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  • 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 howboth sides are the

  • same so why do anythingand 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,

  • Octopussylied 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 forlady”.

  • 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 wasone 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 isin 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 anold 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

  • Mizequivalent for tired parents, but either way, their connection was solid enough to

  • enable treason.

  • Tallmadge warned the governor of Connecticut, who supplied West Point, tobe 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 tolady”, 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 ofseveral 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!

When most people think of a three-digit spy, 007 comes to mind - the super famous, and

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How Agent 355 Changed the Course of the American Revolution

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    Summer posted on 2021/06/22
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