When most people think of a three-digit spy, 007 comes to mind - the super famous, and
super fictional, James Bond.
However, there is a historic spy that also went by a three number code, Agent 355: a
spy so good at staying hidden from the enemy that to this day, we still don’t know who
she is.
Craziest of all?
She operated at a time when women were basically considered property and barely had the opportunity
or rights to do much of anything.
Agent 355 was a female spy who worked during the American Revolution; and she may be one
of the top reasons that the US won its independence.
The year is 1778.
The Declaration of Independence was signed two years ago, epically pissing off King George
III and the Loyalists who wished the US to remain loyal to England.
However, the outcome of the war was far from certain at this point.
In fact, any betting man around the world could be forgiven for laying greater odds
on a British win.
Though George Washington was a great commander, and the Patriots clamored for independence,
the US army was inexperienced and disorganized, especially compared to the war machine of
the British Army and Navy.
At that point, England had used its military might to take over a huge chunk of the world
- they couldn't have been too afraid of a group of American rebels in the beginning.
What made battles harder was the fact that, even within the colonies, not everyone agreed
with American independence.
About 45% of the white population supported the Patriots, but about 15-20% supported loyalty
to the British Crown.
The last 35-40% were undecided.
They probably chose to hang back and talk endlessly about how “both sides are the
same so why do anything” and then complain endlessly on Facebook about whoever ended
up winning.
Thankfully this kind of citizen apathy regarding leadership doesn’t really happen anymore.
In any case, the might of British military forces made information gathering, especially
on the American side, crucial to gaining an upper hand.
And who better to gather information than a network of spies.
Thus, the Culper Spy Ring was formed, operating mainly in New York and Connecticut from 1778
to 1780.
The ring was headed by Benjamin Tallmadge, General George Washington’s intelligence
chief.
Washington ordered that the identities of the spies be so secure, that not even he himself
should know who they were.
Just as celebrities trust friends from back home in their entourage, Tallmadge gathered
most of the informants from his hometown of Setauket, Long Island to form the spy ring.
He initially chose a man named Abraham Woodhull as his top agent, but Woodhull’s frequent
trips from outer Long Island to Manhattan attracted the attention of British intelligence.
So Woodhull instead nominated a relative of his living in a Manhattan boarding house for
the job - Robert Townsend.
Woodhull’s nickname was Samuel Culper, Sr., and Townsend’s became Samuel Culper, Jr.
You may have believed that more exotic codenames exist in the world of spies, but unfortunately,
“Octopussy” lied to you.
The Culper Ring grew, and using some nifty new inventions of the time, including invisible
ink, managed to get countless intelligence messages to revolutionary military leaders.
The ring was doing excellent work with gathering intelligence on the British Navy from careless
conversations and tips, but unfortunately, they had almost no luck penetrating the British
Army.
Perhaps the army drank less.
We’re joking….it was British men in the 1700s, we’re sure everyone drank plenty.
Amid these frustrations, Woodhull had an idea.
He wrote in a letter to Tallmadge, “I intended to visit 727 before long and think by the
assistance of a 355 of my acquaintance, shall be able to outwit them all.”
Contrary to what you may think, this wasn’t Woodhull having a stroke on paper.
Woodhull frequently used codes from Tallmadge’s code book to communicate with him.
727 was code for New York.
355 was code for “lady”.
Woodhull did not disclose who his female contact was.
And in fact, to this day, we do not know for sure, though many people have educated guesses
based on research.
However, one thing was for certain; she gathered British Army intelligence better than any
man before her.
Even though this is the only direct written reference to 355, it became clear she was
not a one-time help or casual informant for the Revolutionary Army.
Woodhull disclosed in a later document that 355 was “one who hath been ever serviceable
to this correspondence”, indicating a long-term involvement with the spy ring on the mystery
woman’s part.
Within two months after the first mention of contacting Agent 355, detailed intelligence
reports regarding British Army officers were coming in non-stop to Washington’s headquarters
in Newburgh, New York.
Most of the information seemed to regard Major John Andre, the chief of British intelligence.
