9 Rules of Spying That Nathan Hale Failed to Follow

Techniques & Tech

May 21, 2015
by John L. Smith, Jr. Also by this Author


Journal of the American Revolution is the leading source of knowledge about the American Revolution and Founding Era. We feature smart, groundbreaking research and well-written narratives from expert writers. Our work has been featured by the New York Times, TIME magazine, History Channel, Discovery Channel, Smithsonian, Mental Floss, NPR, and more. Journal of the American Revolution also produces annual hardcover volumes, a branded book series, and the podcast, Dispatches

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…”[1] 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.”[2]

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.”[3] 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.”[4]

Captain Nathan Hale,[5] the young Connecticut school teacher and now a part of Knowlton’s Rangers,[6] 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:[7]

  1. 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.”[8] 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.”[9] 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.”[10] 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.”[11] In modern-day terms, Nathan Hale was not a good candidate to be a spy.
  1. 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.”[12] 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.’”[13] “Why, all the girls in New Haven were in love with him.”[14] 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.”[15] Specifically, “a powder burn from a musket-flash accident on his right cheek.”[16] Nathan Hale, rather than blending in, seems to have caught the attention of everyone who saw him.
  1. 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[17] 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.”[18] 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.”[19] According to Hale’s sergeant, Steven Hempstead, Hale “twice visited Washington to discuss his route, precautions, and cover story.”[20] 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.”[21]
  1. 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.
  1. 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.[22] 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.
  1. 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.”[23] Nathan Hale began to attract attention, a lot of attention and the wrong type of attention.
  1. 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.”[24] 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.”[25] 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.
  1. 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.
  1. 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.[26] 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 house[27]which 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.[28] 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.”[29] 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.”[30]

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.”[31]

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.”[32] 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!”[33]

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,[34] 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…”[35] 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.”[36]

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.”[37]


[1] 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.

[2] 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.”

[3] M. William Phelps, Nathan Hale: The Life and Death of America’s First Spy (New York: St. Martin’s Press, 2008), 147.

[4] 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.

[5] 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.

[6] “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.

[7] 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.

[8] I. A. Stuart, “Colonel Samuel Green’s Picture of Hale as a School-teacher,” January 1847, in Seymour, Documentary Life, 158.

[9] Letter, Leverette W. Saltonstall to Cyrus P. Bradley, January 17, 1837, in Seymour, Documentary Life, 347; also Phelps, Nathan Hale, 69.

[10] Seymour, Documentary Life, 308; and Phelps, Nathan Hale, 143.

[11] 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.

[12] Library of Congress Information Bulletin, “Nathan Hale Revisited” accessed April 12, 2015.

[13] Phelps, Nathan Hale, 27, citing various sources.

[14] 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.

[15] 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.

[16] Kenneth A. Daigler, Spies, Patriots, and Traitors: American Intelligence in the Revolutionary War (Washington, D.C.: Georgetown University Press, 2014), 102.

[17] “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.

[18] 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.

[19] 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.

[20] Johnston, Nathan Hale, 108 footnote 1; and Rose, Washington’s Spies, 17.

[21] Library of Congress Information Bulletin, “Nathan Hale Revisited” accessed April 12, 2015.

[22] 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.

[23] 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.

[24] “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.

[25] 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.

[26] 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.

[27] 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.

[28] The Daughters of the American Revolution contend that Hale’s execution site is near the present day Grand Central Station.

[29] 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.

[30] 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.

[31] Commager and Morris, The Spirit of ‘Seventy-Six, 475. In writings, Washington never acknowledged or spoke of Hale’s mission.

[32] Commager and Morris, The Spirit of ‘Seventy-Six, 475.

[33] Cato, Act IV, Scene 4, quoted in Bartlett’s, and Boatner, Encyclopedia of the American Revolution, 475.

[34] Montresor was “chief engineer of the British army in America.” Boatner, Encyclopedia of the American Revolution, 475.

[35] 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.

[36] 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.

[37] 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.


  • John,

    Perhaps you can help me. I am working on a history of the British Corps of Engineers in America during the Revolutionary War. In reading your article about Nathan Hale ( which I found most interesting and informative) I noted the passage about John Montressor crossing the lines under a flag of truce and informing General William Hull of Hale’s last words. When I went to the references cited for that passage I found that the passage from Hull’s memoir in Commager & Steele identifies the bearer of that news only as “an officer.” Boatner describes Montressor allowing Hale the use of his tent and some writing materials before his execution, but provides no source information for that account. I also went through the Montressor journals but found no reference in them to Montressor having any contact with, or even mentioning Hale.

