American Espionage: 3 Spies of the Revolution

By Nicky M. | Arcadia Publishing

Tales of daring spies and secret agents have captivated American lore for centuries. The history of espionage in America dates back to the days of the Revolutionary War, where agents spoke through cyphers and code to help the Patriots with the War for Independence. Here, we’re exploring the history behind three of the Revolutions biggest spies and spy rings.

1) Nathan Hale

A depiction of Nathan Hale's execution.

Nathan Hale was executed for espionage by British forces in 1776. Reprinted from Spies of Revolutionary Connecticut: From Benedict Arnold to Nathan Hale by Mark Allen Maker, courtesy of the Library of Congress (pg. 112, The History Press, 2014).

Perhaps the most famous Revolutionary-era spy, Nathan Hale was serving as a captain for the Continental Army when he volunteered to go behind enemy lines in September of 1776. The Continental Army had recently been struggling to retain its hold over the New York area, and General George Washington was concerned the army might lose Long Island to the British.

After a crippling defeat at Brooklyn, Washington tasked his commander Colonel Thomas Knowlton with finding a suitable spy to send into British territory. Knowlton struggled at first to find a willing participant, until the 21-year-old Hale offered his services. Hale had reportedly been searching for a way to distinguish himself within Washington’s army, and saw this as his perfect chance to leave his own mark on history.

Unfortunately for Hale, while he was quite brave, he was not an especially skilled spy. Only days after beginning his ruse as a Dutch schoolmaster looking for work, Hale’s suspicious questions had raised several eyebrows in loyalist territory. But it was a conversation in a tavern that did Hale in: there, a British agent approached Hale pretending to also be a patriot spy, and Hale quickly gave himself away. After being arrested as an illegal combatant, Hale was searched, and several classified documents were removed from her person.

Hale was later sentenced to death by hanging for his participation in the plot. He earned his place in history as a martyr for the Revolution during this hanging, where, legend has it, his last words were simply “I only regret that I have but one life to give for my country.”

 2) Anna Strong, Benjamin Tallmadge, and the Culper Spy Ring

Benjamin Tallmadge, who first created the Culper Ring.
Benjamin Tallmadge, who first created the Culper Ring. Reprinted from Spies of Revolutionary Connecticut: From Benedict Arnold to Nathan Hale by Mark Allen Maker, courtesy of the Library of Congress (pg. 122, The History Press, 2014).

After word of Nathan Hale’s fate reached the Patriots, many were reluctant to follow in his footsteps. General Washington still required some intelligence into the British army, however, especially within occupied New York City. In 1778, Washington appointed Benjamin Tallmadge as his director of military intelligence, with the hopes that Tallmadge would be able to find a way to gather information from British officers and loyalists.

Tallmadge’s approach to his task was to establish a spy network made up of only those he was absolutely sure he could trust. He started with childhood friend Abraham Woodhull, who successfully recruited several others to the spy ring, including Robert Townsend, a prominent tavern owner in New York City. Together, Woodhull and Townsend directed the day-to-day operations of the ring as they gathered information on upcoming British attacks and sieges.

Amazingly, in the five years that the network operated, the British took none of its members as American spies. This was due to the complex codes that Tallmadge had created for his operatives to use. These ranged from basic cyphers, to even using an invisible ink that could be revealed with heat or special chemical compounds. Some members, like Woodhull’s neighbor Anna Strong, even had their own special ways of communicating: Strong would hang her clothes in special places on a clothesline to communicate with a courier who ran smuggling mission.

In addition to the ring’s success at remaining inconspicuous, it was also quite successful at uncovering several British plans: most notably, the network has been credited with uncovering British intension to ambush French forces at Newport in 1780.

3) Benedict Arnold

A portrait of Benedict Arnold.

A portrait of Benedict Arnold. Reprinted from Spies of Revolutionary Connecticut: From Benedict Arnold to Nathan Hale by Mark Allen Maker, courtesy of the Library of Congress (pg. 83, The History Press, 2014).

Benedict Arnold was embittered. Although he was a favorite of General Washington’s, he struggled to find promotions within the Continental Army. In 1778, it seemed that things were looking up for Arnold: he was named the military commandant of Philadelphia after it was claimed by the Patriots, and he was rewarded with a lavish lifestyle.

This lavish lifestyle, however, came with some risks. Shortly after moving to Philadelphia, Arnold began courting and later married Peggy Shippen, the daughter of an overtly loyalist family. Arnold quickly found himself mingling with British officers and dignitaries, all known as “dear friends” of his new wife. While no one knows for sure why Arnold chose to defect from the Continental Army, many credit the influence of his very young and pretty wife.

Surrounded by British officials, it was easy for Arnold to be influenced away from his original loyalties. After meeting with loyalist Joseph Stansbury, Arnold crossed the point of no return, and began operating as a British spy within the Continental Army. He kept close contact with Major John AndrĂ©, a key spy for General Henry Clinton, and slowly began relaying information on the Army’s forces, artillery, and strength.

These conversations only grew once Arnold was given command of West Point in 1780, at which point he began to plan a surrender of the major military base to British forces. In exchange, Arnold would be given enough money to pay of his debts to London creditors, and receive a high commission in the British Army.

Unluckily for Arnold, his point of contact was not as inconspicuous as could be hoped. Major AndrĂ© was finally captured by Patriot forces in 1780, with letters on his person that revealed Arnold’s treachery. Disgraced (and attempting to avoid capture), Arnold and his wife fled to Virginia, where he joined the British Army, and was later exiled to Britain after their surrender.