Washington's Spies

by Alexander Rose

  D’Estaing gathered together the remains of his fleet and returned to Newport, where Sullivan had anxiously been awaiting him, having abandoned his own attack during the storm. Now, at last, thought Sullivan, the operation could belatedly begin, but d’Estaing refused to risk his fleet until it could be refitted in Boston. Sullivan pleaded with the admiral to stay just one more day to help, but d’Estaing was adamant. He departed at midnight on August 21.

  Sullivan was livid. He resented “the conduct of the Count” and his officers, who had left “us on an island without any certain means of retreat.” Half his ten thousand men came to the same conclusion and departed quietly back to their homes, prompting General Pigot to sally forth from his fortifications in Newport and launch an attack on Sullivan’s positions. He was eventually pushed away by well-aimed musket volleys, but Sullivan had already decided to quit the island to save his force from disaster. It was a sound decision. The next day, September 1, Clinton himself arrived with ten fresh infantry regiments and two artillery brigades ferried from New York by Admiral Howe, the sailor who, with a force inferior throughout his brilliant defensive campaign, had saved not only Rhode Island but the British fleet and New York as well.4

  On August 27, a few days before Clinton arrived in Newport, Brewster had sent his first intelligence report. He had watched Admiral Howe’s warships, including “the Isis of fifty guns, the Renown of sixty four, the Apollo thirty six,” limp into New York harbor. The Isis and the Renown, in particular, were “much shattered,” which Brewster attributed to them having attacked “two seventy fours” on the high seas. (He was slightly wrong about the Renown, which actually battled a ninety-gunner.) He also reported that about a thousand British troops were around Brookhaven, on the northeast side of Long Island, and they were preparing to move out, while in Huntington’s harbor there were between twenty-six and thirty ships expected to sail for Rhode Island. Meanwhile, “several regiments [had] crossed from New York to Brookline Ferry, and encamped.”5

  While some of Brewster’s intelligence was somewhat old—the Isis and her sisters had come home a week before his report—it was news to Washington. Thanks to his new agent inside them, New York’s blank, forbidding walls had been breached, and intelligence was slowly leaking out. To know where Howe’s fleet was, even several days late, was better than having to guess. And to know that several regiments of British troops were preparing to board transports clearly bound for one place—Newport—as a relief force was priceless.

  Brewster was impressive, no doubt about that, but he needed to be managed. Washington directed General Charles Scott, who had fought at the Battles of Trenton, Germantown, and Monmouth, to handle Brewster and find additional agents. Scott was then in charge of the light infantry—troops selected for their toughness and skilled in scouting and skirmishing—at the forward positions in Westchester and Fairfield counties. Brewster would find it easier to get his messages through Scott than trying to reach Washington directly.6 To aid Scott, Washington chose Benjamin Tallmadge of the dragoons—a unit that worked closely with the light infantry.7 It was the first time Washington had communicated with the errant major since the winter and the imbroglio over the horses. The commander had determined Tallmadge’s term in exile over. He was forgiven.

  Though Scott was nominally in charge of gathering intelligence, he had onerous field duties to attend to, and was not much interested in the job in any case. In late September, Washington was forced to “earnestly entreat” him to “endeavour to get some intelligent person into the City, and others of his own choice to be messengers between you and him.” It was “of great consequence,” Washington reminded him, “to the French admiral [d’Estaing] to be early, and regularly advised of the movements of the British ships of war, at New York; and he depends upon me to give this advice.”8

  Much of the work thus devolved upon Tallmadge, who at least displayed some enthusiasm and aptitude for the task—as well as enjoying some experience thanks to his time with Sackett and Clark. Obsessively observant, he was possibly the only officer in the army whose roster of recruits contained not just the usual, humdrum facts—names, date of enlistments, discharges, and so forth—but a detailed description of each man’s physiognomy, including his eye color, height, build, and complexion.9 He soon told Washington about one potential contact for Brewster—a Long Islander named Abraham Woodhull.

