Curse of the Black Letter: The Document that could have destroyed the Culper Spy Ring

By Michael Mauro DeBonis

Part 1: The Introduction

                                    

When researching historical people and subjects, one may be said to be entering unfamiliar places and landscapes, where none should be expected.  And at this same time the would-be historian(s) very likely will encounter in these regions unknown and foreign persons and peoples.  This is precisely what occurred to one expert mariner Christopher Columbus, when he sailed for Spain in 1492(on a trading expedition to the Far East), and he landed (instead) in the Caribbean.  Columbus erroneously thought he had reached distant India, when in fact the Italian explorer had found the outskirts of North America…a locale foreign and unknown to Europeans at that time.

Unlike Columbus, the legendary Theseus (of classical Greek mythology) had a ball of string with him when he entered the strange and foreboding Labyrinth of the Minotaur to use as an effective guide back to civilization (in case he got lost).  Many times historians, in midst of exploring one trail of investigation, wind up on altogether different roads of study.  Such an instance recently happened to me. 

I was researching any and all biographical data on the patriot and Dutchess County Militia Colonel of the Revolutionary War, 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).  This digest is an incredibly detailed and historically factual account of the New York State Assembly’s and Militia’s legal, financial and military policies, procedures and activities during the outset of the Revolution in 1774, through its conclusion, in late 1783.

Striking out on most leads of historical probing into Colonel Griffin’s origins, I was becoming intensely frustrated and despondent. Thoughts of quitting this enterprise began echoing and re-echoing in my mind.  More importantly, thoughts of escalating my investigative business crowded out the lesser important ones.  It was here that I (luckily) found some success at last.  

Jacob Griffin was becoming more tangible to me as a historic person, whereas before hand, he seemed to me like an obsolescent New York monolith.  I was finding out (while going through Knight’s book) much more valuable information about New York during the American Revolution, than I had previously anticipated.  And my prior study of General George Washington’s Culper Spy Ring would serve me well as an excellent roadmap, specifically for navigating the “exotic” wilderness of Jacob Griffin. 

I started referencing Colonel Jacob Griffin’s name in Mr. Knight’s index, placed at the back of his comprehensive, 337-paged text.  When I reached pages 194-196, a historical revelation came to me.  It was an extensive inventory of New York patriot names (from May of 1780), and a literal who’s who of the Revolutionary Movement in our State.  Illustrious names included are future NYS senator Isaac Roosevelt (formerly of Manhattan, but then living in Poughkeepsie), Abraham Brinckerhoff, future “lieutenant colonel commandant” of the Dutchess County Militia and a future NYS legislator (see page 67, of the Military Minutes of the Council of Appointment of New York State).  Isaac Roosevelt was a distant cousin to President Theodore Roosevelt and he was a direct ancestor to his descendant President Franklin D. Roosevelt.  Like Abraham Brinckerhoff, he was a stellar patriot and a member of the famed “Council of 100,” a New York Colonial group which strove valiantly, during the early years of the Revolution, to remove British authority and presence in America.

Other members on this expansive list of names were the (then) Lieutenant Colonel Jacob Griffin, of the Dutchess County Militia, Judge Selah Strong of Setauket, (Suffolk County) Long Island and the duly noted Culper Ring spymaster Abraham Woodhull, also of Setauket, NY.  No historian is surprised is glean Jacob Griffin’s name on this list, but the names of Culper spy Abraham Woodhull and auxiliary fellow Culper spy Selah Strong strike one’s eyes as particularly unusual and, one may say, spectacularly odd.

Part 2: Let the Spying Games Begin

Jacob Griffin was an unabashed and dogged New York patriot from the get-go of the American rebellion.  His name is noted in several major legal documents from the Revolutionary period, with each one seeking to smack the British off of the American map.  But the inclusion of Woodhull and Strong’s names on this list (and at this very specific time) is very disturbing.  And this is why:

Abraham Woodhull, in being a spy, and, by residing in enemy-occupied territory (Long Island), was literally gambling with his own life.  Spycraft was considered by the British Crown (during the 18^thand the 19^th)centuries as an exclusively capital offense. And it was so by the French and the Spanish Crowns as well at this time.  People practicing espionage and found guilty of it were hence executed. European countries did not waver in their strict and consistent enforcing of this law.  America regarded spying exactly like their European counterparts, and it employed the death penalty (most notably against the British spymaster Major John Andre) whenever it felt necessary.  All sides, therefore, despised spies during the colonial days, and anyone participating in “the black arts” was undoubtedly walking a very fine line. 

General George Washington had recruited Woodhull, of Setauket, in the fall of 1778, to secretly “get the jump” on British troop numbers, strategies and positions in New York City and on Long Island. Abraham’s voluntary decision to spy for the Continental Army would prove very advantageous for the Americans.  Major Benjamin Tallmadge, Washington’s brilliant new head of Army 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 entire Ring, but 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 all their spying duties.  

