Hugh Hughes and Washington’s Retreat: American Principles and Practicalities

The War Years (1775-1783)

March 14, 2024
by Ethan King Also by this Author


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The Livingston mansion was a large frame house with a colonnaded front porch and four marble chimneys.[1] The chimneys were Italian imports and illustrated the worldliness and influence of the house’s prosperous merchant owner, Philip Livingston. Livingston, though, was absent and the house was instead serving as the military headquarters for George Washington’s Continental Army on Long Island. In the Livingston house, late in the afternoon of August 29, 1776, Washington convened a council of war with his senior officers. Washington put forth a critical question: should the Continental Army retreat from Long Island?

View of part of the rebel works around Walton’s House by Archibald Robertson (October 8, 1776) from the New York Public Library. Sketched by a British officer two months after the American defeat, this image displays examples of the small sloops and watercraft Hughes impressed to help evacuate the Continental Army from Long Island.

Washington’s army was in a precarious position. Situated behind a series of forts, redoubts, and abatises at the tip of Long Island, the 9,000-man army was soaked by incessant rains and shocked by the experience of its first battle. At the Battle of Long Island (August 27, 1776), Gen. William Howe’s formidable army of British regulars and German auxiliaries had overwhelmed the Continental Army. Howe had chosen not to follow up his victory and instead employed siege tactics—known as regular approaches—to methodically close the gap on the American fortifications without a frontal assault. The East River, situated in the American rear, remained a potential avenue of retreat for Washington, but this could be cut off at any moment by the positioning of Royal Navy warships in the channel.

Washington’s question initially faced dissent in the council. John Morin Scott, a lawyer from New York, vehemently opposed. He explained in a letter to his friend John Jay, when the retreat “was suddenly proposed, I as suddenly objected to it, from an aversion to giving the enemy a single inch of ground.” Scott’s dissension was more emotional than rational and he soon “was convinced by the unanswerable reasons for [the retreat].”[2] The council unanimously concluded that retreat was necessary, listing in the meeting’s minutes an exhaustive eight-point list on why Long Island was untenable.

The debate, though, mattered very little because that morning Washington had decided to evacuate Long Island. The council of war was a mere formality that lent credibility to a retreat that would doubtless come under scrutiny from the public. Preparations had begun early—the sick and wounded were ferried over to Manhattan under the premise that in the upcoming fight they would be, “an encumbrance to the army” and regiments were informed that they were going to be rotated out for fresh troops from New Jersey.[3] Washington also gave a verbal order to Deputy Quartermaster General Hugh Hughes to gather all the boats he could find to carry the American army to safety. Hugh Hughes’ actions on August 29 were crucial in securing the survival of the Continental Army and showed the difficulties of waging war while adhering to the professed principles of the American Revolution.

Hughes Before the War

Hugh Hughes was born on April 27, 1727, in Pennsylvania. As the youngest son of Hugh and Martha Hughes, his prospects were more limited than his older siblings. His eldest brother, John, received the sizable family farm, Walnut Grove, and established himself as part of the provincial gentry. The younger Hughes, however, was destined for a life as a part of the newly emerging “middling sort”—the master artisans, merchants, and shopkeepers who possessed a small degree of wealth and learning.[4] Hughes pursued a trade as a tanner in New York City and married Charity Smith in 1748.[5]

Unfortunately, Hughes’ semi-prosperous life came crashing down in 1765. Hughes was a cosignatory on a £500 loan for his friend Benjamin Blagge, who was unable to pay back the loan and defaulted. Hughes became responsible for the sizable remaining sum, but he, too, could not pay back the loan in full even after liquidating his assets. Facing debtors’ prison, Hughes went into quasi-hiding and for several years, rarely left his home. One of his friends, John Holt, summed up his situation in 1771, writing that Hughes had “for many years past, made himself a voluntary Prisoner in his own House, where he has supported a numerous Family of Children, by teaching School . . . [the] most considerable English School in Town.”[6] As a schoolteacher, Hughes delved into intellectual study and, as Holt noted, he “greatly improved his own Knowledge.”[7] This intellectual growth allowed him to offer meaningful contributions to the complex political debates arising during the 1760s, which garnered him the respect of his revolutionary peers.

