Forgotten Patriots of the American Revolutionary War: Major Thomas Henley and Raid on Montressor’s Island

Forgotten Patriots: Major Thomas Henley & The Raid on Montresor’s Island

The genius of America starts as from a trance, at her neglect to guard the lives of a Knowlton and a Henly; and then absorbed in melancholy, sighs, “it was a mistake, they were not to have fallen, only upon the decision of the fate of an empire.”[1]

A fledgling government of ‘insubordinate’ colonialists in eighteenth century America, freely called ‘rebels’ by their British overseers, lost some of their finest young officers in the early stages of the American Revolutionary War. Once hostilities erupted, the youthful soldier/citizens proved their intellect, leadership, and bravery on the field of battle. Had they lived, there is little doubt they would be among the textbook heroes and founding fathers of a grateful nation. Few people currently recognize their names and their sacrifice so selflessly given. Within this distinguished group of dedicated patriots may be found:

• General Joseph Warren, medical doctor, political activist, and president of the Massachusetts Provincial Congress. At a young age, he was a tireless leader who poured his heart and soul into an attempt to get England to listen to the colonists’ complaints. Once hostilities erupted, he organized dozens of militia around Boston into a single force with an eye to mold a protracted army of resistance. He perished in June, 1775 during the onslaught of British regulars at the Battle of Bunker Hill, Boston.

Colonel Thomas Knowlton, Connecticut farmer, former member of the famed Rogers Rangers of the French and Indian War. He was brave, brilliant, and was Washington’s pick to head up the new intelligence gathering arm of the army that would later became the federal government’s CIA. He was the favorite of both officers and the rank and file of the new Continental army, one for whom the phrase was coined – ‘You cannot lead from behind.’  He died leading his ‘Knowlton’ Rangers on September 16th, 1776 at the Battle of Harlem Heights.

• Major Andrew Leitch: this father of four was an active patriot and member of the Virginia’s Prince William County Committee. He readily accepted the temporary helm of the First Virginia regulars as it faced the enemy for the first time.  He did so when his friend and the first chosen leader of Virginian forces, the well known and celebrated statesman Patrick Henry – he who had stood before his fellow patriots and claimed ‘give me liberty or give me death’ – resigned from the army because he was passed over as general and was only offered a colonel’s commission of the first Virginia regiment.  In his stead, Major Leitch marched into battle at the head of that astute southern body and paid the ultimate sacrifice along the slopes of Harlem ridge, in the same battle that claimed Colonel Knowlton.

John Laurens, a South Carolina native, was the son of Henry Laurens. As President of the Continental Congress after John Hancock, the father Henry was a wealthy planter who also owned the largest slave trading establishment in North America; in one year alone, this slave trader would oversee the sale of as many as eight thousand African Americans. John did not share his father’s views on slavery. He was resourceful, courageous, and audacious to the point of foolhardiness. Scholar, statesman, ambassador and soldier, John was a close friend of Alexander Hamilton. He, like Hamilton, believed that blacks should be freed in the cause of liberty and given the opportunity to bear arms in the new American cause. He pressed this agenda throughout his political and military career. Tragically, he lost his life on August 27^th, 1782 near the conclusion of the war in a minor action against a British foraging party which became known as the Battle of the Combahee River. A leader among the elite, there is little doubt that he would have had a role in carving out a new republic and would ultimately have claimed high office in government.

• This leads us to Major Thomas Henley (or Henly, both spellings occur in letters and orders written through the early stages of the war). He was one of the least known among these men. Having enlisted early in the war, he advanced rapidly through the ranks and soon became one of the youngest, if not the youngest major in the American army. Like his peers Aaron Burr, and Alexander Hamilton, he was promoted as aide-de-camp to a major general. Smart, quick thinking, affable, and well liked by all, no one doubted that this young man would continue to rise quickly within the ranks and achieve the fame that destiny seemed to hold for him.

