forth once more,
But fearing soon to run ashore….
For this I leave my wonted course,
with you, and seek for aid from verse.90
Maybe it was a less poetic kind of aid Tallmadge thought his friend was asking for, because on June 20 he rode up the dusty track to Hartford, where Governor Trumbull gave him a lieutenant’s commission.91
Only five days after Tallmadge joined up, British warships began appearing in New York Harbor. Throughout the hot, tense summer, more and more arrived, cutting off Long Island, spreading up the Hudson, just out of cannon range. Hale handed out new equipment to his men, preparing for an epic conflict.92 Then, sometime in August, he switched to a company of Rangers to patrol the shores of Manhattan and Westchester. In doing so, he missed the biggest battle on the continent since Europeans had arrived.
On August 22, twenty thousand British troops landed on Long Island and smashed into the American lines, pushing them back across Brooklyn. Those troops not captured or killed barely escaped, retreating back against the East River. Tallmadge had just arrived in Brooklyn and remembered the retreat: “It was one of the most anxious, busy nights that I ever recollect, and being the third in which hardly any of us had closed our eyes in sleep, we were all greatly fatigued.”93 At last they reached Brooklyn Ferry and crept across the river to Manhattan. It was one of George Washington’s most skillful maneuvers, though there is little glory in retreat. Israel Putnam was astonished they had escaped from Long Island, saying the British commander “is either our friend or no general…. He suffered us to escape without any interruption.”94 Meanwhile, David Bushnell of Westbrook sent his Turtle submarine into New York Harbor, attempting to attach mines to the hulls of British warships, but this technological ploy was unsuccessful.
Connecticut’s front with British-controlled New York and Long Island lasted from 1776 to 1783, leading to dozens of confrontations. Connecticut and Parts Adjacent, Geography and Maps Division, Library of Congress.
It was the beginning of a bad season. Throughout the autumn British troops whipped the Continental army off Manhattan and up through Westchester County. Stopped at the line of hills at the southwest corner of Connecticut, they pushed Washington and the main army across the Hudson River and into New Jersey. On December 7, 1776, another British force occupied Newport, Rhode Island, while a huge British fleet patrolled the Sound, effectively surrounding a panicked Connecticut on three sides.95 Things must have seemed bleak indeed. But there was no turning back. These patriots had committed themselves now, through both declarations and blood, through fire and sacrifice. They were bound through comradeship and oaths, through the connections they had created before the war and through the ones they continued to make in the thick of the struggle. And each of them now faced an uncomfortable prospect: victory or death.
The Shadow War
GEORGE WASHINGTON needed information. No one could run a war without it, and now that the British had occupied Long Island, he needed to know what their next move was. He wrote to his generals on September 1, 1776, and told them he needed a “channel of information” through Tories willing to take a bribe, but “friends would be preferable, if they could manage it.”1 The officers filtered this request carefully down through the ranks, until it reached Nathan Hale, who saw in the job a chance to do something positive for the war. After all, he had yet to participate in a battle.
A college friend from Derby named William Hull was stationed nearby, and Hale asked his advice about the job of “assuming a disguise and passing into the enemy’s camp.” Hull argued against it, saying first that spying was “not in keeping” with Hale’s “character,” and then putting down the entire idea, calling this sort of action was “moral degradation.” He asked, “Who respects the character of a spy, assuming the garb of friendship but to betray?” He insisted that it would end Hale’s “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