The Secret Six: Our Spies in the Revolutionary War

When I think of spies, James Bond is one of the first persons who comes to mind. And I can’t think of him without thinking of out-of-this-world high tech, flying cars, magic watches and other indispensable tools of the imaginary spy trade.

So, I was intrigued by Brian Kilmeade’s book, George Washington's Secret Six: The Spy Ring That Saved the American Revolution, especially after reading his book about Teddy Roosevelt and Booker T. Washington. In spite of his sometimes-flippant persona on Fox News, Kilmeade has shown himself to be a serious historian as he works in concert with people who have strong research chops. His writing style is approachable, and his willingness to investigate less well-known topics engages the reader.

So, when I decided to read his book, it was another chance to see the Revolutionary War, not just through lost battles and harsh winters, but also through the bravery and creativity of the men whom Washington enlisted to use as spies, to give the Patriots a valuable edge:

The spies’ contributions included uncovering a British counterfeiting scheme, preventing an ambush of French reinforcements, smuggling a British naval codebook to Yorktown, and (most important) preventing Benedict Arnold from carrying out one of the greatest acts of treachery in American history: his plan to surrender West Point to the enemy. He could not defeat his foe with manpower, arms, or any other show of force. He would have to beat the British in a battle of wits.

Although some historians criticize Washington’s skills as a military leader, he proved to be an excellent leader of his army’s spies. He had fought in the French Indian War and had served as a spy. That experience served him well. He knew the kinds of men he needed to recruit as spies and the knowledge and experience they would require.

The first man he selected was Nathan Hale. Unfortunately, Hale was captured only weeks later and the specifics of his capture as a spy are uncertain. And he was duly hanged. Washington also recruited John Honeyman, who had allied himself with the Crown. But after being captured, Washington convinced him to infiltrate the Hessian troops and he planted a false story; it allowed Washington to defeat the Hessians at Trenton. That concluded Honeyman’s short but successful spy career.

At that point, Washington determined he needed a New York spy ring. Kilmeade tells the story of Benjamin Tallmadge who was the superintendent of the high school in Wethersfield, but when war broke out, he left the school and joined the Connecticut Continental Line on June 20, 1776. Eventually, he encountered an unexpected opportunity to help a young girl who was spying, and he also worked closely with Washington. As Washington got to know him, he picked Tallmadge as his spymaster.

The selection of the Secret Six began.

Kilmeade does an excellent job of telling us about the spies that Washington eventually selected. Each one had his own unique talents, reluctance or enthusiasm about taking risks, familiarity with the physical landscape, creative strategies for avoiding detection, and they all shared a patriotism that was admirable and important to Washington. One of the most intriguing facts was that a woman spy was enlisted; especially fascinating was the inability of researchers, after her tenure, to identify her. But Kilmeade devotes an entire chapter to investigating who the woman spy, called 355, might have been. Unfortunately, he was unable to identify her with certainty.He states at the end:

The one conclusion that is not possible is that 355 does not matter. Even if she did not exist as one person, several women risked their lives to serve, and one unknown friend of the ring was imprisoned following the unmasking of Arnold’s treachery. That heroism deserves to be honored.

Other unusual techniques were used to conduct their work. They had a unique tool, available in limited supplies, to keep their written messages secret: the invention of invisible ink. The spies developed numerous ways to disguise their hidden messages within conventional communications, so that the enemy would have no inkling that there were hidden messages within them.

Another unusual strategy was used for a spy who traveled on the waterways, with the cooperation of a homeowner:

The hanging clothes would appear as just that—wet clothes drying in the sun—to the untrained eye, but to Caleb Brewster, the arrangement of garments and their colors signified different counts of ships and troops, or in which cove it was safe for him to dock his boat, depending on which version of the story one hears.

I found Kilmeade’s book to be a fascinating way to broaden my knowledge about the Revolutionary War and acquaint me further with George Washington and the men who served him as spies. Their techniques were impressive enough that they are taught in the modern introductory training for federal agents.

I highly recommend the book as a supplement for those who are already familiar with the Revolutionary War, and are interested in exploring a key strategy for our victory against the British.