Thomas was from an ancient and reputable family that had set their roots in Charlestown[2], just north of Boston, during the previous century. His date of birth remains unknown.[3] As soon as he came of age, his father sent him to study in London.  When news of the battle of Lexington reached England, Thomas immediately journeyed home. He entered the Continental service in the regiment commanded by Colonel Varnum of Rhode Island. Shortly after, he was transferred to the corps of artillery commanded by Colonel Henry Knox as Lieutenant and adjunct. A rising star among his peers, “he was beloved and respected by the officers, of not only his own corps, but the whole army, and his reputation as a good officer was such, that, a few days before his death, he was promoted to be first Aid-de-Camp to Major-General Heath.[4]“

His life suddenly ended in the early hours of September 23^rd, 1776, in a raid on a British garrison on Montesor’s (now Randall’s) Island, New York City. General Orders dated the day after Major Henley’s death included praise for the youthful officer: “Major Henley, aide-de-camp to General Heath, whose activity and attention to duty, courage and every other quality which can distinguish a brave and gallant soldier, and must endear him to every lover of his country…”[5]  Washington addressed a letter to Governor Patrick Henry from his headquarters on Harlem Heights on October 5^th, 1776. Within his letter he laments the loss of able officers in recent actions. “Since this skirmish, [Battle of Harlem Heights, September 17^th, 1776] excepting the affair at Montresor’s Island, where Major Henley, another of our best officers, was slain, there has been nothing of any material consequence.”[6]

This raid both symbolized the emerging American army’s dedication and willingness to sacrifice, in counterpoint to a strong current of self preservation in untested troops that was deemed cowardice. A letter from an American officer shortly after the affair: “He [Maj. Henley] fell unsupported and unrevenged, owing to the backwardness of the rest of the party. Not for the actions of which ultimately led to the court-martial of two captains for cowardice and misbehavior before the enemy.[7]” After the fiasco at Kip’s Bay, John Adams voiced his frustration in a now famous letter he wrote to his wife from Philadelphia, dated Oct. 8^th, 1776 (famous for his claim that their ‘generals were out-generaled’): “Wherever the men-of-war have approached, our militia have most manfully turned their backs and run away… their panics have sometimes seized the regular regiments… One little skirmish on Montresor’s Island ended with the loss of the brave Major Henley, and the disgrace of the rest of the party.[8] ”  Colonel Samuel Webb best expressed the general mood of the populace in a letter to his brother on Oct. 3^rd. He refers to the expected court-martial of those accused as ‘poltroons’:  “… trying one of the captains… [for] the night young Henly fell… If our people are in a hanging mood, I think he stands a chance to swing.[9] ”

On August 27^th, 1776, General Washington’s army suffered a devastating defeat in the Battle of Long Island at the hands of the crafty General Howe, Supreme Commander of the British Ministrial Forces. The American army was ‘outgeneraled.’ Shortly afterwards, Washington’s troops enacted an incredible escape from Brooklyn over the East River to New York City. At that point, the Americans anxiously waited for the expected invasion of York Island (Manhattan). The blow came on September 15^th at Kip’s Bay. First the Connecticut militia was routed by an intense bombardment from British men-of-war, immediately followed by a full invasion by a division of Hessian and British troops. There was a complete rout of all American defenses stationed along the East River. A third of the American army under General Israel Putnam remained in New York City and was about to be hemmed in. They barely escaped, slipping by the British forces before the trap could be sprung. The very next day, Washington struck back in an unexpected attack upon the British front guard in what became known as the Battle of Harlem Heights. This left both armies facing the other over the Plains of Harlem. Washington’s army, during its desperate flight from New York, left behind much needed supplies. When word came that a large cache of British arms and accruements were lightly guarded on Montresor’s Island,[10] plans were set to raid the garrison. The island[11] was located at the convergence of the Harlem River, East River, and Long Island Sound, which was called Hell’s Gate on account of the strong tidal currents flowing between the land masses making the passage treacherous to shipping. The channel between York and Montresor’s Island was, and remains, narrow.

