In the late summer of 1776, Nathan Hale was a handsome, tall, charismatic twenty-one-year-old school teacher from Coventry, Connecticut with no battle experience but eager to do his duty for his country’s rebellion. “I owe to my country the accomplishment of an object so important…” His accomplishment is well known, but not in the way he expected. According to the CIA, “Hale was the first American executed for spying on behalf of his country.”
Blindly naïve, but boldly patriotic, Nathan Hale is known for breaking the cardinal rule of spying – “Don’t get caught.” But it was that story of his capture and execution that etched Hale into the chronicles of American history. Nathan Hale, by all accounts, was a respected and admirable young man. He just wasn’t a very good spy.
The job of spying in those early war days was generally looked at as dishonorable, something done by “treasonous scum” and the “scourge of the battlefield.” It usually meant using an embedded civilian who was already stationed behind enemy lines to occasionally feed intelligence out. Soldiers, dressed in civilian clothes, were also being used to enter the British-held territory. In New York, Washington had gotten only sketchy results in the value of the intelligence gathered from using informers or spies. In early August 1776, a spy probably named Lawrence Mascoll brought back some useful information about enemy troop strength and provisions on Staten Island. But when Mascoll also said he’d been told the British would strike first at three New Jersey locations, Washington was very skeptical. Washington considered Long Island to be the target (he was right), and so he tended to discount the quality of the intelligence presented to him.
By the beginning of September 1776, George Washington again desperately needed good intelligence, since he was now penned up in Manhattan after the disastrous battle of Long Island. He needed a soldier to walk within enemy lines on Long Island and find out where next General Howe was going to attack… and when… with how many soldiers… and then quickly get back. Washington, aching for intelligence, wrote to General Heath on September 5, 1776, “…every thing in a manner depends upon obtaining intelligence of the enemy’s motions… Much will depend upon early intelligence, and meeting the enemy before they can intrench.”
Captain Nathan Hale, the young Connecticut school teacher and now a part of Knowlton’s Rangers, volunteered without hesitation. He knew virtually nothing about spying, but that didn’t bother him. Had he known the spying rules, ironically, he may have lived through his adventure, but Nathan Hale’s name would have been lost to history. Instead, he is famously known as an American martyr because he unknowingly broke at least nine accepted spying rules.
The spying rules are:
- Have an inherent deceptive trait: This wasn’t really Nathan Hale’s fault. Being a spy might’ve come easier to someone who was a deceptive con-man, but Hale was not. He couldn’t even fake it. The son of minister-farmer Richard Hale, Nathan wanted to be a teacher, but he never lost the deeply-devout religious values within him. In 1774, Samuel Green (a student of Hale’s and later a colonel in the Continental Army) wrote that Hale had “fine moral character.” Elizabeth Poole, a boarder in the same boarding house as Nathan described him in glowing, magnetic terms and said Hale was “free from the shadow of guile” and had “no species of deception… his soul distained disguise.” Fellow Yale graduate and future general William Hull, to whom Hale confided about his spying decision, said spying “was not in his character: his nature was too frank and open to deceit and disguise.” Modern-day intelligence officer and historian G.J.A. O’Toole summarized that Nathan Hale was “completely ignorant of the espionage tradecraft and ill-suited for the job of agent.” In modern-day terms, Nathan Hale was not a good candidate to be a spy.
- Don’t attract attention; blend in: O’Toole continued with his criticism of Hale as a choice for a spy: “He was, first of all, not a man who could easily avoid attention, being above average height and bearing facial scars acquired in a gunpowder explosion.” Hale was “Quite imposing at six feet… ‘light blue’ eyes… set below a full shock of blondish brown hair that, in keeping with the times, was pony-tailed halfway down his back… ‘broad chested,’ with ‘firm muscles.’” “Why, all the girls in New Haven were in love with him.” Nathan Hale’s childhood friend, Asher Wright, reflected on Hale’s character and very identifiable facial scar: “He was too good-looking to go… he could not deceive. Some scrubby fellows ought to have gone. He had marks on his forehead, so that anybody would know him who had ever seen him – having had powder flashed in his face.” Specifically, “a powder burn from a musket-flash accident on his right cheek.” Nathan Hale, rather than blending in, seems to have caught the attention of everyone who saw him.
