Secret Agent 711

Some Background

In August 1775, following hostilities between the colonists and British troops in Massachusetts, King George III declared the American colonies in rebellion.  The declaration prompted Congress to assemble a Continental Army under General George Washington.  Ten months later, in June 1776, Richard Henry Lee proposed a Congressional resolution calling for independence from Great Britain.

As the independence movement gained momentum, Congress convened a five-member committee to write a formal public statement to justify its declaration of independence.  Committee members included John Adams, Benjamin Franklin, Robert Livingston, Roger Sherman, and Thomas Jefferson.  Jefferson authored the first draft, and after making a few suggested changes, a second draft was submitted to Congress on 28 June 1776.[1]  Congress debated the proposed resolution on 1 July.  Two states opposed the resolution, two more signaled indecision, and New York abstained.  Delaware broke the tie vote the next day, and the two states that opposed the resolution shifted to favor it.  The final vote on 2 July was 12 to 0 in favor.

After the vote, a few members of Congress wanted yet another look at the resolution, which resulted in further modifications.  Congress approved the final draft on 4 July 1776.  The Declaration by the Representatives of the United States of America went to press on 5 July.  Congress ordered 200 copies.  On 8 July, the declaration was read aloud in front of the statehouse in Philadelphia.  New York agreed to support the statement on 9 July.  The official “original” was signed on 19 July, except that some members were absent, so the signing continued as the remaining members became available until 2 August.

No one in Congress celebrated the Declaration of Independence.  The mood was subdued; everyone understood that they had performed an act of high treason, and everyone realized the punishment for high treason was death.  Benjamin Rush later recalled that as congressional representatives signed the document, everyone believed they were signing their own death warrant. 

We celebrate our Independence Day on 4 July.  One day prior, British General Sir William Howe led the British Army ashore on Staten Island, New York; the hostilities that had begun in Massachusetts continued as part of the New York and New Jersey Campaign (July 1776-March 1777).  Howe drove Washington’s Continentals out of New York but erred by over-extending his reach into New Jersey.  General Howe could not exert complete control over both.  The best he could do and did do was maintain control of New York harbor.

Tinker, Tailor, Soldier, Spy

General Washington was unable to hold New York, but neither was he finished with Howe.  Throughout his failed campaign, Washington received unsolicited intelligence reports from individual patriots.  After evacuating the Continental Army from Brooklyn Heights, General Washington asked William Heath and George Clinton to set up “a channel of information” on Long Island. 

Heath and Clinton began looking for volunteers for clandestine operations.  One of these volunteers was Captain Nathan Hale.[2]  Soon after signing on for secret service, the somewhat full of himself Hale traveled to New York City under an assumed name.  Unfortunately, not everyone is well-suited for espionage; Nathan Hale was one of these.  The British quickly unmasked Hale and almost as speedily executed him for high treason.

General Washington learned a valuable lesson from Hale’s execution, not the least of which was that for a secret mission to succeed — well, it must remain secret.  He also learned that volunteer spies simply wouldn’t do.  What he needed was a well-organized, discreet, professionally managed “secret service.”

After Hale’s execution, which historians claim deeply affected Washington, he decided that civilian spies would be less likely to attract attention than military officers.  Washington turned to William Duer to recommend someone to lead this effort in New York City.  Duer recommended Nathaniel Sackett.  However, Sackett was hesitant to take risks, and his intelligence (though worthy in some instances) took too long to produce.  Washington soon replaced Sackett with Captain Benjamin Tallmadge, Hale’s classmate at Yale.

In early 1777, Colonel Elias Dayton of the New Jersey Militia established a spy network on Staten Island.[3]  Colonel Dayton’s system eventually tied in with another, known as the Mersereau Ring.[4]

Following their victory at the Battle of Brandywine on 11 September 1777, the British occupied the city of Philadelphia on 26th September.  General Washington thereafter focused much of his espionage efforts within the city of Philadelphia.  Washington recruited Major John Clark, a wounded/recovering veteran of the Battle of Brandywine, to accomplish this.