General William Heath best expresses the reasoning for the raid. He described it in a letter to William Duer (member of New York’s Provincial Congress) detailing the action on Montresor’s Island. He dated it September 22^nd, 1776.[12] “Two seamen, belonging to the La Brune, a British ship of war, which lay near Montresor’s Island, deserted and came to General Heath’s quarters, and informed him, upon examination, that the British had then but a few men on the island, stating the number; that the piece of cannon which had been put on the island was taken back again, on board the La Brune; that there were a number of officers at the house [garrison], in which there was a considerable quantity of baggage deposited [blankets, tents, clothes, and sundry necessities], &c. General Heath supposed that these troops, a guard of enemy consisting (as was supposed) of about fifty,[13] might be easily taken; and, having called the general officers of his division together, took their opinion, who all coincided with him in sentiment. He then communicated his intention to the Commander-in-Chief [Washington], who gave it his approbation.[14]“

The orders were given to Lieutenant Colonel Jackson of Colonel Paul Dudley Sergeant’s regiment[15] in General Mifflin’s Brigade under Major General William Heath.[16] The forces were instructed to depart the night of September 22^nd at 11:00 PM, embarking in flat-boats, which could each hold up to forty men. “They were to fall down the Harlem Creek with the ebb. The time was so calculated that the young flood was to be so much made, at the break of day, as to cover the flats at the Island sufficiently for the boats to float.”[17] In darkness and with extreme caution they were to head northeast and cross the channel to Montresor’s Island once they made the main river. Their surprise attack was to start as soon as they landed on the island.

Most sources agree that 240 American soldiers were involved in this operation.  However, a letter from an officer on Harlem Heights dated shortly after the raid states that there were 140,[18] while a British author of the time puts the number at 300.[19] Though most records concur on the size of the raid, both primary and secondary sources disagree on how many boats were used. Colonel Glover puts the number at six, stating that each was to carry 40 men – which nicely adds up to the total number of men detailed for the raid.[20] Gordon gives the number of boats as five and adds that they [Americans] had two pieces of cannon with them.[21] Both Leggett[22] and Ford[23] state that only three boats were part of the raid. This is confirmed in a letter from General Washington’s Headquarters[24] composed after the raid. An officer and reputedly good friend of Major Henley gave the number of boats as four.[25] Dawson writes “…[they] embark[ed]… on board of three large floats; to be covered by a fourth float, similar to the others and carrying a detachment of artillery.”[26]

Perhaps Brigadier General Heath, overall commander of the expedition, has the final say:  “Two hundred and forty men were destined for the enterprise… They were to embark onboard three flat-boats covered by a fourth with a detachment of artillery with a light three pounder, in case it should be found necessary in retreating from the island.”[27]

According to General Heath, once plans were in place, the two deserters from the La Brune were brought to him. He told them that, “in consequence of their information, an enterprise against the British guard on Montresor’s Island was to take place that night; that he had ordered them to be kept in safe custody until the next morning, when, if their declarations respecting the state of the British on the Island proved to be true, he would give them a passport to the back country, whither they wished to go; but, in case their information was false, he would order them hanged immediately.”[28]  Accordingly, the two prisoners showed no signs of anxiety over Heath’s threat but expressed gratification for the offer of passport. They were fully contented when reassuring the general that what they said was true.

The other principal officer besides Lt. Col. Jackson was to be Major Hatfield of Westchester County.[29] They were in the first boat to land on the island captained by Robert Smith, who was a captain in Colonel Malcom’s regiment.[30] The two other boats were each commanded by Captain Weisner[31] and Captain Scott.[32] Prior to the time of departure, General Heath records in his flowingly written memoir that his aide-de-camp, Major Thomas Henley, requested his commander to allow him to accompany Colonel Jackson and the others. “He [Henley] importuned that he might go with the detachment. He was refused, and told that he had no business there; that he could exercise no command. He grew quite impatient, returned again to the General’s room and addressed him. ‘Pray, sir, consent to my going with the party. Let me have the pleasure of introducing the prisoners to you tomorrow.’ All of his friends present advised him not to go. The General finally consented.[33]  Major Henley would be in the first boat along with Colonel Jackson and Major Hatfield. The original plan called for two other major officers in the first boat besides Jackson, however only one, Hatfield, was to be present. One is suspect as to the timing of Henley’s request as he ultimately served as the third officer in the first boat.

