Washington's Spies

by Alexander Rose

  Joseph Reed, Washington’s adjutant general, accompanied by General Israel Putnam and Captain Alexander Hamilton, rode to meet him. After passing over the letter, he casually added that one Nathan Hale, a captain, had been executed that morning. The next day, without mentioning the Hale incident, Washington accepted the prisoner offer in a letter carried by Tench Tilghman, who was escorted by Colonel Samuel B. Webb and Captain William Hull, who had specifically requested permission to be part of the embassy after Hamilton had told him about Montressor’s information.72 Montressor again confirmed, at Hull’s insistence, that Hale was dead.

  And that was that. Hull was shaken, but few others wished to talk about the humiliating debacle, and no announcement was made to the army, for fear of undermining morale. In any case, there were hundreds of other war dead to handle. Certainly Washington never spoke of the affair, while Colonel Tilghman wrote to his father on September 25 about the meeting under a flag of truce but conspicuously failed to mention Hale. As part of the cover-up, his official listing in the Nineteenth Regiment’s casualty list was simple and sparse: “Nathan Hale—Capt—killed—22d September.”73

  Privately, however, American commanders seethed, and wanted to exact revenge. On October 3, Tilghman told Egbert Benson not to be so soft on the British and any sympathizers who fell into their hands. “I am sorry that your convention do not think themselves legally authorized to make examples of those villains they have apprehended [for] the General [Washington] is determined, if he can bring some of them in his hands under the denomination of spies, to execute them. General Howe hanged a captain of ours belonging to Knowlton’s Rangers, who went into New-York to make discoveries. I don’t see why we should not make retaliation.”74

  No one made the effort to tell Hale’s family what had happened. It wasn’t until September 30 that his brother Enoch, now a preacher, wrote in his diary that he “hear[d] a rumor that Capt. Hale belonging to the east side Connecticut River, near Colchester, who was educated at college, was sentenced to hang in the enemy’s lines at New York, being taken as a spy, or reconnoitering their camp. Hope it is without foundation. Something troubled at it. Sleep not very well.” Two weeks later, on October 15, a maudlin Enoch continues: “Accounts from my brother captain are indeed melancholy! That about the second week of September, he went to Stamford, crossed to Long Island … and had finished his plans, but, before he could get off, was betrayed, taken, and hanged without ceremony.… Some entertain hope that all this is not true; but it is a gloomy, dejected hope. Time may determine. Conclude to go to camp next week.” It wasn’t until October 26, when Enoch rode to White Plains to talk directly to officers of the Nineteenth Regiment, that his brother’s death was confirmed.75

  By every measure, the Hale mission was a fiasco. While the sacrifice of the obscure captain made no difference to Washington’s grand strategy, the bad decisions and poor planning that led to his death reflect Washington’s own confusion as to what his spy’s purpose was. Washington, however, would learn from his mistakes.

  1777, that year which the Tories said, had

  three gallows in it, meaning the three sevens.

  JOHN ADAMS

  As he trudged toward his doom on Sunday morning, Nathan Hale saw swirling plumes of smoke in the distance, to the south, where the city lay, still smoldering where a fierce fire had burned a mile-long swathe the day before. On that otherwise grim Sabbath, perhaps Hale allowed himself a wry smile upon overhearing his guards cursing the rebel arsonists who had, they presumed, set New York ablaze. Now, happily, the only thing the enemy would be occupying was the smoldering sump of a city.1 If the Americans would be forced to camp outdoors during the coming winter, then for Hale it was satisfaction enough to know that Washington had deprived some redcoats of their nice warm billets as well.

