- King Louis the 15th had a secret, an organization so clandestine that not even his own government officials knew it existed.

Thousands of miles away In Russia, one of its most talented spies watched as porters handled two large trunks.

One contained expensive dresses, much like the one they wore, while the other carried all the trappings of a well-to- do Frenchman.

That covert mission was one of the first times this agent presented themself as a woman.

They later became the first legally recognized transgender woman in the history of France, but not before blackmailing the king.

I'm Joel Cook, and this is Rogue History.

Le Secret du Roi, or King's Secret was founded to help King Louis' cousin, the Prince de Conti, become king of Poland, a large and wealthy country that would increase France's dominance in Europe.

But the French Foreign Ministry wanted someone else on the throne, prompting King Louis to launch this covert operation to sway other European powers to his side.

In 1756, the organization targeted an up and coming star to join The King's Secret.

Charles Genevieve Louis Auguste Andre Timothee d'Eon de Beaumont, for your ears and my sanity, will be referred to as Chevalier or Knight d'Eon.

As a lawyer, fencer and diplomat, the Chevalier was recruited to join a king's Secret assignment in Russia, and that's where the legend of the Chevalier d'Eon would begin.

According to Chevalier d'Eon's memoir, their spy mission began when they learned that the Empress Elizabeth wanted to hire an honest, well-informed, prudent, and discreet lady in waiting to assist her in sending coded letters to King Louis.

Europe was on the brink of the Seven Years War, often called the first true World War, and France needed a strong ally like Russia to have any chance of defeating England and Prussia.

Becoming pen pals with Elizabeth could give them a major boost.

d'Eon infiltrated the Russian court under the cover of Mademoiselle Auguste, and served as a lady in waiting to the Empress.

d'Eon said that they initially resisted the idea, afraid of losing the autonomy their masculine identity gave them, but eventually accepted it.

After spending some time training in the deciphering of diplomatic codes and the manners of an aristocratic lady, they traveled to Russia to begin the mission.

The Chevalier stated that they operated under both masculine and feminine identities in Russia, presenting as Chevalier d'Eon, while working openly as a diplomat for the French foreign ministry.

And Mademoiselle Auguste while working undercover for the King's Secret.

In one well-known legend, the Chevalier, dressed as Mademoiselle Auguste, presented the Empress with a book that could be disassembled with a hairpin, revealing a hidden compartment with secret correspondence from King Louis.

d'Eon went over the Empress, and in November, 1757, she agreed to the terms of an alliance with France, Austria and Sweden against Prussia.

When she learned that Chevalier d'Eon was assigned to deliver the treaty back to France, she made them promise to return to Russia and gifted them a diamond encrusted snuff box.

Other members of the Russian court also lamented the loss of d'Eon's special acquaintance with this country.

Though that may have had something to do with the $600,000 d'Eon spent on wine, this mission was such a success that d'Eon was assigned to another undercover operation a few years later.

In the summer of 1762, the foreign ministry sent d'Eon to London to serve as part of a peace delegation, but King Louis, also had secret orders for the Chevalier to covertly gather reconnaissance of the English coast for a potential future French invasion.

But that's where things started to fall apart.

Though the King's Secret had a small budget, the Chevalier had spent large amounts of money on the Russian spy work and now demanded repayment.

After all, spying ain't cheap, but the King didn't want to pay, so d'Eon threatened to leak secret documents, an action that would very likely lead to a new declaration of war from Great Britain.

Unable to openly threaten d'Eon, King Louis opted to kidnap them, deploying French police officers and spies to spirit the Chevalier back across the English Channel.

But d'Eon unmasked the plan and turned their home in London into a fortress, writing, "I have no fewer than eight Turkish saber, four pairs of pistols and two Turkish rifles with which to give him a Turkish brawl."

King Louis most talented agent was forcing him to come to the negotiating table.

While a dramatic Cold War played out between d'Eon and King Louis, the citizens of London speculated on the possibility of other secrets d'Eon might be keeping.

The rumor started with a letter from one gossiper to another, claiming that Monsour d'Eon is a woman and the debate spread like wildfire.

By the following year, Londoners were taking bets on the answer.

The Chevalier responded to these rumors by regularly visiting the coffee houses where the bets were taken and doing as anyone else would, challenging the bettors to duals.

But these public displays of masculinity didn't tell the whole story.

