The Revolutionary War and the Culper Gang
The importance of secret codes during war time did not start with WW II or even WW I. George Washington learned the lesson during the Revolutionary War.
In 1778, on Washington's order, Benjamin Tallmadge organized a spy network in New York City, the heart of the British forces. Tallmadge was to take every precaution that the organization and it's members remain secret and it did. It was so secret that even Washington didn't know the names of members which were: Aaron Woodhull, Robert Townsend, Austin Roe, Anna Strong, and Caleb Brewster. Tallmadge selected a code name for the group, Samuel Culper, with Woodhull as Culper Senior and Townsend as Culper Junior.
A key member, Culper Junior, was a society reporter for an American newspaper and also the owner of a small dry goods store in New York City. The newspaper position gave him access to social functions throughout the city where he could converse with British soldiers without raising suspicion. The dry goods store gave him public and frequent access to other people without raising suspicion.
An elaborate scheme was devised to pass information from NYC to Washington who was at New Windsor in upstate New York. Austin Roe would enter the store and place an order in writing for a John Bolton which was the code name for Tallmadge. Embedded in the order were pre-arranged secret code words from Washington. Culper Junior would respond to Washington's messages and add information which would be hidden in the goods to be picked up by Roe. Roe would take the dispatches on the first leg of the journey, 110 miles to Setauket, New York, the farm of Culper Senior (Woodhull). In a formal arrangement, Roe had leased a pasture and barn from Woodhull and kept cattle there. He would drop the dispatches into a secret box, tend his cattle and leave.
Anna Strong's place was across the bay from Woodhull's farm and near the water. Caleb Brewster owned and operated a whaleboat and when he was due to arrive Anna would place her black petticoat on the clothesline. She would also hang a number of handkerchiefs to describe the time and place for the handoff from Culper Senior to Brewster.
Brewster would cross Devil's Belt to Fairfield, Connecticut and give Benjamin Tallmadge the dispatches. Finally, in a series of mounted dragoons, posted every fifteen miles, the letter would be passed to Washington in New Windsor.
The scheme worked well until the night Tallmadge's group was jumped by the British. In the fray Tallmadge lost his horse and his dispatches. One document was a letter from Washington, dated June 27, 1779, to Samuel Culper. Only one name in the letter was real, that of a George Higday who was scheduled to join the Culpers. The British raided and searched Higday's home but found no incriminating evidence so he was not harmed.
After this incident, Tallmadge increased security by using invisible ink and more elaborate codes. From that date only Woodhull, Townsend, Tallmadge, and Washington had the coded dictionary.
Washington was very unhappy over the near disaster. He remembered September 22, 1776, when young Nathan Hale was hanged by the British as an American spy while declaring that he regretted having but one life to give for his country.
Washington was also aware that spying worked both ways. He knew it was difficult to identify a true patriot versus a loyalist to the crown. To help with this task he established organizations in all the colonies to spy and to find British spies.
In 1780, three American militiamen captured a British adjutant, John André, who was dressed in civilian clothes with a treasonous letter in his shoe from Sir Henry Clinton, the British commander-in-chief, to Benedict Arnold. André was tried by court martial and found guilty. He begged Washington to shoot him as a gentlemen instead of hanging him as a spy but Washington refused and hanged him in Tappan, New York on October 2, 1780.
Benedict Arnold was a well-to-do and highly respected merchant in his community. In late 1774 Arnold suggested that he could capture Fort Ticonderoga in New York from the British and Benjamin Church made him a colonel with instructions to give it a try.
Benjamin Church was a member of both the Provincial Congress of Massachusetts and a member of the Sons of Liberty rebel organization which included such patriot leaders as John and Samuel Adams, Paul Revere and John Hancock. However, Church was really a paid spy for the British general, Sir Thomas Gage. In October of 1775, one of Church's spy letters to Gage was captured and delivered to General Washington. Church was arrested, stood trial for treason and imprisoned until 1777. After his release, Church sailed to the West Indies in a schooner that disappeared at sea.
At the time Church made Arnold a colonel, major general Sir Thomas Gage was both commander-in-chief of British forces in the colonies and the crown's appointed governor of Massachusetts. He was serving in this capacity during the events leading to the battles of Lexington, Concord, and Bunker Hill. Gage was recalled to England in late 1775 and replaced by General William Howe who in turn was replaced by General Sir Henry Clinton in 1778.
John André purchased a commission as second lieutenant in the Royal Welsh Fusiliers in 1771. In September and October 1775, American troops laid siege to his fort at St. Johns (Québec.) He was captured, brought back to Lancaster, Pennsylvania, and treated roughly. His days as a prisoner turned him against the American rebels but he was released. In 1778 André joined the staff of General Clinton who made him head of intelligence in April 1779. André successfully kept track of intelligence from American deserters and British prisoners who had escaped or were exchanged. André's most famous success was the treachery of Benedict Arnold. As a result, Clinton promoted André rapidly and by October 1779 he was adjutant general.