  A few months before the Newport business, Woodhull had been passing through the Sound between Connecticut and Long Island when his boat was stopped by an armed American sloop and he was taken prisoner on the grounds that he had been involved in what was euphemistically dubbed the “London Trade.” Owing to the Royal Navy’s command of the sea, New Yorkers enjoyed a bounty of imported luxury goods: Spanish olives, French mushroom ketchup, jellies, Gloucester cheese, Scottish smoked salmon, German mustard, Russian tongues, walnuts, anchovies, Indian spices, and Italian confectionery were all available at reasonable prices. However, because Washington controlled the rural areas surrounding the city and Long Island, there were shortages of staples. Thus, delicate Chinese tea, grown on the other side of the world, was sold in New York shops, but milk and beef were rationed even as rebel-owned cows nonchalantly grazed across the Hudson in New Jersey.

  A busy black market inevitably evolved, one that paid no heed to ad hoc borders or personal politics. A Hessian officer in New York once wrote that “almost open trade is carried from here with the rebels; at least both sides close an eye.”10 Suffering under the same petty annoyances bred by army rule, the strictest of Patriots were as keen to trade illegally as the firmest of Loyalists if it meant surviving the war—or maybe just treating oneself to a little something. For years resigned to wearing homespun, scratchy dresses and coats to aid the boycott of British goods, and tired of dunking sage in their brew to give it taste, which American did not desire a stash of Ceylon tea and a bolt of lustrous Cathay silk, especially if it only meant exchanging a few pounds of beef and some garden vegetables?11

  Hence the bizarre spectacle of the London Trade, in which hogs, chickens, and beef were smuggled from Connecticut into New York, and gold buttons, cut-glass decanters, and casks of Madeira returned in the opposite direction.12 The simplest way to enter the trade was for customers to sidle up to whaleboatmen docked at one of New York’s wharves or Long Island’s many inlets, grease them the going commission, and hitch a ride. Passengers would be smuggled across the Sound late at night to a quiet Connecticut bay and barter their goods for, say, fresh produce brought there by an enemy boat.13

  The situation for Woodhull, who happened to be a farmer, was somewhat different in that as a rural Long Islander he had access to vegetables and livestock that could easily be bartered for luxuries in New York. Having little use for buckskin gloves and vinegar cruets, Woodhull would sail across the Sound and sell them for hard currency; that is, British pounds, not worthless, Congress-issued Continental dollars.14 For New Yorkers of all classes, it was ready money—money for bribes, money to pay the rent, money to mitigate wartime privation—that was in the shortest supply.

  Illegal trading understandably alarmed Congress, where, quite apart from the financial problems it created by draining cash from already cash-strapped states, many felt that Americans ought to be weaned from their pathetic dependence on imported fripperies. Some representatives also suspected that the sight of civilians enjoying contraband they had acquired from the enemy damaged ill-fed soldiers’ morale; others feared that so many contacts with the British might cause nostalgic royalist allegiances to reappear.15

  Military men, perhaps surprisingly, were often less critical of the practice, believing it too widespread in Connecticut and New Jersey to be worth devoting the resources, already scarce, needed to stamp it out, and arguing that it was vital to buttress civilian morale during wartime—even at the cost of ostensibly succoring the enemy. (Sometimes, though, officers participated in the trafficking, which really was going a bit far. One such was Colonel Sylvanus Seely of t
he New Jersey militia, who ran a lucrative network of smugglers in Elizabethtown.)16

  Washington himself was unperturbed by illegal trading. In November 1777, Governor Livingston of New Jersey had pleaded with him to clamp down on the Staten Island–Elizabethtown route (in which Seely was likely involved), which “plentifully supplied [the British] with fresh provisions.” Clandestine trading with the enemy was bad enough, but Livingston was particularly incensed by the revelation that Americans had begun opening stores solely devoted to fencing smuggled merchandise to the patriotic public. Washington did nothing. About a year later, when he was again begged to investigate a similar situation in Shrewsbury in northern New Jersey, Washington asked General Stirling to look into it and punish anyone he caught—but that was only after Congress expressly instructed him to take the matter in hand.17