  He hadn’t, though. Grumbling mightily that “had I been left to the dictates of my own judgment, New York should have been laid in ashes before I quitted it,” Washington had obeyed Congress’s instruction to leave the city intact when he evacuated.2 From his headquarters on Harlem Heights, Washington had seen the red glare, and was glad: “Providence, or some good honest fellow, has done more for us than we were disposed to do for ourselves.”3

  The fire, which had begun near the docks at Whitehall Slip, rapidly devoured the surrounding houses and stores. At first there was panic. “The king’s officers, uncertain in whom to confide,” distrusted the city’s volunteer firemen, thinking them to be “rebel[s] at heart,” and “franticly hurried them from place to place.” Several officers became so terrified at the holocaust surrounding them they started “beating [the firemen] with their swords,” and even drove a few into the flames, screaming.4

  Some kept their heads. Admiral Howe immediately ordered his navy to weigh anchor and sail downriver—sufficiently far away to avoid being set alight by stray sparks—while rowboats ferried officers and sailors back to the city to help fight the fire. In the meantime, General James Robertson drafted two full regiments of soldiers into makeshift fire brigades.5 They soon discovered that New York had been left defenseless. Short of metal suitable for casting into cannons, Washington had stripped the city of its alarm bells; the British also found many of the water pumps and fire engines were out of order—testament to prewar civil authorities’ sloppiness.6

  Conquering blocks at a time, the fire marched inexorably to the foot of Broadway and turned—when the wind shifted at 2 a.m.—west. By merest chance, the “ship docks, warehouses, and the commercial part of the city” located on the eastern side were left unharmed.7 Some ten hours after its outbreak, the wind having again changed, the fire was finally baffled at Barclay Street by pulling down the houses in its path.8

  The physical and financial damage was enormous, with contemporaries agreeing that between a sixth and a quarter of the city—including five hundred houses—had been razed.9 Thousands were wretchedly “reduced to beggary,” while “many hundreds of families have lost their all” and were “destitute of shelter, food or cloathing.”10 The blow would have fallen still harder—as well as severely hampering British military preparations for at least a year—had General Robertson not diverted the fire engine dousing his flaming house to the nearby docks, thus saving £200,000 worth of army supplies at the cost of his own residence, worth £2,000.11

  The fire was the fruit of a “preconcerted, deliberate scheme” of fifth columnists, covert operatives, and sleepers, suspected the British.12 It certainly looked likely. “A few minutes after the fire was discovered,” the authorities claimed, “it was observed to break out in five or six other places, at a considerable distance.”13 Mr. Chew, one of the army’s assistant commissaries, said that he had seen the original building at Whitehall Slip on fire, and then another—two hundred yards away—“which had the appearance of having been purposely set on fire.”

  The conspiracy theory of the Great Fire was gravely weakened by General Howe’s admission that the “night was extremely windy,” which naturally conveyed sparks some distance. Further, if the fire were the product of a rebel plot, it’s strange that no one thought to start the fire in the commercial and residential heart of New York.14 Instead, the flames blasted a narrow path, originating in the southeast and driving northwest—that mirrored the wind’s shifting direction through the night.

  The truth about how the fire started has only recently come to light. On the night in question, “several of the soldiers’ wives” had gathered together “in a large frame building near Whitehall-dock”—a storehouse adjacent to the Fighting Cocks, an old tavern frequented by British troops and sailors on the town. Hoping to cook some hot food in a fireplace, the women “procured from an adjacent yard a number of pine boards, the ends of which they placed in the chimney, [with] their opposite points rested upon the cedar floor of the apartment.” The “careless gypsies,” having finished their feast, “had withdrawn from the heated and smoky atmosphere within, to enjoy the fresh Seabreeze without.” In the meantime, the flames
, of course, consumed the boards and “the cry of fire was heard soon after.”15

  Although innocent of igniting the fire, or of acting on Washington’s orders, or of organizing a vast plot to burn the city, Continental servicemen (either stay-behinds, escaped prisoners, or deserters who’d had second thoughts) and rebel sympathizers were guilty of taking advantage of the chaos to help the fire along and frustrate efforts to save the city. Indeed, American officers in northern Manhattan took it for granted that “some of our own people” were responsible for spreading the fire. Washington’s own aide-de-camp, Tench Tilghman, told his father that if any of these arsonists were executed it would admittedly be “upon good grounds” (though he assured him that they had acted “without the knowledge or approbation of any commanding officer in this army”).16

