10 Unsolved Mysteries of the American Revolutionary War

Larry Holzwarth - January 3, 2018

Nearly two and a half centuries after the American Revolution came to an end there are still unanswered questions surrounding many of its events. The Revolution was fought both overtly and covertly on many fronts, visible on battlefields, hidden in cities and towns. Secretive spies and double agents operated behind the lines of both armies. Diplomats and foreign agents arranged deals to provide goods and services, in the capitals of Europe and along the docks of port cities. Politicians in the Netherlands, Paris, London, and Philadelphia made arrangements to accommodate each other while advancing their cause.

George Washington emerged as a spymaster of consummate skill, establishing espionage rings so artfully concealed that their true nature and extent remain hidden to history, some of their heroes as yet unknown. Known spies were kidnapped and turned to serve as double agents. In many ways the American Revolution was a civil war fought between men well acquainted with each other, and the eighteenth century ideal of the gentlemen’s code took precedence in their correspondence with each other. The discretion required of the code still holds in many cases. Some events occurred which defied understanding then, and continue to elude it now.

Here are ten mysteries of the American Revolution which historians and scholars have failed to fully explain or understand after more than 200 years of uncovering clues.

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Who fired the shot heard ‘round the world?

The Revolutionary War began on the morning of April 19, 1775, as a small group of militia under Colonel John Parker stood on Lexington Green, nervously eyeing a column of British Regulars who had marched through the night. The Regulars were there to arrest Samuel Adams and John Hancock, both safely out of Lexington by the time the British arrived. Commanding the British troops on the scene was Major of Marines John Pitcairn. Pitcairn approached the American line (although it may have been another British officer on the scene, Army Lieutenant William Sutherland, reports vary) and ordered the militia to disperse.

According to John Parker’s deposition, given under oath after the battle, he ordered his men to disperse. This was not the first face to face confrontation between British troops and American militia, several had occurred and all ended without violence. With Adams and Hancock safe from British arrest, there was no reason for the Americans to escalate the situation. The militia began to break ranks and move away. Then someone fired.

Who fired the first shot? Parker swore that he had given the order not to fire, and as his men began to disperse the British opened fire and moved forward with the bayonet. Pitcairn likewise stated under oath that he had ordered his men to hold ranks and not fire. Once the first round was discharged the stunned Americans hesitated before several returned fire upon the British. According to American witnesses the British demonstrated a lack of discipline preventing their officers from restraining them, Pitcairn’s own report corroborates this allegation.

The British had been escorting a prisoner taken during their march from Boston, Asahel Porter. According to some, Porter took the opportunity to flee and it was a shot at him that started the brief melee on Lexington Green. Other witnesses, from within the British ranks, claimed that the first shot came from off of the Green, from a gunman concealed either in a building or behind a stone wall, rather than from the militia. The British troops, comprised of light infantry, followed their volley with a bayonet charge and were preparing to enter individual buildings when the rest of the British expedition arrived and restored order.

It will never be known who fired the shot which began the Revolutionary War. It really doesn’t matter, as by that spring morning the die had long been cast. The refusal of either side to back down meant that war was inevitable. Perhaps it is fitting that the responsibility for the first shot is unknown to history.

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Who Betrayed Nathan Hale?

Nathan Hale was a young Connecticut schoolteacher in New London when the Revolution broke out, and although the militia unit of which he was a member was soon dispatched to join the New England army at Cambridge, Hale remained behind. A Yale graduate, Hale had been a classmate and friend of Benjamin Talmadge, who persuaded Hale to join the 7^th Connecticut Regiment of the newly formed Continental Army. When the Army moved to New York after the British evacuated Boston Hale went with it, and when the call went out for a volunteer to enter New York City and obtain information regarding the British activities there, Hale answered the call.

An amateur as both a soldier and a spy, Hale was soon caught by British authorities. Differing accounts of his treatment in British hands exist, some say that he was questioned by Sir William Howe himself, others claim that he was interrogated by Major John Montresor. All accounts agree that Hale was arrested with compromising materials in his possession, which confirmed that he had been gathering information for the Americans.

