Washington's Spies
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The Tories escaped falling into Clinton’s clutches, but Treadwell and Ludlum managed to return from Long Island two days later. Clinton “examined them” and dispatched their intelligence to Washington. Despite Treadwell and Ludlum’s bravery, their intel was of little use and of low quality: Troop figures were exaggerated and their revelations were either vague or pointless, or both (i.e., “a party of the Light Horse … seized upon some bread flour and salt which was in a store, but can’t tell the exact place”).32 It was not a successful mission.
During these early days of the intelligence war, Washington focused nearly exclusively on obtaining military intelligence—that is, tactical information on the enemy’s positions and movements—an activity he had himself performed as a young officer during the French and Indian War, and which was regarded in Europe as a respectable pursuit for a gentleman.33 He made no attempt to infiltrate and implant an agent permanently behind enemy lines to report back periodically. Consequently, Washington’s agents were required to operate at night and return before dawn, or at most, spend just a few days out in the cold. The Americans also commonly failed to provide any training or backup for their agents, which is partly why the success in getting Treadwell and Ludlum over was marred by their lack of expertise in knowing what to look for.
Even so, at least Treadwell and Ludlum were in the thick of things, unlike Hale. Soon after the defeat at Brooklyn, Hale—frustrated at having been present at a battle and at a siege and yet never firing his musket at a redcoat, let alone bayoneting one—transferred to another regiment, one guaranteed some action: Knowlton’s Rangers, a new outfit trained for special scouting service. It was commanded by thirty-seven-year-old Lieutenant Colonel Thomas Knowlton, a former farmer who had been a ranger in the French and Indian War and who had fought at Bunker Hill. Courageous to a fault, remembered one of his men, he never cried, “Go on, boys!” but always, “Come on, boys!”34
As early as September 1, Captain Hale was leading a company of Knowlton’s men reconnoitering potential American positions in the north, at Harlem and Hell Gate, though in the absence of the enemy he saw no fighting. It was clear, however, that Howe was planning to attack Manhattan in the very near future, thereby making imperative an accurate appraisal of his preparations on Long Island. To this end, a few days before September 15—when Howe launched an amphibious landing at Kip’s Bay—Washington asked Knowlton to recruit a few spies from amongst his men. This was not Knowlton’s first brush with intelligence: In July he had helped General Mercer dispatch an agent, Captain John Mersereau (“who undertook the service very cheerfully”), to Staten Island.35
Hale, hearing of Knowlton’s inquiries, sought his friend William Hull to discuss whether he should volunteer. When they met, Hale “remarked that he thought he owed to his country the accomplishment of an object so important and so much desired by the commander of her armies,” and asked Hull’s candid opinion. Hull replied that he thought the business of spying a murky and unwholesome one, adding that he thought Hale too open and frank to carry it off in any case. He warned that he would die an ignominious death. “I am fully sensible of the consequences of discovery and capture in such a situation,” mused Hale. “But for a year I have been attached to the army, and have not rendered any material service.” Spying, he agreed, was not an honorable undertaking, but “if the exigencies of my country demand a peculiar service its claims to perform that service are imperious.”36
Washington had his man. And now that man, according to the recollections of Hale’s sergeant, twice visited Washington to discuss his route, precautions, and cover story.37 (Washington vaguely knew Hale, having distributed General Orders on June 16 noting the court-martial of Hale’s second-in-command, a Lieutenant Chapman, for “Disobedience of orders, and refusing to do his duty.”)38 Washington’s previous attempts to gather intelligence by sending men through the “front door”—landing them directly in heavily fortified Brooklyn or on Staten Island—had all proved fruitless; Hale, this time, would sneak in through the back by making his way to Connecticut, crossing the Sound, and landing on Long Island behind (or to the east of) the British encampments in Brooklyn. From his intended destination of Huntington, Long Island, it was about two days’ unrushed travel to Brooklyn, plenty of time for Hale to observe the massive baggage trains trundling west, count the regiments mustering for a final attack, and see when they embarked on the fleet of transports, tenders, and men-of-war congregating at Hell Gate. Importantly, Hale’s orders never stipulated that he was to travel to Manhattan, since at the time Howe had not yet attacked the island. He was only to spy out Long Island and come home.39
Hale’s brother Enoch later heard that Nathan left between the tenth and fourteenth of September. Accompanied by Sergeant Stephen Hempstead, Hale left the American camp and traveled first to Westchester and then, early on September 15, arrived in Norwalk, Connecticut—home ground for Hale and also a place where it was easy to pick up a ride across the Sound to Long Island. In his pocket Hale kept a letter from Washington directing captains of armed craft to take him anywhere he designated. Hale already knew whom he wanted for the task: Captain Charles Pond of Milford, Connecticut, a friend of his from their days in the Nineteenth Regiment.
