The Battle Of Yorktown British Intelligence Failure

The Battle of Yorktown:

British Intelligence Failures

SFC Michael L. Novotny

MI NCOA (Class 15-003)

The purpose of this battle analysis is to discuss how British intelligence failed to capitalize on counterintelligence, surveillance, and military deception tactics during the Battle of Yorktown, ultimately leading to their defeated. The Battle of Yorktown was the last major land battle of the American Revolutionary War and if the British adequately utilized intelligence, the United States may not have gotten its independence. I will analyze the Battle of Yorktown by placing the American Revolutionary War into context, providing a sequenced description of the key events which occurred at the Battle of Yorktown and presenting multiple

points of view. I will then discuss how available intelligence assets affected the battle and present a concise alternate outcome based on supported facts.
The American Revolutionary War
To justly analyze the Battle of Yorktown, it is first necessary to place the American Revolutionary War into context.

The American Revolutionary War was an unfortunate consequence of the French and Indian War which had occurred from 1756 to 1763. Great Britain’s triumph over the French in this conflict came with a great price for the thirteen North American colonies because of the national debt Great Britain incurred from years of fighting. The war debt rose to over 122 million pounds (British monetary unit) and Great Britain decided to reduce this debt through reforming colonial administration and enforcing tax laws. Great Britain’s explanation was that American colonists should pay a share of the cost for their own defense. This led to heightened tensions between the colonies and the colonial government which represented Britain. Tensions continued to mount between after 1963 and in 1775 war between American Colonists and the British was under way. The timeline of events between 1763 and 1781 provide context leading up to the Battle of

Yorktown.
The Battle of Yorktown
Had it not been for the successful defeat of the British at the Battle of Yorktown, Virginia on October 17, 1781, Washington might have lost the war altogether. The Battle of Yorktown proved to be the decisive victory General George Washington and his French allied forces, led by General Comte de Rochambeau, needed. The combined assault on the British Army at Yorktown, consisted of the March to Virginia, the siege, and the bombardment. The battle also involved both land and sea operations. All of which required complex planning and reliance on intelligence collection.
The March to Virginia
The 560 mile march to Virginia was planned in the spring of 1781 and took place in the in mid-August of that year. It was led by General George Washington and the Comte de Rochambeau and consisted of over 3,000 American and 4,000 French soldiers marching from Newport, Rhode Island to Yorktown. At the time American and French soldiers were positioned in Newport, Rhode Island because Washington and Rochambeau were originally planning to attack the British in New York City. This plan was eventually altered once Washington found out that the French naval fleet he needed was sailing towards the Chesapeake Bay, off the coast of Yorktown.
That shift in strategy by Washington is the beginning of the orchestrated unravelling for the British, who were operating on two fronts at the time. General Clinton, who was the commander of British troops in North America, was occupying New York City and General Lord Cornwallis was in control of a British forces in the south, at Yorktown. Washington’s strategic shift to attack Yorktown instead of New York was completely unexpected and certainly deceived General Clinton. Washington used this shift to his advantage by quickly conducting military deception operations. Washington had his soldiers build fake army camps outside of New York City and he also orchestrating for General Clinton to intercept phony dispatches of Washington’s original intent to attack New York City. All the while, the French naval fleet continued towards Chesapeake Bay.
