Washington's Spies

by Alexander Rose

  Whereas Washington, equipped with a staff of private secretaries, and Tallmadge, nursed on Cicero’s cadences and blessed with a Yale education, composed splendidly styled, flowing sentences, Woodhull’s provincialism made his punctuation idiosyncratic and spelling atrocious. He used such words as “doth” and “hath”—antiquated even by the standards of the time—but as time progressed, so too did Woodhull’s abilities. Tallmadge, for instance, never complained about his correspondent’s letters.52

  Woodhull’s first espionage effort was not a masterpiece, but it did contain some useful tidbits, mostly concerning embarkations onto transports by British troops, which Woodhull speculated were on their way to the West Indies. (In this case, he was wrong: British commanders quite often liked to keep the rebels on their toes by marching on and off ships, and up and down hills, to pretend major movements were afoot or for training purposes.)53 Two days later, Woodhull—having overcome his initial reservations—wrote his second letter. The first third of it is meandering, but Woodhull belatedly gets down to the work at hand, even if, as was typical of these early Woodhull letters, he found it difficult to write concisely.

  Because Tallmadge lacked a permanent agent in the city, Woodhull performed double duty by acting as Brewster’s liaison in Setauket and then traveling to New York every few weeks to pick up news. Woodhull hated making that trip: It was by far the riskiest aspect of his job, for not only did villains, Tory plunderers, and British patrols infest the fifty-five-mile road to New York, but worse, he had to leave his aged parents for several days at a time, stay in expensive (for him) inns on the way, and travel by himself in the cold and through the muck. Most irritatingly, each person who wanted to travel from Brooklyn to Manhattan aboard a ferry was required to show a passport to the guards at the gate, and to leave most had to obtain a two-shilling permit from the authorities, who were apt to be suspicious of unfamiliar Long Island farmers who rarely brought any produce.

  On October 31, at one British checkpoint where he was routinely questioned, Woodhull “received their threats for coming there that make me almost tremble knowing … my business.” After that little scare, Woodhull’s innate caution prompted him to tell his chiefs to “destroy every letter instantly after reading for fear of some unforeseen accident that may befall you and the letter get into the enemies hands and probably find me out and take me before I have any warning.” (Woodhull would have suffered an apoplexy had he ever discovered that Washington’s staff, despite Tallmadge’s assurances that his agent’s wishes were being carried out, actually kept his letters for administrative reasons—so allowing us to read them today—though Woodhull’s real name was never used at headquarters.)54

  Woodhull followed up with an unhelpful observation that some regiments of Loyalist militia had refused to embark for a destination that was a “profound secret.” He was luckier on other matters: A fleet had recently arrived with stores and provisions, and there was “forage and wood sufficient for their needs this winter.” It was crucial to Washington to know the status of the British supply fleet, as well as the quantities of fuel and oats the army had available. An abundance of such things, or evidence of stockpiling, signaled a renewed campaign in the coming season.

  For their part, locked even as they were into their island fortress, the British authorities were alarmed at how vulnerable they were. The city they occupied absolutely depended on the outside world. Before the war, while New York (like the rest of the colonies) imported far more than it exported, after 1776, the city exported virtually nothing and became, instead, a vast urban parasite quarantined from the rest of the continent and its traditional inland trade routes. The army had to import even its footwear. General Howe announced on January 26, 1777, for instance, that the fleet had brought “16,000 pairs of soles, 250 sets of shoemaker’s tools, 14 dozen lbs. of shoemaker’s thread, 40 lbs. of shoemaker’s bristles, 200,000 shoemaker’s pegs, and 450 lasts.”55

  Any provisions that could not be supplied from Long Island had to be imported by sea, by what was known as the “Cork Fleet,” as it sailed from Ireland, the army’s westernmost port, several times a year.56 The overriding importance of this victualing fleet to the survival of the British empire in America was a constant source of worry for city and military officials. “What would become of us should a Cork fleet miscarrie—which sooner or later may be the case—the army wou’d eat up the market and the inhabitants wou’d starve,” wrote an alarmed David Sproat, Commissary of Naval Prisoners, to Joseph Galloway in London.57 William Eden, the undersecretary of state, solemnly warned Sir Henry Clinton that “if the Cork Fleet fails … there can be no doubt that our removal [from New York and America] must take place.”58

