Washington's Spies

by Alexander Rose

  Brewster, characteristically, had little time for such legalities and tackled the problem directly. His particular bugbears were Captains Glover (who had helped kidnap General Silliman) and Hoyt, his accomplice, who prowled the seas around Setauket. While Brewster was picking up a Culper letter at 2 a.m. on August 17, 1780, “I was attacked by Glover and Hoyght [sic]. I left one man taken and one wounded. We killed one on the spot. The man that was taken went after water. I shall want two men before I come across again. I have got two boats in fine order. I wish you send me seven men and I engage to take some of their boats.”63 A few days later, without waiting to hear back from Tallmadge, Brewster went over with three boats “in search of Glover and Hoyght, but could hear nothing of them. They never stayed to bury their dead man. They carried another away with them mortally wounded.” Still, the fact that the “cussed [Tory] refugees are so thick I can’t go amiss of them” persuaded Brewster to try his luck once more with the wily duo, but when he crossed again a week later, they had disappeared.64 He would have to bide his time.

  His efforts did not entirely go unrewarded. The British troops on the Island had become distinctly lackadaisical, and Brewster thought it “a fine time to take some of the officers. They are out with their hounds every day.” Indeed, as Brewster holed up in Selah and Anna Strong’s back garden in Setauket waiting for Woodhull, “there came a lieutenant of 17th Regiment within gunshot of us” who was out hunting. Brewster and his men pulled the officer down from his horse and were hauling him back to Connecticut, “but he begged so hard I thought it not best to take him as it was so near [Strong’s] house.” Pity was not among Brewster’s virtues, but he correctly perceived that if the lieutenant were kidnapped, the British would strengthen their guard in the area, not only casting suspicion on Mrs. Strong—Woodhull’s occasional accomplice—as a harborer of rebels but making it still more difficult to pick up Culper letters. As it was, the freed lieutenant would assume his assailants were thieves who chanced upon him rather than whaleboatmen on a more sensitive mission.65

  Brewster would be luckier—though Glover and Hoyt continued to evade him—the following February, when he was cruising off Long Island with three whaleboats. As they prepared to leave, he spotted a “boat rowing from eastward. I lay concealed till she came opposite to me when I detached one of my boats in pursuit.” It turned out that she was a Tory privateer with an eight-man crew. Back in Connecticut, he sent the prisoners (Captain Joseph Trowbridge, Henry Gibbs, Benjamin Prescott—who had already been jailed for illicit trading, but had escaped—James Smith, a captain in the King’s Militia Volunteers, Thomas Davis, Thomas Wilson, Christopher Young, and Job Mosier) under the care of a corporal and six men to General Parsons’s headquarters for safekeeping.66 Unfortunately, two of them escaped along the way, presumably to plunder again.67

  Brewster’s adventures notwithstanding, taking on the privateers one by one would not deter their future attacks. The Americans needed to hit their center of operations, to sever the head from the limbs, so to speak. In this respect, the Loyalists were vulnerable. While the Patriot whaleboatmen dispersed their forces by using the Connecticut seaports of Stratford, Fairfield, Norwalk, Stamford, and Greenwich as their bases, Tory privateers—who now conglomerated under the official-sounding moniker of the “Board of Associated Loyalists”—camped just outside Fort Franklin at Lloyd’s Neck, Long Island, an elevated promontory between Oyster Bay and Huntington. Sir Henry Clinton maintained a garrison—at one point numbering five hundred—there for the purpose of protecting these guerrillas.68 When they weren’t at sea, Woodhull complained, “parties of them” hid in the woods “laying wait for the unwary and ignorant” and then deceived them by “putting on the character of people from your shore.” They had recently “carried off 10 or 12 men and stripped their houses lately from about 20. The roads from here to [New York] is infested by them, and likewise the shores.”69

  Eliminating this nest of piracy became, for obvious reasons, of key importance to the Americans. In 1779, General Parsons planned an attack, but at the time he had only the frigate Confederacy and the ship of war Oliver Cromwell available—vessels too valuable to risk in a raid, quite aside from their bulk barring any hope of surprise—so he gave it up.70 “Having a great desire to break up this band of freebooters,” Tallmadge revived it in early September of that year, when he daringly took 130 of his dismounted dragoons across the Sound in a small, sleek armada of sloops and whaleboats commanded by Brewster, landed near the Tories’ camp at 10 p.m., and took them completely by surprise. He destroyed their boats and burned their huts, netted several prisoners, and returned to Connecticut without the loss of a single man.71 This would be but the first of Tallmadge’s great amphibious raids.