It wasn’t until September 5, 1781 that the French fleet, commanded by Admiral Comte de Grasse was confronted by a British fleet, commanded by Admiral Thomas Graves, at Chesapeake Bay. After three days of the two naval fleets engaging in only moderate fighting, the French were reinforced with additional vessels and the outnumbered British fleet returned back to New York. This victory ceiled the fate of General Cornwallis by blocking any chance of escape by sea. The first phase of the Battle of Yorktown was essentially complete and the British were now in a vulnerable position.
In examining key events within this phase of the battle from the point of view of the British, one can better understand why they did not fare well. The first key event was General Washington’s deception operations. General Clinton ordering General Cornwallis to detach certain units and promptly send them to New York City in preparation to defend against an attack from Washington. Little did Clinton know, this attack would never happen. This decision reduced General Cornwallis’ forces and as a result, left Cornwallis only moderately prepared for his follow on assignment at Yorktown and the Chesapeake Bay.
The second key event was the French victory at the Chesapeake Bay. General Clinton initially received intelligence from General Cornwallis that a large French fleet was heading to the bay. Unfortunately for the British, neither Clinton nor Cornwallis knew how large the French fleet was. This put the British fleet commander, Thomas Graves, at a vast disadvantage. The British ships returned north, leaving Cornwallis to suffer the consequences. During the first phase the British were caught off guard by Washington’s deception tactics and then they underestimated the French navy at Chesapeake Bay. This aided in Washington’s siege and bombardment of Yorktown.
Siege and Bombardment
The French navy’s success in the Chesapeake Bay allowed for French transport ships to deliver artillery, siege tools, and soldier through the Chesapeake Bay. By late September of 1781 General Washington was in command of over 7,800 French soldiers, 3,100 Militiamen, and 8,000 Continentals. This gave Washington further momentum as his Continental Army and French Allied Forces surrounded General Cornwallis in Yorktown. Between September 28 and October 17 the siege and bombardment phase persisted.
For over two weeks American and French forces gradually worked to surround the British at Yorktown. Early on in the siege a scouting party discovers that General Cornwallis had already abandoned ground fighting positions in order to consolidate forces in fortified positions. This allowed American and French forces continue to maneuver even closer. Eventually American and French fighting positions were dug and by October 7 the French completed their gun and artillery placement. By October 16 American and French fire intensified and in desperation, Cornwallis attempted to evacuate his troops across the York River, but this endeavor was mostly unsuccessful. On the morning of October 17 Cornwallis surrendered and the Battle was over.
When examining this defeat from the point of view of the British one must wonder if conserving financial loss was the most important factor. Early on in the siege General Cornwallis he had received a letter from General Clinton which promised a relief force of 5,000 men, but by the time General Clinton sent more reinforcements it was too late, General Cornwallis had already surrendered. At this point war was proving to be lengthy and costly for Great Britain. It is quite possible that once Great Britain lost the Battle of Yorktown, they no longer wished to incur more war debt replenishing their lines. Another aspect to take into consideration is that Great Britain was also engaged in military conflicts in India, Gibraltar, the West Indies, and Ireland around the same time period as the American Revolutionary War. All of these factors might have been the reason why the British Parliament negotiated to end the war against the United States in March of 1782.
British Intelligence
During the Battle of Yorktown there were a number of missed intelligence collection opportunities which the British could have used to defeat Washington and his French allies.

