Summary
Chapter One
Nathan Hale was a young man attending Yale with his best friend Benjamin Tallmadge in the years of escalating tension before the Revolutionary War. After graduation, the two men both became school teachers. Hale enlisted in Connecticutâs Seventh Regiment on July 6, 1775, about three weeks after the Battle of Bunker Hill. Shortly thereafter, the Seventh was sent to Long Island, where General George Washington was expecting the arrival of British troops, under the command of General William Howe, at any time. When the British arrived, the Americans retreated to Harlem Heights, and then further north. Washington began seeking someone to go behind enemy lines for information. By September 1776, Hale was leading a group of Rangers, and he volunteered to conduct a covert mission. Unfortunately, the arrival of his ship caught the notice of Robert Rogers, an American ranger in the British army. Rogers approached Hale in a tavern and pretended to be a fellow Patriot, whereupon Hale, believing himself in the presence of a comrade, confessed his espionage mission. Hale was promptly arrested, and his death warrant signed by General Howe. He was hanged September 22, 1776.
Need to Know: The Patriots were informed immediately of Haleâs death, and were obviously angry and dismayed, but Washington used this as a learning experience to improve the methods and secrecy of his spies in the future.
Chapter Two
With Washingtonâs troops having retreated to Harlem, some well-meaning Patriots thought it better to set fire to Manhattan rather than cede it to the British. A few of these Patriots were caught and executed in the streets by British soldiers. Afterward, New York City fell into a derelict state of shanty towns and black-market trading. Amid clashes at White Plains, Trenton, and Princeton, New Jersey, Washington conducted a search for reliable spies. One came to him from New Yorkâs Committee for Detecting and Defeating ConspiraciesâNathaniel Sackettâwho would work with Nathan Haleâs classmate Benjamin Tallmadge, and Major John Clark. Messages were carried to Setauket on Long Island, to Connecticut, and on to Washington (then, stationed in New Jersey). Sackett sent men into Long Island pretending to be Loyalists in order to get closer to British troops and report back. Washington fired him after only a few months of service, although it is unclear why. British and American troops alike were aware that there were spies among them, and executions over mere suspicions were frequent.
In the summer of 1777, British General John Burgoyne set out from Canada, hoping to unite with the troops of two other contingents, General Howeâs and Sir Henry Clintonâs, and separate New England from the rest of the colonies. Burgoyne was defeated in battle near Fort George, and when his expected reinforcements did not come, he was forced to surrender. In Pennsylvania, General Howe engaged with Washingtonâs troops near Brandywine, en route to capture Philadelphia. The Patriots were forced to retreat. Washington continued to run spies, some of whom were feeding the enemy false information. Upon Major Clarkâs retirement, Benjamin Tallmadge, now a major with an impressive tour of duty under his belt, stepped into his place as spy recruiter. The British found their position in Philadelphia too precarious and abandoned the city. General Howe resigned as commander-in-chief, and Henry Clinton was promoted.
Need to Know: Sackett virtually invented the espionage long game. Whereas before, spies were sent on brief missions to peek behind enemy lines and quickly report back, Sackett was the first to plant moles with invented identities to stay among the enemy for extended periods of time.
Chapter Three
In August 1778, French Admiral Charles-Hector, Comte dâEstaing, engaged with the forces of Admiral Howe (brother of General Howe) near Newport, Rhode Island, and was forced to retreat. Shortly thereafter, Washington began receiving reports from Lieutenant Caleb Brewster, a former whaleboatman, through Tallmadge, charting the movements of Howeâs fleet. Tallmadge also recommended a friend of his to join the spy ring, a farmer named Abraham Woodhull who had been passing freely through enemy lines as a smuggler, before he was caught and arrested by the Americans. Washington had him freed from jail to join his team of spies, which they would call the Culper Ring, a reference to Woodhullâs code name, Samuel Culper, later âCulper Senior.â Woodhull, Tallmadge, and Caleb Brewster were all from Setauket originally; Calebâs father had been the town minister, and when he resigned, his congregation was taken over by Tallmadgeâs father. Woodhull preferred life on the family farm, but he was motivated into action by the death of his cousin Nathaniel, a general who had been captured by the British army and suffered horribly from negligence in prison, dying of a gangrene infection. Woodhull officially joined the spy ring in October 1778, making reconnaissance trips to New York and reporting back to Tallmadge and Washington. In November, he filed a detailed report of the locations, numbers, and movements of the British troops stationed on Long Island.
Need to Know: It was paramount that Brewster, Woodhull, and Tallmadge grew up together in Setauket because o...