  The camp may have gone but Fort Franklin, however, still stood. In August 1780, prompted by General Parsons, who had sent in a spy, Tallmadge began pondering with Caleb Brewster and Woodhull a scheme to attack it. To this end, the latter provided a rough diagram of the fort on August 6, but Washington did “not think it advisable under present circumstances. Although the enemy appear to be small, dispersed parties, yet the risk in an attempt more than counterbalances the advantage which might be obtained.”72 Tallmadge, however, was already nursing doubts about “the character” of the agent Parsons had sent in, and it was greatly to his relief that Washington again refused to approve it. Afterwards, Tallmadge learned, “that on the night we had appointed to cross, a large body of the garrison were stationed at the place appointed for our landing, which probably would have annoyed us greatly.”73 The agent had betrayed them. If nothing else, Tallmadge learned from this experience to trust only his own spies and no one else’s, especially Parsons’s, who recruited men of shadowy, shifting loyalties, by-products of the Sound’s guerrilla raids and whaleboat wars. It would soon emerge as one of the most valuable lessons of all—when the spy code-named “Hiram,” the most adept triple agent of the war, began operating.

  Arnold’s defection had also prompted Tallmadge to plot a suitable revenge to lift the deflated spirits of the Patriots. For some months, Woodhull had been describing the state and readiness of the local troops in uncomplimentary terms. One time, for instance, Woodhull noticed that “there [are] about 50 refugees at and about Tredles farm near Smiths Town [who] possess a small fort, two field pieces, but are under no command [since] each man thinks himself [his own] captain … and are disagreeing continually. Good judges say they can be taken at any time with ease and is thought they will leave that quarter soon, if they should not be attacked.”74 On September 4, 1780, to give another example, thirty-four Queen’s Rangers had recently left Setauket. “For God’s sake attack them,” pleaded Woodhull, “you’ll certainly be successful, if you are secret about it. Trust not to small boats at this season, you have three strong vessels on your shore that will be sufficient to bring five hundred men. Setauket is exceedingly distressed.”75 Nothing came of it, but in late October Woodhull noticed a nearby foraging force of 150 wagons accompanied “with a very small guard of militia troops,” about seventeen. “Yourself [Tallmadge] with fifty men might do as you would with them. They are much off their guard. I think if you undertake and call on me you will do something handsome.”76 The foragers left before Tallmadge could organize a quick hit-and-run, but by that time the colonel was cooking up a raid that would truly shock the enemy.

  It had been Woodhull who, some time before, had first mentioned that at Coram—seven or eight miles inland from Setauket—the British were stockpiling hay, forage essential for running their war machine.77 In the first few days of November 1780, Tallmadge asked Brewster to call on Woodhull for more details. On November 6, Brewster returned with news, gleaned from Woodhull (who had ridden there for a look), that three hundred tons of hay had already been gathered for transport to New York. And there was more. Tories from Rhode Island had confiscated General John Smith’s house at Smith’s Point, at Mastic, on the south shore of Long Island, about eight miles further on from Cora
m, and had built a formidable triangular stockade they had christened, patriotically, Fort St. George. At two corners were strong-houses, the third consisting of Smith’s house fortified with a deep ditch and encircled by sharpened stakes protruding at a 45-degree angle. The stockade itself was “quite high” and every post was “fastened to each other by a transverse rail strongly bolted to each.” Once work was completed, Fort St. George would likely prove a nettlesome irritant. As it was, the British were already using it as a safe storehouse for wood, “stores, dry goods, groceries, and arms” due to be exported into New York, and it was not far-fetched to predict that oceangoing privateers would soon seek protection in its bay. Tallmadge immediately urged Washington to let him mount a raid “with about 40 or 50 dismounted dragoons” to destroy the stockpile and the fortress in one ambitious (and highly risky) swoop.78

