Knocking Down the Myths of Agent 355

Her Half of History is Lori Baker’s podcast about notable women in various times. Recently she’s been sharing episodes about women involved in espionage.

I like her take on the Culper Ring and whether those spies included a female agent, source, courier, or cover. You can glean her basic conclusion from the title of that episode: “Agent 355: Washington’s Mostly Mythical Spy.”

The historical record of espionage is always sparse, for obvious reasons. We know that Maj. Benjamin Tallmadge invented a code for his agents that used the number 355 for “lady” and the number 701 for “woman.”

We also know that Abraham Woodhull used the number 355 once, in a letter dated 15 Aug 1779. That dispatch referred to bringing a lady along on a trip into New York because the security was getting stricter.

As Baker says, per her transcript:

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. . . .

Culper…wrote “355,” the code for lady. Much has been made of the fact that he did not write 701, the code for woman. . . . [Using 355] 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…[who] may have been willing to pretend she was his wife. . . .

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.

Baker is also skeptical of the family lore about Anna Strong signaling Continental spies in Long Island Sound—and rightfully so, I think. I’ve never been able to figure out the practical logic of that tale, which Pennypacker published a century and half after the war without specifying a source.

Modern American culture thirsts for examples of women active in historical events. In the last century, the extremely sparse documentary tidbits about 355 have been spun out in all sorts of adventures: Agent 355, Turn: Washington’s Spies, The 355, Y: The Last Man. Those stories proudly present themselves as fiction. Most histories of the Culper Ring contain a large amount of fictional speculation as well.

(The picture above appears on Wikipedia’s page for Agent 355, which treats the competing claims too credulously. Its caption says it shows “Agent 355, as depicted in an 1863 issue of Harper’s Weekly.” In fact, that magazine article was about Antonia Ford, who gathered information for Confederate commanders in the U.S. Civil War. The original caption, “General [J.E.B.] Stuart’s New Aid,” has been cropped out. Such is our interest in seeing Agent 355, if such a lady ever existed.)

“By the assistance of a 355”

I liked this Smithsonian article throwing cold water on the idea that the Culper spy ring included a woman known as “355.”

As Bill Bleyer writes, the number 355 was in the ring’s codebook as the symbol for “lady,” but that number appears on the record of the spy network only once:

Of the 193 surviving letters written by members of the ring, only one contains a reference to any woman. A coded letter from chief spy [Abraham] Woodhull to [Gen. George] Washington, dated August 15, 1779, includes this sentence: “I intend to visit 727 [Culper code for New York] before long and think by the assistance of a 355 [lady in the code] of my acquaintance, shall be able to outwit them all.”

There’s no evidence of how this lady might help Woodhull, what her real or putative relationship to him was, or what came of that visit—if it ever took place. We do know the codebook had different entries for “lady,” “woman” (701), and “servant” (599), indicating that Woodhull referred to an upper-class woman.

Woodhull and other long-time agents had pseudonyms because they made many appearances in the letters. There was no pseudonym for a woman, and, again, this is the only mention of a 355.

Bleyer discusses the various ways authors have imagined “355” while claiming to write nonfiction. Morton Pennypacker, who first identified the Culper codebook and figured out the ring members, described a lady who was “Townsend’s mistress…arrested, imprisoned on the infamous British prison ship Jersey and given birth to Townsend’s illegitimate son onboard before dying.”

In their book with no citations, Fox talking head Brian Kilmeade and writer Don Yaeger placed “355 in the social circle of British spymaster and legendary party-thrower John André.“ Once again, she ends up on the Jersey. As historian Todd Braisted has noted, we have the names of everyone detained on the Jersey because the Royal Navy kept careful records, and there were no women.

In Washington’s Spies, Alexander Rose portrayed Anna Strong as active in spying out of Setauket, New York. Pennypacker had been the first to bring Strong’s name into the story, printing family lore about her signaling Patriot boats with her laundry in a way I’ve never understood the logic of. Strong was related to Woodhull. But the evidence she took part in spying is beyond thin, much less that she was the 355 of August 1779.

