Washington's Spies

by Alexander Rose

  Woodhull was terribly shocked by his idol’s coldness. He “intimates [that we] hath been of little service,” Woodhull complained. “Sorry we have been at so much cost and trouble for little or no purpose. He also mentions of my backwardness to serve. He certainly hath been misinformed. You are sensible I have been indefatigable, and have done it from a principle of duty rather than from any mercenary end.” Woodhull, now out quite a lot of money, had to add that he “perceive[d] there’s no mention made of any money to discharge the remaining debts, which hath increased since I saw you.”79

  As quickly as Washington’s anger had erupted, it passed. A little less than two months after he had shut down the Ring, he reactivated it upon hearing that a naval squadron under General Jean Baptiste Donatien de Vigneur, Comte de Rochambeau, was nearing Rhode Island. “As we may every moment expect the arrival of the French fleet a revival of the correspondence with the Culpers will be of very great importance,” and he asked Tallmadge to see if he could engage “the younger” and “prevail upon the elder to give you information of the movements and position of the enemy upon Long Island.”80 Rochambeau, Washington hoped, would be less feckless than d’Estaing, and he might be willing to participate in a New York venture.

  Tallmadge arrived in Fairfield on the morning of July 15—after gently reminding Washington that they were “something in arrears to [Woodhull], and in order to enable him to prosecute the business, it may be necessary to afford him a small supply of money.”81 Brewster, luckily, was hanging around the harbor, and agreed to sail to Setauket that night, but when he landed, Woodhull was too sick to leave his bed. Austin Roe, however, was available, and the next day he rode for New York to ask Townsend, first, whether he was interested in employment, and second, if he knew whether the British were aware of the French fleet’s imminent arrival.82

  What Roe brought back was explosive. So imperative was the intelligence that Townsend deigned to break his own rule and compiled a letter written in stain, hidden between the lines of an order for merchandise purportedly sent by the long-suffering Colonel Floyd—who unwittingly proved his usefulness once again. Cleverly, so as to provide Roe with a legitimate alibi in case he ran into a patrol, Townsend included a letter to Floyd saying, “Sir, I recd, your favor by Mr. Roe [which is crossed out but can be read] and note the contents. The articles you want cannot be procured, as soon as they can will send them. I am, Your humble Servant, SAMUEL CULPER.”83

  Unfortunately, the stain letter has been lost, but Woodhull, still ailing, paraphrased its contents in the package he gave to Brewster—along with the most urgent note he ever penned: “The enclosed [from Townsend] requires your immediate departure this day by all means let not an hour pass for this day must not be lost you have news of the greatest consequence perhaps that ever happened to your country.”84 Townsend, apparently, had warned that the British were aware that the French, carrying vital arms and troops, were close and were intending to ambush them. “Admiral Graves with six ships of the line,” had just arrived, and had been “joined by three more out of New York [and] has sailed for Rhode Island,” where the French had landed. “Also 8,000 troops are this day embarking at Whitestone for the before mentioned port.”85

  In fact, unsuspected by anyone, Clinton had known that Rochambeau’s “six French ships of the line, several frigates, and a number of transports with six thousand troops are expected at Rhode Island in two or three weeks to act under General Washington” since June 12, which had given him plenty of time to plan a welcome party. His spy was General Benedict Arnold, who had been told all the details by Washington a few days before he betrayed them to his new British masters.86 (Clinton also had an agent in Rhode Island who would send a map detailing the exact location and names of the French ships in the bay, as well as an estimate of their troop strength.)87 As it usually took weeks to muster a force together, collect provisions, and gather the necessary transports—so making it obvious that some movement was afoot—Clinton’s foreknowledge had allowed him this time to make his preparations on the quiet. If all went well, Rochambeau’s soldiers—tired after their long voyage, unfamiliar with the terrain, and camped out in the open—would be surprised by Clinton’s redcoated veterans and put to flight while the Royal Navy pounded the French squadron. Such a bloody blow after d’Estaing’s embarrassing performances would surely cool Paris’s ardor for her American allies. Washington would again be left to face the lion alone—and it was doubtful this time whether he would be able to pull off another Trenton or Princeton.

