Nathan Hale Statue

Not Just One Life

Nathan Hale’s statue in City Hall Park honors the Revolution’s most famous spy and one of its earliest martyrs. The 21-year-old Patriot, hung by the occupation government in today’s Midtown, underscored the importance of espionage for the rebels, particularly in New York, the most salient location for learning about British movements and intentions. George Washington’s spy ring on Long Island has gained even more fame, marking the birth of American espionage. But this is only part of the story. Intelligence-gathering was far more common done by everyday, anonymous, unsung heroes of the cause. Knowledge typically passed mouth to mouth, through both formal and informal communication networks. Waitresses overhearing conversation between officers in a tavern passed information onto rebel informants. Slaves moving goods from city to country reported on the British army’s health. Families permitted to cross battlefield lines to visit relatives shared observations in conversation and correspondence.

While less glamorous than official spy-craft, this form of espionage was pervasive and valuable. Spies were everywhere in the region. And espionage worked both ways. Washington believed Loyalist spies (including the “half-tories” in his army) reported his every move, at least in the Neutral Ground. The people of greater New York watched each other nervously, reporting on neighbors if they saw anything irregular. Gov. Clinton lamented upstate, “the communication between this place and New York is entirely open to the Tories and they, I am afraid, make too much use of it.” But rebel espionage also included the growing disenchantment with British rule among the neutral and the loyal. As early as Oct. 1778, the governments issued proclamations and laws, hoping to stem the flow of gossip, rumor, and information.

Lady Rebels

Because they were less suspected than men, women often used their daily errands to gather information. As historian Judith van Buskirk notes, female networks — particularly of New York’s wealthy families, so often divided into Loyalists and Patriots — “far exceeded the contribution of famous spies like Nathan Hale or the few well-known” members of the Culper Ring like Anna Strong. One of New York’s early commandants became so suspicious of the activity, he tried to inhibit women from crossing over from New Jersey, saying “the Women who come into this City under pretext of bringing Provisions to the Market are rather employed to carry out Intelligence.” By 1780 the government declared that anyone, male or female, caught lurking near rebel territory would be court-martialed for espionage.

Women served often as British spies, too. Lorenda Holmes carried messages to Gen. Howe’s forces and smuggled Loyalists into the city across rebel lines in 1776. Margaret “Peggy” Shippen appears to have conspired with British spymaster Major John André in turning Benedict Arnold against the rebellion. Miss Jenny, a French seamstress in the British military, alerted Gen. Clinton of Washington’s plan to recapture New York. Over the years, New Jersey continually shrank the list of persons able to venture into the city, down to Gov. Livingston and the Council of Safety.

Despite such actions, espionage thrived. Military leaders were often prone to be disarmed around women. And the British also let wealthy rebels, like the Alexanders or Jays, visit family in the city. Upstate in havens for wealthy Loyalists like the elder Robert Livingston’s 160,000-acre Manor, traditional roles flipped. Men such as William Smith Jr. were confined, while wives and daughters came and went. But women hardly regarded this activity lightly. They frequently set upon each other for directly or indirectly helping one side or the other.

Slaves And Spies

Because they had to conduct daily errands, slaves travelled greater distances than most, picking up news earlier and later in the day. And because they lived in the homes of wealthy merchants, artisans, officers, clergy, and governors, they were also frequently privy to elite conversation. Both factors made them ideal spies.

Little is known about these men and women. But they spied at great risk. Perhaps the best known is James Armistead Lafayette, a Virginian slave who received permission to enlist with the Marquis de Lafayette’s unit. The French asked him to pose as a runaway to gain entrée to Gen. Cornwallis’s headquarters. Because of his extensive knowledge of the land, he was accepted without suspicion — into the heart of British planning.

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Cato Howe was perhaps the most high-level Black spy in New York, one among several in the Culper ring. His owner Hercules Mulligan joined the Sons of Liberty at King’s College, where he converted Alexander Hamilton to rebellion, fought with soldiers at Golden Hill, and helped topple the statue of King George at Bowling Green. Mulligan provided textiles for British and Hessian soldiers, from his shop near Hanover Square, and during the occupation he used Howe to ferry messages to Hamilton, Washington’s unofficial chief of staff, and to conspire with the rebel financier Haym Solomon, detained on a British prison ship as a translator. Howe was jailed and tortured after raising suspicions, but like Lafayette he won manumission after the war for his services.

Hercules Mulligan (left) and Haym Solomon (right)

People of African descent spied for the British, too. Benjamin Whitecuff, a freeborn Long Islander who joined the Black Pioneers on Staten Island during the Battle of 1776, spied for Gen. Clinton for two years. Later, he was hanged by rebels, saved by the British, captured and sentenced to hang again, then rescued and granted sanctuary in London.

Culper's Crew

Operating principally around New York, the Culper Spy Ring maintained fierce secrecy and used a variety of deceitful tactics to gather information about British military and diplomatic intentions and relay their findings to Washington. The crew used cyphers, invisible ink, and masked letters to uncover enemy strategy, troop movements, and provisioning centers. Fed information by revolutionary sympathizers in the city like the tailor Hercules Mulligan, or wartime opportunists like the King’s printer James Rivington, the Ring usually travelled along the northern coast of Long Island, or row-boated across the Sound to Connecticut, to divulge information to Continental units stationed outside the British military headquarters. Its leaders resided in Lloyd’s Neck, a haven for Loyalist refugees from the “Tory towns” of southern Connecticut.

The Value of Spying

Historians continue to debate the value and impact of espionage on the Revolution. Despite the sensationalism, Culper Ring intelligence rarely decided battles. Nor did it profoundly shift the councils of war. The same has been said for later uses of espionage, many times.

And yet spying, and the harsh treatment of spies, clearly served as powerful inspiration and propaganda. The execution of Hale, and of the prominent British spymaster André, were milestones that shaped the war palpably. After the latter’s death, it was the hated Oliver DeLancey, head of the Cowboy raiders in greater New York, who became the leader of British intelligence.

The “Turtle” provides another example of high drama with questionable utility. David Bushnell and (/or) Isaac Doolittle designed the vessel, which innovated underwater propulsion and clock-activated explosives, at the outbreak of the Revolution. Washington funded the project and rebels made several attempts to use the weapon against British ships in New York’s harbor. All of them failed, but it did mark the first use of a submarine in war.

  • On spying in support of the colonial rebellion, see Morton Pennypacker, General Washington’s Spies on Long Island and in New York (The Long Island Historical Society, 1939); Alexander Rose, Washington’s Spies: The Story of America’s First Spy Ring (New York: Bantam Books, 2006).

    On James Rivington’s intelligence-gathering activities, see Catherine Snell Crary, “The Tory and the Spy: The Double Life of James Rivington” William and Mary Quarterly 16 no. 1 (Jan. 1959): 61-72

    On female spies, AnnMarie Lesco, “Breaking From Tradition: Female Spies In The American Revolution.” PhD Dissertation, 2015

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