Presbyterian, Patriot, Spy: Benjamin Tallmadge and the Culper Spy Ring


It might have gone something like this: He clench-ed his jaw and crumpled the letter in his fist. The audacity, the treachery, he thought. How could Arnold believe him capable—or willing—to do such a thing? Join Arnold in his treason? He, Benjamin Tallmadge, was no traitor. Cowards and blackguards like Benedict Arnold might turn, lured by royal silver and glittering promises, but he never would. Tallmadge spat and nearly threw the wad into the fire, but thought better of it. No matter the letter from Benedict Arnold to Benjamin Tallmadge arrived three months after Arnold’s treason, the foul invitation would remain another red mark in Arnold’s ledger.
Benjamin Tallmadge was the second son of a Presbyterian minister in the coastal Long Island town of Setauket. He was a bright, energetic child, accepted to Yale at the ripe age of twelve, although his father kept him home until he matured a bit more. So when he entered Yale at fifteen, he arrived about the same time as another young man who would become his good friend, Nathan Hale. The two young men distinguished themselves as fine scholars and jovial pranks-ters.
As it did with Hale, the sound of liberty’s drums beat hard in Tallmadge’s ears. Just a few years out of college found Benjamin rising in the ranks of the Continental army. Although his father had hopes that Benjamin would enter the ministry, the elder Tallmadge understood all too well the need for young men to stand up in the face of British oppression. The little village of Setauket and her surrounding neighbors had been acquainted with such oppression when British soldiers commandeered the Presbyterian church as their headquarters, ripping apart gravestones to use as fortifications in the Battle of Setauket. Her sister congregation in South Haven did not fare much better: the British gutted her building and used it as a stable for the British regiments who quartered nearby in the homes of reluctant Whigs. Long Island had been ill-used by the British, and Benjamin Tallmadge was unhappy about it.
Setauket, known in later history as Brookhaven, bred a tight group of individuals, bound by a shared Presbyterian faith, common worship, and patriotic principles. Tallmadge’s own father “alternately denounced the idolators, the damned, and the Episcopalians from his Presbyterian pulpit…”1 Reverend Tallmadge’s other son was among those who signed a petition to raise arms against Britain after Lexington, vowing “‘never to become slaves’ to tyrants.”2 It was from within this band of longtime friends and neighbors that one of the American Revolution’s best kept secrets was born.

Setauket’s Secret Weapons
Setauket’s children nursed her fair share of grievances against the crown. William Tallmadge, Benjamin’s older brother, also served with the American forces. His service, however, was not long-lived. While Benjamin, under Washington’s command, retreated from the British invaders on Long Island, his brother William starved to death on one of the Crown’s infamous prison ships in New York harbor.3
Abraham Woodhull, Benjamin’s Setauket neighbor, still smarted with the knowledge that his much respected older cousin, General Nathaniel Woodhull, had been captured by the British and injured in the Battle of Long Island. Once in British custody, General Woodhull suffered at the hands of clumsy surgeons who botched the amputation of his injured arm. They then struck the General for refusing to say “God save the King” and saying instead, “God save us all.” He died of his wounds on a cattle ship-turned-brig. Abraham also did not relish the harassment he received from the British for engaging in a little harmless smuggling. Like other residents of Long Island, a place rich with produce and livestock, Woodhull supplemented his family income by passing goods to occupied, urban Manhattan.
Caleb Brewster was born for the sea. A physically imposing young man with a carefree attitude, Brewster left his Setauket home to serve on a whaling vessel. When he returned, the British had overrun his island home, desecrating the Setauket Presbyterian church where his great-grandfather was the founding pastor generations before.4 Brewster—a descendant of the Brewster of Pilgrim fame—vowed to make life miserable for the British any way he could.
Austin Roe was a childhood friend of Tallmadge, Woodhull, and Brewster. Austin Roe’s family bought a large home on the northern coast of Long Island from the Woodhull family—and converted it into a popular tavern. No doubt many British soldiers whiled away the hours under Roe’s roof during their occupation of Setauket. Roe had no choice but to serve the British officers, but he didn’t have to like it.