The Chevalier's private clothing orders from the same time period showed several women's items such as corsets, shifts and taffeta cloth labeled, for me.

But the betting continued and became so intense that one case made it all the way to the high courts of London where the chief justice ruled in favor of those who bet that the Chevalier was a woman.

Months later, the judge had a change of heart, and throughout the case, permanently forbidding any betting on a person's sex, due to the invasive and injurious nature of the act to an innocent third party.

When King Louis the 15th died and his grandson king Louis the 16th took the throne, things changed for d'Eon.

Disgusted by the King's Secret, and boosted by the anger of the French people, the new King Louis demanded the dissolution of the organization, but the Chevalier d'Eon and their blackmail threats, still stood in the way of a smooth transition.

A year into his reign, the New King approved a plan , known as The Transaction, which required the Chevalier d'Eon to return the King's Secret documents and maintained their silence about the secret invasion plans.

In exchange, d'Eon would receive a lifetime pension of 12,000 pounds per year, reimbursement for debts and public recognition of their request to be acknowledged as a woman.

But the catch was, d'Eon had to give up their men's clothing forever.

The contract, which d'Eon accepted in November, 1775, was backdated to their 47th birthday as an act of rebirth, and declared the masculine presenting Chevalier d'Eon a ghost.

From now on, Chevalier d'Eon would be Chevalliere, or Mademoiselle d'Eon.

King Louis announced the transaction to the public in 1776 but why was it so important to let the public know?

Let's see what Kaz Rowe has to say about this.

- The reasoning behind the transaction can't be uncoupled from the complex ideas surrounding gender in France in this time period.

The 18th century saw many radical shifts in gender constructs, but was still heavily based on medical and anatomical beliefs, dating as far back as ancient Greece.

Hippocrates wrote about biological sex as existing on a continuum where there was one sex with different forms placed in a hierarchy.

Because of this, with a gender connected to this continuum, 17 to 18th century French society believed that sex itself was fluid and masculine biological traits could therefore appear in women if the right environmental stressors came up and vice versa.

At the same time, cross-dressing was a serious offense.

In particular, if done by a woman trying to claim a man's role.

This made things complicated for sapphic women, for example.

Intimate relationships between women weren't seen as a threat until one of them dressed in mannish clothes or took on a male type role in the act.

Then it was a serious offense worthy of legal punishment.

But it's also a complicated problem because at the same time, cross-dressing in openly recreational contexts like masquerade balls was both popular and widely accepted.

So although these ancient ideas of the sexual continuum persisted in d'Eon's time, the two sex model was coming into place and this shifting uncertainty, is partially why d'Eon was viewed first as a spectacle, then with disgust, even after the transaction, seemed to put some certainty to the question of d'Eon's true sex.

The transaction operated almost literally as d'Eons new birth certificate, a poignant tool for d'Eon as the revolution loomed and the roles for both men and women were once again thrown into question.

- But how did d'Eon feel about the situation.

Though the terms of the transaction required d'Eon to present only as a woman, and they acknowledged that they were a woman, following the high court ruling.

They continued to wear their men's military uniform in London.

It wasn't until October of 1777, well after their arrival back in France, that d'Eon finally donned women's clothing permanently.

At a dinner held in honor of their transition later that evening, they told the seamstress who designed the clothing that, "You have killed my brother, the Dragoon, and I'm in great pain over it."

After the French Revolution, d'Eon lost their pension and began conducting performances in Great Britain where they fenced in women's clothing, an unusual sight for the time.

In 1785, they began writing their memoir in which they acknowledged that they were able to live half their life as a man and half as a woman, and seemed to be at peace with that balance.

Historians have questioned the validity of d'Eon's cross-dressing story for over a century, with some theorizing that d'Eon overstated their experiences at Empress Elizabeth's well-known masquerade balls, while others argue that d'Eon never went undercover as a woman at all.

The Chevalier d'Eon's memoir, now available to the public, is often written off as non-factual due to lack of supporting evidence.

But when it comes to covert operations, sometimes there is no paper trail.

Gender non-conformity has been part of the human experience for thousands of years, but the way historians acknowledge and interpret the people that make up that lineage, still seems to be undecided.

Be honest.

Even now you're probably thinking, well what was the Chevalier d'Eon's identity?

And to that I would answer, the Chevalier d'Eon's identity was that of a deep thinker, a mold breaker, and one heck of a spy.

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