8.3 Agent 355: Washington’s Mostly Mythical Spy

Agent 355: Washington’s Mostly Mythical Spy

The Culper Spy Ring operated in British-held New York and funneled intel to General George Washington. Agent 355, the only woman among them, will probably never be conclusively identified. Was she Anna Strong? Was she a New York socialite? Was she someone else entirely? Here’s the story of what we know.

This episode is part of the the series Women in Espionage.

Full Transcript

This whole series is about shadowy figures, and none of them are more shadowy than Agent 355. She is so incredibly shadowy that if she had been anyone else I would have told myself to give that one a pass, there’s not enough to go on for an episode.

But Agent 355 has been so puffed up by other historical writers and filmmakers. The one I’m most familiar with is the AMC Turn series, subtitled Washington’s Spies. Some history buffs get all hot a bothered when a film isn’t 100% historically accurate. I don’t understand that view. In my mind, when you label something as fiction, then telling a good story is your top priority. Turn is a really good story, so I don’t care whether it’s historically accurate or not. But my podcast is labeled as history, not fiction, so I don’t get to inflate Agent 355’s role that much, as much as I would like to.

So here is the story of the Culper Spy Ring, and if it takes a distressingly long time to get to any female members of it, well, that’s because historically speaking, it did take a distressingly long time for any women to get involved. Right. So here we go.

The year is 1778. General George Washington and his ragtag Continental Army had survived a winter at Valley Forge, but there was no doubt that formidable obstacles remained. One of those obstacles was a British army squatting in Manhattan, which was kind of important. Not as important as New Yorkers like to think. . .

Okay, just kidding. It was important. Washington, who was not a New Yorker, thought it was important.

Washington had a long list of things he needed: more men, more money, more food, more allies, but also more information. He desperately needed to know what his adversaries were up to, and he had no good way of finding out. Several abortive attempts at espionage had ended badly, most famously with Nathan Hale who was caught and was reported to have said “I only regret that I have but one life to lose for my country” before he was hanged. Undoubtedly brave and inspiring and all of that, but Washington still had no intel.

On August 7, 1778, Washington received a letter from a Caleb Brewster offering to deliver reports on the British (Rose, 67). Brewster was a thrill-seeker living a life of adventure. He was originally from Setauket, a small community on Long Island, which was held by the British. But Brewster was currently on the Connecticut side of the sound, which was held by the Americans.

The letter he wrote has unfortunately been lost, so we don’t know exactly what he had to say for himself, but we do have Washington’s response, in which he said:

Let me entreat that you will continue to use every possible means to obtain intelligence of the Enemy’s motions—not only of those which are marching Eastward, upon Long Island, but others—In a more especial manner, I have to request, that you will, by every devise you can think of, have a strict watch kept upon the Enemy’s ships of war, and give me the earliest notice of their Sailing from the hook—To obtain speedy and certain intelligence of this matter may be of great Importance to the French Fleet at, and the enterprize on, Rhode Island; for which reason, do not spare any reasonable expence to come at early and true information; always recollecting, and bearing in mind, that vague, and uncertain accts of things, on which any plan is to be formed or executed is more distressing and dangerous than receiving none at all—Let an eye also be had to the Transports, whether they are preparing for the reception of Troops &ca—Know what number of men are upon Long Island—whether they are moving or stationary—what is become of their draft Horses—whether they appear to be collecting of them for a move—How they are supplied with Provisions—what arrivals—whether with Men, or Provisions—and whether any Troops have Imbarked for Rhode Island or else where within these few days.

(From George Washington to Lieutenant Caleb Brewster, 8 August 1778)

I mean can you hear the desperation in his pen? That’s quite a lot Washington was asking for, and he soon appointed a Benjamin Tallmadge to manage Brewster and this correspondence.

Benjamin Tallmadge. Source

Brewster was a good find, but the truth was that his ability to get the info was limited. He was brave enough to regularly cross the Sound to Long Island, but he was a known Patriot. He couldn’t stay in British territory, nosing about. What was needed was a Patriot who wasn’t known to be a Patriot. Someone whose legitimate business made it perfectly natural for them to stay in British territory with their eyes and ears open.