A Dangerous Proposition
And there were many others in Setauket and her environs that endured many such offenses once the British forced American troops out of Long Island and New York altogether. The loss of New York was a serious blow to Washington and the Continental Army. Together with the failure of Nathan Hale’s deadly mission in September 1776, Washington had to rethink his strategy in New York if he were to have any success against the British. Although Washington understood well enough that accurate, timely intelligence was crucial, the Nathan Hale fiasco was one he did not wish to repeat. Gone were the days of sending a lone man into enemy territory for a quick mission and out again with reliable information. Washington had been one such spy in the French and Indian War some years earlier. What he needed now was something more sophisticated. And he knew just the man for the job.
Washington approached Benjamin Tallmadge, a discreet and promising young major in his command, with an unusual proposition. He wanted a man or two actually embedded in British territory who could pass information off to the American side without raising too much suspicion. Many commentators have tried to discern the exact nature of Washington’s religious convictions. Whatever their nature, the General time and again turned to devout Christians when he had a job requiring unquestioned loyalty.
For Tallmadge, that loyalty would last well beyond the end of the war, and occasioned one of those rare insights into the nature of Washington’s Christianity.
“While he lived, I was fully satisfied that his equal was not on Earth, and since he has died, public testimony to his worth, has exceeded even the most sanguine expectation. Altho’ from a long and tolerably intimate acquaintance with him, I have been abundantly convinced of his attachment to the Christian System; yet had he been explicit in his profession of faith in and dependence on the finished work of our glorious Re-deemer for acceptance and pardon, what a conspicuous trait would it have formed in his illustrious character.”5
Washington charged Tallmadge with finding a man of such loyalty as his own. This informer must be a man of upright character, patriotic principles, and steely nerves. He must know Long Island geography like the back of his hand—and smuggling routes and paths out of the way of watchful British eyes would be a plus. And he must be someone who Benjamin Tallmadge knew well and would trust with his life. Benjamin reached out to the people and place he knew best for help, his Setauket friends.

Abraham Woodhull was first on Tallmadge’s short list. Woodhull, in 1778, took up his official capacity as a spy. His job was relatively simple: travel from Long Island across the water to Manhattan under the pretense of visiting his sister and brother-in-law, who ran a boarding house there. Linger around town where he could hear the buzz about troop movements, caches of munitions and supplies, and anything else that might be useful, and take that information back to Setauket. From there, a courier would transport the intelligence to Tallmadge who would pass it to Washington. Woodhull was also tasked to find others to participate in this intelligence network—men like him who could be discreet. Understandably, Woodhull was nervous. There was much about the plan that could tip off an observant British soldier or Tory sympathizer. Frequent trips to New York, the interception of any suspicious correspondence, misplaced faith in a weak spy ally could wreck the whole business.
Woodhull recruited two other Setauket men for the job, both well-suited to the task at hand. The first, Caleb Brewster, was an obvious choice. Brewster garnered a reputation for being a Long Island tough. For fun, he frequently led mini-raids on British units stationed along the Long Island coasts. He was intimately familiar with the Long Island Sound and the best sea routes to take to Connecticut without crossing paths with the British. And he was brave, if not a little fool-hardy. During the five years of the spy ring’s operation, Brewster never used a pseudonym or was captured by the British. Brewster’s job was simple: ferry the intel from Woodhull across the Sound to Washington’s man, Tallmadge.
Austin Roe was Woodhull’s other recruit. Nicely situated in a popular tavern, Roe heard all the gossip on troop movements and other military chatter. He couriered that news to the next link in the network. Together with the information that Woodhull gathered from Manhattan, Roe could give a fuller picture about British movements to Tallmadge and Brewster could report on maritime activity.
To aid in secrecy, Woodhull and Tallmadge agreed upon a no-name policy. Even General Washington would not know the identity of the men working for him. Instead, they crafted rather bland pseudonyms. Benjamin Tallmadge would be John Bolton. And Woodhull, Samuel Culper. The men also devised a numeric codes for locations and people. No easily identifiable phrases were to ever appear in any correspondence. The cherry-on-top, however, was the invisible ink. A decade earlier, John Jay’s brother (yes, that John Jay, American’s first Chief Justice) was fooling around in his laboratory with some chemical compounds that dried invisibly on paper. The mixture, known as Sympathetic Stain, allowed the Culper ring to write “invisible” messages to one another. They hid these messages on everything from innocuous family letters to grocery lists. The recipient need merely apply a counter-agent to release the stain and read the message.
