The Legend of Agent 355

Hayley Milliman - Content Lead

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September 1776.

The Continental Army was in some seriously deep sh*t, and George Washington was learning the hard way that his ragtag group of forces wasn’t quite up to the challenge of defeating the world’s mightiest military power, no matter how young, scrappy, and hungry they were.

After kicking the British out of Boston a few months earlier, Washington had marched his army down to Manhattan, correctly predicting that his foes would want to use the city as a base for their powerful navy.

Unfortunately, the Continental Army’s success didn’t hold, and the British easily defeated the Americans in New York, forcing Washington to withdraw to New Jersey and Pennsylvania. Worse than that, the fighting had shown that Washington was facing some serious challenges, not the least of which were that his army was inexperienced, undisciplined and kind of cowardly.

If the Americans were going to win the war, Washington needed to gain the upper hand.

So who did he call on for help?

No, not (just) a lyrically-gifted Alexander Hamilton.

Washington knew that spies were the key to defeating the British: if he could figure out the British plans, he could beat them at their own game.

One of the spies that would help win the war for Washington was a mysterious woman, known today only as Agent 355.

The Name Is… We Don’t Really Know, Actually.

Now that we think about it, it’s kind of weird that James Bond went around just telling everyone his name all the time.

Before we get to the story of Agent 355, we want to acknowledge that there’s basically no historical consensus on who Agent 355 was, what she did, and what happened to her.

But you know what?

We think that that’s the hallmark of a pretty bad*ss bitch (or bitches — there are some theories that suggest that “355” was actually a call sign that referred to a number of different well-connected women).

After all, the whole point of being a spy is that no one discovers your real identity, so the fact that we still, 250+ years later, have no idea who Agent 355 was means that she must’ve been pretty damn good at her job.

Now that we’ve established that, in the quest to learn the truth about Agent 355, we’re basically Jon Snow (aka, we know nothing), let’s take a look at one of the most popular theories about her life and work.

Not All Heroes Wear Tricorn Hats

Where were we?

Ah, right.

September 1776.

The Continental Army had just escaped from New York, leaving behind control of one of the most strategic ports in the country and what was left of their pride. George Washington, stuck in New Jersey and probably hating it, needed to devise a new strategy that didn’t solely rely on his untrained and unreliable forces.

Though spies were looked down on at the time (apparently, spying wasn’t “gentlemanly”), Washington saw their value and was realistic enough to know that he needed every advantage he could get to defeat the British.

Over the next few years, several spy rings fed intelligence to Washington. One of them, established in 1778, was known as the Culper Ring.

The Culper Ring was pretty legit, as far as spy rings go: they used invisible ink, they had aliases, they encrypted all their letters. While most of the members of the Culper Ring were men, they did recruit women.

One of the women the Culper Ring recruited was Agent 355.

Here’s what (we think) we know about Agent 355:

  • Her family was super important. Agent 355 came from a prominent Tory family, which meant that her family was loyal to the British. This put 355 in a great place to gather intelligence about British activities, because she was socializing with British soldiers and sympathizers in her daily life.
  • She was a really good spy. 355’s handler was a man named Abraham Woodhull, who praised her work, telling George Washington that 355 was “one who hath been ever serviceable to this correspondence.” That’s actually the only thing we know for certain about 355: because Woodhull wrote this performance review in a letter, we have proof positive that she kicked a ton of *ss.
  • She was caught by Benedict Arnold. As if anyone needed more of a reason to hate famed traitor Benedict Arnold, in the fall of 1780, Arnold became suspicious of 355. Arnold was right to be nervous; he was, after all, getting ready to sell out West Point to the British and, since Agent 355 was a baller, she probably knew about, or at least guessed, Arnold’s deception. Arnold captured 355 on suspicion of spying and imprisoned her on a British prison ship.
  • She was a seriously bad*ss bitch. Like everything about Agent 355’s life, we know very little about what happened to her in prison. Here’s what we do: when Arnold took 355 aboard that British prison ship, she was pregnant. 355 not only gave birth to a baby aboard the prison ship, she also refused to give up any information about the other spies in the Culper ring to Arnold and his minions.

Most sources suggest that Agent 355 died aboard that British prison ship. But by refusing to give in to her captors and protecting the identities of her fellow spies, Agent 355 kept the dream of American Independence alive.

It’s Time to Include Women in the Sequel (And the Prequel, and the Original Source Material)

If you thought you were getting out of this article about the American Revolution without a Hamilton GIF, you were wrong.

When we think of the Revolutionary War, we think of the Founding Fathers. We picture George Washington leading a charge; we imagine John Hancock signing his name with a flourish; we envision Alexander Hamilton engaging in epic rap battles stealing cannons.

We rarely, however, think of the many women who played a large part in establishing the foundations of the United States. We forget about how Betsy Ross convinced George Washington to change the stars on the flag from six points to five. We ignore how Abigail Adams and Angelica Schuyler, two of the greatest thinkers of the time, offered influential opinions to the men who would later go on to publish those opinions.

And we never even hear about women like Agent 355, who devoted their lives to the cause, only to die, alone and anonymous.

It’s high time that we start to remember and tell the stories of these bad*ss bitches, even if, like Agent 355, they were so damn good at their jobs that there’s barely enough to tell.

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