Caleb Brewster (as an active duty Continental Army officer) was outside Abe Woodhull’s authority and he would take his orders directly from Tallmadge and Washington only.  Brewster, Tallmadge, Woodhull and Strong all got along exceptionally well.  Each of them had a common enemy in England, and none of them would waste any time squabbling amongst themselves while trying to rid the American homeland of their snooty and tyrannical British cousins. 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 (with the exception of shy and erudite Robert Townsend, who was of Oyster Bay, and not of Brookhaven Town, like the other Culpers).  

Each of the Culper spies were hence putting their heads in the proverbial lion’s mouth, with each engaging in espionage against British redcoats and self-serving Loyalist Tories.  If caught, every one of them would fatally hang from the gallows, as did fellow patriot Nathan Hale, 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 report (covertly) back all they saw to Washington and his aids.  This would then permit the Continentals to always stay one step ahead of their British adversaries.  From their inception in late 1778, through their end in late 1783, the Culpers were mainly successful and they constantly provided 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 lowly 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 horrible experience badly disturbed Woodhull, who was nearly found out (about his spying) in his travels, but he subsequently resumed his hidden and subtle efforts to oust the British from Yankee soil.

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 British monarch 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, as a British garrison was stationed at Setauket from late 1776-November of 1783.  Yet under the cover of being a Tory…Woodhull would be able to do ample damage to his British masters.  And during his tenure as Culper cell-leader, Abraham Woodhull would, in fact, give the British forces much harm and grief.  However, if Woodhull or any of his fellow (Culper) spies did anything to expose themselves to needless attention, or unwanted scrutiny, eagle-eyed redcoats would be willing and able to swoop in for the kill, swiftly and mercilessly. Their spy ring would collapse like bunch of imperiled dominos, bringing the Culpers to certain doom.

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 rat-infested British prison-ship, which was docked in New York City.   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 (Setauket).   

Part 3: The Culper Ring in 1780

The War for American Independence in 1780 was one for which the British and their Yankee enemies were trapped in a vicious and a long-enduring stalemate. Adding further to growing American worries as to when and if their joyless and bloody conflict with England would ever end, their Continental currency’s worth was non-existent. 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, during their savage and sanguine war for freedom.

Woodhull had to be paid in British currency, as Alexander Rose notes between pages 98-99, in his book Washington’s Spies.  If Abe Woodhull was paid in Continental dollars by Washington, while living well within British lines, Woodhull’s spying would be instantly rendered useless…and Abraham would have much to explain to Tory and Crown forces. Washington hence paid his confidential informant in British coins, allowing Woodhull to do his spycraft as he should do it, under the radar and in more of a mitigated degree of safety. The always-thrifty Woodhull (who paid for his spying activities many times out of his own pocket) was generally appreciative to his great General.

Despite the dire circumstances America and the Continental Army faced in 1780, the Culper Spy Ring would not let up their close inspection of Sir Henry Clinton and the rest of Britain’s army.  It was intelligence snatched up from the keenly thinking and always-elusive Samuel Culper, Jr. (Robert Townsend) in Manhattan (at James Rivington’s coffeehouse) that allowed Washington and the Continental Congress to learn of a massive British forging operation going on, in early 1780. British Governor of New York, William Tryon, was running the counterfeiting ploy.  And it was in New York City that the British were attempting to devalue American dollars.  

The Culpers expedited this news to the General, who then instantly informed every Continental delegate.  Congress promptly recalled and voided all its paper-issued currency, thereby saving itself totally from (financial) ruin.  This successful legislative action was carried out on March 18^th, 1780. American economic confidence was nearly shattered, but Yankee grit held the fledgling nation together.  Loans and subsidies from France and Holland, given by those governments the next year, to the United States, would fund the Continentals’ war efforts in the interim.   

More Culper “victories” followed in 1780.  In July, Sir Henry Clinton, the British Commander-in-Chief, decided to launch an offensive against the French naval fleet, then anchored in Rhode Island waters.  This British action would have ambushed the French forces, even before they had any opportunity to land any substancial troop numbers, on American soil.  The Culpers, who again, secretly warned General Washington immediately, stopped the action.  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 prematurely stopped on the water by his subordinates, to stop a Yankee invasion that would never come. The American ruse allowed the French forces to effectively land all their forces on rebel soil, allowing the Franco-American alliance to come to fruition.  

In spite of these huge gains over the British, by Washington and his Culper spies, the British kept applying severe pressure on all fronts to subvert and to end American resistance.  In September (1780) British Major John Andre (Head of British Military Intelligence and Benjamin Tallmadge’s enemy counterpart) effectually turned American Major General (and Commander of Fort West Point) Benedict Arnold to Britain’s side. Arnold’s insatiable appetite for coin and self-adulation were the main causes for his vulgar and unexpected defection.