General Heath’s memoir explains what occurred as the boats silently entered the mouth of the Harlem River: “Notice had been given to the guards and pickets on the York-Island side, not to hail the party as they went down[Harlem Creek].” Unfortunately, the lower sentinel had not been so instructed. He was nearly opposite to the point where General Heath was to be;[34] and just at the instant when he arrived [assuming the sentinel], had challenged the boats, and ordered them to come to the shore. From the boats they answered, ‘Lo! we are friends.’ The challenge was repeated. The answer was, ‘We tell you we are friends; hold your tongue.’ The sentinel called again, ‘If you don’t come to the shore, I tell you I will fire.’ A voice from someone in the boats was, ‘Pull away!’ The boats went on, and the sentinel fired his piece, giving the alarm.[35]

What occurred next is best related in Henry Dawson’s account found in his 1886 text on the war in New York entitled Westchester County New York During the American Revolution: “… the enemy does not appear to have been disturbed; and the three floats ran up to the place appointed for the landing, without serious opposition and at the appointed time.”[36]  Most accounts give the time to be around four a.m. General Heath writes that “just as the glimmer of the dawn was discoverable.”[37]

William Gordon’s 1801 rendition of the American Revolution states that the Americans were fired upon as they crossed the channel: “the Brune frigate [British man-of-war] being at anchor near the island, fired at the boats in the dark, and sunk one.”[38] Henry Beatson writes three years later in his treatise on the war that the boats were “briskly” fired upon and one of them was sunk “full of men.”[39] Interestingly, both men are British scholars writing during a time when sentiments in England were still strongly bitter towards the war. Retailers knew that any treatment glorifying the British military and their actions during the war would do well among booksellers. Nowhere is it recorded in firsthand accounts or in early histories on the war by Americans that a British ship fired on the boats.

Dawson continues: “But, there, a new and entirely unlooked-for obstruction was encountered. The orders were that the float which contained the three commanding officers should run ashore, between the other two; that the two majors should jump ashore, one to the right and the other to the left, and take command of the men who were on those two outside floats, respectively, while Lieutenant-colonel Jackson should retain the command of those who were on the central float; and that the three parties should act in concert. The officers and those who were on the central float sprang ashore, as they were expected; received and repulsed a charge which the enemy’s guard made on them; but failed to receive the slightest support from those who were on the other two floats,[40] who, instead of landing, sullenly “lay upon their oars.” The enemy, seeing that disaffection, rallied, and returned to the charge, with great spirit; and the Americans, those from the central float, finding themselves deserted, returned to their own float, with heavy loss; and the entire expedition withdrew from the island – whether the fourth float, on which were the artillery and which was intended as a covering party, performed any service, is not now known, as nothing whatever has been said of it, in the narrative of the encounter and retreat.”[41]

Colonel Glover wrote despairingly[42] that after having repulsed the enemy, “those of the first boat called to the other boats to push and land, but the scoundrels, coward-like, retreated back and left him [Henley] and his party to fall a sacrifice.”[43]  Colonel Tench Tilghman lamented that those in the first boat “drove off the guard at the water side, with ease. The other boats rowed back as soon as the firing began, though they were repeatedly called after. This dampened the spirit of the first boat’s crew, who could not be prevailed upon to stay.”[44] General Heath notes in his memoir: “The field officers landed, and the men from their boat. The enemy’s guard charged them, but was instantly driven back. The men in the other two boats, instead of landing – lay upon their oars. The British, seeing this, returned warmly to the charge. The Americans, finding themselves deserted, returned to their boat…”[45]  For whatever reason, Colonel Jackson and the crew of the first boat fought hard, achieved the first directive by beating back the enemy’s guard, and then were abandoned by the rest of their force at the most critical stage of the raid.

