Culper Spies: Curse of the Black Letter

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Col Jacob Griffin portraitI was researching the biography of Dutchess County Revolutionary War Militia Colonel Jacob Griffin. I was having a hard time of it.

By sheer accident I came upon an old historical text entitled New York in the Revolution, as Colony and State: Supplement. The book was compiled and written during the years 1895-1901, by a former New York State comptroller Erastus C. Knight (and others). It’s an incredibly detailed account of the New York State Assembly’s and Militia’s legal, financial and military policies, procedures and activities from the outset of the American Revolution in 1774 through its conclusion in late 1783.

Colonel Jacob Griffins TavernThe book contains an extensive list of New York patriots (from May of 1780) – a who’s who of the Revolutionary Movement in our State. Illustrious names included future NYS Senator Isaac Roosevelt (of Manhattan, but then living in Poughkeepsie) and Abraham Brinckerhoff, future “lieutenant colonel commandant” of the Dutchess County Militia and a future NYS legislator. Roosevelt was a distant cousin to Theodore and ancestor of FDR and a member of the famed “Council of 100,” a New York Colonial group which worked, during the early years of the Revolution, to remove British authority from the Colonies.

Other names on the 1780 list were the (then) Lieutenant Colonel Jacob Griffin, of the Dutchess County Militia; Judge Selah Strong of Setauket, Long Island; and Culper Ring spymaster Abraham Woodhull, also of Setauket.

Let the Spying Games Begin

Jacob Griffin was an unabashed and dogged New York patriot from the get-go of the rebellion. His name is noted in several legal documents from the Revolutionary period, each one seeking to smack the British off of the colonial map. But the inclusion of Woodhull and Strong’s names on the May 1780 list is interesting.

Abraham Woodhull, a spy residing in enemy-occupied territory (Long Island), was gambling with his life. Spycraft was considered by the British Crown (during the 18th and the 19th) centuries as a capital offense (as it also was by the French and the Spanish crowns). Guilty spies were usually executed. Americans regarded spying in the same way and employed the death penalty (most notably against British Major John Andre). All sides despised spies during the colonial days, and anyone participating in “the black arts” was walking a very fine line.

Major Benjamin TallmadgeGeneral George Washington had recruited Abraham Woodhull in the fall of 1778 to secretly provide British troop numbers, strategies and positions in New York City and on Long Island. Woodhull ’s decision to spy for the Continental Army would prove very advantageous for the Patriot cause. Major Benjamin Tallmadge, Washington’s new head of Amy Intelligence, had been the one to facilitate Woodhull (and Caleb Brewster’s) inclusions into what was swiftly becoming the clandestine and intrepid Culper Spy Ring.

Tallmadge would carefully and competently direct the ring, and Woodhull would act as his second in command (in the field). This is to say that Woodhull would direct signal person Anna Smith Strong (wife of part-time Culper spy Judge Selah Strong), couriers Austin Roe and Jonas Hawkins, as well as fellow spy and intelligence-gatherer Robert Townsend, in carrying out their spying.

Caleb Brewster (as an active duty Continental Army officer) was outside Abe Woodhull’s authority and took his orders from Tallmadge and Washington. Brewster, Tallmadge, Woodhull, and Strong all seem to have gotten along well. Each of them had a common enemy in England, and none of them would waste time squabbling among themselves while trying to rid the colonies of the British. The Culpers also all shared a common history and friendship, with each being born and raised in Setauket. The Culper Ring was truly a close-knit group (perhaps with the exception of Robert Townsend, who was of Oyster Bay, and not of Brookhaven Town, like the other Culpers).

Each of the Culper spies were putting their heads in the proverbial lion’s mouth, with each engaging in espionage against British redcoats and Loyalist Tories. If caught, they would probably hang, as Nathan Hale has in the autumn of 1776.

The Culpers’ job was to attack the British Army’s nerve center in New York City (York Island, precisely) and covertly report back all they saw to Washington and his aides. This would permit the Continentals to stay a step ahead of their adversaries. From their inception in late 1778, through their end in late 1783, the Culpers were mainly successful in providing Washington with valuable data on the King’s forces. But the Culpers themselves experienced their fair share of close calls.

Jonas Hawkins was soundly searched by redcoats, while attempting to enter New York City in the summer of 1779. The almost-always antsy Hawkins left the Culper Ring that same September. In the spring of 1779, some Long Island highwaymen robbed the ever-wary Abraham Woodhull of all of his money during one of his many forays to Manhattan, from suburban and rural Setauket. This experience disturbed Woodhull, who was nearly uncovered, but subsequently resumed his efforts to oust the British.

Caleb Brewster and Abe Woodhull did in fact sign the Brookhaven Town’s List of (pro-patriot) Associators in May of 1775. This document sought to give full authority to the relatively nascent Continental Congress, while also attempting to undermine British power in the Colony of New York. Benjamin Tallmadge could not sign his name to this list, as he was then living in Connecticut and no longer residing in Setauket.

