Deception and secrecy are underlying themes that run through recent news about everything from covert funding of right-wing influencers in the US to the remotely programmed detonation of Hezbollah pagers and walkie-talkies in Lebanon.
The shadow world of spying may conceal the identities of people involved in operations like these for a time but eventually we will likely learn who directed them and more about how they were carried out.
In the meantime, there’s a rich history to explore of US intelligence efforts going back to revolutionary times.
This Sunday, September 22, marks the 248th anniversary of the execution of Nathan Hale, the 21-year-old novice spy recruited by General George Washington’s army to help divine the intentions of the British expeditionary force in the early months of the Revolutionary War.
In America’s founding mythology, Hale is often considered the nation’s first spy, though his career in intelligence lasted only a few weeks.
Hale’s mission is commemorated in a statue unveiled by the CIA on June 6, 1973, at its Virginia headquarters. The date was 200 years after Hale’s graduation from Yale, which had commissioned the original version of the sculpture by Bela Lyon Pratt.
“The statue captures the spirit of the moment before Hale’s execution. A 21-year-old man prepared to meet his death for honor and country. His hands and feet bound, face resolute, and gaze fixed on the horizon,” the CIA said.
Since 2022, another American’s statue has occupied a place of pride at the agency’s Langley, Va. headquarters campus — it honors Harriet Tubman. The CIA described her as “a symbol of freedom and an intelligence pioneer.”
While examining the role of today’s intelligence community for a post earlier this week, I was drawn to learn more about these two Americans who are venerated by the CIA.
The vividly contrasting stories of Hale and Tubman give us clues to the role of spying in American history. They show the risks facing secret agents, the crucial importance of securing knowledge about what your enemies are planning, the necessity of good tradecraft and the perishability of information.
Hale’s life
Little is known of the details of Hale’s journey as a spy, but a vivid portrait of the young man emerges from an 1856 biography by Isaac William Stuart, titled “Life of Captain Nathan Hale, the martyr-spy of the American revolution.” Stuart’s effusive book describes Hale as a paragon of virtue, intelligent, affable, generous, athletic and empathetic and “a favorite with the ladies.”
Born in Coventry, Connecticut, Hale was the sixth of 12 children. His father was “a man of sterling integrity, piety and industry,” a farmer, church deacon and member of the General Assembly. His mother was “a lady of high moral and domestic worth,” Stuart wrote.
After Yale, young Hale began teaching school in East Haddam, Connecticut, and quickly proved to be a success in that field, moving on before long to a bigger role at a school in New London.
Stuart noted that Hale was about five feet, 10 inches tall. “His figure was elegant and commanding. He had a full broad chest, full face, light blue eyes, light rosy complexion, and hair of a medium brown.” (The statue by Pratt isn’t a reliable depiction of what Hale looked like; it was based on a model chosen by the sculptor decades after Hale’s death.)
When the battles of Lexington and Concord erupted in April, 1775, Hale was among many young Americans eager to join the cause. At a town meeting in New London, Hale spoke up decisively: “Let us march immediately and never lay down our arms until we obtain our independence!” he is reported to have said.
He enlisted as a lieutenant in the Seventh Connecticut Regiment, under Colonel Charles Webb’s command. Though he was promoted to captain in 1776, Hale did not engage in any “military successes, of dazzling splendor” as the war ground on. He did win plaudits for his effective leadership of troops. At a time when citizen soldiers were tempted to return to their farms and villages at the end of their enlistment periods, Hale noted that he “promised the men if they would tarry another month they should have my wages for that time.”
Stuart sets the scene for Hale’s recruitment as a spy. “The disastrous battle of Long Island had been fought, and the American troops, filled with despair, had retreated to the Island of New York [Manhattan].”
One fourth of the revolutionary troops were “on the sick list.” One in three lacked a tent. Supplies for the coming winter were scarce. And the 14,000 troops fit for duty were dwarfed by a well-equipped British force on Long Island with more than 25,000 troops and ample ships.
What would the British, encamped in Brooklyn and posing a threat of invasion to the west, do next? Washington needed the answer and asked his officers to find someone who could provide it.
‘Companion of darkness’
Spying was viewed as “ignominious,” and a “fraud unworthy of an open, manly enemy,” Stuart observed.
“The spy is the companion of darkness. He lurks — he hides —or if he moves in the light, it is behind walls, in the shadow of trees, in the loneliness of clefts, under the cover of hills, in the gloom of ditches, skulking with the owl, the mole, or the Indian.” And to be caught as a spy in wartime was certain death.