  Washington, too, sensed a strategic opportunity to denude the British of their supplies just as winter was settling in: Without fuel, the despicable Arnold would have to endure a most unpleasant few months as the temperature dropped. Thus, he told Tallmadge in a letter written on November 11, the hay at Coram “is of so much consequence that I should advise the attempt to be made. I have written to Col. Sheldon to furnish a detachment of [100] dismounted dragoons, and will commit the execution to you.” Brewster was to accompany him. Regarding Fort St. George, however, if it can be done “without frustrating the other [aim] or running too great a hazard … I have no objection—what you must remember [is] this is only a secondary object.”79 Not for Tallmadge it wasn’t, who quietly determined to attack the fort after he heard from Brewster (and Woodhull, indirectly) that “their remains about forty Ruffigeus yet at Mastick on Mr. Smith’s place. They have no connon, nothing but muskets.”80 For the time being, Fort St. George was an easy mark.

  On November 21, at four in the afternoon, Tallmadge met his hundred chosen dragoons at Fairfield and took them across to a place called the Old Man’s, a few miles east of Setauket. At 10 p.m., after they had silently marched five miles inland, a fierce wind began to blow, driving rain hard into their faces. There was nothing for it but to return to the beach, where the whaleboats had been concealed in the bushes, and shelter under them for the night. The next night, the rain having abated, they set off again and were within two miles of Fort St. George by 4 a.m. Tallmadge divided his company into three, he commanding the major part, and two subalterns “of high spirit” (one was Lieutenant Thomas Tredwell Jackson, who left a bloodthirsty memoir of the event) taking the balance. They were to circle around the fortress and conceal themselves until they heard the enemy “fire upon my column.” By dawn, all were ready. Tallmadge’s “pioneers”—commandos skilled at breaking through stockades—surged forward first and got to within forty yards of the wall before a formerly drowsy sentry rather foolishly left the stockade, “halted his march, looked attentively at our column, and demanded ‘Who comes there?’ and fired.” But “before the smoke from his gun had cleared his vision, my sergeant, who marched by my side, reached him with his bayonet, and prostrated him” (as Tallmadge delicately put it).

  The sentry’s shot was the signal to charge. The two other detachments “all seemed to vie with each other to enter the fort,” Tallmadge later wrote. Lieutenant Jackson recalled in greater detail that he scrambled out of the ditch surrounding the southeastern stronghouse only to meet Brewster with his blood up barging through the main gate. All this had been achieved without loss and without an American musket fired. Brewster, and Jackson’s unit of fifteen men, stormed the stronghouse: “The poor dogs had not time to rub their eyes, or gasp before they were obliged to cry quarters.” Soon after, the remaining stronghouse and Smith’s house were taken, at which point “the watchword, ‘Washington and glory,’ was repeated from three points of the fort at the same time.” It was too soon for celebration. “While we were standing, elated with victory, in the centre of the fort, a volley of musketry was discharged from the windows of one of the large houses, which induced me,” said Tallmadge, “to order my whole detachment to load and return the fire.” Even so, the diehards barricaded themselves in, obliging Tallmadge to send his pioneers to break the doors down with axes. “As soon as the troops could enter, the confusion and conflict were great.” Those who had fired after the fort was taken, and its colors struck, “were thrown headlong from the windows of the second story to the ground.” “Having forfeited their lives by the usages of war,” judged Tallmadge, “all would have been killed had I not ordered the slaughter to cease.” After that, the victors destroyed “an immense quantity of stores” and demolished “the enemy’s works.” Tallmadge is guilty of omitting a few unpleasant facts in his sunny report, though Jackson alluded to them when he wrote to a friend that there “was a scene … of war my eyes never beheld nor description cannot equal. The cries of the wounded in the agonies of death. The screeching of the women and children while the parent and friend were entreating pity and compassion, called forth every tender feeling.” Tallmadge never mentions these “women and children,” but the Loyalist journalist James Rivington, in his story in the Royal Gazette of December 2, did. Rivington reminded his readers that “a body of respectable loyal Refugees … who were establishing a post in order to get a present subsistence for themselves and their distressed families” manned Fort St. George. Taking into account Rivington’s politics, and his habitual spinning of the news, it cannot be true that these “respectable loyal Refugees” were quite as angelic as he said. Fort St. George was, after all, a legitimate military target whose garrison continued to fight after the colors were struck; even so, Tallmadge seems to have lost control of some of his men temporarily. One woman, for instance, was “barbarously wounded through both breasts, of which wound she now lingers a specimen of rebel savageness and degeneracy.” As for the sentry who had fired the first shot and was “prostrated” by the sergeant’s bayonet, he was Isaac Hart, formerly of Newport and once an eminent merchant, who, after falling to the ground, was “wounded in fifteen different parts of his body, and beat with their muskets in the most shocking manner in the very act of imploring quarter, and died of his wounds in a few hours after.”81

  What to do with the haul of prisoners, some fifty, including a colonel, a captain, a lieutenant, and a surgeon? They were pinioned two-by-two and forced to carry heavy bundles of “dry goods.” At 8 a.m., Tallmadge’s company left whatever was left of Fort St. George and marched away. The colonel selected about a dozen men and together they took horses from the fort while the rest, with the prisoners, were ordered to rendezvous with them at a spot “at the middle of the island.” Tallmadge and his now-mounted dragoons (including Brewster) rode to Coram, “made a vigorous charge upon the guard placed to protect” the stores of hay, “set it all on fire,” and left to meet the rest. By four o’clock that afternoon, the company reached the shore and pulled their boats from their hiding places, and nine hours later they were all safely back in Fairfield. Not a man had been lost, and just one was badly wounded. The enemy, however, suffered seven killed and wounded, most mortally.82

  For this mission, Tallmadge received the thanks of Congress. More personally, Washington congratulated him on the success, particularly the destruction of the hay “which must … be severely felt by the enemy at this time.” Tallmadge must accept his commander’s “thanks for your judicious planning and spirited execution of this business” and asked that “you will offer them to the officers and men who shared the honor of the enterprise with you.” (As a reward, Washington allowed his “gallant party” to split “the little booty” they had acquired.)83 Just as heartfelt, and as deeply appreciated, was Woodhull’s excited letter of November 28: “I congratulate you on your success within the bounds of 729 [Long Island]. The burning the forage is agreeable to me and must hurt the enemy much.”84 Still better news followed: In January 1781, Woodhull went to New York for the first time in months and saw Townsend. The latter, he said, “intends to undertake the business again in the spring.”85


  With that knowledge, not even a letter of mind-boggling impudence Tallmadge received from Benedict Arnold could dampen his mood. The missive, originally written on October 25, but not delivered until late January, was an invitation to come over the water. “As I know you to be a man of sense, I am conscious you are by this time fully of opinion that the real interest and happiness of America consists in a reunion with Great Britain.… I have taken a commission in the British Army, and invite you to join me with as many men as you can bring over with you. If you think proper to embrace my offer you shall have the same rank you now hold, in the cavalry I am about to raise.”

  Arnold’s letter so disgusted Tallmadge he wasted no time sending it directly to Washington, while noting that “I am equally a stranger to the channel through which it was conveyed, the reason why it was so long on its way, or the motives which induced the Traitor to address himself thus particularly to me.”86

  Andre’s death prompted a reformation of the British counterintelligence system under his successor, Major Oliver De Lancey of the Seventeenth Light Dragoons, and his aides, Captain George Beckwith and Colonel Beverley Robinson. De Lancey—he who had knavishly struck General Nathaniel Woodhull in 1776—was described in 1775 as “a lusty, fat, ruddy young fellow, between twenty and thirty years of age.”1 Immediately after taking over, he directed that more attention be paid to acquiring political and tactical intelligence. Unlike the American setup, in which case-officers like Tallmadge looked after their own small networks and conceived their own ciphers and procedures, De Lancey ensured that his aides shared sources, dealt with agents on a rota, and used the same standard codes. This meant that none of them was indispensable; if one manager was captured, his agents and codes wouldn’t disappear with him. The American system’s disadvantage was that if Tallmadge was taken out of the picture, the Culper Ring would have instantly gone dark and silent. On the other hand, because he dealt with his assets personally, Tallmadge knew his men’s characters, fears, and desires far better, and could coddle and chastise them more effectively than his British counterparts. The Culpers, too, trusted Tallmadge implicitly, and he them, unlike the British managers and their agents, who maintained more of a cold business relationship. Another systemic difference is that while Washington insisted on cross-referencing overlapping, and often tedious, intelligence reports to sift out exaggerations, De Lancey preferred to file reports in chronological order in an Intelligence Book—an idea inherited from André.2