It is worth mentioning that in today’s world of spy thrillers and high-tech intelligence agencies, some of the Culper Ring’s tactics may seem rather ho-hum. But in Washington’s day, the Culpers’ bag of tricks was radical. Spying was dangerous business and looked upon with incredible scorn. It was below a gentleman, and it always carried a death sentence if one was caught in it. Washington’s desire for a local, embedded spy network was unconventional. Secret names, coded messages, the multiplicity of players meant a compartmentalization of information: no one person knew everything; therefore, the capture of one would not necessarily shipwreck the operation. The Culper Ring was also among the first to use dead drops—Brewster, Woodhull, and Roe would often leave packets of intelligence in an agreed-upon hidden location for another member to pick up at a later date. And in some accounts of the Culpers’ adventures, another Setauket citizen, Anna Strong Smith, used her laundry line to send coded messages to the ring. Black and white pantaloons signaled to Brewster which Long Island coves were under British watch and whether there was a packet to pick up. Of course, the Culpers dealt with the limits of their time and circumstance. Slow travel, New England’s notoriously unpredictable weather, and constant British scrutiny made their successes all the more impressive.

Of Counterfeits and Kings
Abraham Woodhull was “absent on business” when the troops came to his home in Setauket. Woodhull’s frequent trips to Manhattan eventually raised the suspicion of a British officer stationed on Long Island. Woodhull’s unavailability did not stop the British from sending him a message to cease and desist: the soldiers beat his elderly father, a former Setauket judge and a pillar of the church, into a bloody pulp. This scared Woodhull into recruiting one more member—this time someone outside of Setauket—Robert Townsend.
Robert Townsend had no love for the British. His Quaker family, like many others, had been ill-used. But Robert had not worn his patriotic sympathies on his sleeve. He was a Manhattan businessman, a merchant-shop owner, and he moved easily in Tory highbrow circles. A laid-back sort of man, Townsend felt he did not have anything better to do. He agreed to be Tallmadge’s eyes and ears in New York. Townsend, code named Culper, Jr., decided to add one more job to the list: reporter. In order to gain even greater access to British intelligence, Townsend landed a job with a Tory publication, the Royal Gazette, run by James Rivington, a man popular with the aristocracy, whom Townsend would later recruit as a Culper spy. Townsend’s assignment was to hobnob with the elite, including officers and aristocracy, and collect gossip for the society column. He was only too happy to oblige. His only request to Culper, Sr.? Never to let Washington—or anyone—learn his true identity.
One of the first major plots the Culpers discovered was a counterfeit operation. Continental currency struggled to keep up with the more valuable influx of British coin. In addition to the depreciating supply, America’s debts to foreign sources and her own military weighed heavily on her and threatened to alienate a lot of soldiers short on pay. While the British had long practiced counterfeiting, they never saw the widespread success they’d hoped because something was always just a little off. The paper wasn’t right or the currency press plates were a little tweaked. However, Robert Townsend heard a rumor he thought worth passing on: the British had secured a large stock of Continental currency paper from a storehouse in Philadelphia.6 In spring 1780, Congress yanked the colonial bills from circulation and narrowly avoided financial ruin thanks to the Culper Spies.7
Just months later, however, the Culpers achieved an even greater success. Louis XVI agreed to send a small, but much needed, fleet of ships to America’s aid under the command of Marshal Rochambeau. Unfortunately, the Americans weren’t the only ones privy to this arrangement; the British knew, too. What was unclear to both parties was exactly where the French would land. When word finally reached the Americans that the French were to land in Rhode Island, Washington was still in a quandary: he didn’t know exactly what the British knew about the whole operation. He especially needed to know if the British knew where the French would land or whether they would engage the British fleet. In a race against the clock, Austin Roe traveled non-stop for 55 miles on horseback from Long Island to New York to give Townsend their new orders: find out what the British know about the French fleet and what they’re doing about it. Townsend combed New York for information for four days. And the news he sent back to Washington was dire, indeed.