  Woodhull’s package, courtesy of Brewster, arrived in Connecticut on the morning of July 21, a Friday, but Tallmadge could not be found. Brewster roused a dragoon and ordered him to rush the letters to Washington’s headquarters. Washington, too, was away, and the dragoon left the package with Alexander Hamilton, who deciphered the dispatches and grew alarmed at their contents. At 4 p.m., with Washington still touring the lines, he made the decision to pen a letter for Rochambeau, the French commander, stating that he had “just received advice … that the enemy are making an embarkation with which they menace the French fleet and army. Fifty transports are said to have gone up the Sound to take in troops and proceed directly to Rhode Island.” He sent express riders to catch up with the Marquis de Lafayette, who, unsuspecting that the British had caught wind of the landing, had left headquarters on the seventeenth and was leisurely wending his way to Newport to rendezvous with Rochambeau to help coordinate Franco-American operations.88

  When Washington returned to camp that evening, Hamilton filled him in. The next evening at 9 p.m., Tallmadge, now having returned, was told by Brewster of what had happened; after forwarding the intelligence to Washington (who already had it, of course), Tallmadge urgently requested Generals Robert Howe and William Heath to steel themselves for a possible British attack.89

  Washington, however, had shrewdly seen an opportunity to launch an attack of his own on the British. Knowing that Clinton would have to denude New York of troops for his expeditionary force, so leaving it vulnerable, Washington commissioned several senior officers to appraise the possibility of taking the city. Opinions were mixed, but tended to be negative; even emptied of troops, New York remained a formidable stronghold. Colonel Jean Gouvion of the Engineers thought that a siege could work but that it would take “forty or fifty days” to break through the fortifications, even if they were, as he judged, weak and poorly constructed. Washington would need, he continued, at least forty cannons, large amounts of ammunition for troops, a thousand shells for the artillery, plus another hundred for the mortars. It couldn’t be done, in other words, before Clinton had returned from his hunting trip to Rhode Island.90 Generals Greene and Knox were similarly pessimistic about the logistics of the operations, with Greene saying that the only way success could be achieved would be if Washington forcibly requisitioned supplies from the public—a politically difficult decision. In sum, “the time is by far too short to make the necessary preparations for such an important expedition.”91

  It was a moot point, in any case. “Though I seriously intended to attack New York if Clinton had gone to Rhode Island,” Washington later told Lafayette, ultimately Clinton did not vacate New York.92 “In the hope that I might yet be in time to undertake something offensive against the enemy,” the British general explained to London in August, “I determined as speedily as possible to put a body of troops afloat in the Sound, ready for operation to the eastward, if further information should warrant it, and not too distant to return rapidly, and act against the rebel army, should they, in my absence, form an enterprise against these posts.” Adverse headwinds at Hell Gate, it seems, “conspired to retard the arrival of transports at Frog’s-neck,” and he was only able to embark most of his troops on the twenty-seventh, during which time “all hope of success from a coup de main were of course wafted away.” Like Washington with his New York plan, Clinton lacked the artillery and ammunition needed for a protracted siege of Rhode Island, and he chose to stay a
t home. Like Washington, too, Clinton enjoyed a secret service, and knew that his foe, “by a rapid movement, had, with an army increased to 12,000 men, passed the North-river, and was moving towards King’s-bridge, when he must have learned that my armament had not proceeded to Rhode-Island. He (I apprehend in consequence of this) re-crossed the river, and is now near Orange Town.”93