Agent 355 must have had close access to him, as the reports seemed to become sparer and
less detailed between December of 1779 and May of 1780, when Major Andre left New York
for Charleston.
However, when Andre returned, the information flowed as easily as before.
In fact, the Revolutionary Army was about to get one of the biggest scoops of the war,
and uncover a traitor whose name lives on in infamy.
In the spring of 1780, Washington received his most alarming report from Agent 355: an
American general is “in compact with the enemy”.
The British planned to use him to capture West Point; even then, the most important
military fort in America.
For those who stayed awake in their high school US history class, you might already suspect
that shortly after this message, General Benedict Arnold gained command of West Point.
Arnold was negotiating with British intelligence officer Major Andre to surrender the famed
military academy site for money.
See, Arnold and Andre knew each other through Arnold’s wife, Peggy Shippen.
In historical accounts, Shippen is described as an “old Philadelphia theater friend”
of Andre’s.
We don’t know if this means that they liked to attend theatrical plays often, or that
they spent high school putting on off-key renditions of the 18th-century’s “Les
Miz” equivalent for tired parents, but either way, their connection was solid enough to
enable treason.
Tallmadge warned the governor of Connecticut, who supplied West Point, to “be guarded”
against some unexpected stroke, and know that the enemy probably already knew of American
forces and supply lines in the area.
None other than Alexander Hamilton, of Lin-Manuel Miranda fame of course, revealed that during
the summer of 1780, the American side continued to intercept letters between Andre and Arnold
thanks to their spy.
Eventually, in September of 1780, Major Andre was arrested.
He confessed to his crimes and was subsequently hanged.
Arnold was notified of Andre’s arrest before he got apprehended and quickly fled.
Thus, Agent 355’s information led to the capture of a senior British intelligence officer,
as well as the exposure of Arnold’s treason, and best of all, prevented West Point from
falling into British hands.
So this leads to the next logical question: who was Agent 355?
And how did she manage to access sensitive information from the British Army when almost
no one was able to before?
Many US historians theorize that Agent 355 was a member of a wealthy Loyalist family.
This would have given her easy and privileged access to senior British officers.
Moreover, the fact that “355” translated to “lady”, which at that time denoted
a certain social class in addition to a gender, reinforced the idea that 355 probably came
from a rich or socially prominent family.
Another fact many historians seem to agree on is that 355 must have somehow been close
to Major Andre.
After all, secrets flowed freely from 355 when Andre was in town, and seemingly stalled
in the few months he was in the South.
Thus, it’s likely that she was getting most of her information from this British officer.
Lending further credence to this theory is the fact that Andre was known to have a weakness
for women.
Not necessarily in the lewd way you just thought of, though he was considered the most eligible
bachelor in New York at the time - equivalent to today’s “Sexiest Man Alive”, we presume.
It’s more that he underestimated women’s capacity for doing…..well….much of anything,
really.
For example, in 1777, the British were occupying Philadelphia and Andre held a top secret meeting
in the Darragh house, where he was temporarily quartered.
Housewife Lydia Darragh snuck up the stairs and simply listened in at the door - that’s
how lax his sense of security was around women - then reported back to George Washington
that the British Army was about to attack.
When Andre and his men started their offensive, it quickly became obvious that Washington
had been warned and was well prepared to head off the British Army.
Enraged, Andre questioned every single member of the Darragh household to see who could
have delivered the message.
Every single member...except Lydia.
You see, after his questioning, Andre was sure that the Darragh family shared his Loyalist
views, so he saw no need to question Lydia as he believed wives all held the same political
views as their husbands.
No, seriously, that’s what he thought.
Clearly he never spoke to the couples who filed for divorce after the 2016 election.
However, this general misogyny that existed at that time sometimes worked in female spies’
favors.
Women weren’t generally vetted, checked, or suspected as often as men.
And since many senior officers didn’t think much of womens’ intellectual abilities,
they spoke more freely around them.
There’s another theory about Agent 355 as well, though it doesn’t necessarily bring
us closer to understanding her identity.
Many people thought she might have been the aforementioned spy Robert Townsend’s common-law
wife.