Hempstead observed, several decades later, that at Norwalk, “Captain Hale had changed his uniform for a plain suit of citizen’s brown clothes, with a round, broad brimmed hat; assuming the character of a Dutch [i.e., New York] schoolmaster, leaving all his other clothes, commission, public and private papers with me, and also his silver shoe buckles, saying they would not comport with his character of schoolmaster, and retaining nothing but his college diploma, as an introduction to his assumed calling.”40
Traversing the Sound had turned dangerous. Ruthless smugglers and gunrunners, for both sides or just for themselves, now abounded, and British patrols scouted for rebel privateers. Pond, however, was an old hand at evading (and avoiding) trouble, having been given command of the fast four-gun sloop Schuyler in May, while he was temporarily seconded from the army. Its big sister was the fourteen-gun Montgomery, under Captain William Rogers, and together, throughout the summer of 1776, they had patrolled the coast between Sandy Hook and Montauk. Pond plundered a valuable English merchantman off Fire Island on June 19, but once the British controlled Long Island, the Merlin, Cerberus, and Syren began stalking these Congress-approved privateers in earnest.41
Particularly feared among these British commanders was Captain William Quarme, an adept hunter-killer commanding the sixteen-gun brig Halifax, which often carried a complement of Rangers for the dirty work.42 Cruising off Huntington, on Long Island’s north shore, at 4 a.m. on September 17, Quarme heard word that two Continental vessels—Schuyler and its escort, Montgomery—had been spotted the day before, lurking suspiciously. According to the ship’s log, Quarme “sent the tenders and boats armd to serch the [Huntington] Bay for two rebel privateers haveing interlagence of them.” Quarme tarried at Huntington until the next day, when, at 6 p.m., “the tenders and boats returnd not being able to find any rebel privateers.”43
By dropping anchor at 4 a.m., Quarme had missed Schuyler and Montgomery by mere hours. Having left Norwalk on the sixteenth, the two privateers waited off Huntington until inky blackness fell, then Hale was rowed ashore, and they raced home before the dawn of the seventeenth revealed their presence. The vessels had only a few miles’ head start over the Halifax, but that was more than enough to discourage any pursuit.
As the Halifax weighed anchor, one man aboard—his senses sharpened by decades as a frontiersman, warrior, and ranger—suspected something murky afoot. Why had two Continental vessels appeared so close to an enemy-held shoreline and vanished before sunup? Could they have dropped off something—or someone? He resolved to keep a beady eye peeled for anything untoward. The man’s name was Robert Rogers, and he was a killing gentleman.
Rogers had once been described by a subordinate “as subtil & deep as Hell itself … a low cunning cheat
ing back biting villain,” and by a superior (General Thomas Gage) as a man who would “stick at nothing.” He had been born of yeoman farmer stock on the New Hampshire frontier forty-five years before, and at the age of fourteen, saw his first action in 1744–45 after French-backed Indians raided settlements, stripping corpses, scalping them, and then jerking out the entrails before quartering the limbs and severing the genitals. Having imbibed some knowledge of the techniques of the local Pennacook Indians, Rogers volunteered to help track the killers. Over the next decade, Rogers associated with Indians, Indian fighters, and hunters, and learned to make his way through the immense, mostly unexplored wilderness of valleys and hills, gorges and forests, lakes and rivers.44
By the beginning of the French and Indian War, Rogers was a captain in a New Hampshire regiment, and honed his skills at reconnaissance by probing the French positions a hundred miles distant from his own lines. Already, Rogers was not averse to rough soldiering, recalling that during one of these missions he and a companion tried to capture a Frenchman for interrogation, “but he refused to take quarter so we kill’d him and took of his scalp in plain sight of the fort.” He scouted and raided in all weather, from the mosquito-tortured summer to the freezing winters—when even the hardiest of eighteenth-century armies put aside their muskets. He was notorious for aggressively pursuing his enemies, as well as for his equal-opportunities policy of recruiting Indians into his unit, to serve alongside the ruffians, Irish, and Spaniards he also thought fit to employ.