- Travel with forged papers under a cover alias: Not only did Nathan Hale travel with no forged papers and not under an assumed name, he carried with him his Yale diploma with his real name inked on it. Hale’s cover story for being on Long Island would be that he was a Dutch school teacher looking for work. Although no record exists (records are rarely kept on spy meetings), it’s very likely that Hale had met with George Washington in early September to receive instructions and to hear “the points on which Nathan was to obtain information.” It would’ve been in that meeting with Washington where Hale’s cover story and travel plans were worked out to “cross over the Sound and land on Long Island.” According to Hale’s sergeant, Steven Hempstead, Hale “twice visited Washington to discuss his route, precautions, and cover story.” And what of his mysterious absence from his own military unit? Another mess-up. G.J.A. O’Toole says Hale’s chain of command, “arranged no cover story to account for Hale’s absence from the Rangers, most of whom already knew what Hale was to do in any case. The possibility that the British might have their own spy in the American camp seems not to have occurred.”
- Treat your surveillance area as enemy territory: As Hale landed in Huntington, Long Island to begin his fifty-mile walk toward Brooklyn the morning of September 16, he knew the island civilians were mostly New York Dutch, who were privately pro-rebel, but publicly neutral. But Connecticut Loyalists who had run for their lives to the safety of Long Island were also all around. Although Hale had grown up in Connecticut and had been stationed in Manhattan for over four months earlier in the year, it was always possible that people could know him by sight. We know he stood out in a crowd, but Hale was hoping no one on Long Island would recognize him. An additional risk was that Nathan’s Loyalist cousin, Samuel Hale, was known to be working with General Howe and was somewhere in the Long Island area. All of these factors just reinforce the point that Hale should never have been selected to go on this particular spying mission.
- Assume “Murphy’s Law” and abort the mission if necessary: It was just Hale’s bad luck that a fire broke out over in Manhattan in the early morning of September 21, 1776. It turned out to be the most devastating, wind-whipped inferno New York City had seen in 150 years, destroying at least one thousand structures. The British authorities everywhere were on heightened alert looking for an arsonist in their midst or one who was trying to escape the area. By then, Hale was actually already back to his agreed rendezvous point on the sandy Huntington beach, facing Norwalk, Connecticut. But residents of Long Island were uneasy about the fire and were watching for any strangers in the neighborhood. In another stunning “Murphy’s Law” blow, there was no way Nathan Hale could’ve known at that point that his entire spying mission was no longer needed. While Hale had been sailing from Connecticut under cover of night to begin his espionage operation, the British had attacked at Kip’s Bay and the Battle of Harlem Heights had happened. Washington didn’t need to know what Howe was planning anymore. He knew; time had moved on, but there was no way to get the “abort mission” word to Hale.
- Don’t jeopardize your mission; know when to get out: Nathan Hale had made it safely back to Huntington bay and was waiting for his extraction vessel during the agreed night of September 21 or 22. He already had the intelligence gathered that he had been sent to collect. His mission was accomplished. He could just sit in hiding at an inn until it was time to sneak off of the island. But he didn’t. He kept poking around and asking questions like, “whether the Long Island inhabitants were friends to America or not.” Nathan Hale began to attract attention, a lot of attention and the wrong type of attention.
- Assume no one is your friend: Nathan Hale’s suspicious behavior and questions in Huntington had already attracted the local attention of British Army Major Robert Rogers, the American-born commander of the famous fighting unit, “Rogers’ Rangers.” Rogers, to put it mildly, was a physically brutish, hard-drinking, gambling, ruthless loner with an “elongated nose, bulgy eyes, and pockmarked face” along with a “brutal, bloodthirsty reputation.” But he also had the alter-ego, con-man gift for schmoozing victims and fooling them into thinking he was a friend and compatriot. Rogers had gotten wind of a possible spy who had landed some days before; maybe it was that questionable Dutch school teacher asking a lot of suspicious questions in town? Rogers moved in to take a closer look at his prey. Nathan Hale had been pointed out to Rogers by a tavern person that night. Hale was sitting alone having a drink. Rogers, dressed in civilian clothes, sat down and quickly started telling Hale what he wanted to hear: that he was a fellow patriot soldier and dedicated to the American cause. Nathan Hale bought it and began to quietly tell Rogers about his secret spying mission.