After the Stamp Act Crisis in 1765, Hughes became embroiled in the colonial resistance movement. He shared his beliefs with other patriot leaders—notably Samuel Adams, John Adams, and Thomas Young—in continued correspondence. He wrote to Young in 1772 chiding Boston for acting with too much restraint and complained of the “ignorance of the common people” in New York for their failure to fully grasp their dire political situation.[8] To Samuel Adams in 1775, he discussed the full implications of the American cause, which led him to the conclusion that slavery must end. Hughes wrote, “if we contend for liberty, let us show that we are worthy of it by diffusing the Blessings of it to the whole human race.”[9] His staunch political beliefs created divisions within his own family, particularly with his older brother, John Hughes, who with the patronage of Benjamin Franklin was appointed stamp collector of Philadelphia in 1765. The brothers’ political differences, according to Hughes’ friend Holt, caused “a Breach between them, that seems to be irreparable.”[10]

Hughes used his connections established during the resistance movement to gain an appointment in the Quartermaster’s Department of the Continental Army upon the outbreak of war. Hughes was appointed a commissary of military stores in New York on February 16, 1776, and then Deputy Quartermaster General in the Continental Army on May 11 of that year.[11]

The Retreat

The order Hughes received on August 29 was delivered by Joseph Trumbull around noon. Hughes was ordered to gather every boat “from Hellgate in the Sound, to Speygten Duyvel in the Hudson . . . and have them all in the East Harbor of the city by dark, without letting it be known for what purpose they were impressed.”[12] The timely completion of this task was critical because Washington possessed only a small number of boats. These boats had been sufficient to ferry small contingents of men between Long Island and Manhattan during the prior months, but Washington’s goal of moving the entire army to Manhattan in one night would be impossible without the addition of many more boats.

At least one other Continental officer was assigned to gather boats too. William Heath, a New Englander, was given orders to collect boats in his area of command, which stretched from Kingsbridge to Fort Washington on Manhattan. Heath was told, “We have many battalions from New Jersey which are coming over to relieve others here [Long Island]. You will please therefore to order every flat-bottomed boat and other craft at your post, fit for transporting troops down to New York as soon as possible.”[13] Here again is the attempt to cover up the retreat with the explanation that troops on Long Island were being rotated out for fresh troops from New Jersey in preparation for battle. Even in direct orders to a Continental officer, complete secrecy was upheld.

Heath would later write in his memoirs that “the real intention of their [the boats] use was fully understood,” but his memories may have faded.[14] In a letter to Washington the morning after the retreat, Heath seemed completely taken aback. He wrote, “A very Extraordinary Report has Just Spread here, whether true or false we are as yet uncertain, That Long-Island is Evacuated by our troops.”[15] Regardless of whether Heath fully understood the situation, he acted swiftly and forwarded all boats in his department towards the harbor.

Hughes, meanwhile, rode along the coastline of the East River. Any boat he came across, he hailed and sent to New York Harbor.Hughes explained, anything “that could be kept afloat, and had either oars or sails, or could be furnished with them” was taken into service.[16] Most of the boats were small. Major Abraham Legget referred to the boats that carried his men over as “battoes,” a term also used by Joseph Plumb Martin, a young soldier from Connecticut.[17] Batteaux, derived from the French word for “boat,” were shallow, flat-bottomed boats generally used to move cargo. However, Hughes also seized at least one sizable ship, the sloop Middlesex, which was returning home after delivering flour to the Continental army.[18]

Hughes’ task was made more difficult because most boats that normally resided in New York’s harbor had been relocated to anchorages a safe distance from the city, out of fear of British naval bombardments. He personally rode fifteen miles up to Hell Gate, while to cover the other side of Manhattan he “availed myself of the ardor and activity of some of my fellow-citizens” to impress boats in the Spuyten Duyvil Creek.[19] Considering Hughes relied on private citizens instead of soldiers for assistance, these men must have been people Hughes personally trusted, perhaps from collaborating with them during the pre-war resistance movement. Within eight hours, Hughes collected over fifty boats for Washington’s use.

The retreat commenced at nightfall with all the boats in place. John Glover’s Continentals, mostly fishermen and seamen before the war, handled the boats during the crossings. The militia and less experienced Continentals were ferried off first, while the remaining regiments shifted their positions to fill the gaps. Washington’s most trusted troops, Continentals from Maryland, Delaware, and Pennsylvania commanded by Thomas Mifflin, were assigned the rearguard. As more troops left for Manhattan, the rearguard’s position grew increasingly perilous throughout the night. Ayale graduate, Benjamin Tallmadge, described it as, “one of the most anxious, busy nights that I ever recollect.”[20]

By daybreak, most troops were in Manhattan, but Mifflin’s rearguard remained on Long Island. Fortune, however, smiled on the American cause and a fog so intense that you “could scarcely discern a man at six yards’” settled in.[21] The added hours of cover allowed the entire Continental Army, apart from a few heavy cannons mired in mud, to cross the East River unnoticed.