  As for the British, they were well aware of illegal trading’s negative political and economic impact on Congress, and turned a blind eye—so long as traffickers didn’t get too greedy and run guns across the Sound. Thomas Jones, a respectable New York judge, was all in favor of the trade, for, among other advantages, “the merchants had a large vent for their merchandise.… It assisted the royal army, and it distressed rebellion.”18

  Woodhull, unfortunately, had been caught red-handed during one of the periodic swoops urged by Congress. Hence his imprisonment in Connecticut. He was detained some time before Governor Jonathan Trumbull, with whom Tallmadge had put in a quiet word, issued a permit for him to return home. Before he left in late August, Tallmadge and Woodhull had a talk about the latter joining Washington’s new secret service. Woodhull’s extracurricular activity hadn’t bothered Washington; in fact, he quite approved of the practice in this instance, for if you could smuggle goods, you could also smuggle information. Already, several American spies had masqueraded as traffickers during the war, bringing home minor intelligence picked up on their trips into enemy territory. Alas, smuggling’s fat profit margins proved too tempting for some of them.19 Washington accordingly complained that agents were “attend[ing] more to their own emolument than to the business with which they are charged,” and wanted to “take proper measures to curb this extravagant passion for gain” among his spies.20

  Woodhull, promised Tallmadge, was not cut of the same cloth. On August 25, an impressed Washington said that “you should be perfectly convinced of the integrity of W—— previous to his embarking in the business proposed. This being done I shall be happy in employing him, but there will be an impropriety in his coming with you to headquarters, as a knowledge of the circumstances in the enemy might blast the whole design. You will let me see you this afternoon—if you can come to dinner at three o’clock I shall be glad.”21

  At that dinner, Tallmadge assured his chief of Woodhull’s “integrity” and trustworthiness. Actually, if anyone was a security risk, it was Washington, who had used the first letter of Woodhull’s real name in his letter. Henceforth, with Scott’s approval, Tallmadge adopted a set of aliases: Tallmadge became the anodyne “John Bolton,” and Woodhull, “Samuel Culper.” Washington, Scott, and Tallmadge collaborated to invent the latter code name. Samuel Culper’s reversed initials are those of Charles Scott, while Washington lightheartedly amended the name of Culpeper County, Virginia—where, aged seventeen, he had worked as a surveyor back in 1749—to “Culper.” As for the first name, Benjamin Tallmadge’s younger brother was named Samuel—a friend of Caleb Brewster’s who the year before had helped convey messages from Major John Clark during his sojourn on Long Island. At this precise time, Benjamin was agitating on his behalf with Governor George Clinton to promote him; he chose a name not only on his mind, but also a kind of in-joke between him and Brewster.22 Brewster himself preferred to forgo an alias: Being a bluff and reckless fellow willing to take his chances, he always insisted on scrawling his real name, in very prominent letters, on all of his correspondence.

  The course of relations between the more capable Tallmadge and his distinctly inferior superior, Scott, were not running smooth at this time. Scott was a notoriously difficult boss with a history of undermining his subordinates if he deemed them a threat to his position. In April, he had repeatedly reported one such, Colonel John Parke, for being absent without leave “and even when present inattentive to your duty.” Washington had him arrested, but found no one willing to second the charges. At his hearing, Parke was found guilty of being occasionally absent without leave but cleared of being inattentive. It was a minor matter and Parke was restored to his command. When Parke wrote to Washington to explain his position, he hinted enigmatically that the stories of his dereliction of duty were due to “the misrepresentations of enemies.” Washington knew full well whom he was talking about.23

  Tallmadge had always maintained a chilly formality with Scott and vice versa, but soon Scott was going out of his way to squelch Tallmadge. At the end of October, the already brittle relationship between the two came close to snapping when Tallmadge told Washington that Brewster was delivering messages to him, but that Scott was ignoring them because, as Scott explained, the intelligence was not received “through the proper channel” and therefore “I did not give credit to it.” There was no apology for calling his own deputy an “improper” channel, though Scott knew—and was no doubt irritated by the fact—that Tallmadge was one of Washington’s favorites.24

  Even apart from their personal clashes, Scott and Tallmadge could not keep working together for much longer without destroying whatever little existed of the American intelligence service. They each represented fundamentally incompatible approaches to spying. Tallmadge had learned from Nathaniel Sackett how to disguise agents as enemy sympathizers using realistic cover stories, and from John Parke that a spy could nestle within the breast of an unsuspecting foe for months, perhaps years, at a time—provided he enjoyed a secure chain of communication back to base. Tallmadge ambitiously envisaged combining these two approaches to create a network of agents-in-place permanently embedded in occupied New York and running to Long Island, then across the Sound to his headquarters in Connecticut, where the intel would be digested and passed upstairs to the commander-in-chief—with Tallmadge’s summary and analysis attached.