Hale identified himself as an officer in the Continental Army, which further damaged his position as he was behind enemy lines out of uniform, by definition a spy. Hale had been operating in the city in the guise of an unemployed schoolmaster looking for work, at some point either his cover was blown or he let slip an indiscretion which revealed his true purpose. The information on his person was enough to convict him as a spy, and Hale was hanged on September 22, 1776.

What information he obtained and how he was discovered have never been adequately explained, although several conflicting accounts exist. One is that he was recognized by his cousin Samuel Hale, a Loyalist who revealed Nathan’s identity and rank within the Continental Army to British authorities. When these authorities questioned Hale his inexperience led him to reveal compromising information. Another is that he was captured by Major Robert Rogers, of Rogers’ Rangers fame.

In this account, written by another Connecticut schoolteacher of questionable veracity, Rogers overheard Hale in conversation in a tavern and, suspicions aroused, pretended to be a spy in order to entrap him. His ruse succeeded when the beleaguered Hale, alone and ill-prepared for his mission, revealed his true purpose to Rogers. Whether there is any truth to the tale is uncertain, that Hale went bravely to his death is the only thing known for sure of his brief mission in New York.

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Who Burned New York City in 1776?

George Washington’s first military campaign in the summer of 1776 was a disaster. Trying to defend the city of New York against the larger and more experienced British Army, without the support of a Navy, was a mistake which was largely forced upon him by the Continental Congress. In its aftermath, Washington was forced to withdraw across New Jersey, his army growing weaker by the day due to desertions and disease. British commander Sir William Howe meanwhile established garrisons at points in New Jersey and prepared to spend the winter enjoying the entertainments of New York.

Prior to Washington’s withdrawal the city of New York, then mostly huddled on the southern tip of Manhattan Island, was ravaged by a fire which destroyed almost one third of the buildings constituting the city, along with several docks and other port facilities, all of immeasurable value to the British. The fire began the night of September 20 and burned into the next morning. Several eyewitness accounts of the fire exist, from both British observers and American prisoners held on ships in the harbor. None agree on how the fire started.

It began, according to an American prisoner, in a tavern in Whitehall, and most of the city between Broadway and the Hudson was destroyed. The British occupiers immediately suspected arson, with Sir William Howe directly saying so in his report to London. More than 200 citizens were arrested by the British and questioned regarding the fire’s origins. Some Americans too believed the fire to have been deliberately set, citing the fact that it appeared to begin in multiple locations almost simultaneously.

After evacuating New York, Washington had met with both members of the Continental Congress and his staff to discuss strategy. During the meeting the possibility of destroying the city by fire was discussed, in order to deny the advantages of possessing it to the British. The idea was rejected but the fact of the fire occurring so soon afterward has led to speculation that Washington allowed the idea to go forward, looking the other way as it was carried out by other officers.

No official explanation of the cause of the fire was ever issued, and the British used the conflagration as an excuse to maintain martial law in the city, refusing to return it to civilian control, for the remainder of their occupation, which did not end until 1783. Washington specifically denied involvement even as he approved of the fire’s impact on the British occupiers. To this day it remains unknown whether the New York City fire of 1776 was an accident or an act of arson.

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Who was agent 355?

The Culper Ring was a group of spies and espionage agents, officially run by Benjamin Talmadge but in many instances managed by Washington himself, which operated in and around New York City throughout the Revolutionary War. The ring itself was led by Abraham Woodhull, a Long Island farmer who operated under the alias Samuel Culper.

Culper and Talmadge (who were neighbors before the war) used several agents and a complex system of communication to keep Washington informed of activities and plans of the British occupying troops in and around New York. Agent 355 was recruited by Woodhull, and her identity was not revealed to any other members. This has led to more than two centuries of often conflicting speculation as to who she was, or even that she was possibly more than one person.

Agent 355 provided Culper, and through Culper Talmadge and eventually Washington, the information that a high ranking American officer was negotiating with the British to hand over the American stronghold at West Point. Although Benedict Arnold’s involvement was not suspected prior to his involvement being revealed, Washington’s increased scrutiny of the post was an indication that he was aware of something amiss. Agent 355 and the Culper Ring were also responsible for informing the Americans of British plans to counterfeit Continental currency, and of British plans to attack French forces in Newport, Rhode Island.

