2. Historical background Information Though the codes used by the Culper spies were elementary by today's standards, they apparently were good enough for the Revolutionary War. It wasn't until 1939 that historian Morton Pennypacker revealed the Culper secret code system for the first time. He said that Major Benjamin Tallmadge, Washington's spy chief, prepared codebooks for four people: Washington, Abraham Woodhull, Robert Townsend, alias Culper Jr., and himself. He took hundreds of words from a commonly used dictionary of the day, then assigned numbers to each word.

3. DBQ Essay Question: What were the activities of the Culper Spy ring? What were they trying to accomplish? How did they accomplish it?

4. F earing that their messages might get intercepted by the British, the Culper spies quickly resorted to both secret code and invisible ink. Here is the beginning of a coded letter sent by Abraham Woodhull, alias Culper Sr., to Gen. George Washington. ``729 29 15th 1779. ``Sir. Dqpeu Beyocpu agreeable to 28 met 723 not far from 727 & received a 356... Every 356 is opened at the entrance of 727 and every 371 is searched, that for the future every 356 must be 691 with the 286 received.'' Translated, it reads: ``Setauket August 15th 1779 ``Sir. Jonas Hawkins [an early messenger] agreeable to appointment met Culper Jr. not far from New York & received a letter... Every letter is opened at the entrance of New York and every man is searched, that for the future every letter must be written with the ink received.'' Document #1

5. Questions on Document #1 Why were the letters written in secret codes? _______________________________________________________ _______________________________________________________ _______________________________________________________ Who was Culper Sr. And what was his involvement with the spy ring? _______________________________________________________ _______________________________________________________ _______________________________________________________

6. Document #2 After Their Revolution Was Won Here is what happened to the chief players in the Culper Spy Ring: Benjamin Tallmadge (1754-1835) settled in Litchfield, Conn., where he became a merchant. He represented his district as a Federalist in the U.S. House of Representatives from 1801-1817. He died in 1835 at age 81. Abraham Woodhull (1750-1826) returned to his farm. He served as judge of the Court of Common Pleas for six years, then was named a Suffolk County judge, 1799-1810. Robert Townsend (1753-1838) returned to his Oyster Bay home, continuing his work as a merchant and helping to manage the estate of his father, Samuel Townsend. Austin Roe (1749-1830) continued operating Roe's Tavern in Setauket. In 1798 he moved to Patchogue, where he founded Roe's Hotel. Caleb Brewster (1747-1827), who settled in Fairfield, Conn., was pensioned by Congress for gallantry in action in a whaleboat raid. For many years he was the captain of a revenue- cutter (an armed government vessel used to prevent smuggling) in the New York area. Anna Smith (Nancy) Strong (1740-1812) remained on Strong's Neck in Setauket after her husband, Selah, was released from a British prison in New York and took the children to Connecticut. At war's end the family was reunited in Setauket, where the family property was restored to its former status as St. George's Manor.

7. Scaffolding questions on Document #2 Which spy continued similar activities after the war? _____________________________________________________ _____________________________________________________ _____________________________________________________ Which spy was the most unlikely participant and why? _____________________________________________________ _____________________________________________________ _____________________________________________________

8. Document #3 Veiled Messages Here is a sampling of the secret code used by Gen. Washington, Benjamin Tallmadge, Robert Townsend and Abraham Woodhull. Each of the four men had a codebook of hundreds of commonly used words that were assigned two- or three-digit codes: Code Translation 15 advice 60 better 73 camp 121 day 156 deliver 151 disorder 178 enemy 745 England 174 express 230 guineas 286 ink 309 infantry 317 importance 322 inquiry 345 knowledge 347 land 728 Long Island 349 low 355 lady 356 letter 371 man 727 New York 476 parts 585 refugees 592 ships 660 vigilant 680 war 691 written 708 your *Each letter had a substitute for spelling words a = e b = f c = g d = h e = i f = j g = a h = b i = c j = d k = o l = m m = n o = p p = r q = k r = l s = u t = v u = w v = x w = y x = z y = s z = t

9. Scaffolding Questions on Document #3 Name two methods used for encoding letters?_______________________________________________ How did the spies keep track of their codes? _______________________________________________ _______________________________________________ _______________________________________________

10. In order to pass information from New York City to George Washington in up-state New York without being caught, the Culpers created an elaborate scheme. Document #4

11. The way it worked is this: as Townsend gathered information about the British soldiers in New York City, Austin Roe would drop by the store every once in a while to buy goods for people on Long Island. At the store, Roe would put in a request in writing from a John Bolton. Bolton was the code name for Tallmadge. Townsend would give Roe the requested goods and Roe would leave. Then Townsend would sneak out back when no one was looking, and run up to his small room, close to the shop. There he would read what Tallmadge had written and answer the letter. Roe would show up again at Townsend's room and take the letter back with the answers. Hiding the letter within the package, Roe, a courageous man, not afraid of riding great distances, would ride as fast as he could the 110 miles to Setauket, New York where he would hand off the letter at its first stop. Document #4 continued