Tallmadge found his man. Abraham Woodhull was a farmer from Setauket, a small community on Long Island. It just so happens that Tallmadge was also from Setauket and so was Caleb Brewster. They knew each other already, which has to have helped.

According to author Alexander Rose, Woodhull got dragged into this because he was caught red-handed smuggling goods across the Sound and Tallmadge got him released. Admittedly, I have not been able to identify the source of that tidbit. But certainly many people (Caleb Brewster among them) were doing exactly that. The realities of the British naval superiority meant that in New York, you could get Spanish olives, Scottish smoked salmon, German mustard, and Indian spices, but if you wanted a plain piece of beef or a gallon of milk you might be in trouble. Across the Hudson on the vast American-held continent, the situation was reversed. Naturally, there was a good deal of illicit trading going on to rectify that inequity.

Tallmadge and Washington were not much fussed about Woodhull’s smuggling. Far more important was that anyone who could smuggle goods could also smuggle information. At any rate, Woodhull was released a Washington wrote to Tallmadge that:

You should be perfectly convinced of the Integrety of W—— previous to his imbarking in the business proposed—this being done I shall be happy in employing him—but there will be an impropriety in his coming with you to head Quarters, as a knowledge of that circumstance in the enemy might blast the whole design.

(From George Washington to Major Benjamin Tallmadge, 25 August 1778)

This was a highly dangerous idea. Remember what happened to Nathan Hale? Woodhull had no desire to lose even one life for his country.

To protect everyone involved, Woodhull’s name was never again to be written. He became Samuel Culper. Tallmadge was to be John Bolton. Brewster was to be Caleb Brewster. Apparently he didn’t want a code name.

When Woodhull returned to Setauket, he swore his loyalty to the Crown to allay suspicion. And then he began the first of many letters in October of 1778. (Scott, 29; To George Washington from Brigadier General Charles Scott, 29 October 1778).

Setauket was not exactly the center of British military command, so every few weeks Woodhull traveled 55 miles into Manhattan and back. Ostensibly he was going to visit his sister Mary, who had married a mill owner there, and perhaps he traded his produce as well. But he hated going. The trip itself was dangerous. His aging parents needed him, and the expenses were daunting for one of his limited means (Rose, 88).

Speaking of means, there was the question of payment. There was no prestige at all in doing this job. James Bond had not yet made espionage sexy, and the truth was being a spy involved lying, deceit, theft, all manner of dirty, underhanded tricks, and constant, constant threat of capture, torture, and death. Woodhull would do it, but he declined to be paid for his trouble. He did so out of conviction, not for anything so grubby as financial greed. His convictions were rooted in a love of liberty, but substantially helped along by a thirst for vengeance. His cousin had been imprisoned and abused by the British army (Rose, 85).

So no salary needed, but he did need help with expenses. He was not rich. So he kept detailed accounts even though that wasn’t exactly safe, was it? (Rose 96, 98).

By January of 1779, Woodhull could write a letter, deliver it to Brewster, who took it across the Sound to Tallmadge, who read it, analyzed it, and sent it on to Washington’s headquarters all inside of one week (Rose, 102), which was not too shabby. Woodhull had provided the names, the corps, and numbers of troops in New York. The numbers were neither made up nor exaggerated, which was all too common with spies (Rose, 94). Washington was very pleased.

In theory, Tallmadge was copying out all these letters before sending them on. Then he would destroy Woodhull’s so that nothing would linger in his handwriting, which would be extremely dangerous. Actually, Tallmadge got bored. Or busy, let’s say busy. It sounds better. Anyway, he neglected that part of the agreement, and Woodhull didn’t know.

Woodhull had plenty of reason to be concerned about his handwriting because Tallmadge was attacked. He got through all right, but his post was stolen, so it’s a very good thing the missing letter referred to Culper, not Woodhull (Rose, 112).