John Andre was captured by Americans, shortly after his meeting with Arnold, to turn over blueprints for West Point. He had been captured traveling incognito through Westchester County’s countryside, while returning to Clinton’s headquarters at New York.  With the damning evidence in his boots being discovered, Andre could only offer bogus excuses to Continental Army officers interrogating him.  Spying, as said earlier, was (and still is) a very perilous and dirty business.  Major Benjamin Tallmadge could not be fooled: neither could Washington.  Tallmadge noticed Andre’s military gait as he paced to and fro in his temporary quarters, awaiting his fate.  This Andre failed to conceal.  Beagle-like Benjamin was not duped and he noted this in his Memoirs, on page 36.  Andre, under protest, was subsequently tried and hanged as a British spy (which, in fact, he was).  

Though West Point had been thoroughly safeguarded by the Continentals, Arnold’s treachery had far-reaching affects.  American morale, which was teeter tottering before his defection, had plummeted.  This was transitory, however.  Andre’s capture and his execution slowly hardened Continental resolve.  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 situated on the Great South Bay, near modern-day Smith’s Point. The attack was conducted from southern Connecticut (under cover of darkness) and its ambush was perfectly carried out, despite horribly bad weather conditions.  To top off this success, Tallmadge and Brewster (as part of the same military operation) hustled over to King George 3^rd’s magazine of hay and forage at Coram. There they again ambushed the redcoats guarding the magazine’s stores and they set over 300 tons of hay ablaze. This ungodly inferno forced Sir Henry Clinton to remain in New York City, marooned with his cavalry and army for the entire winter.

Clinton could not feed his horses, even if had wanted to, for the commitment of any possible anti-American military operations.  Tallmadge and Brewster had deprived him of the means to do so. And the Continentals’ success had been 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 gave to Tallmadge and Brewster secret info. (British and Tory troop numbers and the structural layout of the Fort, etc.)…The Culpers came across for Washington, this final time, in 1780.  They would have more success in 1781, as well.

Part 4: The Nature of The Black Letter   

The “Black Letter” is not simply a list of prominent New York State patriot names. It is 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 America, in its own Revolution.  The monies (therefore) garnered by the petition of the Black Letter would be used (by the Continental Congress) to pay for the Continental soldiers in assisting the French Navy’s landing at Rhode Island, as well as all other future Franco-American combined military operations against Great Britain.

The lenders (all signers, or co-signers of the Black Letter) 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.”  Hence every signer of this list was not only supporting New York State against the British Crown, but also more importantly, was supporting the Thirteen American States as a whole, against England and all of her dominions.  The goal and substance of The Black Letterwas made further subversive and traitorous by a compact created by America to be assisted by a foreign power (France) in America’s crusade to kick King George III from her shores.  

Every American patriot petitioner on the Black Letter’s list was thus committing treason against England.  If found out at all by British authorities, any and all would face fierce and mortal punishment by redcoats and Tories.  But this statement, though entirely factual, is a proverbial overstatement of the obvious.  This is why:

Part Five: Truth and Consequences

Signatories and endorsers of the Black Letter’s list, did by the nature of their autographs and the content of their petition, bring certain peril upon themselves, their families and their homes and property.  But most of these signers committed this act of treason firmly outside of British lines, with any possible danger rising at them being severely mitigated.  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.  And with Woodhull especially, as spy Culper Senior, had simply upped the odds of any possible hurt coming his way, at British hands.  Selah, who had already personally felt the pain and anguish of the Crown’s spite and ill-temper, was also increasing any and all potential dangers he could face, from British and Tory agents.  If discovered by the British, Woodhull and Strong would have been promptly executed. Their homes and money would all have been confiscated and their families would have definitely been displaced, or very likely imprisoned.

One of Washington’s sharpest tools (the Culper Spy Ring) he used to cut Britain’s puppet strings over the American people would have been instantaneously rendered visible and useless.  With Culper Sr. and Selah Strong out of Britain’s way, Anna Smith Strong (Selah’s wife and Culper Ring signal person) would also have been removed permanently from the Culper Spy Network.  And without Anna Strong included in the Ring, fellow Culpers Austin Roe and Robert Townsend (Culper Junior) would have swiftly abandoned all of their espionage efforts for Washington.  It would have been a British intelligence coup of undeniable significance and it was have easily and dreadfully eclipsed Nathan Hale’s discovery and undoing from 1776. The Culpers would have become extinct overnight and (then) Major Benjamin Tallmadge would have had to drastically reform and re-strategize his espionage plans.  If the Culper Ring had ever fallen, the Ring’s demise would have certainly done tremendous damage to the Continental Army’s morale.  George Washington’s esteem also would have taken a big hit.  And the discovery of the Black Letter would all have been to blame for it. 

