Washington's Spies

by Alexander Rose

  These problems were not entirely Clinton’s fault. He was a product of the conventional military establishment, where spies were regarded with distaste, and in any case, there was little need for them in the European battlefields. The American theater, however, confronted British commanders with unique intelligence problems. The post service, for instance, was almost nonexistent, especially across enemy lines, and its lack of centralization foiled the kind of Black Chamber mail-intercepting operations common in Europe. Though bribes and baubles could still work their magic on the more mercenary of colonists (Benedict Arnold sold West Point for today’s equivalent of half a million dollars and the promise of a knighthood), the leading ideologues remained barbarically immune to such blandishment.

  Further complicating intelligence gathering, an ornery, diffuse population of constantly shifting degrees of loyalty lay spread over an area comprising one million square miles. In America, soldiers and militiamen foraging for food and supplies as they traversed the countryside was a time-honored necessity. In Europe, by contrast, tradition dictated that the military forgo foraging on the march, which forced generals to stick to roads and navigable rivers so that their supply lines could keep up with them. Any commander who took his army more than five days’ march from a depot risked being cut off.

  During wartime, then, collecting intelligence about the enemy’s movements was not of prime concern since there were only certain, defined routes along which an army could travel, and topographers could thus accurately predict how long a formation would take to reach its destination. “The best way to discover the enemy’s intent before the opening of a campaign,” counseled Frederick the Great, who knew his onions, “is to discover where he has established his provision depot. If the Austrians, for example, made their magazines at Olmütz you could be sure that they planned to attack Upper Silesia, and if they established a magazine at Königgrätz, the Schweidnitz area would be threatened.”

  In Europe, the mark of a great captain was not his talent for deception or for divining intentions, but his ability to outmaneuver opponents on known ground and defeating them in the field as they marched and wheeled in lines and columns. In America’s vast geographical spaces, however, armies (and guerrillas) could hide, live off the land, travel cross-country, appear out of nowhere, strike, and vanish. Possessing advance or intimate knowledge of what the enemy was doing, or was planning to do—the raison d’être of espionage—became of vital importance.

  For both sides in the Revolutionary War, however, the pursuit of intelligence was initially hampered by the fact that no one was quite sure how to do it. There were no textbooks available on the principles and methods of agent (and double agent) recruitment, flipping sources, penetrating networks, verifying walk-ins, establishing dead drops, hiring cutouts, arranging secure data transmission, managing “black” budgets, finding safe houses, and inventing cover stories, let alone collecting, analyzing, and evaluating information.

  Military writers had, of course, historically paid homage to the virtues of espionage. Frederick, Marshal de Saxe, and Julius Caesar had all stressed the need for spies, and everyone was familiar with the biblical story of Joshua sending agents to “spy out the land,” but none had bothered to dictate practical instructions to their successors. Even as late as 1832, when On War appeared, the Prussian military genius Carl von Clausewitz cursorily cited the importance of intelligence while pointing out that “many intelligence reports in war are contradictory; even more are false, and most are uncertain,” and left it at that. He managed only to advise commanders to “trust their judgment.” Lacking instruction manuals, therefore, commanders in America were obliged to fashion a system of trial and error to evolve their secret services.6 In hindsight, it’s easy to illuminate the obvious mistakes made by both sides, but, to give Clinton and Washington their due, they were generally willing to learn from them.

  Clinton, for example, improved his system as he gained control of particular areas, allowing him the time to establish spy networks in place. In May 1779, Clinton appointed Captain John André, his aide, as his specialist intelligence officer—the British equivalent of a Tallmadge. It was a radical step taken not because the general had experienced a brain wave, but for the more prosaic reason that Clinton, as supreme commander, was overwhelmed with work and needed to delegate some of it to a trusted subordinate. André may have been a dilettante but at least he was an efficient dilettante. He immediately put affairs on a sounder footing by extracting intelligence reports from the mass of general correspondence that daily arrived and filing it in chronological order in a hardbound book. Belatedly, one could at last distinguish intelligence (albeit of varying quality) from ordinary military orders, lists of promotions, transcripts of courts-martial, and other ephemera. André, unfortunately, went no further with his reorganization, and reports continued to go unevaluated. The “Intelligence Book” was dropped for lack of interest in August 1779, and only resumed the following July, when André began to concentrate heavily on news from the West Point area provided by his ace, Benedict Arnold, who became André’s sole focus in the months leading up to his defection.7