The efforts of Hughes and Heath had fitted Washington with the means to make his daring escape from Long Island. Hughes’ role was particularly important and burdensome. He wrote, “I never once dismounted from . . . 12 o’clock at noon till 10 o’clock the next day.”[22] But these exertions paid off, creating within a single afternoon a flotilla of boats capable of transporting a 9000-man army over the East River in one night.

Legal Troubles

Years later, the legality of Hughes’ actions would come under scrutiny. Impressment, as a practice, was frowned upon by many because it clashed with core principles of the American cause. The concept that men, according to George Mason’s heavily influential draft of the Virginia Declaration of Rights, “can not be taxed, or deprived of their property for public Uses, without their own Consent,” was considered a sacred value.[23] Impressment—the involuntary seizure of property—was, especially after 1778, nonetheless extensively used to supply the impoverished Continental Army. It was a contradiction to the American cause—one of many including slavery, a strong central government, and a powerful, professional army—that made winning the war and creating a strong country possible, but not necessarily consistent with its professed values.

Most states did enact laws that legalized impressment but limited its scope, and worked to protect individual rights. “An Act Authorizing the Person Administering the Government of this State, to Grant Warrants of Impress,” passed on June 23, 1780, in the New York State Legislature, laid out the proper legal procedure for impressment. It granted the power to local justices of the peace, “whenever he shall deem the emergency and occasion to require . . . to grant warrants of impress.”[24] Continental officers with these warrants were then “impowered to break and enter” into any location where the warrant’s specified provisions were suspected to be and seize the provisions.[25] The officer would then provide a receipt to the owner and the officer would be responsible for compensating the goods or services at the current market price.[26]

According to this, Hughes had acted illegally in 1776. He had not been granted a warrant of impress and, more importantly, many of the owners never received compensation for their boats—most of which were captured by the British in the ensuing months. But since in 1776 no law was in place that regulated impressment, the courts demanded instead that, to avoid prosecution, Hughes provide evidence that Washington ordered the seizure of the boats. Hughes wrote to Washington in July 1784 to explain his predicament and request a written order. He wrote, “I am compelled to solicit your Excellency to favour me with a written Order for that particular Service, or a Certificate of the verbal One.”[27] Despite the business-like tone of the letter, Hughes’ frustration could not help but seep through. He grumbled, “I never expected to be prosecuted for obeying your Excellency’s Orders that were evidently and eventually the Preservation of the Army.”[28] Hughes’ heroic achievement had turned into a painful burden.

Washington responded three weeks later with a testimonial of Hughes’ conduct. From Mount Vernon, he wrote, “I have no doubt therefore of your having received orders to the effect, and extent you have mentioned, & you are at liberty to adduce this letter in testimony thereof.”[29] Hughes avoided prosecution, but the experience must have felt like a betrayal for the sacrifices he had made. For the boat owners, too, who never received compensation for their involuntary losses, it must have felt like a betrayal too. They had subscribed to a cause that promised protections of their rights from the infringements of King George and his ministry. Yet, those rights had been infringed upon by the very cause that promised to secure them.

Unfortunately, these were the realities of war. The delicate balance between securing the rights promised by the American cause and taking actions that would allow the Continental Army to prevail on the battlefield was a paralyzing issue throughout the war. The problematic contradictions derived from the promises of America and the actions needed to win the war illustrate how America prevailing without completely abandoning her original principles was remarkable. Nathanael Greene summed up these issues aptly in a letter to Thomas Jefferson written about the impressment of horses during Greene’s 1781 campaign in Virginia. Greene wrote, “Particular situations and particular circumstances often make measures necessary that have specious shew of oppression, because they carry with them consequences pointed and distressing to individuals.” Greene concluded, “it is to be lamented that this is the case, but pressing emergencies make it political and sometimes unavoidable.”[30]


The remainder of Hughes’ life was spent unsuccessfully attempting to receive pay for his services during the war. He claimed he was owed $8,570 of wages, but this was rebuffed multiple times by Congress and the Treasury Department because Hughes could not provide a full account of his transactions in the Quartermaster’s Department.[31] Matters were made worse when in January 1789, a fire burned down his home and consumed most of his personal papers, which ended any real opportunity for compensation. Hughes passed away on March 15, 1802, in Tappan, New York, on his return home from one final, failed attempt at petitioning Congress.

Throughout his life, Hughes remained hopeful of the future for America. He saw America as “an asylum for the small remains of expiring liberty in the old world, where anarchy and aristocracy, those implacable enemies to the rights of men have long stalked truth and justice out of countenance.”[32] Even so, Hughes and most Continental officers recognized that the way in which America would achieve this noble aspiration had to, at times, undermine their cause’s professed principles. Hughes’ heroic actions on Long Island highlighted these contradictions in play during one of the most critical moments of the American Revolution.