In 1780, reports from Agent 355 ceased. This has led some to believe that she had been captured by the British and placed aboard one of the prison ships in New York Harbor, with some historians speculating that she gave birth aboard the vessel. Neither seems likely, especially if one subscribes to the theory that 355 was in fact more than one person.

That her identity was never revealed, including after the war, lends credence to the theory that she was the daughter of a prominent Loyalist, desirous of remaining anonymous even after the issue had been decided. There is little likelihood of the true identity of Agent 355 ever being revealed, since the caution exercised by Woodhull and Talmadge to protect her identity has held for more than two centuries.

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The Mystery of Silas Deane

Silas Deane was appointed by the Continental Congress to serve as a secret envoy to France in March, 1776, tasked with obtaining financial assistance from the French government. Deane worked closely in Paris with Pierre-August Caron de Beaumarchais, a member of the court of Louis XVI and the author of the plays The Barber of Seville and The Marriage of Figaro. Deane was instrumental in approving an act of sabotage on British docks, paid for through an advance of a little money, and helped negotiate treaties with the French, assisting John Jay and Benjamin Franklin.

Deane also recruited the Marquis de Lafayette, Baron Johan DeKalb, Casimir Pulaski, and other soldiers of fortune to serve in the American cause, often with the tacit support of Benjamin Franklin, who wrote letters of introduction to the Congress. In 1778 Deane was recalled to America and before Congress was accused of malfeasance. For the next two years he battled the charges, which had been leveled by Arthur Lee. John Jay served as Deane’s counsel and legal defense.

In 1780, with the charges still not fully resolved and his reputation damaged, Deane returned to France with the permission of Congress to settle his affairs there and to gather more evidence in his defense. In early 1781 letters written by Deane were “intercepted” by the British. These described the American situation as hopeless and suggested a reconciliation with the Crown. Forwarded to Sir Henry Clinton, British commander at New York, they were soon published in Loyalist and Patriot newspapers.

Deane remained in Europe after the war ended, until 1789 when he made plans to return to the United States to rebuild both his reputation and fortune. In the aftermath of the war documents purported to be Deane’s secret diaries describing his dealings with the British surfaced in Paris; these were purchased by Thomas Jefferson to keep their contents from becoming public, since they also revealed British double agents who had been employed by the Americans during the war.

Deane sailed for the United States in 1789 and after a short time at sea the ship he was in was forced to return to port after heavy winds damaged its rigging. While aboard in port Deane died on September 23. Speculation that he was poisoned to prevent information he either knew or had documentation supporting began with his death, although no incriminating documents were found. It has continued ever since.

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Who told the Patriots in Boston that the British were coming in April 1775?

The story of Paul Revere and other riders roaming the Massachusetts countryside on the evening of April 18, 1775 is well known, although widely mythologized. A question not often asked is how did Revere, Joseph Warren, and other Patriot leaders know of the mission undertaken by the British Army that night? How did they know with unerring accuracy that the British were bound for Lexington to arrest Adams and Hancock, after which they would move on to Concord to seize or destroy military stores cached there?

The answer is, of course, that somebody told them, which changes the question to discover whomever it was that so informed them. Patriot spies were liberally scattered throughout Boston, and often information could be assembled from snippets gathered here and there, as when assembling a jigsaw puzzle. But the information available to the Patriots that night was detailed down to the order of march, nearly all of it obtained by Dr. Joseph Warren.

Dr. Warren had an informer which he had relied on in the past, but only in matters of the greatest importance. Warren never revealed this informer’s identity, that information died with him on Breeds Hill a few short months later. But there is little doubt that he sought out this informer before the British departed on their march to Lexington, indeed he informed Revere that he would. It was from Warren that Revere learned of the British departure across the Charles River, causing him to warn compatriots in Charlestown by hanging two lanterns in the Old North Church.