In August 1778, Lieutenant Caleb Brewster of Norwalk, Connecticut, volunteered to provide General Washington with intelligence.  Washington found Brewster’s initial report quite helpful, so to expand Brewster’s usefulness, Washington appointed General Charles Scott as Brewster’s handler and tasked him to find additional spies, if possible.  Captain Tallmadge became General Scott’s principal assistant.  As it happened, both Tallmadge and Brewster were acquainted with Abraham Woodhull of Setauket (Long Island); Tallmadge suggested that Brewster recruit Woodhull to help channel information through the network.

Abe Woodhull was probably an ideal spy because he was a convicted smuggler.  Tallmadge may have reasoned that if the British suspected Woodhull of smuggling, it was unlikely that they would also suspect him of espionage.  Woodhull was in prison when Tallmadge made him the offer: his freedom in exchange for working for Tallmadge.  Once Woodhull agreed to the arrangement, Washington arranged his release from prison with Governor Jonathan Trumbull.  To protect Woodhull’s identity, Tallmadge gave him an alias: Samuel Culper, Sr.

Tallmadge and Scott had differing views about the best way to run an espionage ring.  Scott preferred single-mission agents — men he could send out on a mission, afterward returning to Scott with a full report, and whom he could then assign to subsequent missions.  Captain Tallmadge had a different idea: he wanted stabilized agents to collect information and pass it along (via courier) to Scott’s headquarters.  Both methods were effective, and both ways were hazardous.

After Scott lost sixty percent of his “single mission” agents, whom the British captured and executed, General Washington reasoned that since Tallmadge had not lost a single agent, his method of collecting and transmitting secret information was “best.”  When General Scott resigned his post, Washington replaced him with Tallmadge.

Woodhull/Culper proved his ability in October 1778 by providing Washington with valuable information about British activities in Philadelphia.  To assist him, Woodhull recruited his brother-in-law, Amos Underhill.  Underhill and his wife Mary (Woodhull’s sister) ran a boarding house and pub catering to British soldiers.  British soldiers do two things very well: they drink a lot, and they talk a lot.  Underhill’s initial problem was that Washington thought his initial reports were too vague.  It wasn’t enough to listen to what the British soldiers had to say; Washington expected Underhill to validate what they said, as well.

The process of conveying information to Brewster was dangerous, complex, and time-consuming.  When Brewster had information for Tallmadge, it was hand-carried from Staten Island to Setauket and then from Setauket to Tallmadge’s headquarters at Fairfield, Connecticut — a distance of 188 miles, 30 of it across Long Island Sound.  To accomplish this feat, Woodhull recruited two couriers: Jonas Hawkins and Austin Roe.  Their task was to carry messages between Woodhull and Brewster.  It was up to Brewster to deliver messages to Tallmadge.  Crossing the Long Island Sound in a small boat was no easy task.  Brewster had six “drop” sites.

Mary Underhill (who some claim was actually Anna Strong) assisted her husband by posting pre-arranged signals to indicate which spies had information to submit.  For example, if Mary hung a black petticoat on her wash line, Brewster had arrived in town.  If she hung up some quantity of handkerchiefs on her clothesline, it told the courier which of Brewster’s six drops the information was to go.  Is this true?  We aren’t sure, but it does indicate how intricate the spy network was (and had to be).

The British were many things, but stupid wasn’t one of them.  The British knew about Washington’s spying campaign.  They suspected Abraham Woodhull, Amos, and Mary Underhill, and they were keen to capture General Scott.  The British knew; the Americans knew that the British knew, and this made American spycraft all the more difficult because the British didn’t need indisputable proof of high treason.  Reasonable suspicion would be enough to send a spy to the gallows.

Everyone in Setauket with a role in Washington’s spy network became nervous when the British arrested John Wolsey, a known smuggler, and a master of self-preservation.  Sure enough, John Wolsey made a deal with the British.  In exchange for his liberty, he agreed to tell what he knew about Abraham Woodhull.  As it turned out, however, all Wolsey knew about Woodhull was something he’d overheard a lobsterback say … which was that Woodhull was suspected of being involved in a spying ring.

Wisely, Abe Woodhull was a cautious man who realized that he was operating on borrowed time.  With men like Wolsey running his gob, Woodhull was prudent to worry about his safety.  British Colonel John Graves Simcoe led his Queen’s Rangers to Setauket to look for Woodhull, who at the time was in New York.[5]  In the process of looking for Woodhull, Simcoe arrested his father, Judge Richard Woodhull, and had him tortured, inflicting him with grievous injuries to obtain information about his son.  A loyalist militia officer, Benjamin Floyd, who was married to a member of the Woodhull family, vouched for Abraham, which gave Simcoe pause in his investigation.  Subsequently, Woodhull conveyed to Tallmadge that he was not able to continue operating as a Continental spy.

