One of the most captivating and controversial parts of the Culper Spy Ring's history is Woodhull's possible female recruit. Her role has been the center of much of the recent debate over the Culper Spy Ring, and historian Alexander Rose, who did compiled the history of the Culper Spy Ring through the original manuscripts, suggests perhaps these letters refer to Anna Smith Strong, a woman who is said to have signaled the presence of Caleb Brewster to Abraham Woodhull. Rose suggests Woodhull planned to have Strong accompany him on trips to Manhattan.
However, this is highly unlikely, given that Strong was already in a dangerous situation, being the remaining guardian of a leading Patriot's estate. She had recently called in many favors with powerful family members to free her husband on parole from the prison ships in New York, and he was living in Connecticut. She would not want to jeopardize his safety, and any departures she made from the estate would be rather suspicious since her reason for being there, rather than with her family in Connecticut, was to protect her home. Signaling could readily be accomplished from her home, but traveling to New York is not a logical role for Strong, whose traditionally credited role of signalwoman would have required her participation from very early on.
Regardless of who Woodhull was referring to, he did write on August 15, 1779, in the midst of Townsend's struggle to acquire decent military intelligence, that he intended to travel to New York City soon, and expected to be able to "outwit them all" with the "assistance of a 355 of my acquaintance." Woodhull frequently used code numbers to replace words from Tallmadge's code book, and in this instance 355 was the number used for the word "lady." The choice of the word lady suggests a person of status in this time period.
There are no other references to a lady, although the Culpers did occaisionally refer to reports from other "sub-agents" and if she was working as a spy with them, her reports may have been written up as part of these, often attributed to "friends." In October of 1780, Woodhull did write of the capture of several friends in Arnold's spy hunts, "including one who hath been ever serviceable to this correspondence," suggesting there was a person working with the ring who contributed more than was typical of their "friends." After Andre's death and while he was gone, Culper intelligence was never the same, which has contributed to the suggestion that the British captured the Culpers' best agent--a woman closely connected to Major John Andre. Supporters of the female agent theory are also quick to point out Townsend's emotional devastation after the capture of these people, which family records suggest he never recovered from.