So there were many American officers who turned down the assignment. Captain Nathan Hale said, “I will undertake it.”
He noted, “for a year I have been attached to the army, and have not rendered any material service, while receiving compensation for which I make no return….if the exigencies of my country demand a peculiar service, its claims to the performance of that service are imperious.”
One of Hale’s friends, Captain William Hull, “tried to talk Hale out of carrying out the mission and facing what he considered a guaranteed death,” as Mary Tsaltas-Ottomanelli wrote,
“To be a good spy, you need to be a good liar — a skill Hale likely hadn’t perfected. Hale also couldn’t help but carry himself like a soldier and did not easily blend into a crowd. He had a powder burn on his cheek, a most unusual and suspicious scar for a schoolteacher.”
“To be a good spy, you need to be a good liar”
“Hull didn't believe Hale was right for the mission, writing that it was ‘not in his character; his nature was too frank and open to deceit and disguise, and he was incapable of acting a part equally to his feelings and habits.’”
After receiving “particular instructions” from Washington, Hale left the American camp at Harlem Heights and journeyed to Norwalk, Connecticut, where he boarded a sloop for the eight-mile journey across Long Island Sound to Huntington, Long Island.
Connecticut was friendly to the revolutionary cause while Long Island was controlled by British loyalists. Hale had taken off his silver shoe buckles and had put on a plain brown suit with a broad-brimmed hat to pose as a teacher.
Landing on a beach in or near what is now the village of Huntington Bay, he walked more than a mile to a harbor-side settlement where a sympathetic resident let him rest. Then Hale began his spying mission, traveling west across Long Island, gathering information about the deployments of the British army as it prepared to advance on Washington’s encampment.
Armed with his findings, Hale then headed back east to the Long Island shore, where he planned to wait for a boat to ferry him back to safety in Connecticut.
In Stuart’s account, Hale spotted a craft approaching, only to discover at the last minute that it was British. Attempting to hurry away, Hale stopped when he saw the crew raise their muskets as one shouted, “Surrender or die!”
Hale was seized and taken to a British ship, the Halifax, lying at anchor behind Lloyd Neck. He had hidden the fruit of his spying — “plans and memoranda” in his shoes. Stuart wrote that Hale jotted his notes in Latin to make them less accessible to unschooled readers — and this evidence of treachery to the British cause “proved his strong accusers,” Stuart wrote.
Tricked
Alexander Rose offers a completely different version of what happened to Hale in his book, “Washington’s Spies: The Story of America’s First Spy Ring.”
If Hale was the first spy, he fell victim to the first counter-intelligence op. Hale was hookwinked by Robert Rogers, a ruthless mercenary veteran of the French and Indian War who a subordinate once called “a low cunning cheating back biting villain.”
In this telling, Hale arrived at a roadside inn on Long Island and sat down for dinner. On the lookout for a spy, Rogers joined him, sharing war stories and masquerading as an American rebel hiding in loyalist-controlled territory. In fact, he was working for the British.
“Rogers’s stratagem persuaded Hale that he had found a friend, and one who could be trusted with his secret…they discreetly raised their glasses and toasted Congress, whereupon Hale confided everything about himself and his mission.” He got Hale to repeat his admission to a larger group the next afternoon, and the American spy was quickly manacled.
“For a bloodied warhorse like him, bagging this Hale, straight out of Yale with a year’s drill duty on his card, had been too easy,” Rose wrote.
What made Hale’s effort particularly futile was that by the time he had finished, the British had already made their move, seizing control of Manhattan. Hale’s “entire mission…was a waste: Washington did not need intelligence on enemy positions in Brooklyn when the enemy was directly in front of him, shooting, but by then Hale was out of contact.”
Whether it was on a boat dispatched by the Halifax or on Rogers’s own boat, Hale was taken to Manhattan. The spy and his captors arrived on September 21 at British commander General William Howe’s headquarters at Turtle Bay, now the site of the United Nations. By Stuart’s account, Hale didn’t try to deny what he was doing, but rather “confessed himself an American officer and spy” and was sentenced to die by hanging the following morning at daybreak.
“His gait, as he approached the gallows, in spite of his pinioned arms, was upright and steady,” Stuart wrote. “At the very moment when the tightening knotted cord was to crush the life from his young body forever,” Hale said, “I only regret that I have but one life to lose for my country.”
Or did he? Other sources have cast doubt on it.
“Hale was not a very good spy, but he was a patriotic and likeable young man with many good friends who, over the years, kept his memory alive,” wrote Nancy Finlay, former Curator of Graphics at the Connecticut Historical Society.