Thomas Gage was the military governor of Massachusetts, as well as the commander of the British troops, and it was he who made the fateful decision to send the troops to Lexington and Concord. Gage’s wife was Margaret Kemble Gage, New Jersey born, and according to some historians, a patient of Dr. Warren’s. These historians and others believe that it was Mrs. Gage who gave Warren the information which started the militia on the road to meet the British.

There is little hard evidence supporting this assertion, and it presumes that a professional officer would discuss detailed military operational information with his wife prior to the fact. Gage himself later commented that only two people other than himself were aware of the plan prior to orders being issued. He never stated specifically who they were. Somehow Warren received exact information about the British expedition. How he did is still a mystery.

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Was Charles Lee a traitor along the lines of Benedict Arnold?

When the American Revolutionary War began the most experienced soldier in North America was Charles Lee. Lee had served with the British Army in America and Europe (including in Portugal under John Burgoyne) and with the Polish Army during the Russo-Turkish War. He found himself in agreement with the Americans in their dispute with the Crown, and settled in Virginia in 1775. He fully expected to be named to command all of the American forces against the Crown in 1776, and when that command went to Washington, Lee was offered second in command, which contributed to his contempt for Washington and his troops.

Lee served, although not with distinction, and with his experience his counsel was considered of value when Washington summoned his officers for their advice. Lee commanded the forces which successfully repelled the British assault on Charleston, South Carolina, early in the war, allowing him to call himself the “hero of Charleston.” After the New York Campaign Lee bombarded sympathetic members of Congress with letters suggesting that Washington be demoted and overall command given to Lee.

Lee withdrew his troops across New Jersey at a plodding pace rather than keeping up with those of his commander, and in December 1776 he was captured at an inn in New Jersey by cavalrymen under Banastre Tarleton. Lee was paroled by the British, but remained in their encampments for a time, until exchanged for captured British general Richard Prescott. After Lee returned to the Continental Army he demanded the command of the attack at the Battle of Monmouth, and so botched it that it nearly became another American rout. Washington assumed personal command and managed to hold off the British counterattacks for a tactical draw.

Washington relieved Lee on the field that day, and a court martial later made his removal permanent. Lee died before the war ended. For several decades speculation over the period of time he spent in British custody – especially as a former British officer – and whether he provided information to the British to aid them has grown. Much of the evidence is circumstantial. Lee was contemptuous of George Washington, contemptuous of American troops, and believed that he was more capable of leading the Continental Army than any other of its officers.

When he returned he did not at first demand the command at Monmouth and in fact turned it down until he learned of its full size, at which time he demanded it as his military due. In the event he did little to push the attack, which had achieved surprise. Whether Lee was a traitor to the American cause, merely incompetent, or what Washington called him on the field of battle – “a damnable poltroon” – remains a mystery.

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Why didn’t the British burn Monticello?

In 1781 British troops launched numerous raids throughout the state of Virginia, many of them led by Benedict Arnold, then serving his new masters at the head of both Loyalist and Regular troops. Raids throughout the state were commonplace and with the war having lasted six years, both sides were prone to brutal actions against their enemies. The burning of towns and farms, confiscation of property, release and recruitment of slaves, and wanton destruction of public buildings became a fact of life in Virginia.

In late May a British column thrust into Albemarle County, aimed directly at Monticello, the residence of Thomas Jefferson. With the possible exception of George Washington, there was no more hated rebel from the British perspective than Jefferson, and the opportunity to capture the author of the Declaration of Independence was too good for the British to pass up.

British troops ascended Jefferson’s little mountain outside of the town of Charlottesville on the morning of June 4, 1781. Jefferson was warned as the British were beginning to ascend, he had a leisurely breakfast before departing just ahead of the British troops, relocating to his plantation at Poplar Forest. When the British attachment of cavalry sent from Charlottesville arrived on Monticello’s manicured lawns it was to find slaves busily hiding the silver and other valuables.

The British were commanded by Banastre Tarleton, who had remained in Charlottesville with the bulk of the British troops. The detachment at Monticello was led Captain Kenneth MacLeod. MacLeod thus had the home and property of one of the leading proponents of the Patriot’s cause at his mercy, opposed only by a handful of unarmed slaves.