Claire Bellerjeau in Espionage and Enslavement in the Revolution: The True Story of Robert Townsend and Elizabeth proposed that 355 was a woman who escaped slavery on Long Island named Elizabeth or Liss. But the only mention of “a 355 of my acquaintance” came from Woodhull while that woman had been enslaved to the family of another Culper ring spy, Robert Townsend. Also, an upper-class white man like Woodhull wouldn’t identify Elizabeth as a lady.

The many stories about 355 reflect our own society’s wish to imagine an active, daring female spy—and to solve the mystery of that number.

A Season of Turn

The A.M.C. television series Turn reached the end of its first season Sunday, and I filed my review of that episode at Den of Geek. Earlier in the week the website published my article on Maj. Richard Hewlett, which I wrote before guessing that the Battle of Setauket, New York, would provide the climax for the season.

My whole collection of writing about the show is linked from here. I tried to avoid spoiling the big revelations in each episode in case you’re still catching up. Also, check out Rachel Smith’s Turn to a Historian blog for excellent analysis of the historical facts behind—in many cases, almost invisible in the distance behind—the show.

Early on in the show’s run I had to reconcile myself to the many historical liberties the show’s creators had taken, from launching the Culper Ring in 1776 to giving two principal characters anachronistic bushy beards as a way to signal they stood outside ordinary norms and differentiate them from the other men. There are so many deviations from the historical record or historiographical questions to point out that those essays could fill a season unto themselves.

But I realized that simply noting those changes was not unlike pointing out that Bucky Barnes died while trying to stop Baron Zemo’s rocket, and not by falling off a train as in the new Captain America movies. That may be true—hey, it is true—but not in the “Marvel movie continuity.”

Similarly, it seemed wiser to consider the Turn continuity to reflect a different universe from the real one. The same characters were playing the same basic roles in the same basic storylines, but they looked different, the timeline was changed, and knowledge about one world didn’t necessarily apply in the other. Given the cast-limiting budget, the show’s production values, use of period music, and generally strong performances kept it generally entertaining.

My biggest disappointment with Turn, therefore, wasn’t with the historical accuracy but with the way some characters’ motivations seemed to shift as the plot demanded. The character at the center, Abe Woodhull, is obviously torn in several directions—politically, romantically, familially. But his choices remained so opaque that, for instance, his getting involved in a duel seemed to be driven more by the producers’ thought that a duel would be dramatic than by anything we’d seen Abe do up to that point. Secondary characters worked better since they could be “flat,” in E. M. Forster’s formulation, and maintain their motivation.

It’s not clear whether there will be a second season of Turn. Certainly there’s plenty of inspiration available: Gen. Benedict Arnold’s name keeps coming up, and we haven’t yet seen the spy inside New York City who operated as “Samuel Culper, Jr.” The show could also shift its focus to Philadelphia in 1777-78 with another set of spies; Benjamin Tallmadge and John André were there, too. But to get to do any of that Turn has to satisfy viewers with good character-driven drama.

Reviewing Every Twist and Turn

Last night saw the launch of A.M.C.’s new spy drama Turn, followed closely by the launch of my review of that show at Den of Geek. I don’t type that fast; I got an advance look at the first episode. So did Michael Schellhammer, and his review at the Journal of the American Revolution went up last week.

Turn was inspired by Alexander Rose’s Washington’s Spies, a history of the Culper Ring operating in British-occupied New York City and Long Island from 1778 to the end of the war. And by “inspired” I mean the creators took names and basic circumstances from that history and went off in their own direction to find drama. For example, the show begins in “Autumn 1776,” two years before the spy ring got organized. (And I’m not sure why.)

As the weeks pass, I’ll be supplying Den of Geek with reviews of more episodes and periodic articles about the history behind the show, hoping to help viewers keep them separate. I don’t want to criticize Turn’s makers for fictionalization when their job is to keep us watching. But I am interested in what the entertainment industry thinks is necessary for a compelling story.

For example, the real Abraham Woodhull wasn’t being tugged in different directions within his family; his father was a Patriot, but the show turned him into a Loyalist for drama. The real Abraham Woodhull was only ten years old when Anna Smith married, and there’s no evidence he carried a torch for her. The show is not only driven by their unfulfilled relationship, but it gives him a wife and baby boy for more drama.

If that drama becomes more compelling, especially in rounding out the characterizations of the British army antagonists, then I think Turn will fulfill the promise of its source material and production values.