Brian Kilmeade and Don Yaeger. George Washington’s Secret Six. Sentinel, 2014.

Brian Kilmeade turns history into great story-telling. George Washington’s Secret Six tells a gripping, even page-turning story about a group of New York based Patriot spies during the American Revolution. The idea became simple; the execution of the idea, not so simple.

Washington, Commander of the Continental Army, needed intelligence, especially about British activities around New York City, which was occupied by the Redcoats during most of the war. He learned the hard way with the hanging of Nathan Hale just a few weeks after Hale had volunteered. He needed insiders who knew their way around and were above suspicion. They also needed an effective way to communicate and to keep their identities secret, even from each other.

The secret six were known as the Culpers or the Culper Ring. Two of the men involved adopted the pseudonyms Culper, Sr., and Culper, Jr. The authors say there were actually seven in the ring, but only six have been identified today. The woman known as Agent 355 has never been identified. That is how well they kept their identities. The only reason we originally knew anything at all about the ring was that one of the men, Benjamin Tallmadge, wrote his memoirs for his children. The memoirs were not published until 1858, eighty years after the ring was established and thirteen years after Tallmadge had died.

Then in 1939, historian Morton Pennypacker published the surviving letters of Washington to and from members of the Culper ring. Some of the identities were still unknown then, but further evidence has identified all six of the men referred to in the letters. All had some kind of skill but also were generally above suspicion because they were locals. Hale was from Connecticut and suddenly appeared in Long Island. The Culper spies lived in New York City or Long Island and for the most part kept the livelihoods they had before the war.

Tallmadge was an officer in the Continental Army and had proven himself as a scout. A native of Brookhaven, Long Island, New York, he knew his way around the area and knew many of the people there. He recruited some of the others including a Long Island neighbor, Abraham Woodhull. Woodhull had inherited a family farm and minded his own business. One of his married sisters lived on Manhattan, and he would visit her fairly regularly. From such travels and talk with people who worked on the water, he could provide reliable information about British positions and naval vessels.

Robert Townsend worked in New York City but had family in Oyster Bay, Long Island. His family home there had been taken over by a British officer. Townsend was something of a loner, but he observed and listened and was able to report on British activities both in the city and on the island.

Caleb Brewster and Austin Roe were Long Islanders who also had connections. Roe ran an inn on Long Island and was able to observe and report on many things he heard and saw there. (As an aside, I happen to know there are still Roes living on Long Island.)

Brewster was a longshoreman and sailor whose job was not only to observe what was going on along the coast but to ferry people and letters to Washington across Long Island Sound to Connecticut. From there, he or someone else would travel west, north of the area of British occupation, to Washington’s headquarters.

James Rivington, like Townsend, worked in New York City. He had family in England and ran a newspaper and publishing house in the city. The newspaper supported the Tories, and British officers and officials frequented his establishment. He was able to pass much information on to Washington. He gave Washington a British code book, so that Washington was able to anticipate British movements. We do not know whether Rivington actually printed the book for the English, a good possibility, or obtained in some other way, maybe from Agent 355.

The authors tell us that the ability to crack British codes was especially significant at the Battle of Yorktown. Rivington’s cover was so effective that after the war, Washington had to personally intercede on his behalf to assure others that Rivington was truly a patriot.

And then there is Agent 355. We know she was a woman who circulated among the British elite in New York. She was able to pass on both political and military information. At some point something happened to her. Robert Townsend was one person who knew her true identity and from his correspondence was very upset when she was exposed in some manner. An afterword (to the paperback edition) names seven women who might have been Agent 355, but no certain ID has been established.

Once the spy ring was fully operational by 1779, things began to turn around for the Continental Army. Washington could operate on reliable intelligence—the Culper Ring was by no means his only source, but many times information from the ring would confirm what other sources had been telling him. Not only was their information critical as the fighting moved south, culminating in Yorktown, but information the ring provided was instrumental in exposing Benedict Arnold and John André.

One interesting detail provided apparently by the Culper letters was that Washington really did not want to execute Major André. He would have preferred to swap him for Arnold, but the British refused, so André was tried and executed as a spy.

Indeed the ring would not have succeeded nor would there be any Culper papers if it had not been for the invention of a proprietary invisible ink formulated by John Jay, himself, of course, a New Yorker, patriot, and future Chief Justice of the Supreme Court.

Indeed, we are reminded throughout the book that while spying was essential, it was considered a breach of the rules of war. As with Nathan Hale, captured spies were usually executed summarily. Some think that that may have been what happened to Agent 355. There were a few women captured by the British and taken to prison ships. Possibly that is what happened to her. On the other hand, one name that pops up also is Peggy Arnold, Benedict’s wife.

According to an article in The Smithsonian, however, the whole idea of 355 being an agent is likely a myth. 355 was simply the code term for “lady.” It suggests she was rather merely a lady of Woodhull’s acquaintance who knew a few things. The truth may be somewhere in among these speculations, but to this day, no one knows.

This is overall a fascinating tale, with or without Agent 355. Enjoy!

P.S. One general observation made by Kilmeade and Yaeger was not specifically about the spy ring but about the nature of the American Revolution. We can learn something from that today—something that might apply to some of America’s overseas military ventures and even something that makes us wonder about Russia’s invasion of Ukraine.

In those [nation vs. nation] battles, it was all about might; the armies fought until someone was finally overpowered. Or, as happened so often in new territories, one army fought…until the other population was simply eradicated. Washington realized that this revolution was different. King George respected no one and recognized no authority…His increasingly oppressive laws and his silence in the face of organized protests had made that clear. Yet the king would not seek to completely decimate the population of the colonies; dead subjects cannot pay taxes.

No, this war would be different…It would not be a fight to the death, nor could it be simply a clash of armies. If the Americans wanted to emerge victorious from this conflict, they would not try to overpower their enemy; they would simply refuse to back down or go away. They did not need to be conquering heroes—they just needed to survive. (19)