- Guard against your own weaknesses: A more experienced spy would never have fallen into Rogers’ befriending trap, but Nathan did. As we’d learned, Hale did not inherently have the ability to deceive, and he perhaps felt a secret, non-deceitful bond with Rogers, a fellow American soldier. A worldly Hale could have guarded against this gullible weakness of his, but he didn’t. There was one other flaw that Hale may have had that was left from his Yale college days. Though pious, it’s reported that Nathan still liked alcohol. It’s very plausible that Robert Rogers, a well-known life-long alcoholic, bought some drinks for Hale that night which possibly could’ve opened Hale up for a more confidential and damning conversation. Rogers invited Hale to breakfast with him the next morning. Hale accepted for some reason. Rogers was setting the scene to spring the trap.
- Safeguard your notes using an unbreakable code, in a form instantly discarded: The next morning, September 21, 1776, Nathan Hale showed up at Rogers’ Huntington tavern quarters. The diary of Consider Tiffany has given history the details of the ensnarement and arrest of Nathan Hale. Tiffany’s pages show that after some breakfast table chit-chat, Rogers stood and arrested Nathan Hale in a loud and indignant voice. Hale was taken outside where a company of Rogers’ soldiers were waiting to tie Hale’s legs and hands. He was taken from Long Island, across the East River to the Beekman housewhich was General Sir William Howe’s new headquarters on Manhattan Island. Hale was searched and all of Hale’s notes and drawings of British troop strength and fortifications were found tucked under the sole of his shoe. To be secretive, Hale had apparently written all of the incriminating notes in Latin, a language Hale had learned at Yale. But Latin was a language many people from upper schooling also knew fluently, and so the British broke the “code” instantly. A military soldier caught in civilian clothing was a spy and that’s exactly what Hale was accused of by Howe. Eventually, Hale confessed and said he’d been sent by Washington on the secret mission. Spying was a crime punishable by death. Without benefit of a trial, Howe ordered Nathan Hale to be hung at the break of day.
The next morning, September 22, 1776, Nathan Hale was marched up the Post Road to an orchard which is today at approximately Third Avenue and 66th Street. A rope with a noose was fitted around Hale’s neck and the rope was swung over a tree limb. Hale was ordered to climb the ladder and the ladder was kicked away. According to the diary of Lt. Frederick Mackenzie, Hale, “… behaved with great composure and resolution.” In the middle of the page of Howe’s orderly book for “22 September 1776,” wedged between paragraphs of normal administration notes, an aide simply wrote,
“A spy from the enemy by his own full confession, apprehended last night, was executed this day at 11 o’clock in front of the Artillery Park.”
Although Nathan Hale was denied his request for a Bible and clergy to be with him, he was allowed some last words just before he swung to his death. His reported famous final words are what have put him into the annals of American history. But at the time, any immortal words said weren’t covered in the news item of a contemporary paper:
“This day, one Hale, in New York, on suspicion of being a spy was taken up and dragged without ceremony to the execution post, and hung up. General Washington has since sent in a flag, supposed to be on that account.”
It was only five months later when the February 13, 1777 Essex Journal newspaper from Newburyport, Massachusetts reported Hale, “at the gallows, … made a sensible and spirited speech” and his last words, “If [I] had ten thousand lives, [I] would lay them all down, if called to it, in defence of [my] injured, bleeding country.” Some historians today feel that any phrase Hale may have included in his final words was inspired from the very popular play at the time, Cato, by Joseph Addison, “What pity is it / that we can die but once to serve our country!”
