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.)