My historical novel, To Outwit Them All, (Iron Stream Media, October 2025) is inspired by the true story of George Washington’s Culper Spy Ring, which operated in Long Island and New York City at the height of the American Revolution, between 1778 and 1781. The novel takes the reader on a suspenseful journey back to when spies not only lingered in the shadows of the brothels but danced amid the lamp-lit ballrooms of New York high society.

To Outwit Them All is told through the eyes of the lone female member of the Culper Ring, who is known to this day only by her code name, 355. In the story, however, her name is Betty Floyd, cousin to Robert Townsend, aka Culper Junior. We know that Townsend was a store owner and reporter, using his positions to gather intelligence for the Patriot cause.

The idea for the novel began when I perused a list of important women in American history. One name stood out, or rather, a number—355. I wanted to know more, so I studied all I could find about the Culper Ring and this elusive lady. In addition to resources such as Washington’s Spies by Alexander Rose and George Washington’s Long Island Spy Ring by Bill Bleyer, I poured over obscure articles in the New York Public Library’s historical collection and peppered New York and Long Island historians with questions.

One book I discovered was George Washington’s Secret Six by Brian Kilmeade and Don Yaeger, which lists several possible candidates for 355, why each might have fit the bill, and also why not. One was Betty Floyd, and although there are few concrete facts about her, what we do know led me to consider the possibility of her involvement with the Culper Ring and write her story.

Betty was born on Long Island in August of 1758, a distant cousin to Robert Townsend and the niece of William Floyd, a signer of the Declaration of Independence. She was at the right age to be acquainted with future Culper Ring members and their families in addition to Townsend, who all grew up near Setauket, a village in central Long Island.

In 1778, when Betty would have been 20, a coded letter was sent to Benjamin Tallmadge, George Washington’s Director of Intelligence and founder of the Culper Ring. The letter came from Abraham Woodhull, aka Culper Senior. In the letter, Woodhull states, “I intend to visit (New York) before long and think by the assistance of a (lady) of my acquaintance, shall be able to outwit them all.”

Who was this lady who would outwit them all, and ultimately have a significant role in the Culper Ring?

It seems Woodhull knew her and believed she would be instrumental in helping the Culper Ring “outwit” or outsmart the British, who were then occupying the city. This lady (or 355 in the Culper code) must have been living in New York at the time. With Robert Townsend already in New York, it would have been relatively easy for him to bring his younger cousin Betty into the Ring, who may have known Woodhull from Setauket.

If Betty was 355, she would have socialized with the many British officers in New York, gaining their trust and gleaning intelligence to pass on to Townsend, who would add the information to his own reports to Washington. One such officer was undoubtedly Major John André, Britain’s Director of Intelligence, well-known among the ladies for his charm and good looks. As Betty danced and flirted with André, he may have let secrets slip, never suspecting the young lady on his arm was one of the spies he was urgently trying to catch.

Original records have been lost, yet there is some evidence that a Betty Floyd died aboard the Jersey, one of the British prison ships anchored near Brooklyn in Wallabout Bay. Roughly two dozen women were imprisoned aboard the hellish ships, with over 8000 prisoners in total. Elizabeth (Betty) Floyd was a common name, but why was she a prisoner? Had she been arrested for spying? If she was Townsend’s cousin, it would explain why he evidently was deeply troubled around the same time and temporarily left the city.

Records also show, however, that a Betty Floyd with family connections to Robert Townsend died in New York in 1820, at the age of 62. Were they two different people? Or what if Townsend’s cousin Betty truly was an imprisoned Culper spy, but didn’t die on the Jersey?

Except for 355, all of the six main Culper Ring members have been named. There are several theories about her identity, and although they are compelling, none have been proven, and we may never know her real name. In addition, some experts believe the number 355 in the Culper Ring’s code stood for any lady, not a particular person.

After the war, none of the Ring members wished to be named or wanted any notoriety. If the mysterious 355 was indeed Betty Floyd, she may have covered her tracks so well that she will never be found out.

Authors of historical fiction are often unable to find all the answers to their questions. They use what records exist and then may fill in the blanks by piecing together other information. As we approach the 250th birthday of our nation, let us take a fresh look at the mysterious lady behind some of the most covert actions to aid the Continental Army, leading to independence—and consider Betty, the Signer’s young niece, whose story can finally be told.