It’s likely that Hale said more than just a single, immortal sound bite when given the chance to speak. But it’s from the memoir of Nathan’s friend, General William Hull, where we get that last fabled phrase. The day after Hale’s hanging, British Captain John Montresor, under a white flag truce, crossed lines and met with Hull to bring a letter proposing a high-ranking prisoner exchange. Montresor also told Hull of Hale’s execution and that “he was calm, and bore himself with gentle dignity…” Then he also told Hull that Nathan Hale’s last words were, “I only regret that I have but one life to lose for my country.”
To make a statement, Nathan Hale was left hanging for three days by the British in the hot September weather before he was cut down. He was buried in an unmarked grave, somewhere near present day Third Avenue, between 66th and 46th streets. His remains have never been found. But his memory can be found everywhere in America.
In the long run, it doesn’t really matter if Nathan Hale was a good spy or bad spy or what his exact words were. The important thing is that he was a young, dedicated patriot-spy who wanted to do what he considered to be an important job for his country. He was someone who backed up whatever words he did say with his honor and his life. The CIA reminds all onlookers that Hale’s statue standing in the courtyard of their headquarters, “serves as a constant reminder to CIA employees of the duties and sacrifices of an intelligence officer.”
 Memoir from Hale’s friend, William Hull, in George Dudley Seymour, Documentary Life of Nathan Hale: Comprising All Available Official and Private Documents Bearing on the Life of the Patriot (New Haven, CT: privately printed, 1941), 308.
 Central Intelligence Agency, “The CIA Campus: A Walk Outside Headquarters”, https://www.cia.gov/news-information/featured-story-archive/a-walk-outside-headquarters.html accessed April 9, 2015. A “statue of Nathan Hale stands guard between the CIA Auditorium (also known as the Bubble) and the Original Headquarters Building (OHB). It serves as a constant reminder to CIA employees of the duties and sacrifices of an intelligence officer.”
 M. William Phelps, Nathan Hale: The Life and Death of America’s First Spy (New York: St. Martin’s Press, 2008), 147.
 George Washington to Major General William Heath, September 5, 1776, New York, in John Fitzpatrick, ed., The writings of George Washington from the original manuscript sources: Volume 6, Library of Congress, 2001; and http://etext.virginia.edu/etcbin/ot2www-washington?specfile=/texts/english/washington/fitzpatrick/search/gw.o2w&act=surround&offset=6731366&tag=Writings+of+Washington,+Vol.+6:+To+MAJOR+GENERAL+WILLIAM+HEATH+New+York,+September+5,+1776.+&query=intelligence&id=gw060027 accessed April 27, 2015.
 Ironically it was one of Nathan Hale’s Yale classmates who may have inspired Hale to enlist as a captain in the Nineteenth Regiment of Foot on January 1, 1776, none other than future spymaster Benjamin Tallmadge. In a letter to Hale, Tallmadge ended with, “We should all be ready to step forth in the common cause.” Letter, Tallmadge to Hale, July 4, 1775, Connecticut Historical Society; and Phelps, Nathan Hale, 75.
 “Today’s Army Rangers, Special Forces, and Delta Force trace their origins to Knowlton’s Rangers. This unit was the first American military intelligence organization.” Thomas B. Allen, George Washington, Spymaster. How the Americans Outspied the British and Won the Revolutionary War (Washington, D.C., National Geographic Society, 2004), 168. Also “Washington established a unit known as Knowlton’s Rangers, under the command of Lt. Col. Thomas Knowlton, to carry out reconnaissance and raids against British facilities. This unit was the first American military intelligence organization… The ill-fated American spy Nathan Hale was recruited from this early Ranger force.” CIA Library, by P.K. Rose, “The Founding Fathers of American Intelligence,” https://www.cia.gov/library/center-for-the-study-of-intelligence/csi-publications/books-and-monographs/the-founding-fathers-of-american-intelligence/art-1.html accessed April 18, 2015.
 The International Spy Museum web site lists the well-known rules for spying commonly called the “Moscow Rules”, supposedly developed by the CIA during the Cold War. This article’s list uses those rules plus variations of other “dead simple and full of common sense” rules set forth in genre books by authors like John le Carré, Robert Ludlum, and Tom Clancy. http://www.spymuseum.org/exhibition-experiences/online-exhibits/argo-exposed/moscow-rules/ accessed April 12, 2015.