Who, and how many defended the island? Dunlop writes they were received by ‘vollies’ from about seventy highlanders. Gordon gives the number as eighty highlanders and Colonel Glover believed the Americans from the boat, numbering around forty faced imposing odds: “The enemy… 150 of them rushed out of the woods and attacked them again at 30 yards distance.” Only the English scholar Robert Beatson,[46] in 1804, notes that the British unit facing Colonel Jackson’s men was none other than part of the seventy first highlanders. They were raised under the command of Colonel Frazer and first assembled in Glasgow in April, 1776 where they soon embarked for America. Though not fully trained, General Howe placed them in the front during his attack in Long Island on August 27th. Judging well from the experience he had had of Fraser’s Highlanders in the seven years’ war, he gambled that their bravery, if engaged before being disciplined, would make up for their lack of discipline. In what was known as the Battle of Brooklyn, they fully justified the expectations of their general.[47]  Colonel Jackson and his crew had faced not just a small body of men, as assured by the two deserters, but a large, well equipped formidable foe.

American casualties, all from the only boat that fought on the island, were heavy. The total number varies, but it is safe to say perhaps as many as half those in the first boat were killed, wounded, or made prisoners. Dawson writes that “Lieutenant-colonel Jackson received a musket-ball in his leg.[48] That Major Thomas Henley was shot through the heart as he was getting into the boat; that Major Hatfield was missing; and that the [total] loss of killed, wounded, or missing was fourteen.”[49] An American officer wrote that Captain Hubbart… paymaster… [was] killed.[50] Tilghman wrote that “…they had a considerable number of men killed; and left a Major and twenty-two men wounded, who were made prisoners. Their commandant was also wounded.”[51]  Benson Lossing agrees that there were twenty-two casualties.[52] A letter from Harlem Heights stated that every officer was either killed or wounded with the loss of half their men.[53] From Washington’s headquarters it is recorded that fourteen men were killed, wounded, and missing.[54] Leggett states likewise.[55] Colonel Glover writes dramatically that “Major Henly carrying off Col. Jackson was shot dead as he was putting him into a boat, and not a single man of the eight but was wounded. One of them died at the oar before they landed on the main.[56] Lossing writes that Henley was shot while leading his men.[57] The expedition’s commanding officer, General Heath, records in his memoir that “… Major Henly, as he was getting into the boat, [a musket ball was shot] through his heart, which put an instant end to his life. The boat joined the others, and they all returned, having, in the whole, about fourteen killed, wounded, and missing. Since Henley’s corpse was returned to York Island, and, according to Beatson, the Americans left their dead behind, it is most likely that Henley was shot and killed as he was either getting into the boat or already in the boat.

The only detailed British description of the raid was written by Beatson twenty eight years after the battle; it conflicts with the American account. The claim of the British warship firing on and sinking one of the American boats has already been noted in this article. “The others made good their landing on the island, and attacked the troops posted there, who consisted only a company of the 71^st regiment; but they behaved with such courage and firmness, that they [Americans] were quickly repulsed and driven back to their boats… twenty-two men wounded, who were made prisoners.” Beatson is the only source that gives the British loss: “In this skirmish, the 71^st regiment had four men killed and six wounded.”[58]

General Heath best expresses the frustration felt throughout the army by the failure of the raid. “Had only one of the other boats landed her men, the success would have been very probable; but the two would have insured an execution or the whole plan, in the opinion of all concerned.”[59] Those who commanded the other two boats were strongly condemned. Tilghman writes: “A very strict scrutiny is making into the conduct of the officers who thus shamefully deserted their leader, and it is expected they will meet the fate their cowardice deserves.”[60] Gordon simply writes that the men behaved most scandalously while Dawson is more prolific: “There was a wide-spread sorrow expressed for the death of Major Henley, who appears to have been a general favorite; and the cowardice of those who held back their support was as widely reprobated…”[61] Perhaps Colonel Glover expressed the worry of the general command over the impact of the crew’s behavior on the rank and file: “The officers who commanded the other boats are all under arrest and will be tried for their lives. In short, if some example is not made of such rascally conduct, there will be no encouragement for men of spirit to exert themselves.”[62]

