“bright career” and end in “ignominious death.” Hale listened to this advice but decided that he needed “to be useful, and every kind of service, necessary to the public good, becomes honorable by being necessary.”2
The faithful Sgt. Stephen Hempstead accompanied Hale, leaving Harlem Heights and traveling to Norwalk, Connecticut. Hale handed a “general order” to Captain Pond of one of the sloops there and silently slipped across the Sound with Hempstead. At Huntington, Long Island, Hale changed his uniform to a suit of plain brown, “assuming the character of a Dutch schoolmaster,” keeping only his college diploma with him as evidence of his qualifications for that job. Hempstead sailed back to Norwalk, and Hale walked in disguise toward Flushing. He began drawing maps and taking notes on British positions.3
The following events are unclear, but Hale might have been betrayed by his cousin, who, though he denied it, fled to England. Nathan may also have revealed himself to Col. Robert Rogers, a double agent. Whatever the case, he was discovered and brought to Sir William Howe. Now in possession of a smoldering Manhattan, Howe ordered the spy executed, and on the morning of September 22, 1776, Hale was brought to a makeshift gallows in Artillery Park. While waiting amid the haze of smoke from the fires, he was allowed to write letters to his father and commanding officer. Then he was taken to the gallows, where the provost marshal took the letters and destroyed them, refusing him either clergy or Bible. According to Frederick Mackenzie of the Welsh Fusiliers, Hale maintained his “composure and resolution.” The hangman asked if he had any last words, which he did, “saying he thought it the duty of every good officer, to obey any orders given him [by] his Commander in chief; and desired the spectators to be at all times prepared to meet death in whatever shape it might appear.” And then he offered a paraphrase from Joseph Addison’s play Cato, probably learned in those more joyous hours in the Linonian Society at Yale: “I only regret that I have one life to lose for my country.” Later that day, a flag of truce discussing the exchange of prisoners reached headquarters. George Washington, Alexander Hamilton, Israel Putnam, and William Hull received the messenger, who had witnessed Hale’s execution himself and reported it to the group of American officers. A shocked Hull tried to hold back the tears in front of his superior officers.4
Hale’s body was left hanging, and a few days later some mischievous British soldiers added a board painted with the words “General Washington” to the grisly scene.5 His death was a reminder that despite the honor codes of war at the time, this was not only a war of gentlemanly conduct, parleys, and soldiers in formation firing at one another. It was dirty and brutal, and the methods by which it was carried out were just as horrific as or worse than any modern war. The casualty lists are deceptive, usually giving only the soldiers killed in pitched battle. People rarely died in battle—they died later of gangrenous wounds, of smallpox, of pneumonia. Men froze to death in winter camps and women suffered enemy soldiers’ brutality.
It might be helpful to separate the war into three smaller wars, into actual battles fought by armed regiments, the struggle for money and supplies, and the shadow war of spies and prisoners fought in the back country, often by ordinary citizens, in which loyalty and courage was tested in a completely different way. Nathan Hale had been one of the first casualties of that war, at which the British had long been experts. George Washington knew that he had to improve his own chances, and after Hale’s death decided to set up a semi-official Secret Service Bureau. There was a problem, however. Spying was thought the lowest of the low, “ignominious” as William Hull put it. What man would lead it? The answer was Benjamin Tallmadge.
Nathan Hale’s reputation grew in the decades after his death as his story was elevated to myth. Here, the British commander destroys documents before ordering his execution. Cunningham Destroying Hale’s Letters, in Benson Lossing, The Two Spies (New York: Appleton, 1897), University of Bridgeport Archives.
Why would a promising young soldier in the dragoons decide to become Washington’s spymaster? Perhaps it had something to do with his best friend’s death. Perhaps he wanted to prove that such activity was not ignominious. But years later Tallmadge remained circumspect about his activities as George Washington’s chief intelligence officer, stating, “I opened a private correspondence with some persons in New York (for Gen Washington) which lasted through the war. How beneficial it was to the commander-in-chief is evidenced by his continuing the same to the close of the war. I kept one or more boats continually employed in crossing the Sound on this business.”6 In such understated remarks he was referring to taking charge of the network of spies that Washington was using, primarily in New York City.
Tallmadge’s career in the regular army is impressive, though not as impressive as Benedict Arnold’s. In June 1776 he joined the army in New York to wait for the British fleet and took part in those awful battles in which the overwhelming force of British redcoats pushed General Washington and the American brigades off Long Island, then off Manhattan, and back to the heights of Westchester County. He was promoted to captain in December of that year by George Washington himself, having been one of the few to have fought bravely throughout the terrible campaign. During that winter, while the exhausted army rested in New Jersey, he returned to Weathersfield to train a regiment of dragoons. In the spring of 1777, at the head of his regiment, he marched from Weathersfield all the way to Morristown, where he joined Washington in that season’s campaign. By July he had been promoted to major and became a field officer in the regiment. He took part in all the combat in Pennsylvania during that autumn, fighting at Brandywine and Germantown.7 As commander of his light dragoon company, Tallmadge was praised by Congress.8
But he began doing much more. While Washington and his men suffered at Valley Forge, Tallmadge and detachment of dragoons spent their time galloping around the no-man’s-land between the camp and Philadelphia, fighting off patrols of British light horses. This appears to have been largely cover for espionage work. On one occasion at least he rode to Germantown and met a female spy, who had ventured into Philadelphia on the pretense of selling eggs. As he was talking to her, a British patrol arrived, and he grabbed the woman and galloped with her for three miles before letting her off at a safe place.9
As the northern war settled into a standoff, he began his other work in earnest. By 1778 he corresponded with “Samuel Culper,” the name assumed by the two chief spies in New York, Abraham Woodhull and Robert Townsend, while his own code name was John Bolton or simply #721. He received constant intelligence as to British troop strength and position. They used invisible ink invented by John Jay’s brother James, and by 1779 Tallmadge was even using a cipher code similar to ones used by the British. Pocket dictionaries with this code were used by his spies to decode and encode messages.10 Meanwhile, he kept up an extensive correspondence with George Washington, keeping the commander in chief apprised of all the intelligence. Though not strictly written in code, this correspondence remained vague and indeterminate, with lines like “You will be pleased to observe the strictest silence with respect to ____ as you are to be the only person intrusted with the knowledge or conveyance of his letters.”11
He had a difficult job. The British had the best secret service in the world in the eighteenth century, with professionals who stuffed messages inside hollow silver bullets that could be swallowed if necessary. But no matter how good they were, spies still had a dangerous job. Israel Putnam caught one and wrote to the Tory governor of New York, William Tryon,
Sir—Nathan Palmer, a lieutenant in your service, was taken in my camp as a spy; he was tried as a spy; he was condemned as a spy; and you may rest assured, sir, he shall be hanged as a spy.
I have the honor to be, &/C.
ISRAEL PUTNAM.
P. S. Afternoon. He is hanged.12
Luckily for the British,