Luckily, the document 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 these two locales.  The NY State Assembly was thus conducted between Albany and Poughkeepsie, during these aforementioned years, because the central Hudson Valley was properly and safely guarded by American forces.  The NY State Assembly was relatively unimpeded to carry out its manifold duties as a result.  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 very likely they did so.

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 that Culper spymaster Abraham Woodhull and fellow (part-time) Culper spy Selah Strong’s massive sacrifice to support the Continental Army, in addition to both spying and enduring very horrible living conditions at Setauket during the years 1776-1783, when British soldiers occupied their small seaside town (and pilfered from it, oftentimes) at an extra risk of their own lives, is solidly tangible and ubiquitously truthful.

The two Culpers made their donations only in British currency and not in the almost worthless Continental dollars.  If they did so the other way around, it would have brought needless scrutiny on them (or worse) by the British right away, since Woodhull and Strong both lived in an American town manned by a British and Tory garrison.  If caught at any time with Continental money (again) trouble would have quickly ensued for both, by the British.  How did they make their gifts available to the New York Assembly?  In secret of course, and it is undoubtedly Caleb Brewster (mariner, smuggler and soldier par excellence) who was to do the job.  Brewster’s unstoppable bravery and huge skills of stealth would guarantee a successful delivery to the NY State Assembly in the Hudson Valley, by Brewster journeying from across the Long Island Sound at Setauket (Suffolk County). Brewster would first land at Connecticut after leaving Setauket.  From there, Brewster would pass into Dutchess County (NY).  Austin Roe would never make such an land-based errand on horseback, as the route would have been much too long, dangerous and susceptible to roving enemy (redcoat) patrols and wandering cutthroat highwaymen, that freely abounded everywhere on Long Island at this time and haunted the Island’s many rural roads.

The Black Letter was a particularly damning document, which directly incriminated Abraham Woodhull and Selah Strong with funding and encouraging American anti-British and pro-French military operations in their theatre of the War. Woodhull as assistant spymaster to John Bolton (Major Benjamin Tallmadge) was markedly putting his life in perilous circumstances (as they were already previously due to Abraham’s spying). This put the entire Culper Spy Ring in further jeopardy…but it simultaneously emboldened and enhanced the American war effort against the British.  That Culper Senior’s benefaction to the Continental Congress involved Selah Strong is irrelevant.  Strong was a man with a vital sense of mind, body and person, who was not bullied into doing anything he was not formerly willing to do by himself. In this capacity, Judge Selah Strong was as Abe Woodhull and Jacob Griffin were, fearless, feisty and unrelentingly patriotic.  That the rest of the Culper Spy Ring did not fall in this process is not only remarkable, it is concrete proof of Abe Woodhull’s superb (spying) skills of cunning, deception and his iron-willed desire to remove from America the British parasites that were then thriving on Long Island at the expense of all Long Island patriots.

And yet despite any counter-arguments that may seemto suggest otherwise (many signers of the Black Letter were given NYS government jobs after the War) 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.  During this time the signers of the Black Letter no longer took a gamble on Great Britain and its monarch (King George 3^rd), but they all proudly took their chances on the revolutionary idea of America.  242 years later, the democracy they founded is still here, and Americans are still struggling to define who they are and what their country still is…and as long as we do, democracy will thrive.

***Author’s 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 6^thDutchess County Regiment were rewarded for their honorable sacrifices to liberty (even apart from the financial requests made by the NYS Assembly in the Black Letter).  

The Continental Congress and the NYS Assembly thus had ample funds and other resources to pay back Mr. Griffin, Abraham Woodhull, Judge Selah Strong and Abraham Brinckerhoff, once the Revolution was over.  There is absolutely no historical record stating that the NYS and the Federal governments did not make these reparations to soldiers and minutemen.  As far as we know, historians can trace through NY State militia and Continental pension records, which men were paid and which ones were not.

I called the Black Letter, as such, not for the black ink of the document’s typography, but rather for the document’s direct implications of Culper spies Abraham Woodhull and Selah Strong, in supporting America’s Revolutionary War effort, apart from their roles as agents of espionage…efforts, which obviously, could have endangered the very productive and secret Culper Spy Ring. 

About the Author:  Michael Mauro DeBonis is a poet and a historian from Long Island, NY.  A graduate of both SUNY Stony Brook (B.A. English) and Suffolk County Community College, Mr. DeBonis’ first work appeared in The Village Beacon Record and The Brookhaven Times Newspapers.  Michael’s latest work (poetry and prose) may be found in the New York History Review and The New York History Blog (prose only). Mr. DeBonis is dedicated to studying and to learning the history of the great State of New York.