12. Scaffolding Questions on Document #4 Which spy gathered information about the British? ______________________________________________________ ______________________________________________________ ______________________________________________________ How did they get this information to the continental officers? ______________________________________________________ ______________________________________________________ ______________________________________________________ Who rode the 110 mile distance to Setauket?______________________________________________________

13. Document #5

14. Transcription Fairfield Nov. 6th 1780 Dear Sir I proceeded from this place on the 3rd and returned this afternoon, the time appointed to go over again is on the 10th instant. There is three Hundred Tons of Hay at Coram collected from South Hold,Southampton and East Hampton and taken at Coram, which is expected soon to be carried away by the enemy, at New York. Should be glad if you would inform me as quick as possible whether you would have me go and destroy it or not. I can do it without interferring with my other business. Is reported in New York that the _____ ______ is taken, and generally believed here. Am sir in Haste every red Mark and ends with Your most obedient Humble Servant Caleb Brewster Click Here For Homepage Document #5 transcript

15. Questions on Document #5 What does Caleb Brewster want to destroy? ____________________________________________________ ____________________________________________________ ____________________________________________________ Why would he want to destroy this item? ( what use might it be to the enemy? ____________________________________________________ ____________________________________________________ ____________________________________________________

16. June 27, 1779 -- George Washington to Benjamin Tallmadge (Page 2 of 3, private) From the Clinton Collection Document #6

17. June 27, 1779 Route of the letter from Washington to Talmadge Document #7

18. Questions on Document #7 What were the patriots trying to do with British letters?___________________________________________________ Were the British doing the same thing? How can you tell from the map? ___________________________________________________ ___________________________________________________ ___________________________________________________

19. Document 8 Timeline June 27 George Washington wrote Benjamin Tallmadge and the Culpers a letter discussing the prospect of another aid, George Higday. Unfortunately the letter was captured, so Higday was not able to help. George WashingtonBenjamin Tallmadge August 14 Congress proposed terms of peace with the British, including independence and British evacuation of American territories. After long debate about the terms, Congress named John Adams negotiator on September 27. September 3 - October 28 A French fleet and American troops unsuccessfully tried to capture Savannah, Georgia. October 11-25 The British abandoned Rhode Island.

20. Questions on Document #8 What happened to the letter that Washington wrote to Talmadge on June 27 th ? _______________________________________________________ _______________________________________________________ _______________________________________________________ What was the letter supposed to accomplish? _______________________________________________________ _______________________________________________________

22. Explain how a message passed between three different people and places step by step. __________________________________________________________ __________________________________________________________ __________________________________________________________ __________________________________________________________ __________________________________________________________ __________________________________________________________ _________

23. Some of the Achievements of the Culper spy ring By Pat and Rob Sisler In our last installment we spoke of those in Washington’s spy ring and the role each played: Abraham Woodhull(Culper Sr.), Robert Townsend (Culper Jr. ) Austin Roe (The Paul Revere of Long Island), Philips and Nathaniel Roe( who picked up information and shifting droppoints) and Caleb Brewster( who rowed the messages across the sound) In addition Major Tallmadge in Connecticut saw to it that Washington got the messages. What did the spy ring achieve? Alexander Hamilton's friend Hercules Mulligan operated a tailor shop on Wall Street where he outfitted British officers. He picked up information on a plot to kidnap Washington and passed it on to the Culper ring, thereby foiling ( ruining) the attempt and saving Washington's life. Robert Townsend’s sister Sarah in oyster Bay, kept his shipping business going. From her vantage point on the shore she kept the Culper ring informed on the movement of all British ships on the Sound. This information was passed on to Washinton. General Simcoe was was quartered I the Townsend house and Sarah listened carefully to his conversations, especially those about Major Andre and his friend Gustavus selling out to the British. Washington again needed his valuable Culper ring. He persuaded Tallmadge to send Brewster to Setauket to get a message to Culper Jr. That his services were required. Brewster waited in the strong mansion with Anna Strong for a reply. This was the same Nancy Strong that was supposed to hang messages on her clothesline to alert Benjamin Woodhull as to where courier Caleb Brewster was. A Black petticot meant he was in and red kerchiefs signaled where from Mount Sinai to Old Field. Benedict Arnold believing that the Revolution was doomed, wanted to sell his allegiance to the British and as commander of West Point wanted to turn his fort over to the British. When Major Andre was apprehended along the Hudson with the plans of West Point on his person hi was brought to Major Tallmadge. The latter suddenly realized that previous information relayed by the Culpers theat something was ffot related to this event. Putting two and two together he suddenly connected Benedict Arnold with Gustavus. Arnold was unmasked but got away his accomplice Major Andre was hanged. The British had planned to capture Washington while he was en route to Newport to meet the French. The Culpers relayed this to Washington who changed his route and sent a force to the old route to meet his kidnappers. When Washington learned for the Culpers that the British fleet planned to attack the French in Newport he planted a false message in British spy circles and saying that he was to attack New York. Signals along the Sound to the departing British vessels called them back to defend New York from and attack that never came. The French flett was thus saved from a superior force.

24. Scaffolding Question on Doc. 10 List three problems the Culper spy ring averted through their spying activities. _______________________________________ _______________________________________ _______________________________________ _______________________________________