  The nightmare came close to realization in the summer of 1778, when food reserves had run so low there were just five weeks’ worth left and British commanders even debated abandoning the city. But thanks to Woodhull’s letter, Washington—much to his chagrin—learned that the fleet had arrived with enough supplies for six months. Only there wasn’t. Graft and thievery, the twin banes of the British army, would whittle six months’ supplies down to just three months’. Greed, as usual, played a role: An investigation found that barrels of what purported to be government-approved “fine flour” actually contained “sweepings of stores and bake houses, rags, papers, and old hats,” while some military contractors mixed sand with flour or sent shortweighted barrels of beef, disguising their fraud by placing stones at the bottom.59

  Despite the bad tidings he brought, Woodhull was hoping this would be his last trip. “Blessed be God,” cheered Woodhull on his return, I’ve been “particularly successful in engaging a faithful friend and one of the first characters in the City to make it his business and keep his eyes upon every movement and assist me in all aspects and meet and consult weekly in or near the City. I have the most sanguine hopes of great advantages will accrue by his assistance.”60

  Woodhull’s mysterious “faithful friend” was Amos Underhill (1740–1803), a former mill owner in Glen Cove whose property had been razed by the British during the Battle of New York.61 Soon afterwards, he moved into the city, became a merchant of sorts, and bought a house. By 1778, with a baby on the way, he and his wife, Mary, were forced to take in occasional boarders. They, like so many others, had been hit hard by the steep increases in the cost of living caused by the war. So tight was the financial situation that even Woodhull—who was Underhill’s brother-in-law through Mary (1745–1815), Abraham’s older sister—had to be charged £3 per week to stay with them.62

  In September 1775, the normal peacetime price for a family-size portion of flour was 20 shillings; by 1781, it would be more than 70 shillings. Over the same period, beef rocketed from 65 shillings a pound to £8, while the price of fresh vegetables soared 800 percent. And this was before factoring in rent increases of 400 percent, caused by a combination of a housing shortage after the Great Fire and New York’s burgeoning wartime population.63

  New York’s inhabitants were compressed into a tiny area, an inverted triangle measuring half a square mile.64 There were about 25,000 residents in 1776—including 3,137 free, freed, and enslaved blacks, as well as Scots, Irish, Germans, Jews (some 300), Spaniards, and Portuguese—but this figure did not account for soldiers. In May 1776, 8,767 American troops were deployed in and around the city; by August, there were no fewer than 20,375 American and 34,614 British servicemen in the area, all demanding food, fuel, and shelter.65 Within the month, the vast majority of civilians had fled the fighting, leaving just 5,000 living in the spookily deserted city. (Among those who remained, whoever’s soldiery was in town, were the 500 hopeful prostitutes plying their trade in what was known as “Holy Ground”—it was land owned by the Church of England—that occupied the area later occupied by the World Trade Center.)66

  Over the coming years, tens of thousands of civilians dribbled back. Whenever the British retreated to New York, a ragged, hopeful procession of Loyalists accompanied them. Those from Con
necticut and New Jersey arrived first—by early 1777, the city’s population had swollen to 11,000—and another 3,000 streamed in after the British evacuated Philadelphia in 1778. In 1783, on the eve of the British evacuation, there were 33,000 inhabitants.67

  There were also, of course, the king’s troops, who were rotated in and out of action as the fortunes of war required. In January 1777, immediately prior to Washington’s victory at Princeton, there were 3,300 soldiers in New York, rising to 5,000 in November after General Burgoyne’s surrender at Saratoga, and rising again to 9,000 in July 1778 following Clinton’s withdrawal from Philadelphia. Eighteen months later, owing to British success in the South, the number of redcoats had fallen to 4,000, but in August 1781, on the eve of Yorktown, it had more than doubled, to 9,700, before reaching 17,200 in December 1782, that imposing figure ironically heralding the collapse of Britain’s American empire.68 Even then, these numbers were underestimates. For example, if one includes in the July 1778 figures (i.e., 9,000) the cohorts of new recruits, deserters, Royal Navy sailors, Marines, privateers, soldiers on sick leave, Loyalist militiamen, and freebooters working off the books, the number was actually about 20,000.69