But Woodhull, in late October of 1778, swore an oath of loyalty to King George III, shortly after joining the Culpers. He dwelt deep inside British-controlled domains, and to seem a Washington sympathizer would have proven quite hazardous to his health and his well-being. This conviction was logically reinforced by a British garrison stationed at Setauket from late 1776-November of 1783. Yet under the cover of being a Tory, Woodhull could do ample damage to the British. During his tenure as Culper cell-leader, Abraham Woodhull would, in fact, give the British forces much grief.

In 1776, Judge Selah Strong of Setauket became a Suffolk County, NYS militia officer, one year after fighting first commenced between patriots and British forces, in 1775. Shortly before the War, Strong was also a Suffolk County delegate to the New York provincial Congress, serving as an undaunted and dedicated Whig. By the end of 1778, Selah was jailed by the Crown as an anti-British troublemaker, serving his sentence aboard a British prison-ship. Anna Smith Strong, his wife and full-time Culper Spy, directed a successful release of her husband from his miserable bondage by shrewdly and effectively “reaching out” to some of her influential friends. By 1780, the newly freed Selah Strong (“Esquire,” as Caleb Brewster referred to him) was elected as President of the Town of Brookhaven (from Connecticut soil, ironically) and he was quietly living back home with his wife at Strong’s Neck in Setauket.

The Culper Ring in 1780

The War for American Independence in 1780 was a stalemate. Adding further to growing American worries as how the conflict with England would end, their Continental currency was worthless. Soldiers in Pennsylvania and New Jersey mutinied against Congress and Washington, between late December of 1780-January of 1781. The American Commander-in-Chief would swiftly and keenly put these “in-house” insurrections down. But two things were clear: American soldiers were unhappy about getting paid with valueless notes and the infant nation was (as a whole) barely getting by.

As Alexander Rose notes in his book Washington’s Spies, Woodhull had to be paid in British currency.  If he was paid in Continental dollars they would useless and hard to explain. Paid in British coin, Woodhull could remain under the radar.

It was intelligence by Samuel Culper, Jr. (Robert Townsend) in Manhattan (at James Rivington’s coffeehouse) that allowed Washington and Congress to learn of a massive British forging operation in early 1780. British Governor of New York, William Tryon, was running the counterfeiting ploy. The British were attempting to devalue Patriot dollars in the City of New York.  The Culpers expedited this news to the Washington, who informed every Continental Congressional delegate. Congress promptly recalled and voided all its paper-issued currency, thereby saving itself from financial ruin on March 18, 1780. (Loans and subsidies from France and Holland would eventually help fund the Continentals’ war).

More Culper victories followed. In July, 1780, Clinton launched an offensive against the French naval fleet, then anchored in Rhode Island waters. This action would have ambushed the French forces before they had any opportunity to land. The Culpers secretly warned Washington. While General Clinton was en-route to Rhode Island, via the Long Island Sound, Washington and his Continentals feinted an attack on the city of New York. Clinton was held up on the water by his subordinates moving to stop an invasion. The American ruse allowed the French forces to effectively land all their forces, bringing the Franco-American alliance into fruition.

The British applied their own pressure. In September, 1780 British Major John Andre (Head of British Military Intelligence and Benjamin Tallmadge’s enemy counterpart) effectually turned Benedict Arnold, then a Major General and Commander of Fort West Point, to the British.  John Andre however, was captured shortly after meeting with Arnold, while traveling incognito through Westchester County’s countryside returning to Clinton’s Headquarters at New York. With the damning evidence in his boots, Andre could only offer bogus excuses to Continental Army officers interrogating him.  Andre, under protest, was subsequently tried and hanged as a spy.

In late November 1780, Culper spies Caleb Brewster and Benjamin Tallmadge launched a daring raid against Fort St. George (at Mastic, Long Island), a British garrison on the Great South Bay, near modern-day Smith’s Point. The successful ambush was conducted from Southern Connecticut under cover of darkness, despite bad weather. To top off this success, Tallmadge and Brewster (as part of the same military operation) hustled over to Coram, where they ambushed the redcoats guarding over 300 tons of hay, and set it and the other stores ablaze. The inferno helped force Sir Henry Clinton to remain in New York City, marooned with his cavalry and army for the entire winter.

The Continentals’ success was bolstered by accurate intelligence reports mainly gathered by Culper, Sr. (Abe Woodhull) but also by William Booth, an alleged Tory and the Superintendent of Fort Saint George, who provided information to Tallmadge and Brewster on the Fort and troop numbers.