In 1756, William Shirley, commander-in-chief of the British army in North America, commissioned Rogers to command the “Independent Company of Rangers,” a newly formed unit whose mission was “to make discoveries of the proper routes for our own troops, procure intelligence of the enemy’s strength and motions, destroy their … magazines and settlements, pick up small parties … upon the lakes, and keep them under continual alarm.” There’s little doubt that “Rogers’s Rangers” were a tough bunch. Kitted in coarse, woolen green jackets and canvas trousers, they wore brown leggings up their thighs, buttoned, like spatterdashes, from the calf downwards, and were shod in moccasins (an idea borrowed from the Indians). Betokening the Scottish origins of many of the Rangers, they adopted the flat bonnets of their homeland, with caplike hats for the officers. Along with the usual musket, powder horns, bayonet, and canteen distributed to regulars, they wielded tomahawks and knives.
A day in the life of a Ranger could be a terrifying one. During one winter mission deep in the woods, Rogers and seventy-four of his men were ambushed by the French and their Indian allies. As they ran low on ammunition, the heavily outnumbered Rangers heard the French (in Rogers’s words) “calling to us, and desiring us to accept of quarters, promising that we should be … used kindly.” If they didn’t surrender soon, however, “they would cut us to pieces.” Rogers defiantly shouted back that he and his Rangers would be the ones doing the cutting, only to be shot “thro my wrist which disabled me from loading my gun.”
After a firefight lasting five and a half hours, it now being nighttime, Rogers and his officers decided to carry off their wounded and vanish into the hinterland. Unfortunately, they had overlooked some of the wounded, including Private Thomas Brown, who found two other casualties, Captain Speakman and a soldier, Baker, also left behind. Brown crawled into the underbrush to hide, whence he saw an Indian first scalp Speakman alive, and then kidnap Baker, who tried to commit suicide but was prevented.
Speakman, lying there with the back of his head peeled off, his brain exposed, and his blood soaking into the snow, saw Brown and “beg’d me for God’s sake! to give him a tomahawk, that he might put an end to his Life! I refus’d him, and exhorted him as well as I could to pray for mercy, as he could not live many minutes in that deplorable condition, being on the frozen ground, cover’d with snow. He desir’d me to let his wife know if I lived to get home the dreadful death he died.” Brown was soon captured anyway and later saw Speakman’s head stuck on a pole, staring glassily out at the wilderness. Baker was never heard from again. Brown, however, did witness another Ranger stripped and tied to a stake by the Indians, who thrust pine skewers into his flesh and set them alight. As for Rogers, he got the rest of his broken men back to the fort—with heavy losses, but that was not unusual in the Rangers. His friend, Captain Abercrombie, was sportingly sanguine about the affair, telling Rogers that “I am heartily sorry for Spikeman [sic] … as likewise for the men you have lost, but it is impossible to play at bowls without meeting with rubs.”45
After the French and Indian War, Rogers married Elizabeth Browne, a minister’s daughter, and began an unillustrious career of being dunned constantly by creditors as a result of business ventures gone sour. No matter what Rogers did—land speculation, fur trading, trying to discover the Northwest Passage, or organizing a lottery to build a road in New Hampshire—it never quite panned out. In the mid-1760s, he moved to London, where his military exploits and rough frontiersman demeanor still made him a minor celebrity. By all accounts, he enjoyed the metropolitan lifestyle, perhaps a little too much, for he was committed in 1771 to the “Prince of Prisons,” the Fleet—a debtors’ jail—where he began drinking heavily.