  Though these numbers made life most unpleasant, Woodhull could also take solace in the realization that, owing to the flood of strangers and outsiders, he might easily blend into the background and evade recognition by alert British sentries. Though that fact greatly reassured him, Woodhull was not yet comfortable sneaking around as a spy, and tended to exaggerate to buttress his confidence. Thus, Woodhull boosted Underhill’s importance in order to impress Washington and Tallmadge. By no means could his kinsman, upstanding and respectable as he was, be described as “one of the first characters in the City.”

  Even so, his chiefs were pleased at Woodhull’s acquisition of an asset in New York, but not so much about the vagueness of their man’s intelligence: the destination of the army being a “profound secret,” for instance. On November 18, Washington instructed Tallmadge to tell Woodhull to “ascertain the following facts with as much precision, and expedition, as possible.” These included which corps were in Manhattan and which on Long Island, whether any forts and strongpoints were being built in Brooklyn opposite Manhattan, the names of the commanders on Long Island, where they were based, whether the troops were ready to move, and other humdrum basics. He didn’t care, having been burnt before by spies plucking numbers from the sky, about Culper’s estimates of troop strength, since “I can form a pretty accurate opinion of the numbers from” knowing simply which corps were present. If his spy complained about the workload, Washington airily opined that discovering the location of sundry units was “a piece of knowledge that a man of common abilities may come at with precision by taking a little pains.”70

  It was a moot point, replied Tallmadge, because “I have been hourly waiting for two days” for the latest Culper letter. Getting information was one thing, receiving it quite another. “I am confident the failure must be attributed to those employed in crossing the Sound for such dispatches, as [Woodhull’s] punctuality heretofore in fulfilling all appointments … leaves no room to doubt.” The problem lay not with Brewster, but with his crew—most of whom could only be used if their commanding officers allowed them time off from their military duties to work “freelance” under Brewster, who had been released from the artillery for secret service. Unfortunately, the rub was that if sailors were detailed to work on the Culper missions exclusively, someone would eventually shoot his mouth off in a tavern that something secret was afoot. Tallmadge said he was about to ride to Fairfield, where Brewster was based, to try to work something out.

  In the meantime, it was crucial to keep Brewster as the sole liaison between Tallmadge and Woodhull, for the latter’s “extreme cautiousness, and even timidity, in his present undertaking would not admit of having his business made known to any persons who are not at present his confidantes.” So jumpy was Woodhull that if his role were “communicated to any other persons he would most probably leave his present employment immediately.” The same principle applied to Woodhull’s letters. Though Tallmadge didn’t fear that Culper’s spying will be “made public at camp,” if people at headquarters were “made acquainted with his present situation [it] would make him extremely unhappy, and as he [said] when he embarked in the business, he should leave the Island immediately” and flee to American-held Connecticut.71 To which Washington immediately confirmed: “You will be pleased to observe the strictest silence with respect to C——, as you are to be the only person intrusted with the knowledge or conveyance of his letters.”72