  Born in 1750, André was the son of a cold Swiss merchant and an exuberant Parisian mother. He grew up in Geneva but, after training in languages, music, dancing, and mathematics, left for London to work in his father’s firm. Thankfully, when he was nineteen, André’s father died, and he inherited a nice little fortune, thereby relieving him of the burden of labor. He got engaged to an Anna Seward, but she broke it off, believing he lacked “the reasoning mind she required.” Bored, and newly single, André bought a second lieutenant’s commission in a smart regiment, the Royal Welch Fusiliers, but transferred as a full lieutenant to the Seventh Foot, which was headed for Quebec in late 1775. Taken as a prisoner during the siege of Fort St. Johns shortly after, André charmed his captors and was exchanged after the Battle of New York in 1776. He soon became a staff officer at General Howe’s headquarters, serving as a translator for the Hessian troops. When his benefactor left for England, he joined Sir Henry Clinton’s staff in 1777–78. Clinton took a shine to him and André became the British commander’s first friend and confidant. In three years, he had advanced from being a mere subaltern in the Fusiliers to Clinton’s adjutant general, the eighteenth-century equivalent of chief of staff.8

  In many respects Captain John André resembled Captain Nathan Hale: Both were gentle and graceful, and artistic and talented; both, too, were unsuited to espionage (André once admitted he, like Hale, was “too little accustomed to duplicity” to succeed in the game).9 The André-Arnold correspondence even mirrors that which passed between the Culper Ring and its manager, with its manifold examples of crossed wires, elementary mistakes, and petty irritations.

  Both teams used an alphanumeric substitution code, Tallmadge’s being based on his own Code Dictionary, and André’s on William Blackstone’s legal Commentaries, a copy of which he and Arnold possessed.10 Soon after making contact, they began using it as their common sourcebook (with Joseph Stansbury, a London-born Loyalist in Philadelphia, as their intermediary, and the Reverend Jonathan Odell in New York, who decrypted the messages).11 “Three numbers make a word,” instructed André, “the 1st is the page the 2nd the line the third the word.”12 So “general,” which could be found in Blackstone on page 35, at the twelfth line, eight words from the left, became 35.12.8.

  There were two fairly obvious drawbacks to the scheme—quite aside from the risk of someone discovering what the sourcebook was—as André and Arnold soon found. First, Blackstone had to have actually used the term. Otherwise, they were laboriously obliged to spell out the word, each time scratching through the last digit to indicate that this number referred not to a whole word but to the placement of a particular letter on the line. Since Blackstone never alluded to, say, “Poughkeepsie,” the correspondents were often confronted with daunting strings of numbers for a single word (sixty, in Poughkeepsie’s case). Second, even if Blackston
e did use the word, it might require enormous stamina to find it. Arnold, rather enterprisingly, managed to dig up “militia,” but only after he’d ploughed through 337 pages of legalese. Arnold and André tried it once and gave up, turning instead to the 21st edition of Nathan Bailey’s Universal Etymological English Dictionary, which not only contained every common word, but also listed them, of course, alphabetically.13