After Andre’s hanging and Arnold’s escape, Townsend and several other spies went into
hiding for a few weeks until everything blew over.
When he returned to New York however, the first news he heard via a letter Woodhull
wrote to Tallmadge was of the arrest of “several of [their] dear friends”...including 355.
Furthermore, the rumor was that Agent 355 was pregnant at the time of her arrest.
However, brave as always, she refused to crack under questioning, divulging nothing of her
spying activities, nor even the identity of her child’s father.
Townsend’s reaction was immediate, emotional, and extreme.
He went straight to Woodhull’s house out in Setauket and swore to immediately stop
spying and gather as much money as he could by stealing from every business to which he
had connections, including his own father’s.
Townsend went on to steal 600 pounds in ten days - a value of around $156,000 today.
Many suspected Townsend might have been amassing money to ransom 355’s freedom, and that
of his possible child.
However, a happy ending was not to be for the spy couple.
Allegedly, Agent 355 was held on the HMS Jersey in New York harbor, where conditions were
so terrible most prisoners succumbed to disease or other causes of death within a few months.
Certain stories relay that Agent 355 died on that ship, but not before giving birth
to a baby boy.
After her death, by all accounts Townsend spent the rest of his life as a single, depressed
alcoholic.
This romantic story is sometimes disputed by other sources.
Many historians including author Alexander Rose argue that there is no record of a birth
on the HMS Jersey, and women at the time generally weren’t kept on prison ships.
Other historians believe it’s more possible Agent 355 was Sarah Townsend, Robert Townsend’s
sister...and, we hope, not also his common law wife.
What’s the proof for this?
Well, British officer John Graves Simcoe was stationed at the Townsend home, where it would
have been easy for Sarah to overhear sensitive information.
Furthermore, Simcoe received frequent visits from Major Andre of the British army, who
it seems most of the intelligence leaks came from.
Perhaps most tragically of all, it appears Simcoe was in love with young Sarah.
In fact, a written letter professing his love is now considered America’s first ever valentine.
Sarah did not choose him as a valentine at the time, likely due to her strong Patriot
beliefs.
However, she never married, and after her death, many report that she still had Simcoe’s
valentine letter among her possessions.
This led many to believe that the two had a flirtation, and Sarah, at least in part,
returned Simcoe’s feelings.
We never knew the Revolutionary War contained so many Hallmark Channel stories within it.
Another suspected candidate for Agent 355 was Anna Smith Strong.
Strong would help signal the position of another Culper Spy Ring member, Caleb Brewster, using
handkerchiefs on her clothes line.
Brewster raided British shipping on the Long Island Sound, and therefore had to be a bit
sneaky about where he landed his boat, what with all the angry British captains looking
for him.
Strong would help designate a safe haven for Brewster, then use the handkerchief code to
tell Woodhull of Brewster’s location, so Woodhull could pass on dispatches about the
location of other British boats.
The reason some believe Strong may have been 355 is because her husband was captured and
held at the HMS Jersey, where Strong was allowed to visit him to bring him food.
This may have caused the confusion about identifying Agent 355 as being on a prison boat that generally
didn’t hold women.
Another woman historians suspect of being Agent 355 was Elizabeth Burgin.
At first glance, Burgin appeared fairly ordinary to outsiders; a war widow trying to raise
three children on her own.
After being approached by the Culper Spy Ring, letters show that her efforts helped free
200 Patriot prisoners from British prison ships.
However, even though she was part of the spy ring and deeply devoted to helping the Revolutionary
War effort, there isn’t much additional evidence for her specifically being Agent
355.
So what is the real story of Agent 355’s life and death?
Was she ever captured?
Was she one of the many, many women who laid their lives on the line for the Revolutionary
cause, but have mostly been left out of history books?
Even with all these unanswered questions about Agent 355, one thing is certain: her help
was invaluable to George Washington and the American fight for independence: finally obtaining
British Army intelligence, exposing a traitor, and saving America’s most important fort
from falling into enemy hands.
Who do you think Agent 355 really was?
Let us know in the comments below!
In the meantime, learn more hidden facts and history by clicking on this video here, or
this one right over there!