  Whereupon Woodhull filed a report on November 23 that exceeded Washington’s expectations. Not only did he provide names, corps, and movements (“the second division under Brig. Genl. Cambell that have laid some time at Sandy Hook … are to sail this day” and “the cannon and field pieces are removed from the common [in New York] to Fort George”) but, disobeying the general’s instructions, Woodhull added precise numbers: “the whole of the Kings troops on York Island including outposts, doth not exceed three thousand five hundred men” but the “best of their troops are on Long Island.” Thus, “there is about 300, most of them Hessians, at Brooklyn Ferry. 350 New Town, British; 1500 British, Jamaica; 800 Yeagers [Hessian Jägers], Flushing; 200 Jerico, most of them Dragoons; 400 foot, 70 Dragoons Oyster Bay; 150 Lloyd’s Neck, [new] Leveys; 400 Hempstead, Dragoons.” Unlike the inflated figures habitually produced by other spies, Woodhull’s estimates rang so true, a skeptical Washington could not help but be impressed.73 “His account has the appearance of a very distinct and good one and makes me desirous of a continuance of his correspondence,” declared the general. But then he, as had Tallmadge, fingered the issue that would vex the Ring throughout the war: How to get the intelligence through, on time and securely. “At the same time, I am at a loss how it can be conveniently carried on as he is so scrupulous respecting the channel of conveyance.” He left it up to Tallmadge to come up with a scheme “in which the purpose of procuring his intelligence with expedition can be answered.”74

  Tallmadge never quite succeeded in reconciling Washington to Woodhull’s (understandable) obsession with anonymity and safety. Security and timeliness were incompatible virtues—there would always be a trade-off between them. Whereas Woodhull’s primary concern lay in keeping his neck out of a tightening noose, the general, preoccupied with winning battles, was rather more concerned with receiving timely intelligence about the enemy than about the personal comfort level of his agents, especially one as pernickety as Woodhull was turning out to be. Washington, even so, was willing to go halfway: “If you think you can really depend on C——s fidelity, I should be glad to have an interview with him myself; in which I could put the mode of corresponding upon such a footing that even if his letters were to fall into the enemy’s hands, he would have nothing to fear, on that account.”75 (The meeting did not happen, Woodhull being reluctant to raise suspicions by being away from Long Island for so long.)76

  Aside from the tardiness of his correspondence, two tics, both of them irritating to Washington, characterized Woodhull’s letters. First, he liked to add his personal views. So, for instance, in November he attends a meeting of Loyalists, and noting that “with much satisfaction [I] beheld their dejected countenances,” he pompously declares that “I am firmly of opinion that a sudden attack of ten thousand men would take the City and put an end to the War.” There was “not much to be feared from the inhabitants” of Manhattan, he casually appends, as “the whole City [is] seized with a panic and a general dissatisfaction.”77 By December, Woodhull had convinced himself that if Washington waited but four months, “I am confident they will go themselves, Yes I am firmly of opinion and it is become general belief that in half the time we shall have the news of Great Britain acknowledging American independence.”78 Washington soon learned to filter out Woodhull’s grand strategic visions.

  Still, Woodhull’s ruminations, especially his more mordan
t ones, provide an insight into what normal Americans thought of the British and their own political leaders at the time. “I cannot bear the thoughts of the war continuing another year,” wrote Woodhull, “as could wish to see an end of this great distress. Were I to undertake to give an account of the sad destruction that the enemy makes within these lines I should fail. They have no regard to age, sex, Whig or Tory. I lament to hear [of the] civil dissensions among you [the Congress] at Philadelphia. I think them very alarming. It sinks the spirits of our suffering friends here and pleases the enemy. Cannot the disturbers see that they are working their own ruin. Is there no remedy to apply. Better had they be cut off from the land of the living than to be suffered to go on.”79

  The second annoying thing was more serious. Money. Woodhull was fanatical about getting his expenses reimbursed. Amazingly, for someone so strident about every other aspect of his security, Woodhull kept a cash book notated with the costs incurred by his espionage: travel, lodging, and food, mostly.80 Though no doubt he kept it safely hidden, maintaining an itemized ledger was, of course, a major breach of the regulations. In one respect, however, it was a necessity: Woodhull, as he often pointed out, was not wealthy, his expenses were considerable, and hard cash was difficult to come by.

  But Woodhull (and his colleagues) were adamant about one thing: They did not serve for pay, and would not accept any reimbursement apart from money rightfully owed to them for expenses. Had they been offered cash, they would have haughtily rejected it. Indeed, they—Woodhull, in particular—were ashamed of being spies, and never termed themselves as such, instead referring to spying as “this business” and other euphemisms.