  Unlike Tallmadge, who insisted on using anodyne aliases (“John Bolton,” “Samuel Culper”) and simple code numbers, André preferred to assign colorful biblical names to people and places: Carlisle, Pennsylvania, for instance, became “Rome,” the Susquehanna River “Jordan,” Indians “Pharisees.” Occasionally, his waspish sense of humor emerged, such as calling Congress “Synagogue” and Fort Wyoming, of all places, “Sodom.” For himself, Arnold selected “Gustavus” or “Monk” for his aliases (after the seventeenth-century Scottish general who had restored monarchical rule to England, for which signal service he received a knighthood, a barony, an earldom, and a dukedom from an exceedingly grateful Charles II), while André broke from his own practice and, quite foolishly, used “John Anderson,” or sometimes “James Anderson”—both names bearing too close a resemblance to his own. For a time, André used a cipher almost identical to Tallmadge’s, in which, starting from the number 50, words were converted into digits; he even made the same mistake as Tallmadge by listing the words alphabetically, not randomly, so rendering the cipher relatively easy to crack.14

  In some of their correspondence, as Townsend did with his letter to “Colonel Floyd,” André and Arnold disguised the real meaning of their words within harmless contexts: a business deal between two crooked merchants, for instance, or “the complexion of affairs [of] an old woman’s health.”15 André, like Tallmadge with Woodhull, cajoled and chided his secret servant, though, unlike his American counterpart, he did not quite trust him and it took several months of Arnold’s importuning to persuade him that he had stumbled onto a bona fide, highly placed, and voluntary mole. The primary difference between Arnold and the Culper Ring, of course, is that the general was a mercenary entrepreneur, continually demanding more money for his treachery while his masters tried to gauge how fertile their man’s supply of intelligence was likely to be.16 André was perfectly blunt about what he desired: “Dispatches to & from foreign Courts, original papers, intimation of channels thro’ which intelligence passes” plus “taking possession of a considerable seaport and defeating the troops assigned to the defense of the province.” (At one point, he asked, “Could you obtain the command in Carolina?” though in that case Arnold one-upped him by offering possession of West Point.)17 In reply to Arnold’s pleas for more money, André remained businesslike, telling his spy that “services done are the terms on which we promise rewards; in these you see we are profuse; We conceive them proportioned to the risk.”18

  It was only in late August 1778 that Arnold’s thirty shekels—twenty thousand pounds for West Point and its garrison, with a guaranteed minimum of ten thousand pounds should the plot fail but he came over anyway—was agreed, and André (now a major) and Beverley Robinson (who had been running agents on the Hudson and knew the area) arranged to meet their contact on the Hudson River to finalize the terms on September 11.19 That plan was aborted when a British patrol boat fired on Arnold’s barge as it neared Dobb’s Ferry. For a week, they waited, and Arnold enticed his manager with the intelligence that Washington was in the vicinity and likely to visit him.20 If all went well, not only would this key fortress fall into British hands, but so too would its three-thousand-strong garrison, plus, best of all, Washington himself.

  On September 20, a second attempt was made. André and Robinson sailed upstream aboard H.M.S. Vulture, but could not make contact that night. The next evening, Arnold’s intermediary, Joshua Smith, collected André, who was inexplicably posing as a merchant while dressed in regimental uniform, and brought him ashore to a grove at Haverstraw, on the west bank of the Hudson.21 Upon meeting “Mr Anderson,” recalled Smith of André’s “youthful appearance [and] the softness of his manners,” he “did not seem to be qualified for the business of such moment. His nature seemed fraught with the milk of human kindness.”22

  At about two in the morning, André—still outfitted in his regimentals—discussed the topography and defenses of West Point with Arnold, who was waiting nervously a little north of Haverstraw. By the end of their long conversation, by which time daybreak was imminent, Arnold accompanied André and Smith to the latter’s house to continue their talks, the plan being for him to leave the major in Smith’s care until the following night, when he could be rowed back the six miles to the awaiting Vulture. It was only during the ride to the safe house that André realized, having seen in the dawn’s early light a sentry post, that he was within American lines—dressed in the kit of an enemy officer. In the meantime, Arnold gave him a pass to travel unhindered through American territory, sketches of the fort, and maps of its artillery positions, all of which André hid in his stockings.