In a letter to Tallmadge in late June, General Washington suggested considering Mr. George Higday as a possible replacement for Woodhull.  Unhappily for Higday, the British intercepted Washington’s letter, which prompted Colonel Banastre Tarleton’s raid into Tallmadge’s camp.[6]  Tarleton captured several documents, all confirming what the British already knew: Washington had spies.   Mr. Higday’s espionage career was over before it began.

Tarleton’s raid also convinced Abraham Woodhull that his early decision to retire was a wise and prudent course of action.  However, before his retirement, Woodhull did manage to recruit a new spy, a man named Robert Townsend.  Mr. Townsend’s alias was Samuel Culper, Jr.

Robert Townsend had several reasons for joining Washington’s spy network.  He was first of all motivated by Thomas Paine’s pamphlet Common Sense.[7]  He was also put off by British harassment of his family (because of their religious affiliation) — and because Abraham Woodhull was an excellent salesman.  As a devoted Quaker, Townsend could not participate as a soldier. Ordinarily, this belief system might have also prevented him from joining the spy network. Still, a schism between religious and political Quakers (aided by Paine) pushed Townsend into the “political camp.”[8]  There was one more provocation: Colonel Simcoe of the Queen’s Rangers seized the Townsend home and converted it into his headquarters.

Mr. Townsend was a businessman.  He owned a trade goods store and a coffee shop in partnership with Mr. James Rivington.  Mr. Rivington was the publisher of a loyalist newspaper, and Mr. Townsend was one of his regular journalists.  As a merchant, coffee shop owner, and reporter, Townsend had access to numerous British officers and NCOs and their places of patronage.  As a contributor to a loyalist newspaper, Townsend had credibility within loyalist society — such that British loyalists were happy to talk to him.  Both Townsend and Rivington formed the core elements of the Culper Ring in New York City.

Despite the stress of espionage, which produced strained relations within the Culper Ring, the effort produced more information than any other American or British intelligence network during the war.  American espionage focused on British troop movements, fortifications, and operational plans.  For example, the Culper Ring foiled British plans to ambush the French in Rhode Island.  Arguably, this information saved the Franco-American alliance.  Culper also uncovered the correspondence between Benedict Arnold and British Major John Andre, General Clinton’s chief intelligence officer.

To clarify what General Washington wanted from the Culper Ring, he provided them with specific instructions (see a special note below).

Townsend wasted little time energizing his spy activity.  Nine days after accepting Woodhull’s “offer of employment,” Townsend reported that two divisions of British infantry were preparing for an expedition to Connecticut.  In 1780, Townsend discovered a plot by British officials to ruin the American economy by circulating counterfeit currency.  He reported that the British hierarchy was optimistic about an imminent end to the war.  Townsend’s timely reporting permitted Congress to recall all of its money then in circulation.

Throughout his employment, Townsend remained suspicious of everyone and every circumstance.  To safeguard the identity of his spies, Tallmadge utilized several protective measures.  In addition to pseudonyms, Tallmadge also developed a system consisting of seven-hundred sixty-three numbers.  The number 745 represented England; 727 for New York; Robert Townsend was 723, and so forth.

Robert Townsend’s conduct of spycraft was both astute and sensible.  How sensible?  How good was Townsend at keeping secrets?  Townsend died on 7 March 1838.  He was 84 years old.  When he died, he took everything he knew about the Culper Ring with him.  What we know of Robert Townsend was only revealed in 1930 by American historian Morton Pennypacker.  Not even General Washington knew the identities of his spies.

And none of his spies knew that General Washington was Agent 711.