    I would very much like to nail this bit of the history of the British Engineers during the Revolution. If you could point me toward any other references to the Montressor/Hale connection that I could dig into, I would appreciate it very much.

    All the best,

    Norm Fuss

    1. Norm – thank you for the note and of the interest in poor Captain Hale. What you’re touching on is representative of some of the evolved facts and truths that surround a folk hero such as Nathan Hale.

      I had picked up additional material on John Montresor (I’ve seen the last name spelled with one “s” and two “s” in various books and references) in Boatner’s “Encyclopedia of the American Revolution”, as you also referenced, on page 475 within the “Nathan Hale” entry. Montresor of course, also has his own entry on pages 729-730… but with no mention of the Hale encounter. Maybe Boatner figured he’d already covered it in the Hale entry, or maybe in talking about Montresor’s engineering career, (and within Montresor’s own journal) a side-bar about Hale was off topic?

      The material that I chiefly sourced in this phase was from Hull’s daughter, Maria Hull Campbell, who published her father’s memoirs in 1848, 23 years after Hull’s death (end note 35). As with any source, one has to weigh the preponderance of the evidence and just because a source is old or written by a family member doesn’t always make it true. In fact sometimes red flags go up because of that. For instance Hull had been on record as saying Hale only went to Long Island. In his daughter’s memoirs, she said her father had claimed that Hale went to both Long Island and “York Island” (Manhattan). I had also assumed that dual-island scenario when I went into writing this story. In the course of research, I was persuaded beyond any doubt that time-line wise, Hale could not have made it to Manhattan in the known time he was on Long Island. So this is just a small example of the logical, hazy and sometimes-bewildering facts that researchers as yourself need to sift through.

      An excellent, updated book discussing Hale, Hull and Montressor (spelled with two s’ in the book) is Alexander Roses’ “Washington Spies: The Story of America’s First Spy Ring”. I found that M. William Phelps’ 2008 book “Nathan Hale” is spotty on truths vs. folklore, but does give Consider Tiffany’s diary a prominent place in the capture story, as it should. It also goes into some depth of the Hull-Montresor occurrences.

      At this time, I also need to express huge thank you’s to JAR’s espionage expert Michael Schellhammer for his invaluable guidance given to me in researching and writing this story. It is because of the superb expertise of Mike that I was guided to a better and more factually-sound story.
      I always feel hesitant about listing someone else’s name as a possible reference for your examination of John Montresor, but JAR editor Don Hagist is beyond all earthly-known expertise when it comes to research access on all aspects of the British Army.

      Good luck and perhaps the story of John Montresor/Montressor would warrant its own JAR article?

  • John, I enjoyed your article. It highlights the period of Washington’s management of the war where he had yet to engage effectively his intelligence expertise. Hale was badly, and terminally, used for no meaningful purpose. In additional to his character being totally unsuited for the work, he received virtually no training and few instructions from either Knowlton nor Washington, if indeed there was such a meeting as Hale’s enlisted servant later claimed. In addition to points you raise regarding operational security issues with his mission, he had served in the New York City area during the British offensive and even paid one individual for some type of intelligence. Yet another strike against him returning as a School Teacher. The blame for this intelligence failure has to lie with Washington as the Commander. Luckily, starting with Trenton, Washington began to focus on intelligence and this “force multiplier” was used effectively throughout the rest of the war.
    At least one Director of Central Intelligence questioned why a statue of a failed spy was posted facing the main entrance to the Headquarters building. Perhaps the answer is not only his willingness to serve his country, but also that there are lessons to be learned from the mistakes committed in his mission.

    1. Thank you for your comments, Ken (and I might point out to readers that in end note 16, I reference Ken’s excellent book “Spies, Patriots, and Traitors: American Intelligence in the Revolutionary War”).

      You’re exactly right that Washington got better with his espionage management as time went on. I ended up feeling that the planning meeting actually happened between Hale and Washington because Hale had to get his mission instructions from someone and there were indications that no one, not even Knowlton, knew what Washington needed in espionage from Long Island. It is said that Washington never mentioned Hale in either words or letters for the rest of his life. Conjecture wonders if Washington felt so badly about sending a brave but naive school-teacher-officer on such an ill-planned mission? Then taking that guilt one step farther, would it be a stretch to think of Washington’s firm order to hang Andre later as “pay back” for Hale? As you certainly know, spy records are obviously not kept.