“It was one of his college friends who attributed to him his famous last words, ‘I only regret that I have but one life to give for my country,’ Finlay noted, adding that the words are based on dialogue from Joseph Addison’s play Cato, first produced in 1713, “and though the play was a favorite of Hale and his friends when at Yale, there is no reason to think that Hale spoke them at his execution.”
“Over the years, as his story was told and retold, history transformed Hale from an obscure and unsuccessful spy into a symbol of selfless sacrifice in the service of his country.”
Rose noted that there is one reliable account of what Hale actually said. A British officer wrote in his diary: “He behaved with great composure and resolution, 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.”
Regardless of the content of Hale’s final remarks, in 1985, the Connecticut Legislature named him the official state hero. Two schoolhouses in East Haddam and New London still stand as monuments, as does the family manse in Coventry.
On Long Island, where a portion of Huntington Town east of the harbor is now known as Halesite, in Hale’s honor, a monument sits across from a traffic roundabout. Hale’s body was placed in an unmarked grave in New York, but there’s a memorial cenotaph in the family cemetery in Connecticut. There’s also a statue of Hale in New York’s City Hall Park.
Harriet Tubman, successful spy
Harriet Tubman’s upbringing couldn’t have been more different than that of Nathan Hale. Tubman, originally named Araminta, was born under slavery on Maryland’s Eastern Shore.
At the age of 5, her owners began to rent her out to other households to perform child care and other domestic chores. “One day, Tubman recalled, she was whipped five times before breakfast—and her neck bore the scars from this incident for the rest of her life,” historian Catherine Clinton wrote in “Harriet Tubman: The Road to Freedom.”
In her early 20s, Tubman resolved to escape to the north. “I had reasoned this out in my mind,” she recalled later. “there was one of two things I had a right to, liberty or death; if I could not have one, I would have the other.”
Reaching safety in Philadelphia, Tubman chose to dedicate her life to rescuing family members and others left behind in the South. She adopted the name of her mother Harriet as her own freedom name.
Tubman helped spirit scores of people out of slavery before the start of the Civil War. “She was certainly the lone woman to achieve such a prominent role” in the Underground Railroad.
“When on a mission behind enemy lines in a slave state,” Clinton wrote, “Tubman demanded absolute discipline. She was not afraid to exert her authority and forced everyone to toe the line. Tubman even carried a pistol and was prepared to use it, which earned her a reputation for toughness.”
When the Civil War broke out, Tubman’s career became even more remarkable.
Union forces granted her “the authority to line up a roster of scouts, to infiltrate and map out the interior” of South Carolina’s low country. On June 1 and 2, 1863, Tubman guided a force of 150 black Union soldiers along the Combahee River, using intelligence she had gathered to help the troops’ ships steer clear of explosives planted by the Confederates. The raid liberated 750 slaves and damaged plantations and warehouses on the river.
“Tubman guided the boats to designated spots along the shore where fugitive slaves had hidden. Once given the all clear, they would approach the waterline to be loaded onto ships to cast their lots with ‘Mr. Lincoln's army.’…The estates of the Heywards, the Middletons, the Lowndes, and other Carolina dynasties were left bereft and humiliated. Tubman's plan was triumphant,” Clinton observed.
“Today, historians consider the Combahee River Raid to be a major intelligence and military success,” the CIA noted.
Tubman’s “gift,” Clinton concluded, “was, again and again, to make her appearance when the enemy least suspected, working behind the scenes. Federal commanders came to depend on her, but kept her name out of official military documents.”
Clinton added, “Her missions were clandestine operations, and as a black and a woman she became doubly invisible.”
Thankfully, Tubman is invisible no more. Her accomplishments are taught in schools and told in books, and there are memorials in New York and Boston, and the Harriet Tubman Underground Railroad National Historic Park in Maryland.
There’s a third statue at the CIA campus — that of William J. (“Wild Bill”) Donovan, founder of the agency’s precursor, the World War II-era Office of Strategic Services, but that’s a story for another time.
Courting luck
In its online tribute to Nathan Hale, the CIA describes a superstition: “The Agency, steeped in tradition, holds to the legend that placing a quarter—which bears the face of Washington whom Hale served under—around Hale’s statue will ensure the safety of officers preparing to leave for an assignment.”
Douglas London, who retired in 2019 from the CIA after a 34-year career, says he never heard of that legend. As a CIA trainee, though, he was told about a different tradition: never to step on the Great Seal in the agency headquarters’ lobby.
In a business as risky as spying, it helps to have a little bit of luck.