General Clinton, Washington’s British counterpart, knew of the French’s arrival in Rhode Island and he began a massive movement of troops out of New York toward the French fleet. This left Washington with a tantalizing opportunity—move American troops into New York and recapture the city while the British defenses were busy elsewhere. It was a grand scheme, but Washington concluded, a foolish one since New York would certainly be able to hold off American advances until Clinton could return and hem in the American forces in. No, Washington would leave New York alone—or would he?
Using the intelligence gathered from the Culpers, Washington let slip that he was making a move on New York—at least, that’s what the British thought. In reality, Washington sent his own fleet of soldiers down to Rhode Island to thwart the British there. Meanwhile, Clinton, frantic that the Americans might capture his New York prize, moved his forces back to New York. The British took the bait, the French landed safely, and Washington reveled in his easy victory brought about by his own intelligence operatives.

A Spy in Their Midst
Some historians believe that Benjamin Tallmadge’s spy ring had a direct hand in exposing Benedict Arnold’s treasonous dealings with the British. A decorated military general, Benedict Arnold was deep in debt and generally pouty about not getting his choice of command. As early as their days together at Yale, Tallmadge believed Arnold was “not a man of integrity.”8 Arnold had struck up a correspondence with the British Army, particularly John Andre, a major under Clinton, that lasted for many months. In letters and at high society New York gatherings, in whispered conversations, Arnold toyed with the idea of siding with the Crown. Although the British promised remuneration for certain turncoat services, Arnold’s relationship with the British was still a rocky one. That is, until, Arnold was able to secure a command of one of America’s most important strategic locations—West Point. West Point, situated on the mouth of the Hudson River, allowed access not only to important waterways, but the whole of the continent. Once in command, Benedict Arnold contracted with the British to sell West Point for 20,000 pounds sterling. Arnold would hand over the plans of the fort to Andre and diminish its fortifications so that the British could easily capture the fort.
Tallmadge’s spies were busy, however. Throughout the course of the summer of 1780, Tallmadge’s “emissaries” intercepted a significant amount of correspondence between Arnold and Andre. Some of the messages between the two went completely missing; others arrived in Andre’s hands as unintelligible babbling, obviously tampered with and altered by the Culper agents. But up to this time, Arnold’s shady dealings were kept quiet from the bulk of the American military officials, even possibly from Washington himself.
After a failed attempt to meet and finalize the West Point deal in early September, Arnold and Andre met just a few weeks later at the home of a questionable man named Smith, who Tallmadge believed sold American and British secrets to the highest bidder. During the meeting, American troops fired at Andre’s ship, The Vulture, which was moored along the Hudson. This forced The Vulture to move down river and necessitated that Andre now walk through the American lines to reach safety behind British lines in New York. Meanwhile, Benedict Arnold rushed back to West Point for a meeting with Washington. Andre, accompanied by Smith, the West Point plans, and travel papers provided by Arnold, made his way back to The Vulture.
Some time into their journey, Smith made his excuses to Andre, and pointed to a fork in the road, indicated what path Andre should take, and ditched Andre. Once Smith was out of sight, Andre promptly chose the other path; he did not trust Smith. So it was an unfortunate event when Andre, dressed in civilian clothing, found himself surrounded by three American ruffians. Andre, supposing them to be at first Tory sympathizers, identified himself as one of them. When that tack failed, Andre attempted to bribe his way around them. After a quick search, the men found the plans and promptly hauled him off to the nearest American garrison, which happened to be Benjamin Tallmadge’s.
Tallmadge was absent when Andre was brought into camp, but Tallmadge’s commanding officer was present—and made a poor assessment of the situation. He sent the papers on to Washington (who did not receive them in time) and he presumed that Andre was really who he said he was—an agent handling important documents for Benedict Arnold. He promptly sent Andre back to Arnold! When Tallmadge returned to camp, he frantically arranged for the retrieval of Andre, but not before Tallmadge’s unwitting superior sent a letter informing Arnold of the events. That night, Benedict Arnold escaped just hours before Washington arrived for his meeting with Arnold.