      In my original draft, I’d uncovered the claim that Hale had paid an unknown person in Manhattan for “the Secret”, implying that the payment was made for information while Hale was on his spy mission… in Manhattan. Because I became convinced of Hale’s presence on Long Island only for his mission, the alleged payment mention went by the wayside for obvious reasons.

      Like you said, William Casey, as CIA director, wondered that surface-level question of why have a failed spy in bronze statue form on the CIA headquarters grounds? Your last sentence, Ken, sums up the obvious very well. Thank you again.

  • John, an excellent article!

    You provide another example that the Continental Army early in the conflict lacked the full range of military capabilities. It took some time (and some foreign expertise) and investment for Washington to develop sufficient engineering, calvary and intelligence capabilities.

    As you point out, Hale was not sufficiently led and trained. Unfortunately for him it took more time for the Patriots to develop a viable intelligence capability. I. Any event he was a committed and courageous patriot.

    1. Thank you, Gene! I think it was either John Adams or George Washington, or both, who bemoaned the fact that the new “Continental” Army was deficient in everything it took to wage a war! Meaning the trained officer expertise; aside from small details such as clothes, supplies, money, and food.

      Folklore and failed mission aside, there can be no doubt that Nathan Hale was a true Patriot and a very brave American. His remarkable demeanor when interrogated and executed stands the test of time and facts when historical correctionists attempt to tear the story down. Thank you again.

  • Hi John,
    Excellent article and great use of sources and footnotes. I really enjoy reading the breakdown that lead to Hale’s execution.

    As the war went on, did spying become more acceptable?

    Was Major Andre executed in retaliation for Hale’s execution?

    Great job and thank you for a great informative article!

  • Thank you, Brian. The answer to your first question – if spying became more acceptable as the war went on – is that I don’t know. Here’s where someone like Mike Schellhammer or Ken Daigler might interject their knowledge. My un-educated guess though is – probably not. Some things didn’t change that much in those days, and the un-noble nature of spying may have been one. My extended guess (and might be entirely wrong) is that it might have started changing during the Victorian era, with the feelings that spying (as during the Civil War) was romantic and fraught with dime-novel danger. Then Ian Fleming’s James Bond character right after WWII took all of that to where we are now. Again – an espionage expert would know much more.

    The hanging of Andre as payback for Hale is what I had alluded to in the reply to Ken Daigler. Again, without a shred of documentation one never knows what went on in Washington’s mind. He was known to give last-minute clemency to some people and to hang others as examples. Very perceptive that you brought that point up though.
    Thank you as always.

  • John,

    Your discussion of spies and the penalties imposed on them got me to thinking about the legality of how they were handled when caught. Turning to Emer de Vattel and his 1758 Law of Nations, which is something that both the British and Americans were aware of, we see this:

    “Section 179. Spies. The employment of spies is a kind of clandestine practice or deceit in war. These find means to insinuate themselves among the enemy, in order to discover the state of his affairs, to pry into his designs, and then give intelligence to their employer. Spies are generally condemned to capital punishment, and with great justice, since we have scarcely any other means of guarding against the mischief they may do us.”

    So, it is not surprising to see the British hanging Hale as they did; consider that they took the view that this was an unlawful rebellion that allowed them to punish harshly without remorse. But with Washington, as he reluctantly did with POWs, we see his hesitancy in engaging in a tit-for-tat response to British actions.

    I don’t profess to be any kind of a Washington expert, but from what I have read and understand about the man, he was not one to take the offensive in matters such as these. Rather, he responded in like manner and only did so because he believed himself forced to do so by the actions of the British. To have done otherwise would have meant harm to his reputation, both within American and British ranks.

    Perhaps the only other thing he could have done with Andre was to jail him for the duration of the war and not respond as he did, but the tenor of the times dictated harsh measures despite whatever his personal feelings might be on this, or many other occasions. Still, I think we can see that Washington was an extraordinarily honorable man, making him, in my estimation anyway, the finest example we have ever seen in our nation’s history of the military/politico persona.

    1. Gary – great discussion about Washington and his treatment of British spies and POWs vs. Washington’s own temperament.

      With Andre, from what I understand, the whole thing moved pretty quickly from Andre being captured (and thereby exposing that arguably Washington’s best general, Benedict Arnold, had gone over to the enemy) to Andre’s trial and hanging.

      Taken in the context of the moment, Washington was in complete shock. Lightly said, Joseph Ellis in “His Excellency, George Washington” stated “He [Washington] was not in a sentimental or generous mood.” More personally, Ed Lengel in “General George Washington” said about Washington having to hang Andre that, “The episode left Washington…severely shaken.” Washington might’ve been a Gibraltar of a person, but maybe was more sensitive about that stuff than the average person might guess. Washington didn’t go to Andre’s hanging.