The British burned a few barns and storage sheds, but other than that they left Jefferson’s home nearly as they found it, an almost inexplicable event given the ferocity they had displayed in Richmond and at other Virginia plantations known to be the property of Patriots. Some have explained the British action – or lack of action – as a result of the chivalry often present in 18^th century warfare. Why the British ignored the opportunity for vengeance against Jefferson was a mystery then and a mystery now.

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Who was Jane McCrea?

During the Saratoga campaign, British General John Burgoyne’s invading army was supported by warriors from the Iroquois Confederation, who were intended from the outset to raid settler’s farms and towns, striking terror in the hearts of the Americans as the British struck south towards Albany. The hope was that the Americans would withdraw in the face of the Indian threat supported by the King’s troops.

When the Indians kidnapped and later murdered a young woman named Jane McCrea, alleged to have been engaged to a Loyalist officer in Burgoyne’s army, it caused an outrage. McCrea had been traveling to join her fiancé when she was attacked. Immediately the American’s exploited the murder as a sign not only of the Indian’s savagery but of the British collusion in brutality. American Commander Horatio Gates sent a letter admonishing Burgoyne and pointing out the damage to the Englishman’s reputation which would result. The ranks of the American army swelled with new volunteers and supporting militia.

After the war and for the more than two hundred years since, the legend of Jane McCrea has continued to grow. Over the years she has become more beautiful, more virtuous, and ever more inclined to support the Patriot cause, rather than the Loyalist cause espoused by her fiancé. Houses have been designated as her residence, signed with hisortical markers, despite no evidence that Jane ever saw the house in question.

Her body, or rather gravesites believed to contain her remains, has been exhumed no less than three times, both for DNA testing and to examine the skeletal remains for evidence of cause of death. Thus far they have been inconclusive.

There is enough contemporary evidence to confirm that Jane McCrea was a real person, and that she died as a result of Burgoyne’s march down the Hudson Valley to his destiny at Saratoga. One member of the community in which she lived described her contemporaneously as “without either beauty or accomplishments.” But there is little evidence to support the story as it was published throughout the United States that summer of 1777, when it did much to garner support for the American Army forming to stop Burgoyne at Bemis Heights. The truth about who Jane McCrea was and what happened to her remains mysteriously veiled.

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What Happened to Benjamin Church?

Dr. Benjamin Church was a Boston physician and surgeon in the days of the Sons of Liberty in that city, active and vocal in his support of the cause of the Patriots. Following the Boston Massacre in 1770 Church treated several of the injured and performed the post mortem examination of the body of Crispus Attucks. He was an early practitioner of cataract surgery, and among his patients was John Adams, then a Boston attorney.

Church was a member of the Massachusetts Provincial Congress and its Committee of Safety, exercising responsibility for preparing the rebellious colony for armed conflict by ensuring weapons and supplies were secreted at various points around the countryside, including in Concord. He worked closely with Dr. Joseph Warren to prepare medical supplies for any coming conflict. After the war began he was assigned as a surgeon with the newly formed army. He reported being arrested by the British authorities in Boston (explaining why he had been seen in conversation with General Gage), released for lack of any evidence of his revolutionary activities.

When Washington arrived in Cambridge, problems within the medical department which by then was being run by Church as Director General compelled the new Commanding General to initiate an investigation. Church asked to be relieved of his duties, complaining that he was the victim of professional jealousy. Before Washington could act, information and evidence arose describing Church’s corresponding with the enemy, in the form of coded messages to General Gage describing American troop strength.

Although Church protested his innocence he was removed from his offices and placed in custody, although he was not incarcerated and was at liberty in the camps after a short time of being held in Connecticut. In 1778 he was banished from Massachusetts and left for Martinique on a packet, which was never heard from again after its departure from Boston.

Evidence unearthed from General Gage’s personal papers more than a century later established a long-term correspondence between Church and Gage, containing details about Patriot activities and plans which pre-dated the war. Church was likely motivated by money, his accounts revealed him to have been deeply in debt. Whether he escaped to a British man-of-war and a new life outside Boston or was lost at sea has never been determined.

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