Washington's Spies

by Alexander Rose

  In the meantime, he fell in love. Or rather, re-fell in love, with the same woman. In his last year at college, Hale had been introduced to Alice Adams, a pretty, vivacious thing, but one, alas, about to be married off to a wealthy man, Elijah Ripley, considerably older than herself. Fortunately for Hale, Mr. Ripley’s talents did not include longevity, and he died on December 26, 1774. Hale waited, decently, until her period of mourning was over before launching his suit. In early 1775, Alice was overjoyed to receive a Hale-penned poem:

  Alicia, born with every striking charm,

  The eye to ravish or the heart to warm

  Fair in thy form, still fairer in thy mind,

  With beauty wisdom, sense with sweetness joined

  Great without pride, and lovely without art….

  The two began to court, but Hale put duty before pleasure.13 Just a few months into his wooing, the Revolution came to Connecticut. The battles of Lexington and Concord on April 19, 1775, galvanized young men into joining the colors—including two of Hale’s brothers, who signed up for the Connecticut militia marching to Massachusetts. Of the thirty-five members of Yale’s 1775 class, for instance, thirteen continued into the ministry, but no fewer than thirteen others joined the Continental army.14

  Inescapably shaped by his background, his milieu, and his education, Hale was by temperament and inclination a pronounced Patriot. Tallmadge, who wrote to him on July 4, 1775, allows us a penetrating glimpse into what two young American idealists felt at the time: “I consider our country, a land flowing as it were with milk & honey, holding open her arms, & demanding assistance from all who can assist her in her sore distress.… [W]e all should be ready to step forth in the common cause.”15

  While Tallmadge would join the Continentals the following year, Hale went to the recruiting station just two days after that inspirational letter was written. It was the same day—July 6—that the governor of Connecticut commissioned officers in the newly raised Seventh Regiment. Hale’s name is on the list as first lieutenant of the third company. The Seventh was commanded by Colonel Charles Webb, whose own first lieutenant was William Hull, one of Hale’s friends from Yale. On September 8, Washington requested Governor Jonathan Trumbull to send his new Connecticut regiments, and within two weeks, Hale was on the march. From his diary—albeit abbreviated, and hurriedly jotted down—we know that the Seventh marched to Providence, then through Massachusetts to Cambridge, headquarters of the American forces surrounding Boston, where they had Gage and his forces bottled up. Once there, the regiment was assigned to General John Sullivan’s brigade at Winter Hill; Hale was promoted to captain-lieutenant, and signed up for another contract of service for 1776 at a time when many refused to reenlist when their terms were up. His regiment was then renamed the “Nineteenth Foot in the service of the United Colonies,” as part of Washington’s effort to mold his gaggle of ragtag militias into a professional volunteer force.

  Hale had missed a great battle on June 17, when the newly arrived General William Howe put to flight the American militia from their fortified positions atop Bunker and Breed’s hills. Howe’s multiple assaults, though eventually achieving their objective, proved abnormally costly in his own men’s lives; of Howe’s field staff, only he remained unshot. One Tory, Peter Oliver, who witnessed the battle, ascribed “the sacrifice of a greater disproportion of heroick officers than perhaps ever fell in one battle” to the Americans’ “savage way of fighting, not in open field, but by aiming at their objects from houses & behind walls and hedges.”16 Two decades earlier, during the Seven Years’ War, Howe had made his name with his dashing attacks; Bunker Hill turned him into an overly cautious commander reluctant to administer the coup de grace to his downed, albeit still dangerous, enemies for fear of having victory snatched from him at the last moment. Though he remained a master tactician—Washington would repeatedly find himself at a disadvantage on the battlefield whenever he was present—Howe’s experience at Bunker Hill convinced him that the Americans, even when seemingly vanquished, were far more potent than his superiors in London realized. Howe’s preferred strategy became one of attrition: Secure one’s base, muster overwhelming numbers, outmaneuver the enemy, defeat him in open battle when necessary, and wait until his army collapsed. To this end, as it became evident to Howe over the subsequent months that Boston was ultimately untenable, he began planning an evacuation to Canada.

  By the time Hale arrived, the excitement was over, and the two armies were in stalemate. Hale spent his time doing virtually nothing during his stay outside Boston. Apart from a few brief bursts of action around him (“Considerable firing upon Roxbury side in the forenoon, and some P.M. No damage done as we hear,” he wrote in his army diary), life was pretty uneventful, even dull—with all the attendant ill effects on discipline that breeds. Indeed, in September the Virginian regiment of riflemen mutinied out of boredom, and when a British doctor visited the New England camp, he described the soldiers there as nothing but “a drunken, lying, praying, hypocritical rabble, without order, subjection, discipline, or cleanliness.”17 In his free time, which was plentiful, Hale played checkers, watched the men wrestle (even placing a few bets on the burlier ones), drank wine at Brown’s Tavern, read whatever books came his way, and listened to chaplains give sermons. He also composed poetry for his Yale friends about army life, and provided an admiring portrait of Washington:

  When coming here from Watertown,

  Soon after ent’ring Cambridge ground,

  You spy the grand & pleasant seat,

  Possess’d by Washin[g]ton the great.

  Though his sense of rhyme failed to scale the Himalayan heights he intended, Hale occupied his hours on duty drilling, sorting out pay disputes, organizing supplies, setting pickets, listing guard rosters—all the humdrum minutiae of army life. “Studied the method of forming a regiment for review, of arraying the companies, also of marching round the reviewing officer,” he noted of one day’s activities.

  In mid-March 1776, short of supplies and awed by Washington’s artillery newly emplaced atop Dorchester Heights, the British finally evacuated Boston and departed for Halifax, Nova Scotia, to recuperate under their new supreme commander, General Howe. Though Washington could not predict when and where Howe would return, he was confident that New York—wealthy, easily supplied, situated between the South and New England, and possessing a magnificent harbor—would be the target. In this, he was right. In their Canadian fastness, Howe and his generals planned to use New York as their base of operations. Ownership would permit him to march north up the Hudson River, thereby severing the fiery New Englanders from their less hostile brethren in the Middle States and the South, and British control over the region would gradually tighten until the rebellion asphyxiated.

  In mid-March, Washington began transferring his forces south to New York. On the nineteenth of that month, accordingly, Hale’s regiment was ordered to leave Roxbury. On the thirtieth, they sailed across Long Island Sound and disembarked at Turtle Bay in Manhattan, at the foot of what is now East Forty-fifth Street.18 Then into the city itself, at the southern end of the island, where they fortified their positions against a possible, and increasingly probable, British onslaught. Throughout May, Hale and his men were stationed on the west side of the Bowery. Shortly after, his unit was rotated out to post guard at the western end of Long Island, a region rife with anti-Patriot sentiment and where the inhabitants eagerly awaited “liberation” from these rebels by His Majesty’s troops, rumored to begin landing on Staten Island in late June.

  Writing to his brother Enoch on May 30, Hale was dismissive of the Long Island Tories, observing that “it would grieve every good man to consider what unnatural monsters we have as it were in our bowels.” He wanted robust measures taken against them. Until that happened, there was more cheerful news to consider: On July 9, when the regiments were summoned to their customary evening roll call, “the declaration of the Congress, declaring the United Colonies FREE, SOVEREIGN, AND INDEPEND
ENT STATES, was published at the head of the respective brigades, in camp, and received with loud huzzas.”19

  How long that independence would last depended on the resilience of the Continentals stockaded in New York City (i.e., what is now lower Manhattan), with a fortified bulwark in Brooklyn. These few were expected to dissipate the fury of an empire. On August 20, we have the last, hasty dispatch Hale wrote (to his brother): “For about six or eight days the enemy have been expected hourly whenever the wind and tide in the least favored. We keep a particular look out for them this morning. The place and manner of attack time must determine. The event we leave to Heaven.”20

  Two days later, General and Admiral Howe—“Black Dick,” the latter, was the commander’s brother—began ferrying their army to Long Island, their intention being to storm the Brooklyn fortifications, cross the East River, conquer Manhattan, and crush the rebellion before Christmas. Hale’s Nineteenth Regiment was sent to Brooklyn, but did not assume front-line positions. His eighty-man company was kept in reserve behind the breastworks, and he witnessed from afar the disaster that befell Washington’s soldiers at the hands of the best army in the world on August 27 and 28, when General Howe felt confident enough in numbers to assault the American positions. Washington’s front collapsed, and on August 30, he evacuated Brooklyn and withdrew to Manhattan. He had lost one island only to be trapped on another. Across the East River, the thin blue ribbon separating Washington and oblivion, an observer could see the tens of thousands of scarlet-clad soldiers and hundreds of troop-transports awaiting a decent tide and a fair wind so they could invade Manhattan. There was nothing else for it but to leave, while they still had the chance. Sooner or later, the British would come and Washington could ill afford to have his army besieged in the city. The decision was quickly made: The Americans would retreat north to Manhattan’s Harlem Heights, whose rocky slopes afforded useful cover for a last-ditch defense of the Revolution.

  Washington and his commanders furiously debated what to do with the abandoned city. The New Englanders wanted to burn it, so as to leave the British with nothing but a blackened husk in which to spend the approaching winter; the New Yorkers, sensibly enough, were reluctant to raze their own property.21

  General Nathanael Greene, a Rhode Islander, favored burning. In a lengthy letter to Washington, he laid out the purely military justifications for doing so: “The city and island of New York are no objects for Us.… Part of the army already has met with a defeat; the country is struck with a panic; any capital loss at this time may ruin the cause.… Two-thirds of the property of the city of New York and the suburbs belongs to the Tories. We have no very great reason to run considerable risk for its defence.… I would burn the city and suburbs, and that for the following reasons. If the enemy gets possession of the city, we never can recover the possession without a superior naval force to theirs. It will deprive the enemy of an opportunity of barracking their whole army together.… It would deprive them of a general market; the price of things would prove a temptation to our people to supply them for the sake of gain, in direct violation of the laws of their country. All these advantages would result from the destruction of the city.”22 He would be proved right in every respect.

  But New Yorkers pressured Washington not to listen to the likes of Greene, and the Convention of the State of New York asked him to ensure that if it came to “the fatal necessity” of destroying the city, then its “twenty thousand inhabitants may not be reduced to misery by the wanton act of an individual.”23 The Convention was referring to a rumor running round the army “that any man is authorized to set [New York] on fire” if the order to retreat was given. Not yet having made up his own mind about what to do, but wanting to soothe their fears of an overzealous arsonist, Washington hedged whether he would give an order to burn-and-retreat. “Nothing but the last necessity and that such as should justify me to the whole world,” he wrote, “would induce me to give orders for that purpose.”24

  For political cover, Washington passed the buck to Congress; if there were to be fallout in later years, the general needed to be able to claim he was following the directions of the nation’s elected representatives. On September 2, in his report to the body, Washington spoke frankly, and despondently: “Our situation is truly distressing.… Till of late I had no doubt in my own mind of defending this place, nor should I have yet, if the men would do their duty, but this I despair of.… If we should be obliged to abandon the town, ought it to stand as winter quarters for the enemy?” Congress replied from Philadelphia the very next day: “Resolved … that no damage be done to the said city by his troops, on their leaving it; the Congress have no doubt of being able to recover [New York] tho the enemy should for a time obtain possession of it.”25

  Washington was off the hook, and the Americans made their preparations to vacate. The issue that now vexed him was, having departed New York, how would he fend off the British once his troops were stretched across middle and upper Manhattan, and living off the land, especially as winter drew on? At least when they were tightly boxed into the city, apart from being billeted in warm quarters, the Americans could leverage their numbers and benefit from their short supply lines. Better still, the enemy’s choice of possible attack strategies was severely limited. At some point, the Howes would have to undertake an amphibious landing, followed by an infantry assault on tenaciously held fortifications—maneuvers fraught with danger and almost certain to result in heavy losses. Still, eventually the Howes would do it, and Washington would be finished. Better, perhaps, to run now and live to fight another day. Accordingly, on September 11, Washington informed Congress that he was “ordering our stores away [so] that if an evacuation of the city becomes inevitable, and which certainly must be the case, there may be as little to remove as possible.”26

  Between September 7 and 15, apart from a few thousand who would depart a few days hence, American troops left the city of New York and marched north. Washington now at least enjoyed a line of retreat into Connecticut or New Jersey should the fortunes of war continue to tell against him, but his first priority was to divine the probable British line of attack. They could come from almost any direction. Across the water, Washington could see with his own eyes the British busying themselves, but would they land in the city and advance up the island, or would they land to his north and drive south, or would they do both and entrap him within their pincers? Perhaps they would do neither and attempt an invasion midway up the island, then divide their forces and take New York at the same time as marching to Harlem. Washington knew Howe was ploddingly slow, but he was methodical, and it was a dead certainty he had something up his sleeve.

  Washington needed accurate and timely intelligence of Howe’s designs and motions. Previous efforts had proved a mixed bag. As early as July 14, General Hugh Mercer—Scotland born, he was a former apothecary from Virginia—regretfully informed Washington that he could find no one suitable to sneak into the British camp (though he did succeed two days later). Five weeks later, General William Livingston—soon to resign his commission to become the governor of New Jersey—said that “very providentially I sent a spy last night on Staten Island to obtain intelligence of the movements of the enemy.… He has this moment returned in safety.”27 The spy, whose name was almost certainly Lawrence Mascoll (Washington’s warrant-book records a payment on August 23 for him “going into the enemy’s line to obtain information”), had visited an “informant” employed by Howe to carry “baggage” who had “heard the orders read and heard the generals talk.”28

  Mascoll brought back some useful intelligence, such as the British army figures, the revelation that provisions were running very low, and the news that the “Tories on the Island are very illy treated lately, so that the inhabitants who at first were all pleased would now be willing to poison them all. They take from them every thing they choose, and no one has any thing they can call their own.” But Mascoll’s assertion that the next attack would fall on New Jersey (at Berg
en Point, Elizabeth Town Point, and Perth Amboy) didn’t impress a skeptical Washington.29 He believed that an imminent strike on Long Island was being prepared, and in that he was right. A few hours after Washington told Congress of his suspicions on August 22, Admiral Howe fired his guns as a signal and his brother launched his invasion with some four hundred vessels.

  On September 1, Washington ordered Generals William Heath, a former Massachusetts farmer (he had urged Washington not to abandon New York), and George Clinton (then serving as a militia commander but soon to become governor of the state) to establish “a channel of information” on the Long Island side. “Perhaps some might be got who are really Tories for a reasonable reward to undertake it. Those who are friends would be preferable, if they could manage it as well.” Then, four days later, Washington wrote again, a little anxiously, to Heath: “As everything in a manner depends on intelligence of the enemy’s motions, I do most earnestly entreat you and General Clinton to exert yourselves to accomplish this most desirable end. Leave no stone unturned, nor do not stick at expense to bring this to pass, as I was never more uneasy than on account of my want of knowledge on this score.… Much will depend on early intelligence, and meeting the enemy before they can intrench. I should much approve of small harassing parties, stealing, as it were, over in the night, as they might keep the enemy alarmed, and more than probably bring off a prisoner, from whom some valuable intelligence may be obtained.”30 Following orders, Clinton managed to get over William Treadwell and Benjamin Ludlum, who had pledged “to run every risk to gain the necessary intelligence.” For good measure, he had conceived a plan to kidnap two Tory neighbors of his, whom he thought might prove reluctant to talk. But never mind, Clinton jauntily assured Washington, “If I can catch them I’ll make them willing.”31