The Mysterious Agent 355

In the fall of 1776, General Washington received grievous news. One of his chief espionage officers, Nathan Hale, had just been captured and executed by the British. Frankly he wasn't too terribly surprised; Hale was a good man, but a horrendous spy. Nor was he the first of Washington's spies to be found out and killed before they could deliver their hard-sought information about the enemy. After receiving news of Hale's execution by hanging without a trial, Washington was most aggrieved and probably more than a little frustrated.

If his army was going to get any kind of foothold in this war, they needed inside intelligence. He'd learned that back in 1754, when his army was taken down from the inside by French spies during the Seven Years' War. While admirable, his espionage efforts so far were not going very well. The handful of volunteer spies he had working for him were untrained, inexperienced, and woefully disorganized. Although good-intentioned, these amateur spies were clumsy, and often not the least bit discreet while doing their jobs. As such, they were often caught red handed and killed on sight. Even if a spy managed to make it back to camp alive, the intel they gathered wasn't always accurate or reliable. The message often got muddled along the way, or was simply bad intel purposefully planted by the British.

Something had to change. Someone would have to take charge, and whip these knuckleheads into shape, reworking their entire spy organization from top to bottom. Out of ideas, Washington immediately consulted a trusted colleague - William Duer - to see if he had anyone in mind suitable for the job. Duer was quick to offer two names for the price of one: Nathaniel Sackett, a former classmate of Hale's, and Benjamin Tallmadge.

It took several years and lots of trial and error, including a falling out between Washington and Sackett, but by 1778 Washington's new network of spies - formally known as the Culper Ring - was finally put in place. The name "Culper" was Washington's own suggestion, named for Culpeper County, Virginia, where he worked as a surveyor in his teens. The hub of the network operated in New York City, which was where the British headquarters was located at the time. The leaders were Abraham Woodhull and Robert Townsend, posing as father and son duo Samuel Culper Sr. and Jr.. Whatever information their subordinates collected was passed along the grapevine to them via couriers Austin Roe and Jonas Hawkins. Townsend and Woodhull then funneled that intelligence to Major Tallmadge - alias John Bolton - who personally delivered the goods straight to Washington.

Although it began in New York City, the Culper Ring eventually extended its reach to include Long Island and Connecticut. From August 1778 to October 1783, the network was invaluable to Washington. They uncovered several plots by the British, including one to counterfeit American money, and an incoming surprise attack on Rhode Island by French officer Lt. General Rochambeau. The largest feather in their cap by far was the discovery of a British spy among Washington's most trusted officers: Benedict Arnold.

The Culper Ring had dozens of members, most of which went by code numbers or pseudonyms to protect their identities. Not even Washington knew many members' real names. This group was made up primarily of civilians, as Washington believed they would more easily infiltrate British regiments than soldiers would. Women were relied upon as often as men to carry information up the chain, as British soldiers usually didn't pay much attention to the fairer sex or a husband and wife traveling together.

One woman in particular, a Long Island housewife named Anna Smith Strong, routinely passed along signals and codes to nearby American soldiers... using - of all things - her laundry line. If she hung up a black petticoat, it meant a spy was back in town with fresh information. The number of handkerchiefs alongside it indicated which of his six prearranged meeting places he'd be waiting at for another agent to collect his gathered intelligence.

Another housewife, Lydia Darragh, found herself playing host to a group of British officers in the second story of her home. When they had meetings, she would listen through the wall and write down whatever she heard, hiding her notes in her teenage son's shirt buttons. Afterwards, her son would leave home to visit his older brother in a neighboring town, and his brother would give the buttons to the Patriot leaders in charge there.

Although many spies' true identities were later found out long after the Culper Ring disbanded, one appears to be lost to time forever: a woman, known only as Agent 355. According to an old Culper Ring codebook, the only hint to her true identity is the word, "lady". It's believed that the moniker was given because she was a woman of means, most likely the wife or daughter of a wealthy Loyalist. Her identity was supposedly kept so tightly under lock and key to protect herself and her family, out of fear of what the King might do if her treasonous ways were discovered. To this day, no name is as yet definitively assigned to this enigmatic woman.

Some experts posit that Agent 355 could have been Anna Smith Strong, but there is no concrete evidence to support this claim. For one thing, Anna Smith Strong's husband was a well-respected Patriot. She also had no known connections to the British aristocracy, as she was of a much lower socioeconomic status. Others have speculated that Benedict Arnold's own wife - Peggy Shippen Arnold - was Agent 355, as she had connections to British society. Again, nothing has been confirmed one way or the other, and this claim is flimsy at best, so who she really was remains a mystery.

One thing that most experts agree upon was that Agent 355 was a master of her craft. She was believed to be very outgoing; pretty and feminine with a sparkling personality, but also exceptionally clever. It is said she was able to outwit any man who dared cross her path. She may have acted as a courtesan or a peddler; a merchant or mistress; a comrade or a confidant. Anything in order to gain her mark's trust, and pump them for every scrap of information they had. It was through her direct efforts that Benedict Arnold's treason was discovered, and she also reportedly played a major part in the mission leading to the arrest of Major John Andrew, the head of the British intelligence operation in New York City.

One popular theory is that she was Robert Townsend's secret lover, and that their closeness allowed her to personally deliver the juiciest and most sensitive information straight to him. The only evidence to this theory is a letter from Woodhull to Tallmadge, detailing the capture of a spy and their subsequent imprisonment on a British prison ship in 1780. Although Agent 355 is not mentioned in the letter, nor is the spy referred to by name whatsoever, Woodhull wrote that the spy in question was "...ever serviceable to [their] correspondence." He also mentioned that the spy's capture had hit Townsend particularly hard.

Further credence to this theory came about in 1808. Townsend's son reported that his father petitioned New York City for a special monument, honoring patriots who had lost their lives aboard British prison ships. While not overtly damning, this piece of the puzzle does indicate that Townsend and someone who died on a prison ship were very close. Possibly more than friends... and many historians are sure that person was Agent 355.

Others are not sold on this theory, however. They believe that the moniker "lady" could have referred to a dozen different female spies instead of just one particular woman. If this is true, there could have been a small army of nameless, faceless women, all carrying the name Agent 355. While several women played key roles in the American Revolution, both in the public eye and in secret, it is widely agreed upon that Agent 355 was one person.

Still, there are others who believe there was no such woman. They simply cannot fathom that a woman like Agent 355 could ever have existed, and that she is nothing more than a myth, made to inspire American girls and romanticize the American War for Independence. Perhaps they are right. Or perhaps, the naysayers only believe her to be a fictional character because her skills of espionage and deception were so expertly honed. The debate is still very much open.

Maybe she was indeed captured, and met her tragic, untimely end on that prison ship. Or maybe she simply faded into obscurity; adopting the role of a caring wife or loving mother, and living out the rest of her days comfortably in a little house in a small, quiet New England town. Perhaps she moved back to England, staying in the limelight as a bubbly, charismatic socialite. Maybe she is just a fairytale. Whatever her fate may have been, one thing remains indisputable. Agent 355 was a bold, fearless individual who used her cunning, her beauty, and her sex to her advantage, all in an effort to help her country become the great nation it was destined to be.