  One such freelance arsonist was Abraham Patten, who would be hanged as a spy in Brunswick, New Jersey, in early June 1777 after bribing a British grenadier to carry four letters to Washington; the soldier had pocketed the fifty guineas and delivered the messages to his superiors. On the scaffold, Patten, who had been living in the city at the time, “said he was a principal in setting fire to New York, but would not accuse any of his accomplices.”17 Another accessory after the fact was a New England captain “seized, with matches in his pocket,” who confessed he was determined to set fire to King’s College.18 This unfortunate was one William Smith—son of a Massachusetts clergyman—who was “sacrificed on the spot to the fury of the soldiers.”19 The captain had been taken prisoner during a skirmish and took it upon himself to do his bit for Washington. Poor Smith wasn’t the only one caught red-handed: Captured the week before, Lieutenant Richard Brown, of a Pennsylvania regiment, was discovered by soldiers “setting fire to some of the houses in New York” and likewise executed in the street.20

  Being thrown into the flames was often the on-the-spot penalty for suspected arsonists (and sometimes looters), though lynchings and stabbings were not unheard of, and there were several instances when individuals were “hung up by the heels, and afterwards had their throats cut” or were bayoneted.21 Women were not excluded from retribution: In fact, the “first incendiary who fell into the hands of the troops” was a female shoved “without ceremony” into the inferno. Soon afterwards, several men seen “destroying a chain of buckets, in order to prevent their being made use of in extinguishing the conflagration” were thrown into the flames after her.22

  Unlike the Great Fire of London in 1666, which cleansed its alleys of beplagued vermin, blasted a millennium’s worth of microbes out of the gutters, and razed the medieval hovels, so giving Sir Christopher Wren the opportunity to construct a modern city atop its ruins, the fire which ravaged New York left large parts of it a macabre pyre. A bustling mercantile metropolis descended into a degenerate mare’s nest, the leading red-light district in North America, the black-market capital of the Revolution. The area around Whitehall Slip, for instance, was never rebuilt, and instead became “Canvas-Town,” a hell where paupers, felons, and prostitutes huddled in burnt-out houses. The glittering balls thrown in the ostentatious mansions of parvenu merchants and hard-faced war profiteers disguised, like a cheap rug, the rotted floorboards of a city torn and conflicted.

  A narcotic, poisonous atmosphere pervaded New York, whose inhabitants were forced to compromise their principles to survive the war. Surrounded by naught but devastation, often forced to flee from their homes by greedy Patriots, and facing an uncertain future, almost every man and woman, no matter how deep his or her attachment to the Crown or to Congress, traded illegally with the enemy. Ambiguity reigned—New York was a city schizophrenically under occupation but one also under siege—and the only means of emerging unscathed was to play both ends against the middle. Citizens tailored their politics, allegiances, and beliefs as circumstances dictated: On one particular morning—June 25, 1775—crowds cheered George Washington as he passed through the city on his way to Boston; that very afternoon, they cheerfully greeted William Tryon, the royal governor, on his return from England.

  The immolation of New York was the one bright spot for Washington that dismal fall of 1776. He would spend the rest of it on the run. Leaving two large detachments at Forts Washington and Lee, the commander-in-chief of a severely demoralized army retreated north of Manhattan, languidly followed—“chased” would be the wrong word—by Howe. At the end of October, the two sides clashed at White Plains, and yet again Washington came off worse. Much to Washington’s pleasant surprise, however, Howe refrained from the kill and turned back to finish off the forts to his rear. On November 7, General Nathanael Greene—the officer commanding Fort Lee—could see the enemy’s camp fires burning across the river.23 It could not be long before Howe, lethargic as he was, reduced Fort Washington and advanced on his own vulnerable outpost. Taking advantage of the respite, Washington withdrew the rump of his army further north to Peekskill, his plan being to circle around, rendezvous with his remaining commanders in New Jersey, and then, hopefully, evade Howe until winter brought campaigning to a halt.