As soon as the expedition returned, the captains of the two boats that failed to put in as ordered were arrested. A court martial was appointed September 29^th to try Captain [John] Weisner [of Col. Nicoll’s regiment of New York levies] and Captain Scott for cowardice and misbehavior in the attack made upon Montresor’s Island on the morning of the 23^rd instant.[63] Only Weisner was found guilty, but the sentence was far from what was expected and condemned by officers throughout the army. In General Orders written on October 31^st at White Plains, NY, “The Court Martial whereof General Beall was president, having found Captain Weisner, guilty of ‘Misbehavior before the enemy in the attack on Montresor’s Island’ – and ordered him to be cashiered with infamy, -The general [Beall] approves the sentence, and orders him to be dismissed from the army.”[64]

The army was dumbfounded. Every man expected the death sentence, if for nothing else than to act as a deterrent for future cowardice. Colonel Glover vehemently writes, “As the case now is, they will always fall a sacrifice, while such low-lived scoundrels, that have neither Honour nor the Good of their Country at heart, will skulk behind and get off clear…”[65] The verdict was unsatisfactory to General Washington. “To convict an officer of the crime of cowardice, and in a case where the enterprise failed on that account, where several brave men fell because they were unsupported, and to impose a less punishment than death, he [Washington] is very apprehensive [it] will discourage both officers and men, and render it, hereafter, difficult, if not impossible, to make an exemplary punishment, and especially in the case of a common soldier, who will suppose distinctions are made by officers in the case of an officer.”[66]

Thomas Henley was buried by Colonel Knowlton’s side and next to Major Leitch, the two officers who were killed in action during the Battle of Harlem Heights just seven days previous to the raid. The spot is indicated in the orders of September 24^th:  “Thomas Henley will be buried this P.M. from the quarters of Major David Henley [deputy adjunct general and older brother of Thomas.[67] ] … below the hill where the redoubt is thrown up on the road.”[68] During the Battle of Harlem, September 16, 1776, troops were throwing up entrenchments across the island at about one hundred and forty fifty street (west of 9^th avenue). This was the first and most southerly of the three lines constructed on the Heights as a defense against the British who had invaded from Kip’s Bay just south of the plains – occupying the hills around the Morris estate. Sauthier’s map,[69] the authority in the case, shows this line with a battery across the King’s Bridge Road, just at the top of what is known as Breakneck Hill. It was on the slope of this hill that Knowlton and Henley were buried with all the honors of war.[70] Lossing mistakenly puts the grave in one of the redoubts on the second line, afterwards including in Trinity Cemetery, but that line was not thrown up when Knowlton was killed.[71]

At the time of Henley’s death, he was among the most popular officers in the army, one on whom all eyes were trained as a future leader who would brand his name on the annuals of history. Yet, because of his early demise in the war, his history is recorded by only a few letters, general orders and the footnotes in aging texts, many times with his last name misspelled. A search on the internet will pull up a few references with only brief mention of Thomas in old texts; more so his brother David since he survived the war and commanded his own regiment, becoming an Indian agent for the southwest. As to the two deserters who assured the American command that the garrison was loosely defended, whether they swung at the end of a rope or buried their conscious in a new life in the western wilderness, history leaves us nothing, not even a crumb or two to follow their path.

Mr. John Jay, President of the Continental Congress (1778-1779), a wealthy NYC merchant, and the nation’s first Chief Justice, suggested the erection of a monument to Knowlton,[72] Leitch, and Henley. The idea was supported by many powerful men at the time. It was decided that no finer site could be found than the spot where Knowlton and Leitch fell in Morningside Park. However, more pressing matters diverted their attention; the important men had more important concerns, and the thought was soon forgotten. Thus, three incredible men who gave every ounce of their souls to the cause of American liberty lie in unmarked graves beneath the busy streets and concrete structures of a city far too busy to remember.

If you would like to read more about the American Revolution in and around New York City, check out these free previews of great books on Amazon

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Source

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Wilson, James Grant & Fiske, John.  Appletons’ Cyclopedia of American Biography Vol. 3. 1888:  Grinnell-Lockwood, New York, NY.

Footnotes: