Washington's Spies

by Alexander Rose

  To this end, he discreetly requested William Duer, a member of New York’s Committee for Detecting and Defeating Conspiracies—the enforcement arm of the political revolutionaries—to recommend a suitable candidate. On January 28, Duer forwarded the name of Nathaniel Sackett, a middle-aged colleague of his on the committee. Not only was Sackett “a man of honor, and of firm attachment to the American cause,” he was, more importantly, “a person of intrigue, and secrecy well calculated to prosecute such measures as you shall think conducive to give Success to your generous exertions.”34 A week later, Washington informed Sackett that the “advantage of obtaining the earliest and best intelligence of the designs of the enemy” and “your capacity for an undertaking of this kind, have induced me to entrust the management of this business to your care.” A monthly salary of fifty dollars was arranged, and Sackett was additionally allowed a secret fund of five hundred dollars “to pay those whom you may find necessary to Imploy in the transaction of this business.”35

  If Sackett succeeded in recruiting agents, he would certainly require a deputy empowered to detail army riders to run their messages to headquarters, as well as able to soothe the snippier colonels annoyed that a civilian was interfering in matters they regarded as their own prerogative. To that end, Washington quietly appointed a freshly made captain, Benjamin Tallmadge of the Second Continental Light Dragoons, as Sackett’s military contact.36

  Tallmadge, dark-eyed, pale, delicately featured, with a prominent nose, a somewhat bulbous forehead, and a disconcerting habit of cocking his head like a quizzical beagle, had enjoyed an interesting war so far. After bidding adieu to his dearest friend Nathan Hale, he had become a schoolmaster in Wethersfield, Connecticut. Most of his letters to Hale between 1773 and 1775 talked about girls (the females in his town were “very agreeable” and he was looking forward to having “a colleague (of the fair sex) settled under me, (or rather over me), for she will dwell in the 2nd loft”), but Tallmadge was slowly being drawn into revolutionary circles. His landlady, a widow of the town’s Congregational minister, introduced Tallmadge to Wethersfield’s first citizens, many of whom—such as Silas Deane and John Chester—would go on to play significant roles in the coming years. Tallmadge also met Jeremiah Wadsworth of New Haven, like him a minister’s son. That contact would prove especially beneficial.37 Still, Tallmadge was reluctant to sign up after the skirmishes at Lexington and Concord in April 1775, telling Hale in May that while “a great, flourishing state may arise” in America, he questioned whether “we ought at present desire it.”38 A June jaunt to see the American lines at Boston, followed by a heartfelt talk with his friend John Chester, now captaining a company of Connecticut militia, removed some of Tallmadge’s doubts and went some way toward persuading him that rebellion was a divine mission. As he told Hale, “Our holy religion, the honour of God, a glorious country, and a happy constitution is what we have to defend.”39 Even so, still beset by worry that expressing Whiggish sentiments was quite a different thing from taking up arms against an anointed king, he refrained from signing up for the colors for another year. By the spring of 1776, it had become almost impossible for a young man of Tallmadge’s upbringing and milieu to avoid the fateful decision. By chance, Chester had just been promoted to colonel, and he offered Tallmadge a lieutenancy. Tallmadge took the commission. On June 20, he proudly donned his dashing new uniform for the first time and prepared to meet the blast of war.40

  Chester’s regiment marched for New York soon afterwards, where it was absorbed into General Jeremiah Wadsworth’s brigade. For Tallmadge, perhaps thanks to his connections, promotion was rapid, and he became the regimental adjutant on July 22.41 In late August, Chester’s regiment was transferred from Manhattan to Brooklyn to await the inevitable British attack. When it came, Tallmadge saw action around Flatbush and found himself, along with the exhausted remnants of Washington’s army, awaiting evacuation at Brooklyn Ferry on the evening of August 29. Tallmadge departed on one of the last boats off Long Island and followed Washington north to White Plains. His eldest brother, William, who had signed on as a sergeant in a Connecticut regiment as early as 1775, did not accompany him: He had been captured during the battle and soon after died of starvation and neglect, aged twenty-four, aboard one of the British prison ships in New York harbor. If Tallmadge still nursed any doubts about the cause he served, they immediately disappeared.

  In early October, John Wyllys, then serving as Wadsworth’s brigade major, was killed in a skirmish, and Tallmadge was raised to his place.42 In this post, Tallmadge first came to Washington’s attention; brigade majors met at the general’s headquarters at 11 a.m. each day to receive their orders, which they would in turn read out to the regimental adjutants. As Washington retreated through New Jersey, however, Tallmadge and many of the New England regiments were directed to stay in northern New York, on the east side of the Hudson, to fend off British pursuit. Rejoining the main body of the army in early December, Tallmadge was offered a captaincy in one of Congress’s four brand-new cavalry regiments, the Second Dragoons, commanded by Colonel Elisha Sheldon. These mounted troopers, who could also fight on foot, were to be deployed by Washington on reconnaissance missions, where they would often skirmish with enemy cavalry undertaking the same task.43 Forty-three men were under the young officer’s command: a lieutenant, a cornet (a commissioned officer), a quartermaster, two sergeants, two corporals, a trumpeter, a farrier, and thirty-four privates.44

  Uniformed in dark blue coats, lighter breeches, and knee-high black boots with silver spurs, the dragoons were crowned with metal helmets—designed to ward off saber blows—stylishly decorated with a white horsehair plume sprouting from their crested peaks. Each man carried a cavalry saber, a pistol or two, and a short musket, while officers, befitting the dashing character of the cavalryman, wore a crimson sash around their waists.45 Immediately after being raised, the regiment trekked to Connecticut to buy horses, so missing the Battles of Trenton and Princeton. Tallmadge ensured that his own troop (one of six) “was composed entirely of dapple gray horses … with black straps and black bear-skin holster-covers” that, he added modestly, “looked superb.”46

  It was while based in Connecticut in these early months of 1777 that Tallmadge first experienced the secret world, its shadows and thrills. There, he served a dual role: His day job entailed being a dragoon captain assigned the chore of purchasing horses for the regiment, while his extracurricular employment consisted of acting as Sackett’s point man for espionage operations across Long Island Sound. Even though Washington’s correspondence with Tallmadge about horses is dull—“I would not wish to have even dark greys, if others equally good could be got; but if they cannot, you may purchase them, and when they change colour by age, we must put them to other Uses in the army”—the fact that the commander-in-chief was writing to a mere captain about such humdrum matters is testament to the trust he reposed in him.47

  Tallmadge’s first mission was to ensure that Major John Clark safely arrived on British-occupied Long Island from the Connecticut shore. Clark was a young, large-built Pennsylvanian lawyer, “fond of fun and frolick,” who volunteered for duty as a lieutenant in 1775 and was noticed by senior officers for his gallantry at the Battle of New York.48 Over the following months, Clark turned to specializing in reconnoitering. General Nathanael Greene, in particular, thought him remarkably talented and audacious, made him his aide-de-camp, and sent him out by himself to probe far ahead of the army and even to scout deep within enemy territory, where he whiled away the lonely hours in the forests and hills reading Beccaria’s Essay on Crimes and Punishments (which contested the era’s emphasis on harsh punishments) and Laurence Sterne’s Sentimental Journey Through France and Italy, an account of the comic, and often amorous, adventures enjoyed by the author’s alter ego, the Reverend Mr. Yorick.49 For a covert expedition to Long Island, perhaps using it as Nathan Hale had as a back way into New York, Clark was just the man.

  Little is known of what exact
ly Clark did there—Clark was so habitually secretive that in the autobiographical sketch he published forty-five years later he omitted any mention of what he was doing between January and September 1777—but he was certainly traveling all along the northern coastal road, from Setauket in the east to Huntington about midway and probably still more west than Oyster Bay.50 On February 25, he paid a whaleboatman who frequently crossed the Sound to carry a message to Tallmadge. In it, he reported that “there were no troops at Satauket [sic], but part of two companies at Huntington.” And that “there are but few who are not friendly to the Cause—That they had beat up for volunteers in the western part of the county but that only three had inlisted.”51

  Setauket at the time was a very small town, remarkable in this context only because it was Tallmadge’s birthplace, and it was where his father still lived. Thus, Clark was assured of a friendly welcome, safe sleeping, and warm food—all the things Hale had lacked. The intrepid Clark spent several more months reconnoitering Long Island, all the while honing his skills at blending into a population and learning from the inside how the British army worked.52 (On June 1, Washington’s private accounts book records that $946 for “secret services” had lately been paid, some of it to Clark, to refund his expenses.)53

  After receiving the message, Tallmadge summarized it for Sackett and passed the new version on to Captain John Davis, of the Second Company, Fourth Battalion, Fourth New York Regiment, for delivery.54 Tallmadge had become acquainted with Davis through his younger brother, Samuel Tallmadge (born 1755), once bound for a mercantile career but currently a sergeant in the Fourth New York’s First Company of the Fourth Battalion.55 Samuel was also great friends with the former ensign—the lowest rank of officerdom—of Davis’s company, Caleb Brewster, with whom he and Benjamin had grown up in Setauket. Brewster was a former whaleboatman by trade, and it may well have been he who carried Clark’s messages across the Sound from Setauket to Connecticut.56 Though Tallmadge’s letter was addressed to Sackett, the latter seems to have been absent and Davis entrusted it to William Duer, who sent on a copy to Washington.57

  Earlier in the year, chafing at the regiment’s inaction, Brewster had transferred to the Second Continental Artillery, an outfit which allowed him plenty of free time to participate in “semi-official” covert operations across the Sound.58 One such was an amphibious raid on August 14 in which Colonel Parsons led 150 armed men in a sloop and six whaleboats—one commanded by Brewster—on an attack on Setauket’s Presbyterian church, recently taken over by a prominent Long Island Loyalist, Colonel Richard Hewlett, to use as a fort. His men had overturned many of the gravestones in the churchyard, destroyed the pulpit, and ransacked the interior. The desecrated church happened to be the one ministered by Tallmadge’s father, and his son approved heartily of Brewster and his friends paying Hewlett a surprise visit (Tallmadge himself couldn’t go, as his regiment had already been recalled to the main army). Parsons did not succeed in taking Hewlett and his men prisoner, but he did give them a good scare: Having beached their whaleboats outside the village, they silently marched to Setauket and sent a flag of truce to the surprised inhabitants of the “fort.” Hewlett refused to surrender and a fierce firefight erupted. After Parsons was tipped off by a friendly local that British warships were on their way, he ordered a retreat to the boats and the raiders scarpered for home, not omitting to steal a few of Hewlett’s horses.59

  In the meantime, Tallmadge had found himself made a major on April 7, 1777, and in early July his regiment rode from Connecticut to New Jersey to join Washington.60 The dragoons ranged widely, frequently encountering the advance parties of their British equivalents. As Tallmadge wrote to Wadsworth, “I have had here & there a horse and rider or two wounded, but have lost none from my troop as yet, though several horsemen have been killed in the same skirmishes with me, from other regiments.”61 So busy was Tallmadge with his regular military duties that his intelligence function fell by the wayside.

  In any case, it mattered little, for Sackett had, during Tallmadge’s absence in Connecticut, turned himself into an astute and imaginative spy chief. Unfortunately for his relations with Washington, he was successful more at inventing new forms of tradecraft than actually acquiring hard intelligence. Most of his agents may have performed poorly, but Sackett’s system protected them, and their secrets, better than had any other until that time.

  On the same day as Tallmadge’s promotion, Sackett compiled a lengthy report for Washington on his progress. Having served on the Committee for Detecting Conspiracies, Sackett would have known a thing or two about double agents and impersonators, but his letter discusses so many advanced techniques—especially for the time—it should be regarded as one of the founding documents of American espionage.

  Following his appointment, he had spent a fortnight “almost desp[airing] of success” until a gentleman pledged to “secure me a proper person to go into the City of New York … who he recommend [ed] to be well educated and a good surveyor and every way calculated for the business.” On the night of March 7, Sackett got him through the British lines, his mission being to “hire a room in the city and get a licence to carry on a secret trade for poultry to enable him to convey me intelligence once or twice a week.” The luckless agent never returned. This particular spy was either a charlatan or a dead man, but Sackett had stumbled onto an important insight: Instead of dispatching scouts or spies when the occasion demanded and having them return the same day with their intelligence, Sackett had been determined to send an agent into enemy territory, to keep him there, to invent a legend (in this case, poultry trader), and to arrange regular communication.

  After that, Sackett found another gentleman who—in order “to enable him to go in under proper circumstances to get the best intelligence”—had “for some time associated with the first rate Tories in these parts and carried matters so far as to get a written invitation from William Bayard [a senior loyalist] now in the City.” Bayard’s son, John, was a colonel in the King’s Orange Rangers and had offered to recommend Sackett’s agent to Colonel Abraham Van Buskirk and Captain Robert Timpany, both of the New Jersey Volunteers. It is unknown what information this anonymous spy amassed, but Sackett’s idea of infiltrating men masquerading as sympathizers and ingratiating them with senior British commanders was a brilliant one.

  Then there was Sackett’s recruitment of a Hessian, resident in America for nearly forty years, who said he would attach himself to members of Hessian regiments in New York and use “such arguments with them as will prevail with great numbers to desert,” and then “make use of the deserters as pipes to convey intelligence.”

  Finally, by posing as a secret friend to King and Country, Sackett went so far as to recruit an unwitting female agent to ferret out intelligence. This woman was the “wife of a man gone over to the enemy” whose grain had been stolen by American troops. When she came to Sackett to complain, he gently counseled her to go see General Howe. “She was pleased with the advice and set off to his lordship to let him know how she was oppressed and to request the time that she might expect relief.” On March 28, she left New York with nothing in hand, and told Sackett—who nodded sympathetically with pursed lips, no doubt—that no relief was in sight, for “there is a large number of flat-bottomed boats in the harbour of New York which are intended for an expedition against Philadelphia and that the British army is going to subdue that city and the poor Tory sufferers here will not be relieved until that expedition is over.”62

  It was a sweet coup, but not enough to save Sackett’s job. He was paid off with five hundred dollars in secret service funds and ceased his involvement in intelligence matters following some kind of fiasco.63 Washington forever remained silent about what happened, though in 1789, when Sackett was importuning the general for a federal appointment (unsuccessfully), he wrote a letter begging Washington to recall his services during the war. In doing so, he left behind a comically obtuse clue as to what precisely ended his career: “I ha
d gone through all those dangers that awaited me in getting a regular plan laid, and was beginning to carry it on with every appearance of success, [but] the Jersey [man fell] in love with his horse, the doctor narrowly escaped with his life, and the whole scheme was frustrated.”64 The mind boggles.

  Washington, too, imbibed some lessons from these first, halting steps toward constructing an effective espionage apparatus. To Sackett he declared that “the good effect of intelligence may be lost if it is not speedily transmitted—this should be strongly impressed upon the persons employed as it also should be to avoid false intelligence.” Not only intuitively understanding that intelligence of the enemy’s designs and movements is only useful if delivered promptly, and that spies often embroidered paltry facts to earn their pay, Washington also grasped the importance of cross-referencing one agent’s reports with other, competing versions (“A comparison of circumstances should be had, and much pains taken to avoid erroneous accounts”) to prevent exaggerations. This was especially crucial when it came to estimating troop strengths, a notoriously tricky science to get right; many a promising offensive had been cancelled when the local commander relied on a report telling him the enemy possessed double or even triple his actual number. One thing Washington did not get right, however: “It runs in my head that I was to correspond with you [Sackett] by a fictitious name—if so I have forgot the name & must be reminded of it again.”65

  There would be fewer of these comic moments in future. By the time Sackett left, the secret war was beginning to turn into an exceedingly nasty one. Over the course of the “year of the hangman,” the Americans became increasingly wary of not only British spies but covert Tories living in the areas under congressional control. When caught, for them the noose inevitably awaited. Perhaps because there were fewer American spies, the British tended to be more lenient, though even they sometimes made graphic examples of those they suspected of passing on information. General Howe, for example, was usually quite lax about delivering such awful punishments, but that did not stop him from hanging “three women, (two of them by the feet, at the head of his army) whom he imagined were spies,” as one observer informed Washington in June.66