  Given the chaotic circumstances, American intelligence was nonexistent. Deserters, who could sometimes bring in useful material about their regiments, had become a rare thing indeed, for no one abandons the winning side. Washington, however, suffered terribly from these turncoats, though one, William Demont, may have single-handedly, if inadvertently, saved the American cause. An ensign in the Fort Washington garrison, he “sacrificed all [he] was worth in the world” and brought plans of its fortifications and artillery emplacements to the British. It was this intelligence which convinced Howe, then north of New York, that of the two fish he had to fry, Fort, not General, Washington was the bigger. By letting his foe escape, Howe lost the opportunity to extinguish the rebellion.24

  Washington’s primary problem, however, lay in not possessing a secure, fixed headquarters. Without one, there was no guarantee that spies’ messages would ever find him. Washington was obliged to forget about acquiring strategic intelligence and instead rely on tactical reports gleaned by scouts riding as close as they dared to the enemy lines. More often than not, they would return with “lame” and “imperfect” accounts of British movements, a result General Charles Lee—one of Washington’s most senior (and supremely talented, at least in his own opinion) officers—ascribed to them not “ventur[ing] far enough.” He was very “far from being satisfied” with the conduct of the scouts, though Washington had no choice but to use them, especially after mid-November, by which time Forts Washington and Lee had fallen, and Washington was being relentlessly pursued through New Jersey by Lord Cornwallis, Howe’s chief lieutenant, who boasted that he would trap Washington “as a hunter bags a fox.”25

  And an exhausted fox at that. Since August, the strength of Washington’s army had fallen from 20,000 to just 3,000 (about half of whose contracts were due to end in December), and he had lost four battles (plus one surrender without a fight—at Fort Lee, where the entering British discovered General Greene had vacated it so precipitately “the pots were left absolutely boiling on the fire, and the tables spread for dinner of some of the officers”; they also found twelve Patriots, “all dead drunk,” who had resolutely stayed behind and liberated the fort’s rum stores).26 “The fact is,” concluded Lord Rawdon, “their army is all broken to pieces, and the spirit of their leaders and their abettors is also broken.” Surely, he ventured, “it is well nigh over with them.”27

  Still, this old fox remained a sly one. On December 12—with Cornwallis threatening to advance on Philadelphia, the seat of Congress itself—Washington ordered Colonel John Cadwalader to “keep a good lookout for spies” and “magnify your numbers as much as possible” should he spot an opportunity to sow some disinformation.28 A little more than two weeks later, the efficient Cadwalader reported that he had sent an anonymous but “very intelligent young gentleman” to Princeton who had found some friendly British officers with whom to share a bottle. They got to talking, and the officers boasted they
had 5,000 men at their command, whereupon the young gentleman cheekily declared that Washington had 16,000 in fine trim. The officers looked shocked, as they had not believed “we had more than 5 or 6000”—itself an exaggeration—that were deserting and in poor shape. His job done, the enterprising agent even brought back a map of the local British deployments.29

  These successes aside, Cadwalader—like Washington and most officers at the time—relied primarily on soldiers sneaking across enemy lines, memorizing troop positions, and returning later that night. “I have sent several persons over for intelligence,” noted Cadwalader on December 15, “& last night sent Capt. Shippen with 20 good men,” and that wasn’t to overlook the “very intelligent spirited officer in the Jersey Regulars” who also went over on a separate mission.30 The British, too, had their sources, though they tended to rely more on the information brought in by such helpful loyalists as Bazilla Haines of Burlington County, who stayed a night in an American camp and subsequently informed his masters that “they had only two field pieces” and that “there were not above eight hundred, near one half boys and all of them militia.”31

  Despite such heroics, the enemy was taken by surprise by Washington’s counterattacks at the Battles of Trenton and Princeton in late December and early January, allowing him a respite after the rigors of the past months.32 With the British withdrawing to New York to reassess their strategy and recover from the shock of being beaten, Washington wintered in the hills around Morristown, where he was finally able to consider his intelligence apparatus, or rather, how to build one that would serve him well in the coming campaign seasons.

  While military officers would continue to handle purely tactical matters and scouting, Washington wanted to recruit more civilians into the nascent service. Whereas soldiers disguised in civvies found it difficult to shed their drill-bred habits of saluting superiors and walking in perfect time, civilians could easily enter enemy-held cities without attracting suspicion, especially if they were locals or possessed the requisite passes. As Washington advised one of his generals at the time, he should gather intelligence “by engaging some of those people who have obtained protections, to go in under pretence of asking advice.”33