Some historians note that Tallmadge was well aware of Arnold’s and Andre’s meeting. Some even go so far as to suggest that he had a hand in stranding Andre on foot with the hope of capturing him himself on the path that Smith had originally pointed him to. For what purpose Tallmadge wanted Andre, we do not know. Perhaps, it was to turn Andre to the American side. Perhaps, it was to gather deeper British intelligence. Perhaps, he shared some sort of kindred spirit with his British analogue. Whatever the case, it is of note that in Tallmadge’s memoirs, he speaks at length of Andre’s final moments, of Andre’s gallantry, and nobility.
Andre was tried and executed as a spy. Tallmadge was incredibly shaken. The significance of Andre’s death could certainly not have been lost on Tallmadge, who was charged with Andre’s care throughout his execution. Here was Britain’s most important and accomplished agent dead, disgraced as a spy, the most ignominious occupation any man could undertake during this era. And now, Arnold was free and angry.9 Tallmadge’s emissaries were in their greatest danger yet. But, ironically, Benedict Arnold invited Tallmadge to desert his Continental post and join the British army. After promising Tallmadge rank and honor among the British, Arnold flatters Tallmadge, “I shall make no use of arguments to convince you to take the step which I think is right. Your own good sense will suggest anything I can say on the subject.” Then he baited Tallmadge with this piece of startling intelligence: “I will only add the British Fleet has just arrived with a very large contingent of troops.”10 Tallmadge was not impressed.

Rivington, the Book, and Yorktown
With Andre out of the picture, the British needed another spymaster to take his place. They found one in Oliver De Lancey, a smart, capable soldier who felt the need to tighten up the noose around the American’s spy network in New York. With the earlier capture of 355 and heightened tensions around New York, Robert Townsend effectively dropped out of the picture, leaving New York an intelligence void. Townsend’s boss and fellow spy, Rivington, however, kept busy with his printing press and The Royal Gazette. It was a good thing for the American cause, too. Imagine Rivington’s delight when he happened upon a copy of a British naval code book—one that would unlock all of the signals British ships flashed to one another.11 And this just in time, for another French fleet was making for the Chesapeake to aid the American cause. Washington snapped up Rivington’s find and couriered it to the French, who used the intel to cut off the British sea power at the Chesapeake. And imagine Rivington’s delight when he realized that his acquisition of the code book led to one of the most decisive blows America dealt to Britain, the one that signaled the beginning of the end of the war, the British surrender to Continental forces at Yorktown. Yet again, the Culpers managed to turn the tide of the Revolution toward liberty.

Before the Culper ring’s great successes, however, Benjamin Tallmadge had already proved his mettle. His role as “John Bolton” necessitated that he behave with great discretion, not only for the protection of the nation, but especially for those he referred to as his “emissaries”—the Culper Spies.12 Yet as mindful as he was of his duty toward those under his care, he always had the good of his Setauket home on his heart.
After the Battle of Long Island, when British troops swarmed through Long Island and on to New York, not much on Long Island was left unharmed in some way by the British. Tallmadge felt deeply the injustices that his fellow islanders suffered. One such victim was Judge William Smith, a respected judge and framer of the 1777 New York constitution. Lord of the historic mansion compound of St. George in South Haven, Smith did not much appreciate the British ousting him from his ancestral home and converting it into a military fort.13 He also did not appreciate having to relocate into the Long Island swamps. And neither did Benjamin Tallmadge. In 1780, sensing an opportunity to deliver a little justice directly to the enemy-occupied Long Island, Tallmadge persuaded General Washington to authorize a small military offensive. Launching from Mt. Sinai near Setauket, Tallmadge led his forces to his target: a large cache of hay held by the British in the little town of Coram. But the way to Coram led past Judge Smith’s home, now christened Fort St. George by the British. Tallmadge all along had the Fort in his sights—burning the hay in Coram would be a bonus. With 80 men, Tallmadge—accompanied by Brewster— stormed the Fort and captured it within minutes. He lost no men. And he burned the hay.