 I. A. Stuart, “Colonel Samuel Green’s Picture of Hale as a School-teacher,” January 1847, in Seymour, Documentary Life, 158.
 Letter, Leverette W. Saltonstall to Cyrus P. Bradley, January 17, 1837, in Seymour, Documentary Life, 347; also Phelps, Nathan Hale, 69.
 Seymour, Documentary Life, 308; and Phelps, Nathan Hale, 143.
 Library of Congress Information Bulletin, “Nathan Hale Revisited – A Tory’s Account of the Arrest of the First American Spy” by James Hutson, http://www.loc.gov/loc/lcib/0307-8/hale.html accessed April 12, 2015.
 Library of Congress Information Bulletin, “Nathan Hale Revisited” accessed April 12, 2015.
 Phelps, Nathan Hale, 27, citing various sources.
 Quote by Eneas Munson (a friend of Hale’s), from James Grant Wilson and John Fiske, Appleton’s Cyclopedia of American Biography (Detroit: Gale Research Co., 1968), 3:30; also Phelps, Nathan Hale, 27.
 Asher Wright, “Testimony” in Seymour, Documentary Life, 316; also John Bakeless, Turncoats, Traitors & Heroes: Espionage in the American Revolution (New York: De Capo Press, 1998), 114; and Phelps, Nathan Hale, 156.
 Kenneth A. Daigler, Spies, Patriots, and Traitors: American Intelligence in the Revolutionary War (Washington, D.C.: Georgetown University Press, 2014), 102.
 “It was a small parchment at that period.” Henry Phelps Johnston, Nathan Hale, 1776: Biography and Memorials (New Haven, CT: Yale University Press, 1914), 112. British Provost Marshal William Cunningham reportedly taunted a future captured spy with his souvenir of Hale’s Yale diploma.
 Henry Howe, Adventures and Achievements of Americans: A Series of Narratives Illustrating Their Heroism, Self-Reliance, Genius and Enterprise (New York: Geo. F. Tuttle, 1860), 20.
 I.W. Stuart and Edward Everett Hale, Life of Captain Nathan Hale, the Martyr-Spy of the American Revolution (Hartford, CT: F. A. Brown, 1856), 88; and Howe, Adventures and Achievements, 20. In regards to where Hale would spy, “He was only to spy out Long Island and come home.” Alexander Rose, Washington’s Spies: The Story of America’s First Spy Ring (New York: Bantam Books, 2006), endnote 39.
 Johnston, Nathan Hale, 108 footnote 1; and Rose, Washington’s Spies, 17.
 Library of Congress Information Bulletin, “Nathan Hale Revisited” accessed April 12, 2015.
 There has been conjecture if Nathan Hale was the arsonist who started the New York City fire. As far as the timeline goes, Hale was on Long Island (in fact, had never left it) when the fire started after midnight September 21. So it couldn’t have been Hale. But to answer that question: if Washington had wanted to set fire to the city he probably would’ve done so as they were leaving. But after asking Congress if the fire could be set upon leaving, Congress told Washington no. It wouldn’t be like Washington to go against the wishes of Congress. One other theory: “The fire may have been set by the Sons of Liberty to do what the Continental Congress had forbidden Washington to do – burn the city rather than leave it to billet Howe’s troops.” G.J.A. O’Toole, Honorable Treachery: A History of U. S. Intelligence, Espionage, and Covert Action from the American Revolution to the CIA (New York: Grove Press, 2014), endnote 8, chapter 4.
 Consider Tiffany, unpublished diary which carries two pages describing Nathan Hale’s capture by Major Rogers in great detail (Library of Congress, Manuscript Division, acquired by LOC in 2000); also Phelps, Nathan Hale, 172.
 “Rogers’ Rangers” was a well-known elite fighting force of the French and Indian War. The regiment Rogers initially commanded during the Revolutionary War was the “Queen’s American Rangers,” but was still referred to with Rogers’ name. In slight conflict to endnote 6, today’s U.S. Army Rangers are said to trace their origins to Rogers’ Rangers. One clarification may be that Rogers’ Rangers were British during the French and Indian War, and Knowlton’s Rangers were American, formed during the Revolutionary War.