Even so, Tallmadge decided code names were not enough. The bottle of invisible ink they all had was difficult to procure and the easier recipes were so easy to reveal, that there was not much point (Rose, 110).

Tallmadge decided they needed a cipher. He wrote out a list of 710 words he thought might be relevant and he numbered them. From a cryptographer’s point of view, he made a major mistake in doing this alphabetically, but he was making this up as best he could without the benefit of a manual. Numbers 711-763 were for proper names, and the first of these was very naturally Washington himself as 711. Culper was 722 (Rose, 121).

A page from the Culper cipher book. Note Samuel Culper (722) and Samuel Culper Junior (723). Source

Around the same time, Woodhull managed to recruit an accomplice. This was a man who lived in Manhattan, which was great news for Woodhull, since it meant he wouldn’t have to go so often himself. It was also great news for Washington, since a man on the spot was bound to hear more than a visitor.

They had learned a thing or two about security during the previous year, so this operative got the name Samuel Culper Junior, or #723. That is all he was ever called. Even Washington himself never knew Culper Junior’s real name. Historians appear not to have known either until the 1920s when author Morton Pennypacker collected a box of Townsend family papers and correlated the handwriting of one Robert Townsend, an otherwise unremarkable New York businessman with the Samuel Culper Junior letters in Washington’s papers (Kilmeade, xvi).

The only known picture of Townsend. A casual sketch by his nephew. I’m amazed at just how modern this looks. Source

Culper Junior was a big help, but even if he wrote the letters, those letters still had to make it out of Manhattan and 55 miles up Long Island to Culper Senior. They did use couriers, particularly one called Austin Roe, but Woodhull also still had to go himself sometimes and the experience was not improving. On the contrary, Woodhull wrote on August 15, 1779, that:

“Every letter is opened at the entrance of New York… They have some knowledge of the rout our letters take. I judge it was mentioned in the letter taken [this means the one stolen from Tallmadge earlier], or they would not be so vigilant. I do not think it will continue long so. I intend to visit New-York before long and think by the assistance of a lady of my acquaintance, shall be able to outwit them all.”

(From Samuel Culper to John Bolton, 15 August).

Finally! Finally! We have arrived at a woman. This brief mention is 100% of the solid, historical record on Agent 355. It is the only time she is ever mentioned. Everything else is either a speculation or an outright fabrication. And oh wow, does imagination run wild.

So here are some of the theories. First, Culper’s letter was written with Tallmadge’s code. So he didn’t write the word “lady; he wrote “355,” the code for lady. Much has been made of the fact that he did not write 701, the code for woman.

In the modern world, woman vs. lady is a mostly meaningless distinction, but not so in the 18th century. At this time, a man (code 371) was an adult male. A gentleman (code 237) was a male who owned property. It was a black and white distinction. You either were or were not a gentleman. It was not an insult to not be a gentleman. It was just a fact. Woman vs. lady was trickier, since women mostly did not own property. But it certainly meant she was either the wife or daughter of a gentleman. That is to say, she had some social standing.

Morton Pennypacker and more recently Brian Kilmeade and Don Yaeger have taken this linguistic nugget of truth and run miles with it. Agent 355 was, according to them a young coquette living in the height of New York society, attending parties with the cream of the British officers. She was also, according to them, a lover of Robert Townsend and later maybe even bore him a child.

Author Alexander Rose calls this an “utterly fantastical and fanciful tale” (Rose, 325), and he is absolutely right. He points out that the letter was written by Woodhull and he says a lady of my acquaintance, not Townsend‘s acquaintance (Rose, 325).

Rose then goes on to inform the reader with absolute assurance that the lady in question was Anna Strong. Anna Strong was a Setauket neighbor of Woodhull’s. Her husband Selah was a Patriot imprisoned by the British, so she had ample reason to despise the British. According to this theory, the soldiers stationed at the entrance to New York were searching the people who fit the spy profile: single men. Which incidentally was a mostly correct profile. Woodhull, Townsend, Brewster, and Tallmadge were all single men at the time. But maybe Woodhull meant they would not search a respectable married man and his wife. So Anna may have been willing to pretend she was his wife. Or perhaps they did search married men but maybe would not dream of fingering the wife herself if she carried the letters.