  Robert Townsend, despite his critical assistance during the Rochambeau affair, was still proving reluctant “to continue the correspondence,” though Washington belatedly authorized Tallmadge to give Woodhull whatever was owed to him as a reward for his good work.94 On August 1, however, Tallmadge brought encouraging news. He had conceived a way of shortening the line by transporting the Culper letters “over at Cow Neck, to the westward of Oyster Bay. If this can be effected, dispatches may be brought from N.Y. to the White Plains [headquarters] in twelve hours [in] emergencies, as the whole land course on [Long Island] would not exceed 22 miles, and the Sound not more than ten miles over.” Townsend had been impressed by, if somewhat guarded about, the idea as he had “near relations living [near] Cow Neck whom if I can also engage, I am sure of Cr. Junr.’s services.” A bonus for Townsend would be that “a change of men through whom letters may pass” in the future might be arranged: Austin Roe, it seems, had been tardy for several meetings with Townsend in the past and the courier’s carelessness had contributed to Townsend’s reluctance to pen letters. In short, Townsend “has consented to give intelligence but does not say how long.”95

  Woodhull by this time was also having trouble with Roe, whom he had begun mentioning in a slightly disparaging tone: “Being still in a feeble state (but mending) was obliged again to have recourse to Austin Roe,” is one example.96 It was also clear that keeping Roe on was proving expensive, according to an invoice sent by Woodhull. He had reimbursed Roe £34, more than double the £15 or so given to Townsend and thrice Woodhull’s own expenditure of £11-odd. (Of the total of £60.18.8, Woodhull had received only £18.18.8, leaving him down £42—a great deal of money.)97 Tallmadge, however, was reluctant to dispense with Roe just yet and reminded Washington, before he made a cost-cutting decision that might prove rash, that the messenger was “obliged always to ride to New York from the place where the boat lands and wait Culper’s answer; his expenses on the road and in the city for himself and horse must be very considerable.”98 Washington agreed to wait.

  Still, the Culper Ring was almost always most effective when Woodhull and Townsend communicated face-to-face rather than using an intermediary. Woodhull received a conciliatory note from his old comrade. Using his clever stratagem of writing to poor Colonel Floyd in the guise of a merchant, Townsend confided that the “articles you wanted” had not been sent because “the office was shut” before “Mr. Roe” finally showed up—a catty little comment—but signaled that he was again open for business, so to speak, by saying “they shall be sent by next conveyance.”99 Woodhull, greatly heartened by Townsend’s thawing, immediately prepared to depart for New York “for the benefit of our 115 [correspondence].”100 Ten days later, Woodhull returned from the city, and was exceedingly “happy to inform you that Culper Junior hath engaged to serve as heretofore.”101

  Washington was “very much pleased that the correspondence with C—— is again opened. I have the greatest dependence in his good intentions and I am persuaded when he pleases to exert himself he can give the most useful intelligence.”102 Tallmadge assured his chief that “respecting the man, he is a gentleman of business, of education and honor,” and was willing to “shorten the route on certain conditions.”103 A commercial animal, Townsend simply wanted to reconfirm that his postwar needs would be taken care of before signing on. “Should [Townsend] continue serviceable and faithful,” replied Washington, “and should the issue of our affairs prove as favorable as we hope, I shall be ready to recommend him to the public, if public employ shall be his aim, and if not that I shall think myself bound to represent his conduct in the light it deserves and procure him a compensation of another kind.”104 The Culper Ring was back, but for how long?

  At the same time as the Culper Ring was resurrecting itself in the late summer of 1780, Sir Henry Clinton was poised to spring a trap. Clinton’s goal in this round against Washington was the capture of West Point, a key American stronghold on the Hudson River that allowed Washington to move men, supplies, and arms between Massachusetts and Connecticut to New Jersey, Pennsylvania, Delaware, and Maryland.1 His agent was General Benedict Arnold, who had persuaded Washington to appoint him West Point’s commander.

  Arnold’s military laurels were undoubted by all. He had fought valiantly at Ticonderoga and had played a decisive role in the Saratoga campaign, at one point daringly, and almost single-handedly, preventing Burgoyne from escaping at the Battle of Bemis Heights. But he was resentful that he was continually passed over for promotion and not given the honors he felt were due him for his brave service. After Arnold was wounded badly in the leg, Washington put him in charge of Philadelphia during his recuperation, and it was while there he grew increasingly discomfited with the French alliance and more comfortable with Tory views, not least because of his engagement to Peggy Shippen, the vivacious daughter of a local Loyalist. Sensing blood in the water, his enemies arranged for a court-martial for two minor misdemeanors, which earned him a mild rebuke from Washington, who was aware of the ludicrousness of the proceedings and tried to salve Arnold’s amour propre with the promise of high command. By then, however, Arnold had mulled too long on the injustices he had suffered and his thoughts had turned to treachery. And it was then that he asked for, and received, West Point.