Post War
At the close of the war, Tallmadge made a special point to visit each of his operatives personally. Spying was risky business, and life after such intrigue would be hard to imagine. Tallmadge’s main concern was the reputation of those in the ring. Abraham Woodhull married Mary Smith, also a Setauket native, and lived a relatively uneventful life after the war, much to his satisfaction. His grave can be found at the Presbyterian Church in Setauket. Robert Townsend never married, though some historians believe he may have fathered a child with 355. He lived out his days in Oyster Bay, near Setauket. Until the 1930s, his identity as a Culper spy was unknown, which is just the way he would have wanted it. Austin Roe continued to operate his tavern, telling stories of the good old days as a Culper spy. One wonders how much fact mixed with fancy in his tales. Caleb Brewster, on the other hand, kept to the sea. In fact, he worked for the newly minted American government chasing down smugglers on the very seas he rode years earlier, terrorizing the British. His commission would later become what today is the U.S. Coast Guard.14 Poor James Rivington was perhaps the most unfortunate living Culper member. He played his Loyalist part so well that, after the war, he was shunned by the very people he worked secretly to defend. He spent over thirty years in a debtor’s prison trying to recuperate from his financial and personal losses.
Benjamin Tallmadge served until the war’s end. He moved to Connecticut, married, had seven children, and served as a Congressman for sixteen years. During that time, Tallmadge not only busied himself with affairs of state, he actively supported the cause of the Gospel in Connecticut and elsewhere. Tallmadge funded two missionary schools, one for Native American children and one for girls, wrote hymns, and participated in the religious awakening the day. Benjamin Tallmadge, speaking of the post war years, was full of the hope of the Gospel when he wrote:
While wars and rumours of war are permitted to disturb the nations, and desolate the earth, the eye of faith beholds the purposes of infinite benevolence continually maturing, and the glorious era rapidly advancing, when the millenial reign of the Prince of Peace shall fill the earth…How strictly and literally true it is that he makes the wrath of man to praise him, and the residue of it he restrains! The glorious footsteps of the great Captain of our salvation are seen in these ends of the earth…15
The Culper Spies are enjoying somewhat of a renaissance in popular culture. From books to television shows and even video games, Tallmadge and his emissaries’ exploits inspire and entertain.16 Yet for Tallmadge, his greatest exploits were not done for entertainment or excitement, but for a small town in Long Island and a community of saints gathered there.

1Alexander Rose, Washington’s Spies (New York: Bantam Dell, 2006), 80.
2 Ibid.
3 Ibid, 44.
4 patriots.html#brewster
5 January 11, 1800 personal letter from Abraham Tallmadge to his friend, the Rev. Manasseh Cutler, reflecting upon the recent death of Washington. Cutler was a Congregational pastor, Continental army chaplain and one of the prime movers behind passage of the Ordinance of 1787, which opened up the Northwest Territories (and which passed in no small part to Cutler bribing a number of congressmen).
6 Brian Kilmeade and Don Yaeger, George Washington’s Secret Six (NP: Sentinel, 2014), 104.
7 It seems a pity to reduce such an important figure to a footnote, but Robert Townsend likely had an accomplice during the currency mission. The facts surrounding the accomplice are murky at best. Historians agree on at least three things. First, the accomplice was never given a code name by the Culpers—just a number, 355. Second, the accomplice was a female. Of her exact social status and identity, there is still much debate. Some even argue she was not a single woman, but a collection of helpful women. Third, she was the only Culper spy to have been apprehended by the British. She, purportedly, was imprisoned on one of the British prison ships docked in the harbor. For an interesting discussion of the possible identity of 355, please see Brian Kilmeade’s and Don Yaeger’s fun and fascinating book, George Washington’s Secret Six.
8 Richard Welch, General Washington’s Commando: Benjamin Tallmadge in the Revolutionary War (McFarland & Company, Jefferson, North Carolina, 2014), 90.
9 Ibid, 99.
10 Ibid, 100.
11 Kilmeade, 189.
12 The Memoir of Colonel Benjamin Tallmadge, details/memoirofcolbenja00tall, 60.
13 history/history.htm
14 2014/07/caleb-brewster-revolutionary-war-hero/
15 The Christian Visitant, Vol 1. 1815
16 wiki/Benjamin_Tallmadge