 Phelps, Nathan Hale, 164. Rogers was a controversial person in history. Seemingly fearless, he nevertheless had a brutal side to him in battle and a reckless side in his personal life. He sued his commanding general, Thomas Gage, for back wages and false imprisonment. The British arrested Rogers for treason. He was acquitted in a trial but went to debtors’ prison. He petitioned George Washington for an American command, but instead Washington had him arrested as a spy. Rogers escaped and went back to the British side forming the “Queen’s American Rangers” just before his encounter with Nathan Hale. Ironically Rogers was played as a good guy by Spencer Tracy in the 1940 film Northwest Passage, but is back to the bad guy persona in the AMC-TV series Turn: Washington’s Spies.
 Until the year 2000, it was generally believed that Hale was betrayed by a Loyalist inn keeper in Huntington, or (the most assumed story), “he allegedly was betrayed by his Tory cousin, Sam’l Hale.” Mark Mayo Boatner III, Encyclopedia of the American Revolution (New York: David McKay Company, Inc., 1976), 475. But in 2000, a diary in the possession of family curator G. Bradford Tiffany was donated to the Library of Congress. It was the diary of Consider Tiffany, a Tory storekeeper from Connecticut, in which he describes with counter-checked factual detail of how Major Robert Rogers lulled Hale into a trap to capture him. The diary is also considered by the Library of Congress “a manuscript history of the American Revolution written during or soon after the conflict.” This diary story itself, is worthy of reading and appreciating: “Nathan Hale Revisited: A Tory’s Account of the Arrest of the First American Spy,” James Hutson, Chief of Manuscript Division, LOC; http://www.loc.gov/loc/lcib/0307-8/hale.html accessed April 18, 2015.
 The Beekman house was way up in the country from lower Manhattan at the time. Today the site is north of the United Nations headquarters, near First Avenue and 51st Street.
 The Daughters of the American Revolution contend that Hale’s execution site is near the present day Grand Central Station.
 Mackenzie spelled Nathan Hale’s name as “Nathaniel Hales.” Frederick Mackenzie, Diary of Frederick Mackenzie, Giving a Daily Narrative of his Military Service as an Officer of the Regiment of Royal Welch Fusiliers During the Years 1775-1781 in Massachusetts, Rhode Island and New York, Volume I (Cambridge, MA: Harvard University Press, 1930), 61-61; and Seymour, Documentary Life, 292.
 Henry Steele Commager and Richard B. Morris, ed., The Spirit of ‘Seventy-Six: The Story of the American Revolution as Told by Participants, Volume 1 (New York: The Bobbs-Merrill Company, Inc., 1958), 475; also Phelps, Nathan Hale, 192.
 Commager and Morris, The Spirit of ‘Seventy-Six, 475. In writings, Washington never acknowledged or spoke of Hale’s mission.
 Commager and Morris, The Spirit of ‘Seventy-Six, 475.
 Cato, Act IV, Scene 4, quoted in Bartlett’s, and Boatner, Encyclopedia of the American Revolution, 475.
 Montresor was “chief engineer of the British army in America.” Boatner, Encyclopedia of the American Revolution, 475.
 Maria Hull Campbell, Revolutionary Services and Civil Life of General William Hull; Prepared from His Manuscripts,… Together with the History of the Campaign of 1812, and Surrender of the Post of Detroit, by James Freeman Clarke (New York: D. Appleton & Co., 1848), 37-38; and Commager and Morris, The Spirit of ‘Seventy-Six, 476.
 Campbell, General William Hull, 37-38; and Commager and Morris, The Spirit of ‘Seventy-Six, 476. These famous last words supposedly passed from Montresor to Hull were penned by Maria Hull Campbell, Hull’s daughter, in 1848. It’s possible that the phrase was invented or embellished at that stage.
 Central Intelligence Agency, “The CIA Campus: A Walk Outside Headquarters”, https://www.cia.gov/news-information/featured-story-archive/a-walk-outside-headquarters.html accessed April 9, 2015.