that having more intel than your enemy makes the difference between conquering and dying.

In 1775, Washington was appointed as commander in chief of the Continental armies by the Second Continental Congress. He elected a man named Thomas Knowlton to organize the very first spy unit of the war. It roughly comprised of 130 men and was called Knowlton’s Rangers.

Knowlton’s Rangers played a significant role at the Battle of Harlem Heights in New York in 1776, by scouting the British advance guard. In the next big fight, Knowlton lost his life but left his legacy behind.

Today his work is honored by the U.S Army intelligence service in the form of a 1776 stamp to represent his unit. His work created the guidelines for the way intelligence organizations work in the country, today.

The Culper Ring

November of 1778, General Washington ordered Benjamin Tallmadge to put together a spy ring in New York City, which has been taken over by the British. This group was called The Culper Ring.

The name was suggested by Washington in honor of a riff on Culpeper County in his home state of Virginia. This group was made up of Benjamin Tallmadge who went by John Bolton and his chief recruit Abraham Woodhull who used the alias Samuel Culper Sr. Woodhull went underground in New York and would timely report to Tallmadge with information about British operations.

In case you’re wondering why such a significant group was so small, let me know it didn’t remain that way. The spy ring grew to include Robert Townsend whose code name was Culper Jr.

He posed as a newspaper columnist and hung out in cafes befriending British officers who wanted to show off and often let important intel slip.

Imagine that, chatting with a man in a coffee shop only to find it was a spy. Who can you trust? It also included a female spy!

This is quite surprising, considering women couldn’t even vote at the time. This female spy named is believed to have gone by the codename Agent 355.

Her real name was Anna Strong. She took her position in Setauket on the coast of Long Island. Her job was to transmit signals to couriers smuggling through Long Island Sound to Tallmadge who was in Connecticut. Her method was artistic!

She hung out her laundry on a clothesline- in full view of British soldiers and boats moving through the Sound. If Anna hung a black petticoat it meant that a message was ready to be picked up.

Then she would hang a number of handkerchiefs- the number each corresponded with a secret pickup spot. Again, something we see every day like clothes on a clothesline being used to send secret messages. That makes me very suspicious of my neighbor!

Later, a spy named Caleb Brewster was added to the Culper Ring. He commanded whaleboats in Long Island Sound and watched for Anna’s signals to determine when and where he could find the message. The Culper Ring continued to prove crucial intelligence throughout the war.

They figured out the British plan to crash the Continental economy by printing massive amounts of fake currency. Which is sort of actually genius, if you think about it.

Culper Ring uncovered the British plan to attack the French ships as they arrived in Rhode Island to help the Americans. Now that is just plain ol’ jealousy!

They revealed the war most notorious traitor- Benedict Arnold!

Arnold surrendered the crucial American garrison at West Point to the British through their top spy John Andre for 20,000 pounds. (*gasp)

Thankfully, Andre was caught with the plans in his shoes. Though Arnold escaped to Britain, Andre did not get a happy ending. More about that towards the end.

The Secret of the Secret Codes

The Culper Ring had code names for everyone. Obviously! Washington was Agent 711. Since Tallmadge was the head of intelligence, he got to make a fancy book called the Culper Code Book, which assigned ciphers to 763 names and words.

For example, the number 219 meant gun. 223 means gold. 701 meant woman. As a person who dislikes math and numbers, I can’t even imagine having to memorize all of those combinations.

Remember John Jay? Turns out he wasn’t the only genius in his family. His brother John invented invisible ink! He created a chemical solution using acidic fluids like lime juice, vinegar, etc. Messages could be written on paper and you wouldn’t be able to tell there was anything.

When that piece of paper was introduced to heat, that writing would appear. This helped Washington to send around information without having the danger of a British officer finding them, or having to rely on a person that might be say killed while they were delivering information.

This makes me think of National Treasure. Where they had a map on the back of the Declaration of Independence. Imagine, something like that, but real.

The Deadly Duo

One of the most useful spies in NYC began his work even before the Culper Ring was established. His name was Hercules Mulligan. He and his sidekick/manservant Cato ran a clothing emporium that served many high-ranking British officers. Though he secretly supposed the Americans, he married the sister of a British officer.

Before the war had started a British loyalist named Alexander Hamilton had been a tenant in Mulligan’s home. Mulligan converted Hamilton to switch sides and become an aide de camp to Washington.

Hamilton went on to recruit Mulligan into the secret spy groups. Mulligan would gather information from his British clients who thought he was on their side, then he would send his manservant Cato to deliver it to Hamilton.

As the war went on, Mulligan saved George Washington’s life. TWICE.

The first night, Mulligan learned from a British soldier that they had a plan to capture Washington. Mulligan quickly sent Cato to inform Washington and he was secured in another location.

The second time was when the British learned of Washington’s travel to Rhode Island and ordered 300 soldiers to capture him. One of the men who ended up on the ship was Hugh Mulligan, the brother of Hercules Mulligan. Hugh informed Hercules who again sent Cato to inform Washington.

Washington remained loyal to Mulligan. He bought most of his clothes from Mulligan’s store, even after becoming president. Mulligan’s store started advertising as “Clothier to General Washington.”

Against All Odds

The story of James Lafayette Armistead is even more intriguing. He was an enslaved African-American who served as a double agent. In 1781, Armistead posted as a runaway slave and infiltrated a British outpost in Virginia. He soon became a trusted informant for the Americans and was positioned to gather critical intelligence.

It is quite interesting, isn’t it? How in history books, we’re taught that African-Americans during this time were doing nothing but working. They’re illustrated as people with no hope, no dreams, no bright futures.

Have you ever noticed that when you read this part of American history, we read about the start of slavery and the end of slavery? What about the years in the middle? Those years when cool stuff like this was happening? Or when other terrible stuff happened?

Anyway, back to the topic at hand. So then, Armistead began smuggling military intelligence to Maquis de Lafayette. Lafayette was the head of the French forces that helped General Washington.

Armistead ultimately won his freedom by gathering intel that the British were attacking Yorktown. When the Americans found out, they set up a blockade around the Yorktown peninsula, which helped them win the battle of Yorktown, the last battle of the war.

Not all Fairytales

Spy work is not all cool gadgets and sneaky looking disguises. It involves lots of danger. During the Revolutionary War, two high-profile spies were seized-one from either side.

At the beginning of the war, Washington found out that the British were trying to capture New York City. He called for a spy behind enemy lines. Benjamin Tallmadge chose Nathan Hale, a fellow Yale classmate.

Hale was in New York posing as an unemployed Dutch teacher when the British captured the city. His identity was eventually uncovered, it is still unclear how and when was hung to his death. At the time, he was just 21. His last words were, “I only regret that I have but one life to lost for my country.”

Though Hale’s death was pretty tragic, it wasn’t the most recognized. The most high-profile spy to be captured was Major John André, the associate of Benedict Arnold. He was arrested with the help of the Culper Ring. John André was so famous that even Washington was nervous about killing him.

However, it was almost crucial that he was killed. John André himself requested to be killed by a firing squad, but his wish was not granted.

Instead, he was hung just like Hale in front of an audience of officials. Reportedly before being dropped from the gallows John André whispered to himself; “It will be but a momentary pang.”

The American Revolution was a crucial period of time for the United States. We won our freedom, from the people we’d hated for so long. It took time, money, but worst of all it took lives. The British fought their own people.

They brought war to keep the peace! Thanks to General Washington and his spies, a free America began slowly prospering into the country we know today.


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