Jeffrey Keeten's Reviews > Washington's Spies: The Story of America's First Spy Ring

"I only regret that I have but one life to give for my country."
Nathan Hale

Statue of Nathan Hale at City Hall in Lower Manhattan.

Courage in the face of imminent demise. There is some speculation as to whether Hale actually said these words or some version of them. At this point it doesn’t really matter, they have become a part of the lexicon of our history. One thing that is not speculated about is that this young man of 21 went to his death displaying fearless gallantry. When the British hanged him for spying on September 22nd, 1776 they also unknowingly condemned a young man by the name of John Andre. George Washington seethed over the execution of Hale, and even though it was several years in the making, he did finally capture the perfect candidate to serve as an eye for an eye.

Nathan Hale was unsuited for spying. He was a Yale graduate, a rather attractive youth, a person that people would notice. One of Nathan’s classmates at Yale was Benjamin Tallmadge, the soon to be leader/handler of the Culper Spy Ring. One of his letters inspired the young Hale to join the rebel cause. Washington was trying to decide what to do about New York, abandon it, burn it, or try and hold it. He realized he needed more intelligence. He asked for a volunteer. Hale still caught up in the zeal of a fresh cause was the only man to step forward. Once in NY he was recognized in a tavern by Major Robert Rogers, one of those men who found the young Hale a bit too privileged. Rogers posed as a rebel sympathizer. Hale, inexperienced and feeling like a fish out of water and probably wanting to impress the crusty veteran, admitted the scope of his task.

Things wouldn’t turn out well for Rogers either, but that is another story.

Let’s flash forward to 1780.


Benedict Arnold an unfortunate traitor.

Benedict Arnold after years of battling his enemies in congress and being passed over numerous times for promotion is about to make a very bad decision. He is nearly bankrupt after using most of his personal fortune to pay his troops and furnish them with supplies. Congress is slow to reimburse him and sometimes even refuses to reimburse his expenditures. He is a legitimate war hero best known for his capture of Fort Ticonderoga. He was a commander that led from the front, a dashing man in the mold of George Armstrong Custer. Confidence and competence exuded from him like a musk. His men would have followed him into the pits of hell if necessary, but men like Arnold also collect enemies. Washington had no doubts about his ability, but he was also tired of the numerous letters of complaints he received from Arnold. He was constantly mediating issues between Arnold and Arnold’s enemies in congress. Washington had a war to win, and though Arnold was important to him, he had other pressing things to worry about.

Arnold was pissed off.

He was also married to Peggy Shippen, a woman from a deeply loyalist family. She was “good friends” with John Andre. (It was rumored that he was also her paramour, but that is on the QT.) Andre was close friends with Sir General Henry Clinton; in fact, being fluent in four languages he wrote a good part of the General’s correspondence. Andre was a handsome man and you would think an intelligent man, but his fiancee broke off their engagement because he lacked “the reasoning mind she required.” Hmmm maybe she was an astute young woman and could see that a life with a dashing, handsome husband might be a life of trouble and heartache.

Because of his connection to the Arnolds and his close association with the General, Andre soon finds himself in the awkward position of carrying dispatches between the two parties. He was the lynchpin facilitating the Arnold negotiations for defection.

Andre is caught with compromising dispatches.


John Andre

Washington finally has the man who will pay the price for Hale. Andre asks for a firing squad, but of course he must be hanged. The American officers who held him captive, which shows how charming the young man was, weeped at his execution. Symbolism negates reason.

Benedict Arnold has always been an interesting figure to me. I read Willard Sterne Randall’s book Benedict Arnold: Patriot and Traitor many years ago and the author certainly poked holes in my previous opinions about Arnold. I’d always thought of him as the ultimate turncoat. In fact on the school yard I can remember using his name to describe a teammate that suddenly switched sides in the rough and tumble football games that often left me bruised, battered, and elated.

He is most assuredly a traitor, but he is also a tragic figure. If he had stayed with the cause schools, roads, counties, and cities would have been named after him. He would have been among the paragon of great soldier patriots. He traded that, out of frustration, for $500,000 and a promise of a knighthood. The thing of it is no one likes a traitor, even the side that benefits from the defection. They can never trust that person and many of them actually despise that person. If his service to his country had been properly recognized. If congress hadn’t been actively trying to destroy his life even to the point of bringing fraudulent charges against him there is no doubt in my mind that he would have stayed a patriot. I might have found myself attending Benedict Arnold High School.

We can really only guess how many Americans were Loyalists or Tories, but the high estimate is about 500,000 or twenty percent of the white population. Only about 19,000 of those men actually picked up weapons to fight against the rebels, so people, with a few angry mob exceptions and an occasional burning of a loyalist home, lived side by side with opposite views of the war. As long as you didn’t actively help one side or the other your life could go on with only the normal stresses of living during a time of war. After the debacle of the Nathan Hale situation it became apparent that it was best to recruit people who actually lived where the intelligence needed to be gathered.


Poster for the show Turn on AMC.

This brings us to Abraham Woodhull. For those that have been watching the series on AMC called Turn this man is the basis for the main character. Major Benjamin Tallmadge is the leader and primary recruiter for the spy ring. He went by the name Samuel Culper. Woodhull signed his dispatches Samuel Culper Sr. and the New York connection Robert Townsend used the name Samuel Culper Jr. Not much imagination being used in the naming of the operatives. None of these men recruited by Talmadge asked for money other than what was needed to reimbursed their expenses.

So Robert Townsend was located in NY. He would pass information to a courier who would leave the dispatch on Woodhull’s property. Woodhull would then add his own observations to Townsend’s. Woodhull’s neighbor Anna Strong would arrange her laundry a certain way to signal that the whaler Caleb Brewster was in the vicinity. Woodhull would then pass the information to him for delivery to Tallmadge. Invaluable information was passed to Washington that certainly had an impact on the future of the war. Washington was always impatient for information arriving quicker, but Townsend and Woodhull were always well aware of the precarious nature of their situation and always errored on the side of caution.

They used invisible ink (gallic acid) that gave the dispatchers some level of security.


Abraham Woodhull to Benjamin Tallmadge.

Alexander Rose has done a wonderful job piecing together what is known about the Culper Ring, and certainly filled in some gaps for this reader. Sometimes the information is sketchy because these men and women after the war just went on with their lives. They didn’t write about their experiences or even talk about it. In some degree there is a feeling of shame associated with spying. The reason they didn’t take pay is because they saw it as a duty not as a way to make money. They were working for a better future for themselves and for their descendents. The life of a spy, no matter which conflict whether it be the Cold War, Civil War, or the Revolutionary War, is a lonely existence. The fears and agitations are theirs alone. To alleviate the stresses by talking to a friend only puts people they care about in danger. They are the unsung heroes, the men and women in the shadows, more worried about results than immortality.

If you wish to see more of my most recent book and movie reviews, visit http://www.jeffreykeeten.com
I also have a Facebook blogger page at:https://www.facebook.com/JeffreyKeeten