This theory seems far more plausible to me than the young New York coquette theory, but at the end of the day Rose does not offer any more proof than the others. Woodhull does not say that this happened. He certainly does not name Anna Strong, and surely she is not the only Long Island resident who could have posed as his wife, if anyone did.

Supporters of the Anna Strong theory all claim another role for her as well. The Strong home was right on the coast, clearly visible from out on the water. According to Strong family tradition, Anna’s laundry line and the placement of a black petticoat was the signal to Caleb Brewster that he should come in and pick up a letter. That is entirely possible, but none of these sources mention how old this tradition is. Because if no one ever mentioned it until the 20th century, it’s highly suspicious. It is, for example, amazing how many traditional ghosts and hauntings suddenly cropped up after ghost tours became commercially viable in older cities. At the end of the day, neither Woodhull nor Strong nor Brewster ever wrote anything down on the subject of a laundry line or a black petticoat.

On the other hand, opponents of the Anna Strong theory have also said ridiculous things against it. Kilmeade and Yaeger say it’s a silly theory because “it seems quite unlikely that the fortyish housewife, mother, and spouse of a well-known Patriot rabble-rouser would have ventured from Long Island to Manhattan to attend parties where she would have rubbed elbows with the Loyalist elite and gained the trust of high-ranking British officers” (Kilmeade, 93).

I have to agree that that scenario seems wildly unlikely, but they seem to have forgotten that there’s no reason to think Agent 355 ever attended a party in her life. That’s the part they made up.

The enormous reading-between-the-lines-to-create-things-that-actually-did-not-happen continues, for on November 12, 1780, Culper wrote that “several of our dear friends were imprisoned, in particular one that hath been ever serviceable to this correspondence. This step so dejected the spirits of Culper, Junior that he resolved to leave New York for a time” (To George Washington from Benjamin Tallmadge, 14 November 1780 (the part quoted is an insert by Woodhull).

This, I have been informed, must mean Agent 355. She was held in the HMS Jersey, the infamous British prisonship! And Townsend was so in love with her he couldn’t cope (Kilmeade, 177).

Actually, we have no idea who Woodhull meant. They had used a number of couriers by then. They had stayed at inns and with family members who had offered them food and shelter. They had talked to people who might have seen any tidbit of information they had missed. The arrest of any of these people might have been enough to put the wind up on Townsend, who knew perfectly well what had happened to Nathan Hale.

He did come back, though, for the Culper ring (with or without Agent 355) continued to write for the remainder of the war, including a great deal of thanking God and Tallmadge for the security which prevented a certain Benedict Arnold from knowing their names. That would have been bad, and he had certainly tried to find out before defecting. But he failed.

On May 5, 1782, Woodhull wrote that “a cessation of arms is ordered, to take place within these lines both by land and sea and terms of peace are given to Congress, but the conditions is here unknown, but generally supposed independence is offered” (Rose, 259). He wrote this months before there was any such official news. The Culper ring was good.

Washington had never managed to retake New York, but he rode into it anyway on November 25, 1783 (Kilmeade, 201).

In July of that year, Woodhull submitted his final expenses, which included £4 for SS, presumed to mean Selah Strong, presumed to really mean Anna Strong (Rose, 264). And it could be so, it really could be, but as I’ve been trying to say, we just don’t know.

None of the Culpers ever blabbed about what they had done. Woodhull’s name was teased out because the early letters were not that secure. Townsend’s name surfaced only by 20th century handwriting analysis. Tallmadge’s identity was known all along, and he even wrote a memoir, but all he deigned to say was “[In 1778] I opened a private correspondence with some persons in New York (for Gen. Washington) which lasted through the war. How beneficial it was to the Commander-in-Chief is evidenced by his continuing the same to the close of the war. I kept one or more boats continually employed in crossing the Sound on this business” (Tallmadge, 29).