  After Arnold’s departure later that day, September 22, an American officer, having noticed the Vulture, decided to shell it with a howitzer, forcing the sloop to sail twelve miles downstream.23 Rowing eighteen miles in a blazing red uniform, even at night, was far too risky an enterprise, and André, “vexed” (Smith’s words), was persuaded to change into civilian dress, and don a round hat and blue cloak, and cross the river at Verplanck’s Point with Smith and his black servant, so he could ride overland to the British lines at White Plains. Eight miles later, an American sentry stopped them and helpfully pointed out that Tory partisans were operating to the south, which was a no-man’s-land terrorized by marauding gangs of Tory “Cowboys” and Patriot “Skinners.”24 Knowing that to continue would invite suspicion, André and Smith kipped near the outpost for the night, and after a breakfast of mush and milk early the following morning (September 23), Smith bade him farewell and handed him forty dollars to get home. André was confident he could make the fifteen-mile journey to White Plains by nightfall. That was the last time Smith saw him.25

  All went well until 9.30 a.m., when, as André consulted a map, John Paulding appeared in the road and pointed a musket at him. In the bushes to either side hid Isaac Van Wart and David Williams, also armed. Paulding demanded André’s name and affiliation. A more hardened case officer would have precomposed the aptest response to a challenge from men equally likely to be rebel Skinners or loyal Cowboys: If the former, his pass from General Benedict Arnold of the Continental army would awe even them and he would be allowed to go; if the latter, the pass would guarantee they took him prisoner and conveyed him under guard to White Plains, where he could prove his credentials and be released. In the event, not unreasonably given the sentry’s warning about Tory activity and that one of the party was wearing an ancient British redcoat, André misjudged the situation, and cheerily declared: “My lads, I hope you belong to our party.” Paulding asked which party that might be. “The lower,” said André, referring to the British side.

  At that, they announced themselves to be Patriots. Startled, André stammered that he was “an officer in the British service on particular business in the country,” and, mustering himself to look impressive, directed that they let him go. They didn’t, instead ordering him to dismount. It was only then that André had the presence of mind to show his permit, but it was too late. Van Wart merely exclaimed, “Damn the pass!” and demanded money. The other two then mugged him—André’s fine, white-topped, London-made boots being of particular interest to David Williams. As they unshod him, they found Arnold’s incriminating plans of West Point hidden within his stockings. Paulding, the only literate one, stumbled through them and cried, “This is a spy!” Still, the highwaymen told André they would let him free if he gave them one hundred guineas, his horse, and his watch, an offer to which he readily agreed. Just as André thought he was home free, one of them suggested that there was nothing to lose by taking him in anyway.26


  The trio trundled him—all the time debating André’s desperate offers of a lucrative reward if they brought him south to New York instead—to the nearest commanding officer, Colonel Jameson at North Castle, who allowed them to keep André’s belongings.27 The twenty-eight-year-old colonel was befuddled, mostly because he had recently received a letter from Arnold informing him that an important friend to the American cause named Anderson might be crossing into Patriot territory from British lines, and here he had an Anderson who had claimed to be a royal officer heading for British lines carrying letters in Arnold’s handwriting.

  Tallmadge, who was out on patrol, was less puzzled than suspicious. In the secret world, as he knew, there was no such thing as a coincidence. He, too, had received a letter from Arnold a week earlier noting that a “Mr. James Anderson”—“a person I expect from New York”—might arrive; if he did, Tallmadge was to “give him an escort of two horse to bring him on his way to this place, and send an express to me that I may meet him.” Ominously, Arnold had added, “if your business will permit I wish you to come with him,” implying that the turncoat believed he might have a bonus for the British to scoop up: the American chief of intelligence.28 Tallmadge, unfortunately for Arnold’s scheme, did not open the letter until September 21—he had been “absent on command by special directions of His Excellency Genl. Washington”—which allowed him to avoid the trap set for him.29 Unluckily for the captured spy, however, the letter’s contents were fresh in Tallmadge’s mind when he heard of this mysterious fellow in custody at Jameson’s headquarters.