  Scott thought more traditionally and wanted to stick to the tried-and-true method of military reconnaissance. He wanted to send in single, disposable spies on quick, Nathan Hale–style missions to observe what they could of the enemy’s deployments and (attempt to) sneak back across the lines.

  The risk inherent in Tallmadge’s “underground railroad” system was that if one member of the network was blown or flipped by the enemy’s counterespionage service, it rendered the rest of the chain useless, whereas if the same happened to Scott’s agents, the loss would be limited to just the unfortunates captured (as happened with Hale). Where Tallmadge held the advantage was that if he could set up such a network, the intelligence it communicated back would be of a far higher quality than that gleaned by any one-time operative. But Scott could counter that simultaneously running several small-scale missions assured more accurate—if lower-level—intelligence because the case officer could verify his agents’ independent estimates of, say, troop strengths, by cross-referencing them against each other. As Washington once wrote, to the leading American cryptographer of the time, “It is by comparing a variety of information, we are frequently enabled to investigate facts, which were so intricate or hidden, that no single clue could have led to the knowledge of them.”25

  For the time being, Washington was not entirely convinced by the merits of Tallmadge’s radical scheme, and instead continued to rely on the older system. On September 10, accordingly, Scott informed Washington that “Capt. Leavenworth is now on the Sound in pursuit of intelligence,” and that Scott had sent in three officers separately—Butler, Parker, and Grayham—to sniff out British positions on Long Island.26 A Captain John Rathburn also went in, to observe the enemy fleet.

  Rathburn and Leavenworth soon returned safely, but Scott f
eared the worst for the other three. On September 12, Scott informed Washington that one of them had been “stopped at the out lines contrary to the usual custom. Leaves it no longer a doubt about the others being detained.” The British had unexpectedly tightened their perimeter, netting the three unlucky spies.27

  Two weeks later—September 25—Washington had belatedly concluded that the traditional system was failing. He needed something new, and discreetly suggested to Scott that Tallmadge’s progressive ideas ought to be tried. He asked Scott to “endeavour to get some intelligent person into the City and others of his own choice to be messengers between you and him, for the purpose of conveying such information as he shall be able to obtain and give.” He now wanted a chain of agents stationed permanently in enemy territory. His choice of chief agent was Tallmadge’s recruit, “Mr. C——,” because if he “could be engaged in a work of this sort, his discernment, and means of information, would enable him to give important advices.”28

  Invigorated by this unexpected support, Tallmadge intended to forge Woodhull and Brewster into the nucleus of a network—what would become known as the Culper Ring—as a showcase for his scheme, and to take effective control of his little band from Scott. As early as October 22, for instance, Tallmadge was in direct contact with Brewster and thence to Washington, thereby neatly excising Scott from the chain of command.29

  He began prepping Abraham Woodhull for active duty. Since Woodhull’s return from Connecticut in the summer, he had been regarded with slightly raised eyebrows by his pro-British neighbors. Tallmadge needed to put their minds at ease that Woodhull was one of them, and as loyal as they were to the Crown—despite his suspiciously early release from prison by the rebel authorities. By coincidence, earlier that month, just before its members returned to London, the Carlisle Commission—fruitlessly sent by Britain to negotiate an end to hostilities—had proclaimed that all those who swore an oath to their sovereign would be pardoned after Congress’s defeat. The spy chief hit upon the crafty idea of having Woodhull “take the benefit of the same and serve as in his present capacity.” Woodhull, now “considered as one of their friends,” would have “a better opportunity of acquainting himself with their proceedings,” Tallmadge boasted to Washington.30