[1]Gabriel Furman, Antiquities of Long Island (New York: J.W. Bouton, 1875), 154.

[2]John Morin Scott to John Jay, September 6, 1776, in H.P. Johnston ed., The Campaign of 1776 Around New York And Brooklyn (Brooklyn: Long Island Historical Society, 1878), 2:36-37.

[3]General Orders, August 29, 1776, The Campaign of 1776 Around New York And Brooklyn, 2:30-31.

[4]Gordon S. Wood, The Americanization of Benjamin Franklin (New York: Penguin Books, 2004), 41-42.

[5]B. Friedman, “Hugh Hughes, A Study in Revolutionary Idealism,” New York History, 64 (1983), 231-233.

[6]John Holt to Benjamin Franklin, October 2, 1771, in W.B. Willcox ed., The Papers of Benjamin Franklin, vol. 18, January 1 through December 31, 1771 (New Haven and London: Yale University Press, 1974), 225-228.

[7]John Holt to Benjamin Franklin, October 2, 1771, ibid., 225-228.

[8]For Thomas Young to Hugh Hughes, December 21, 1772, see

[9]Hughes to Samuel Adams, December 22,1775, in “Hugh Hughes, Study of Revolutionary Idealism,” 242.

[10]Holt to Franklin, October 2, 1771, The Papers of Benjamin Franklin, vol. 18, 225-228.

[11]General Orders, May 11, 1776, in P.D. Chase ed., The Papers of George Washington: Revolutionary War Series 4, April-June 1776  (Charlottesville and London: University of Virginia Press, 1994), 274.

[12]Hugh Hughes, Memorial and Documents in the Case of Colonel Hugh Hughes Deputy Quarter Master General During the War for American Independence (Washington D.C., 1802), 33.

[13]The Campaign of 1776 Around New York And Brooklyn, 1:218.

[14]William Heath, Memoirs of Major-General Heath Containing Anecdotes, Details of Skirmishes, Battles, and other Military Events, During the American War (Boston: L. Thomas and E.T. Andrews, 1798), 49.

[15]William Heath to George Washington, August 30, 1776, in P.D. Chase and F.E. Gizzard eds., The Papers of George Washington: Revolutionary War Series 6, August-October 1776 (Charlottesville and London: University of Virginia Press, 1994), 165.

[16]Hughes, Memorial, 33.

[17]Account of Major AbrahamLeggett, in T.W. Field, ed., The Battle of Long Island with Connected Preceding Events, and the Subsequent American Retreat (Brooklyn: Long Island Historical Society, 1868), 501.

[18]The Campaign of 1776 Around New York And Brooklyn, 1:219n1.

[19]Hughes, Memorial, 33.

[20]Major Tallmadge’s Account of the Battles of Long Island and White Plains, The Campaign of 1776 Around New York And Brooklyn, 2:78.


[22]Hughes, Memorial, 34.

[23]For George Mason’s draft of the Virginia Declaration of Rights, see,the%20extension%20of%20religious%20tolerance.

[24]Laws of the State of New York Passed at the Sessions of the Legislature Held in the Years 1777, 1778, 1779, 1780,1781, 1782, 1783, 1784, Inclusive, Being the First Seven Sessions, Volume 1 (Albany: Weed Parsons and Co., 1864), 264.

[25]Ibid., 265.

[26]For more information on impressment during the American Revolution, see E. Wayne Carp, To Starve the Army at Pleasure: Continental Army Administration and American Culture 1775-1783 (Chapel Hill and London: University of North Carolina Press, 1984), 75-99.

[27]Hughes to Washington, July 31, 1784, in W.W. Abbot ed., The Papers of George Washington: Confederation Series 2, July 1784-May 1785  (Charlottesville and London: University of North Carolina Press, 1994), 17.

[28]Hughes to Washington, July 31, 1784, The Papers of George Washington: Confederation Series 2, 17.

[29]Washington to Hughes, August 22, 1784,The Papers of George Washington: Confederation Series 2, 18n1.

[30]Nathanael Greene to Thomas Jefferson, April 28, 1781, in D.M. Conrad, R.N. Parks, M.J. King, R.K. Snowman, eds., The Papers of General Nathanael Greene: Volume VII, March-July 1781 (Chapel Hill and London: University of North Carolina Press, 1994), 165.

[31]Hughes, Memorial, 30.

[32]Hughes to Daniel Carthy, November 28, 1781, in “Hugh Hughes, A Study of Revolutionary Idealism,” 245.

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