      I think the perfect example of “tit-for-tat response to British actions” of what you brought up is the 1782 incident of Capt. Charles Asgill of the First British Regiment of Foot.

      Apparently a New Jersey militiaman named Capt. Huddy had been hung in reprisal for militiamen executing a Loyalist partisan. To quell the outrage, Washington decreed a lottery of British POWs where the winner (or loser) would be executed in reprisal for Capt. Huddy. When Washington found out some details of the victim, Capt. Asgill, he apparently felt very torn, even though the public and Congress demanded the tit-for-tat killing. Ron Chernow says in “Washington”, “Still haunted by Andre’s execution, Washington didn’t care to execute another sensitive young British officer.”

      The execution was averted when Captain Asgill’s mother pleaded her case to King Louis XVI and Marie-Antoinette (why not go to the top?) and it was arranged for Asgill to be released. It relieved Washington of another apparent emotionally-draining personal crisis.

      Washington was, as you said, an “extraordinarily honorable man.”

      Thank you, Gary!

  • John,

    Thank you for the information on Alexander Roses’ “Washington Spies: The Story of America’s First Spy Ring”. That’s one I don’t have. I plan to go the Rockefeller Library on Monday to see what he has to say about the Montressor/Hale connection. Hopefully he has references to primary source material that mentions the relationship

    1. You’re welcome, Norman and actually if you don’t mind – when you find out more about any primary sources or any additional information about the Hull – Montressor/Hale, please think about keeping this thread going.

      That’s the great thing about this JAR site – your findings can continue to get shared with all others on this subject.

      Happy huntings!

      1. John,

        OK. I think I have been able to verify the Montressor connection to Nathan Hale to a reasonable degree of certainty.

        The Hull memoir clearly states that “an officer” came into the American camp under a flag of truce, that it was that officer who conveyed the news of Hale’s execution to Hull, that he had witnessed Hale’s execution and that he said that he had afforded Hale the use of his tent, given him writing materials, etc. Unless we are willing to discount this material (I think it is credible) it establishes that a British officer who had befriended Hale and had witnessed his execution crossed the lines under a fag of truce and delivered the news to Hull.

        The question is, who was that officer?

        Rose, in “Washington’s Spies” cites only one reference for the entire half page of text dealing with the Montressor/Hale relationship, but it is, in my opinion, persuasive. He cites a letter from Washington to Howe dated 23 September, 1776, the day after Hale’s execution. In it Washington identifies Montressor as the officer who crossed the lines (presumably that day) under a flag of truce with a letter proposing an exchange of prisoners. While conveying news of the execution of a spy to the other side would be unlikely to justify a flag of truce, a proposal to exchange prisoners would.

        So, unless there was another officer who crossed that day in that local under a flag of truce (for which I have no evidence and which I think is unlikely), Montressor is the sole candidate for the officer who delivered the news of Hale’s execution, showed him kindness before his execution and witnessed his execution.

        It’s not “smoking gun” proof, but to me it’s pretty persuasive.

        All the best,


        1. Norman – good job on delving into the Hull/Montressor/Hale connections. From the preponderance of the evidence, I would suspect that you are right that it was Montressor who was the British officer in question.

          Your findings stand with this article for other researchers to consider, as well as for people who are interested in Nathan Hale… and I have since found out there are many!

          Thank you for a great follow-up.

  • The attitude of most “gentlemen”, both colonial and British, seemed to be that spying was an activity best conducted by lesser types. For example, Washington was less impressed with the Culper Ring’s Principal Agents, Culper, Sr. and Culper, Jr., as the war wound down, and King George III lost opportunities to effectively use information on the activities of the American Commission in Paris because he felt his primary penetration of the organization, Edward Bancroft, and Bancroft’s handling officer, Paul Wentworth, were of questionable character. That said, both sides constantly sought intelligence and often used Officers to accomplish these activities. It seems that the use of Officers for traditional, tactical military collection, including recruitment of individuals to report on the enemy, was a more acceptable activity than obtaining enemy plans and intentions by feigning personal loyalties behind enemy lines.

    At the end of the war, and in the period thereafter, Washington did personally thank many of his spies, yet his overall attitude towards what constituted a “gentleman” would seem to indicate he was not completely comfortable dealing with them. As I note in my book, once the fighting ends the value of the infantryman and the intelligence officer is often forgotten.

    1. Well stated, Ken.
      Spying, and the spies themselves, back then just didn’t have that romantic and daring aura that it later took on. Either by the public at large or the officers commissioning the spies.