We still don’t know anything about the identity or even the role of Agent 355. The two theories I’ve given here are the most publicized, but they are not the only theories. Another is that she was a slave woman. But again, no evidence.

If she was the imprisoned coquette, she may well have died in prison. Kilmeade and Yaeger go so far as to tell me quite seriously that Townsend “never… recovered emotionally from the blow” (Kilmeade, 211)! I had some snide remarks to make here, but I’m cutting them, so you’ll have to make your own snide remarks on that subject.

If Agent 355 was Anna Strong, she died in 1812 after living a quiet life with her husband Selah (Rose, 277).

If she was someone else, who knows? It seems highly unlikely that definitive proof will ever surface. In the meantime, let’s leave fictional accounts to those who admit they’re writing fiction.

Selected Sources

Bleyer, Bill. “The Myth of Agent 355, the Woman Spy Who Supposedly Helped Win the Revolutionary War.” Smithsonian Magazine, 21 Mar. 2022, http://www.smithsonianmag.com/history/the-myth-of-agent-355-the-woman-spy-who-supposedly-helped-win-the-revolutionary-war-180979748/. Accessed 17 Aug. 2022.

Casey, Susan. Women Heroes of the American Revolution : 20 Stories of Espionage, Sabotage, Defiance, and Rescue. Chicago, Illinois, Chicago Review Press, 2017.

“From George Washington to Lieutenant Caleb Brewster, 8 August 1778,” Founders Online, National Archives, https://founders.archives.gov/documents/Washington/03-16-02-0282. [Original source: The Papers of George Washington, Revolutionary War Series, vol. 16, 1 July–14 September 1778, ed. David R. Hoth. Charlottesville: University of Virginia Press, 2006, pp. 268–269.]

“From George Washington to Major Benjamin Tallmadge, 25 August 1778,” Founders Online, National Archives, https://founders.archives.gov/documents/Washington/03-16-02-0411. [Original source: The Papers of George Washington, Revolutionary War Series, vol. 16, 1 July–14 September 1778, ed. David R. Hoth. Charlottesville: University of Virginia Press, 2006, pp. 376–377.]

“II. Samuel Culper to John Bolton, 15 August,” Founders Online, National Archives, https://founders.archives.gov/documents/Washington/03-22-02-0039-0002. [Original source: The Papers of George Washington, Revolutionary War Series, vol. 22, 1 August–21 October 1779, ed. Benjamin L. Huggins. Charlottesville: University of Virginia Press, 2013, pp. 47–48.]

Kilmeade, Brian, and Don Yaeger. George Washington’s Secret Six : The Spy Ring That Saved the American Revolution. New York, Puffin Books, 2013.

Rose, Alexander. Washington’s Spies : The Story of America’s First Spy Ring. New York, Bantam Books Trade Paperbacks, 2014.

Tallmadge, Benjamin. Memoir of Col. Benjamin Tallmadge. United States: T. Holman, book and job printer, 1858.  Available at https://www.google.com/books/edition/Memoir_of_Col_Benjamin_Tallmadge/lIRi9_goutMC?hl=enandgbpv=0. Accessed 8/20/2022.

“To George Washington from Benjamin Tallmadge, 14 November 1780,” Founders Online, National Archives, https://founders.archives.gov/documents/Washington/99-01-02-03940. Note that this is listed as coming from Tallmadge because he enclosed Culper’s letter in one of his own. The part quoted was written by Culper. “To George Washington from Brigadier General Charles Scott, 29 October 1778,” Founders Online, National Archives, https://founders.archives.gov/documents/Washington/03-17-02-0654. [Original source: The Papers of George Washington, Revolutionary War Series, vol. 17, 15 September–31 October 1778, ed. Philander D. Chase. Charlottesville: University of Virginia Press, 2008, pp. 635–637.]

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