He spent three miserable years there, and was released in August 1774. The next spring, he was given a belated break and allotted the retirement pay of a full major. Suddenly liquid again, Rogers sailed to America, not only to see his wife for the first time in half a decade, but also because he suspected that his very special talents, degraded through indolence and age though they were, might prove useful sooner than many thought.
When he arrived in September 1775, no one quite knew what to do with him, or what his intentions were. General Gage, the British commander, had loathed him—it was a personal thing—ever since the French and Indian War, so Rogers’s pickings looked a little slim in Boston. The Americans weren’t too hospitable, either. On September 22, the Philadelphia Committee of Safety, suspecting Rogers as a retired British army major (which indeed he was), locked him up for a day.46 He was released only after he promised not to take up arms against Americans.47
Still, Rogers remained deeply in debt, so his strategy was to play both sides to see who would bid highest for his services. Fortunately for him, Gage resigned in October, and was replaced by General Howe, who was far more solicitous of Rogers’s talents. In November 1775, Rogers offered him his services (and heightened his attractiveness by fibbing that the Americans had already “made considerable overtures to him”). Howe was enthusiastic, telling the prime minister that he had asked Rogers to name his terms.48
Rogers, having hooked Howe, went to the Americans in December and sought out Washington, a fellow French and Indian War veteran well acquainted with Rogers’s fearsome reputation. Washington was surprised by Rogers’s approach, for all he wanted, apparently, was to pass through the American lines so he could “go unmolested where my private business may call me.” And then, a casual aside revealed the deeper harmony playing beneath the charming melody: “I have leave to retire on my half-pay, & never expect to be call’d into the [British] service again. I love North-America, it is my native country and that of my family’s, and I intend to spend the evening of my days in it.”49
Washington did not long mull Rogers’s proposal. He was already suspicious. Two weeks before, the Reverend Eleazar Wheelock, the Congregational minister who founded Dartmouth College in 1769, had written him a lengthy note relating the details of a visit from Rogers, who “was in but ordinary habit for one of his character” and “treated me with great respect.” Two of Wheelock’s recollections drew Washington’s attention. Rogers claimed he “had been offered and urged to take a commission in favor of the Colonies but as he was [still] in half pay from the Crown he thought proper not to accept it,” a statement that proved him a liar. If anyone knew whether Rogers had been offered a position in his army, it was Washington. While Rogers’s untruth could possibly be dismissed as bluster or a misunderstanding, the seco
nd nugget was more alarming. Wheelock said two soldiers, recently arrived from Montreal, had remarked that Rogers “had lately been seen in Indian habit” in Canada, which could imply that Rogers was planning to stir up the Indians and cause trouble for the Americans in the north.50
It was all very fishy. After checking out the Canadian rumor, Washington told General Philip Schuyler (head of the Northern Department and charged with the invasion of Quebec) that while he suspected Wheelock’s information about the Indians to be inaccurate, Rogers was anyway “much suspected of unfriendly views to this country, [so] his conduct should be attended to with some degree of vigilance and circumspection.”51 He directed Generals Sullivan and Schuyler to surveil and to “strictly examine” Rogers.52 Unfortunately, like a good Ranger chieftain, the latter had disappeared since his visit to Wheelock.
Rogers reappeared in early February, in New York of all places, then under American control. His intent was blazingly obvious: General Henry Clinton was due to arrive any day to discuss “matters” with the royal governor, William Tryon, who had been obliged to rule New York (what parts weren’t already in rebel hands, that is) from aboard the Dutchess of Gordon, anchored in the harbor. Clinton, born in 1738 and the aristocratic son of a former New York governor, had just recently emerged from a long depression caused by the death of his wife. Ever since his recovery, Clinton—in his youth something of a charmer—had turned into a cantankerous and egotistical, yet paradoxically shy and self-doubting, character who brooked no dissent from his subordinates and had nothing but criticism for superiors. For his part, Howe intensely disliked working with his second-in-command, foisted on him by London. Taken together, the two supreme commanders of the British forces in America—both adequate individually—were the worst possible combination with which to combat as audacious a general as Washington or to fight a new kind of people’s war in a vast military theater far removed from the familiarities of Europe.53