      Even with the thought of someone as alluring as Edward Bancroft, a reckless double spy!

  • Some comments regarding Andre to add to an enjoyable article and good commentary…The cases of Andre and Hale are quite similar especially as to the ending. While Hale looks out over the CIA HQ, Andre rests in piece in an honored crypt of Westminster Abbey. As noted, Hale’s final resting place might be disturbed daily by the rumble of the Lexington Avenue subway line. It should also be noted that Andre got a full hearing before a Board of General Officers and decided André’s fate. Washington simply refused to commute his sentence. However, this had less to do with vengeance and more to do with the refusal of Clinton to turn over Arnold. Clinton made desperate efforts to save his favorite officer and Washington actually delayed the execution to hear out the British. But, in the end, Washington, albeit dismayed over the affection some of his officers had for Andre, had to follow the example of Hale and others originally set by the British. He wouldn’t even approve a firing squad. Not for the time it took to throw a rope over a tree limb would it have taken the British to dispatch Washington and the others who ‘pledged their sacred honor.’ It wasn’t ‘tit-for-tat’ but as the Board of Generals determined Andre was, indeed, a spy and “agreeably to the Law and usage of Nations…ought to suffer death.” For Washington, knowing the importance of Andre to Clinton, he wanted Arnold badly. Perhaps executing Andre would make Arnold’s stature dim (as it did) among his new found ally and whenever enemy anger was directed at Andre’s fate, a bit of that reaction might be directed at Arnold. For more on the Andre story, please see my article For Sale: West Point – Part Two https://allthingsliberty.com/2014/05/for-sale-west-point-2/

    1. Steven – thank you for elaborating a bit more on the similarities and differences in Hale vs. Andre. It also helps to shed more light on Washington’s refusal to pardon Andre or allow him the honorable death of a firing squad. Your article about Andre and Arnold, and how much Washington wanted Arnold because of his betrayal, is a perfect follow-up for the reader in these threads.

      I wonder how many average readers know that John Andre is buried in Westminster Abbey, after his body was moved to that place of honor in 1821?

      Great feedback, Steven. Thank you.

  • Steven, while, as you know, the letter to Clinton regarding a “trade” of Arnold for Andre was written by his aide, Alexander Hamilton, I do wonder Washington’s role in it. He clearly recognized that Clinton could not turn over Arnold without jeopardizing any future defection or even report-in-place volunteers who might later need re-location. There was, of course, also the question of Honor.

    Andre was caught primarily because he was a poor intelligence officer who disobeyed Clinton’s instructions and allowed Arnold, the agent, to run the show. Always a bad idea in the intelligence profession. Hale was just a poorly, if any, trained naïve agent. Had Robert Rogers not entrapped him, there were several other reasons his mission could have been discovered.

    1. Ken – a good summation commentary on the competencies of both Hale and Andre. The success of each respective agents’ mission was directly affected by that critical factor.

      Many thanks.

  • This was not central to the article, but the statement that Long Island’s civilians were “mostly New York Dutch” is inaccurate. Suffolk County, the largest on the Island, and where Huntington is located, had been settled primarily from New England, and was heavily Presbyterian/ Puritan as well as Whiggish in sentiment. No surprise they were generally pro-Revolution. Queens County to the west had a mixture of Dutch and English settled areas, and Kings (Brooklyn) contained the greatest number of Dutch descended inhabitants. Generally speaking, the further one moved west on Long Island the more numerous Loyalists became.

  • Richard – I derived the “mostly New York Dutch” statistic from a number of secondary sources including M. William Phelps’ recent work of Nathan Hale.

    But you raise the realistic question of quantifying an entire population labeling 240 years after the fact. Thank you for bringing that to light.

  • John,
    A good, readily available reference for things New York off Manhattan Island is “The Other New York. The American Revolution Beyond New York City, 1763-1787” Joseph S. Tiedemann and Eugene R. Fingerhut editors. Solid, well-researched articles by excellent local historians.
    I very much enjoyed your presentation of Hale and his mission

    1. Richard – thank you again and I’ll add the Tiedemann / Fingerhut book to my wish list of reference materials. That’s another great thing about the JAR forum – being able to share book tips to other like-minded historians.

      Thank you!

  • John, as a fellow military historian, I found this article useful for my MILH320 class at the American Military University. A number of my students are Global Security or Intelligence Analysis professionals, so this really hits home for them. Keep up the good work and visit my website sometime! JL

Leave a Reply

Your email address will not be published. Required fields are marked *