Better utilization of spies and couriers to perform intelligence activities is the primary downfall of this battle. British spies and couriers were capable of conducting a plethora of intelligence activities such as Counterintelligence, Human Intelligence, military deception, propaganda, and surveillance. In fact, the United States even formed the Committee for Detecting and Defeating Conspiracies in New York between June 1776 in order to apprehend British spies and couriers. This lends some credibility to their overall effectiveness during the American Revolutionary

War.
Spies
The first key event that could have been altered with the use of spies was George Washington’s deception plan in New York. Rather than acting hastily and coming to the conclusion that Washington was going to attack at New York City, Clinton could have utilized spies to conduct surveillance and determine if Washington actually had soldiers waiting outside of New York City. General Clinton could have better utilized his spies to infiltrate Washington’s forces and collect intelligence on his war strategy. Also, considering how easily General Washington’s fake dispatches got the General Clinton, utilizing spies to conduct more counterintelligence operations would have aided in finding out the truth.
It’s quite possible that General Clinton did utilize his spies to the best of their abilities and yet he fell short .
Had General Clinton been able to figure out General Washington’s deception act, Washington and his Army might have been attacked and defeated prior to being able to depart for Newport, Rhode Island. General Clinton also may not have requested the General Cornwallis detach some of his units to send back to New York. Had General Clinton known about the deception well in advance, he could have also
The second collection asset which General Clinton could have better utilized This and he also orchestrating for General Clinton to intercept phony dispatches of Washington’s original intent to attack New York City. Probably the first Patriot organization created for counterintelligence purposes was the Committee (later called the Commission) for Detecting and Defeating Conspiracies. It was made up of a series of groups established in New York between June 1776 and January 1778 to collect intelligence, apprehend British spies and couriers, and examine suspected British sympathizers (www.cia.gov).
Wartime Special Operations:
On the high seas, British supply ships and troop ships often fell to American privateers operating under letters of marque and reprisal from the Continental Congress. Franklin, for example, ran a flotilla of Irish and French privateers from the American mission in Paris. Success in intercepting British vessels was so great that the British accused their captains of taking bribes from the Americans to surrender their ships (www.cia.gov).
Battlefield Reporting: In the beginning of September, de Grasse defeated a British Fleet that had come to relieve Cornwallis at the Battle of the Chesapeake. As a result of this victory, de Grasse blocked any escape by sea for Cornwallis (The American Revolution, 2015).
Admiral Graves‟ British ships met the forces of the French fleet under de Grasse. In order to communicate from one ship to another the British used a visual flag signaling system. The Americans had a copy of the flag code book (Wilcox,____). In the end, with or without the flag code book, de Grasse defeated Graves. The British ships returned north, leaving Cornwallis to suffer the consequences (Wilcox,____).
Counterintelligence (CI):
U.S Counterintelligence:
Another successful American agent was Captain David Gray of Massachusetts. Posing as a deserter, Gray entered the service of Colonel Beverly Robinson, a Tory intelligence officer, and became Robinson's courier. As a result, the contents of each of Robinson's dispatches were read by the Americans before their delivery. Gray eventually became the courier for Major Oliver DeLancey, Jr., the head of the British secret service in New York. For two years, Gray, as DeLancey's courier to Canada, successfully penetrated the principal communications link of the British secret service. Upon completing his assignment, Gray returned to the ranks of the Continental Army and his name was struck from the deserter list, where George Washington had placed it at the beginning of the operation (www.cia.gov).
British Counterintelligence: William Eden, chief of the British intelligence service, recruited Edward Bancroft to work as a double-agent maintaining his contact with the Americans in France and reporting back to the British. Silas Deane, and later Benjamin Franklin, gave Bancroft full access to American negotiations with France. They even hired him as their secretary and unknowingly put a spy on the payroll. In this position, Bancroft copied all the instructions sent to the American commissioners from the Continental Congress as well as U.S. correspondence with the French foreign minister. Much of the information Bancroft provided to Britain pertained to military supplies and shipments from France to America and the progress on a French-American treaty (Wilcox,____).
Washington wanted to keep absolute secrecy as to where they were headed. Washington sent out fake dispatches that reached Clinton, and convinced him that the Franco-American army was going to launch an attack on New York, and that Cornwallis was not in any danger (The American Revolution, 2015).
Deception:
Go back to NSA reference for code ciphering
Alternate Outcome
The British prevent the French blockade on the coast
British Rear-Admiral, Thomas Graves, was placed in command of fleet operations at New York.
There was much interest on the Chesapeake Capes He received word of a strong French Fleet sailing towards New York from the West Indies. There was much correspondence between Graves and Admiral George Rodney, British naval commander in the West Indies at this time During July of 1781 the British started experiencing a series of misfortunes.

The British and their superior Army find out that George Washington is going to attack.
The battle is drawn out and Cornwallis’ Army in Virginia defeats Washington’s Army.
From August 30, 1781 and into next week, almost daily, Cornwallis sent encrypted messages to Gen. Clinton informing him of the arrival of de Grasse and the number of ships involved (Wilcox,____).
Admiral Graves‟ British ships met the forces of the French fleet under de Grasse. In order to communicate from one ship to another the British used a visual flag signaling system. The Americans had a copy of the flag code book (Wilcox,____). In the end, with or without the flag code book, de Grasse defeated Graves. The British ships returned north, leaving Cornwallis to suffer the consequences (Wilcox,____).
Conwallis’s Southern Army marches on Washington’s forces. Cornwallis’s Army in Virginia was already superior in number to the Americans’ and he had two battalions of Germany mercenaries sent by Clinton from New York (Lumpkin, 1981).
Effects of Alternate Future
British Occupation
Economic
Social Loyalists
French Lost French alllies

References:
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Wilcox, J. (n.d.). The Secret Communications of the American Revolution. Retrieved March 19, 2015, from https://www.nsa.gov/about/_files/cryptologic_heritage/publications/prewii/revolutionary_secrets.pdf

The American Revolution, 1763-1783. (n.d.). Retrieved March 21, 2015, from http://www.loc.gov/teachers/classroommaterials/presentationsandactivities/presentations/timeline/amrev/

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