Truth and Consequences

The “Black Letter,” as I’ve come to call the 1780 list, is not simply a list of prominent New York State patriots. It’s an exacting legal and financial document of record and an open petition issued by the NYS Assembly to request from each of its signers a loan to the Continental Congress of five hundred (Continental) dollars each, to be used by the Continental Army, specifically to aid in the French military intervention, on behalf of the Revolution.

The lenders (all signers, or co-signers) are promised to be re-paid by New York State and the Continental Congress, within six months, at an inclusion of interest on their loans of “six percent per annum and secured against a further depreciation.” The patriots on the list were committing treason against England, which brought certain perils upon themselves, their families and their homes and property. But most of these signers committed this act firmly outside of British lines. William Floyd (also a signer of the Declaration of Independence) owned a vast estate at Mastic, Suffolk County. Yet, at the time of the Black Letter’s execution, Floyd inhabited Connecticut, and not Long Island. He and the rest of the Floyds were relatively safe from any potential British harm directed at them. The same could be said of Jacob Griffin, Isaac Roosevelt and Abraham Brinckerhoff, each living entirely within American-held territory.

This was clearly not the case for declarants Abraham Woodhull and Judge Selah Strong. Both, living in Setauket in 1780, were living in strongly gripped British turf.  If discovered,  they would have been almost certainly executed. Their homes and money would all have been confiscated and their families would have been displaced, or possibly imprisoned. The Culper Spy Ring would have been rendered visible and useless. Major Benjamin Tallmadge would have had to reform and re-strategize his espionage plans. If the Culper Ring had fallen, its demise could have damaged the Continental Army’s morale. George Washington’s esteem might have taken a hit.

Original American flagLuckily, the Black Letter never fell into enemy hands. But whose responsibility was it to guard New York State’s security-sensitive information during the Revolutionary War? New York State Assembly officials most definitely had their precious documents guarded by the State’s militias during the War for Independence.

The State’s government could have never convened on Long Island or New York City, as British forces, from late 1776-late 1783, occupied those areas. The State Assembly was conducted between Albany and Poughkeepsie during these years, as the central Hudson Valley was more safely guarded. Did Colonel Jacob Griffin and his Dutchess County Militia safeguard New York’s “top secret” legal and financial documents as part of performing their many military tasks? We may never know for sure, but it is likely they did.

According the U. S. Bureau of Labor Statistics’ consumer price index, $500.00 (U. S. currency) in 1780 would be worth roughly $8, 400.00 dollars in 2016 (U. S.) monetary value. But this figure cannot be relied on at all, since (again) the Continental dollar was significantly deflated and devalued at the precise point in American history. What is worth its weight in gold is Abraham Woodhull and Selah Strong’s sacrifice to support the Continental Army, especially during the British occupation at Setauket (1776-1783).

The two Culpers made their donations only in British currency and not in the almost worthless Continental dollars. How did they make their gifts available to the New York Assembly? In secret of course. It may have been Caleb Brewster (mariner, smuggler and soldier) journeying from across Long Island Sound and passing into Dutchess County. It seems unlikely that Austin Roe would have made the trip by land.

The Black Letter was a particularly damning document, which directly incriminated Abraham Woodhull and Selah Strong with funding and encouraging anti-British and pro-French military operations.  The signers not only did put their money where their mouths were, they all put their lives on the line as well, at a legitimate threat to themselves. They took their chances on the Revolution.

Note: At the close of the American Revolution, an estimated 60,000-100,000 Loyalists were expelled by the Continental Congress from American shores. Many had no time to pack all of their belongings or to take all of their money. Most of these Loyalists relocated to Canada, after the Revolution. But many wound up going to Great Britain and the British West Indies, in the Caribbean. As a result, their vast real estate holdings in all thirteen original colonies, horses, cattle and other livestock were used to compensate Continental soldiers and various state militiamen for their service to the United States against Britain in the Revolution. This is precisely how Colonel Jacob Griffin of Fishkills, NY and other members of his 6th Dutchess County Regiment were rewarded for their sacrifices.

Illustrations, from above: portrait of Col Jacob Griffin; Colonel Jacob Griffin’s Tavern; Major Benjamin Tallmadge (ca. 1778); and original American flag.

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About Michael DeBonis

Michael Mauro DeBonis is a poet and a historian from Long Island, NY. His previous work has appeared in The Village Beacon Record and The Brookhaven Times Newspapers. Mr. DeBonis is a graduate of both SUNY Stony Brook and Suffolk County Community College. He is dedicated to learning and to studying the amazing history of New York State.

2 thoughts on “Culper Spies: Curse of the Black Letter

  1. Michael DeBonis

    Many thanks to John Warren and his staff of the New York History Blog, for allowing me to write about the Culper Spy Ring. John, you did a great job here editing my article!

    Best always,
    Michael M. DeBonis.

  2. Michael DeBonis

    Readers can expect more stories about the Culper Spy Ring from me in the future.

    Best always,
    Michael M. DeBonis


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