On Church's authority Arnold raised a regiment and captured Fort Ticonderoga on May 10, 1775. Arnold returned home triumphantly and joined Washington's Continental Army. Washington then gave him command of an expedition to attack Québec which failed, but Arnold and his men managed to sustain a blockade. During this time, Arnold seriously wounded his knee. For his heroism Congress promoted him to brigadier general on January 10, 1776. Within months Arnold's ego was showing as he threatened to resign when other brigadiers were promoted to major generals, but he was not.
With Washington's encouragement, he joined his forces with others to stop the advance of British General Burgoyne, Colonel Barry St. Leger, and Sir William Howe from the north. Arnold twice made two heroic attacks against the British, leading to Burgoyne's surrender at Saratoga on October 17, 1776. During one of these forays, he was shot in the same leg as before, giving him a serious limp thereafter. Arnold's successes conflicted with his superior, General Horatio Gates (Gates was a pain to everyone around him,) and he was temporality removed from his command.
In 1778 Washington appointed Arnold the military commander of Philadelphia after the British evacuated. In Philadelphia patriots accused him of using using public wagons for private profit and for making money for himself after he closed all the shops in Philadelphia. Patriots also accused him of being to friendly with loyalists. After all, the British had just evacuated Philadelphia, and tensions were high between loyalists and patriots. Arnold then faced a court martial for corruption and resigned his post on March 19, 1779. Soon after resigning, Arnold sold his services to the British.
In May 1779 Arnold sent for Joseph Stansbury, who lived in Philadelphia and opposed armed resistance. Stansbury met with John André who by now was aide-de-camp to General Clinton. In the following months, Arnold provided the British with a variety of military and political secrets.
After leaving his post in Philadelphia Arnold met with Washington and tried to convince him that his troubles as military commander were brought on by loyalist seeking to harm the Continental Army's integrity. Whether Washington accepted this explanation is not clear, but Washington -- ever fair-minded -- gave Arnold the command of West Point which at that time was a small, but very critical, army fort on the Hudson River 90 miles north of New York City.
Arnold's treachery was revealed, however, when André was captured by three militiamen on September 21, 1780. André had a coded message in his shoe from General Clinton to Arnold. The message was an acceptance of Arnold's July 15th offer to surrender West Point for £20,000!
Once the Americans discovered he was a spy Arnold escaped to New York and published a statement to encourage other Americans to join his cause. This failed but he was made a British brigadier and sent on raids into Virginia. His successful attacks against forts in Virginia and New York permanently marked him as a traitor. After General Charles Cornwallis surrendered at Yorktown, Virginia in October 1781, Arnold and his family sailed back to England with Cornwallis. In Britain, he was not trusted with any military commands and failed as a merchant. He died in London in 1801.
THE TEXT OF ARNOLD's OFFER
["Sir Henry" in the following text refers to General Sir Henry Clinton, commander-in-chief of British forces in the colonies.]
July 15, 1780 -- Benedict Arnold to John André (Decoded)
Inclosed in a cover addressed to M[r.] Anderson /
Two days since I received a letter without date or Signature, /
informing me that S[ir]. Henry ------ was obliged to me for intelligence /
communicated, and that he placed a full confidence in the Sincerity /
of my intentions, etc. etc. On the 13th Instant I addressed a letter /
to you expressing my Sentiments and expectations, viz, that /
the following Preliminaries be settled previous to cooperating. - /
First, that S[ir]. Henry secure to me my property, valued at ten thou- /
sand pounds Sterling, to be paid to me or my Heirs in case of /
Loss; and, as soon as that happens [strike out] shall happen, __ hundred /
pounds per annum to be secured to me for life, in lieu of the /
pay and emoluments I give up, for my Services as they shall /
deserve - If I point out a plan of cooperation by which S[ir}. H[enry]. /
shall possess himself of West Point, the Garrison, etc. etc. etc. twenty /
thousand pounds Sterling I think will be a cheap purchase for /
an object of so much importance. At the same time I request /
thousand pounds to be paid my Agent - I expect a full /
and explicit answer - The 20th I set off for West Point. A /
personal interview with an officer that you can confide in /
is absolutely necessary to plan matters. In the mean time /
I shall communicate to our mutual Friend S[tansbur]y all the /
intelligence in my power, until I have the pleasure of your answer. /
July 15th  /
To the line of my letter of the 13th /
I did not add seven.
N.B. the postscript only relates to the manner of composing the /
Cypher in the letter referred to
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