Sources:

1. Rose, A.  Washington’s Spies: The Story of America’s First Spy Ring.  Penguin Books/Random House, 2014.

Special Note:

General Washington’s Instructions:

1. Culper Junior, to remain in the City, to collect all the useful information he can — to do this, he should mix as much as possible among the officers and refugees, visit the coffee houses, and all public places. He is to pay particular attention to the movements by land and water in and about the city especially.  How their transports are secured against an attempt to destroy them — whether by armed vessels upon the flanks, or by chains, booms, or any contrivances to keep off fire rafts.
2. The number of men destined for the defense of the City and environs, endeavoring to designate the particular corps, and where each is posted.
3. To be particular in describing the place where the works cross the island in the rear of the City-and how many redoubts are upon the line from the river to river, how many Cannon in each, and of what weight and whether the redoubts are closed or open next the city.
4. Whether there are any works upon the Island of New York between those near the City and the works at Fort Knyphausen or Washington, and if any, whereabouts and of what kind.
5. To be very particular to find out whether any works are thrown up on Harlem River, near Harlem Town, and whether Horn’s Hook is fortified. If so, how many men are kept at each place, and what number and what sized cannon are in those works.
6. To enquire whether they have dug pits within and in front of the lines and works in general, three or four feet deep, in which sharp pointed stakes are pointed. These are intended to receive and wound men who attempt a surprise at night.
7. The state of the provisions, forage and fuel to be attended to, as also the health and spirits of the Army, Navy and City.
8. These are the principal matters to be observed within the Island and about the City of New York. Many more may occur to a person of C. Junr’s penetration which he will note and communicate.
9. Culper Senior’s station to be upon Long Island to receive and transmit the intelligence of Culper Junior …
10. There can be scarcely any need of recommending the greatest caution and secrecy in a business so critical and dangerous. The following seem to be the best general rules: To entrust none but the persons fixed upon to transmit the business. To deliver the dispatches to none upon our side but those who shall be pitched upon for the purpose of receiving them and to transmit them and any intelligence that may be obtained to no one but the Commander-in-Chief.

Endnotes:

[1] The declaration took the form of a grand jury indictment — allegations not proven, and many that history proves were not even true.  In modern times, one popular axiom is that it’s possible to indict a ham sandwich and such was the case of America’s “indictment” of King George II.  The colonist’s real problem, aside from King George insisting on his prerogatives as Great Britain’s king, was the British Parliament, but since a government legislative body cannot be indicted, Jefferson and other members of Congress decided to make their point by indicting the King.

[2] Hale came from a prominent Connecticut family.  He began his education at Yale at the age of 14, attended classes with Benjamin Tallmadge, and figured rather prominently in the college’s debating society.  He graduated with honors in 1773 at the age of 18 years.  When the British executed Hale, he was 21 years old.

[3] Later, Revolutionary War brigadier general, mayor of Elizabethtown, and member of the New Jersey General Assembly.  He was the father of Jonathan, a signer of the U.S. Constitution.

[4] Started in December 1776, this operation focused on intelligence gathering in New Brunswick and New York.  John Mersereau was the primary supervisor of this effort.

[5] Simcoe, from Cornwall, was the only child in his family to survive into adulthood.  He entered British military service in 1770, participating in the Siege of Boston, New York, New Jersey, and Philadelphia campaigns.  Tradition holds that Simcoe, in ordering his men not to fire on three withdrawing Continental officers, saved George Washington’s life.  He later served as Upper Canada’s first lieutenant governor and was responsible for founding Toronto and for establishing Canada’s judicial system (1791-96).

[6] Contrary to how Mel Gibson portrayed him in the fictional film The Patriot, Tarleton was not so much of a scoundrel as he was a fighter.  He never burned down a South Carolina church filled with parishioners, but he did threaten to torch the home of General Charles Lee of New Jersey unless he surrendered to Tarleton’s authority.  At the Battle of Waxhaw, the 22-year-old captain, commanding provincial cavalry, assaulted a superior force of Continentals under Colonel Abraham Buford.  Buford refused to surrender despite the fact that Tarleton gave him that opportunity on two occasions.  With Buford’s refusal, Tarleton’s force of 149 troops attacked Buford incessantly, killing 113 Americans, wounding 203, and taking prisoners of those left alive when Buford finally agreed to surrender.  The Americans called it a massacre; it was no such thing.  It was war.  Tarleton was not the butcher revisionists have claimed.

[7] Paine argued that any Quaker who believed in pacifism at any price was not a true Quaker.

[8] Religious Quakers were among the strongest supporters of the British during the revolutionary war period. 

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