  Arnold’s enemies had their reasons. Tallmadge, for one, greatly disliked him. He had become “acquainted” with Arnold, he told a friend, “while I was a member of Yale College & he residing at New Haven, & I well remember that I was impressed with the belief that he was not a man of integrity. The revolutionary war was coming on soon after I left college, & Arnold engaging in it with so much zeal, and behaving so gallantly in the capture of [General] Burgoyne, we all seemed, as if by common consent, to forget his knavish tricks.”2

  Arnold, a heroic and valiant soldier, was a low, sly Iago among traitors, but this defector was also the most senior mole in espionage history and a first-class intelligence asset. His betrayal poleaxed Washington. Even his peers, who thought him arrogant and snotty, had respected his undoubted martial talents, and none suspected him capable of treachery of the blackest dye. The British secret service, approached by Arnold in May 1779, ran him until September 1780, when the plot, by merest chance, was uncovered at the very last moment.

  Until Arnold’s recruitment, British intelligence operations had lagged behind Washington’s, whose Culper Ring surpassed anything Clinton, let alone General Howe, had constructed. Washington, too, appreciated the craft of intelligence far more than did Clinton (or other senior commanders), and naturally grasped the need to acquire reports from myriad, often contradictory sources behind the lines, to cross-reference their information to distinguish between fact and fiction, and to analyze and evaluate their timeliness and utility before acting.

  Washington understood that authentic intelligence gathering consists, not of flashy derring-do and glamorous escapades, but of piecing together an intricate, yet most tedious, jigsaw where every “fact” could be interpreted in several different ways. To Lord Stirling (William Alexander), Washington summarized that “as we are often obliged to reason on the designs of the enemy, from the appearances which come under our observation and the information of our spies, we cannot be too attentive to those things which may afford us new light. Every minutiae should have a place in our collection, for things of a seemingly trifling nature when conjoined with others of a more serious case may lead to very valuable conclusions.”3 Washington was always careful to keep a stern lookout for bloviating and unwarranted speculation in his agents’ reports—an inevitable hazard in a game so often played by fantasists and adventurers. He told
Matthias Ogden, an intelligence officer, in 1782: “It is my earnest wish that you impress upon the persons in whom you seem to place confidence, urging them to be pointed, regular and accurate in all their communications.… An account of the nature and progress of their [the enemy’s] public works is of infinite more consequence than all the chit-chat of the streets and the idle conjecture of the inhabitants.”4 One reason why Washington valued the Culpers’ dispatches so highly was owed to their proven veracity and absence of hyperbole.

  The British, conversely, still preferred to use military scouts to reconnoiter enemy positions and to obtain tactical information as frequently as possible. Whereas Washington had appointed Tallmadge as his chief of intelligence and personal liaison with the Culper Ring, Clinton, until late in the day, acted as his own intelligence head and lacked any specialist staff to help him. Small wonder that he put little store in it, while Washington enjoyed the luxury of avoiding such humdrum chores as negotiating terms of service, dealing with uppity agents, and arranging the reimbursement of expenses incurred.

  New York, of course, being the nexus of the imperial war effort, was the navel of all British intelligence operations. Two Loyalists, General Cortland Skinner and Colonel Beverley Robinson, set up their own private networks in their old stamping grounds (New Jersey, in Skinner’s case, and the Hudson River, in Robinson’s), and periodically sent Clinton packages of information and rumor gleaned from refugees, scouts, prisoners, and deserters, but these proved of little use and timeliness as they were jumbled and often contradictory. Consequently, Clinton complained of “too many ill-founded reports” finding their way to his desk.5