Washington's Spies

by Alexander Rose

  During the eighteenth century, there were three distinct types of agent. One kind was perfectly respectable, and weren’t spies per se but military scouts on reconnaissance missions to probe fortifications or map terrain. These intelligence gatherers were heirs to a tradition dating from Homer and the Peloponnesian War. Officers and gentlemen—the two being one and the same at the time—were permitted to practice this kind of “espionage,” one reason being that they were rarely out of uniform, or if they did assume a disguise, it was merely temporary—and physical (such as a wig or cloak). They did not stay behind enemy lines and masquerade as adherents to the enemy cause.

  Washington had been one of these “intelligencers,” as he once said in his journals. In 1753, then a young officer during the French and Indian War, he was ordered to enter the wilderness and discover whether the French were building forts on British soil. As “cover,” he was given a letter from the lieutenant governor of Virginia requesting that the French vacate their positions. Two months later, a uniformed Washington visited Fort Lebouef and, while the French commander was reading the letter, was allowed to wander around freely taking notes and sketching the defenses. In the end, the French ignored the lieutenant governor’s warning and sent Washington home, whereupon he was directed to return and build a fort of his own.

  The second type of agent was more secretive, but just as respectable, for he operated solely within the closed and cramped environments of European palaces and chancelleries. Diplomats, princes, and generals discreetly passed each other scraps of intelligence that eventually reached the ears of the various capitals. It was all very civilized and often took place over dinner.

  Alternatively, the foreign ministries of the European powers conducted their activities through “Black Chambers,” a set of offices whose entrance was usually on a side street off the main building. Aside from the collecting of gossip, most intelligence was acquired by intercepting the diplomatic mails, sliding a hot wire beneath the wax seal or melting it, breaking the cipher, and making copies before re-sealing it.

  The practice was so ubiquitous that the British ambassador in Vienna once complained to the Austrian chancellor that his censors had kept the originals and accidentally passed on the copies. The latter, Count Kaunitz, did not bother denying his interceptors’ activities, lightheartedly remarking instead “how clumsy these people are.” He could afford to be so humorous: The Habsburg Geheime Kabinets-Kanzlei was the best in the world. The sacks of diplomatic dispatches due to be delivered to the embassies in Vienna were dropped off at the Black Chamber at 7 a.m. each day; by 9.30 a.m., they were back at the Post Office ready to go. (Owing to the stress of the job, Viennese cryptanalysts worked shifts of one week on, one week off, but were paid lavish bonuses when they cracked a code: eighteen, once, in a single year.) Over the centuries, the espionage process evolved into a ritual as stiffly stylized as Kabuki, and was viewed as just part of the ancient game played by Great Powers.81

  It was the third kind of spy that was beneath contempt. These were agents who worked for wages, and whose loyalty was always in doubt. They were regarded as lowborn blackguards who insinuated themselves into better society and betrayed their colleagues’ trust by selling information. Permanently embedded in enemy territory and psychologically disguised as “friendlies,” they were the sneaky, shifty toadies who informed on Jacobites, Jacobins, and radicals of various kinds. By their masters, cash was earmarked for bribes (“Without money,” reads one particularly clear-eyed Bavarian instruction of 1773, “one does not get far”), some £67,000 annually in London’s case.82 It was to these characters that Napoleon, always a shrewd judge of character, alluded in his dictum: that the only true reward for a spy was gold. The playwright Ben Jonson also amusingly captured the prevailing image of these creatures:

  Spies, you are lights in state, but of base stuffe,

  Who, when you have burnt your selves down to the snuffe,

  Stinke, and are throwne away. End faire enough.

  Woodhull, a former (if temporary) militia officer and an eminently respectable (if unmoneyed) gentleman related to a martyred general, would have been horrified had he been regarded as a mere, snuffable “light in state” by his heroes, Washington and Tallmadge. Hence he sought to cleanse himself of espionage’s taint by refusing offers of pay, and also his insistence on serving solely out of loyalty to the Cause of Liberty, a theme he repeatedly harped on.83 As for Tallmadge, he, too, remained enigmatically discreet about his spying activities. In his Memoir, written half a century after the Revolution, he had only this to say: “This year [1778] I opened a private correspondence with some persons in New York [for General Washington] which lasted through the war. How beneficial it was to the Commander-in-Chief is evidenced by his continuing the same to the close of the war. I kept one or more boats continually employed in crossing the Sound on this business.” Apart from that sole paragraph, the balance of the sixty-eight-page book is devoted to his more respectable soldierly achievements.84

  Lest Washington ever suspected him of padding his expenses—the sort of thing low-class spies did—Woodhull repeatedly took great pains to explain how thrifty and “as sparing as possible” he was. “I have drawn on you for fifty pounds,” he humbly wrote, “which please accept.”85 Washington, because “all the specie in my possession is with my baggage from which I shall be for some days separated,” could not send the money directly, but mentioned to Tallmadge that “there is a sum about equal to what is now wanted in the hands of Col. Henley, whom I have directed … to pay what he may have, to you.”86 This was money originally allotted to Charles Scott, lately resigned, to fund secret services.

  Though he understood that spying could not be done on the cheap, Washington was always concerned with keeping expenses down. A peculiar difficulty was presented by Woodhull, who required British currency or bullion, not the Congress-printed paper that was both worthless (by 1780, a pound of tea cost five hundred dollars and people used the bills as wallpaper) and useless (how was Woodhull expected to circulate enemy currency in British-occupied territory?).87 As Washington explained, “specie is so scarce an article and so difficult to be procured, that we must use great oeconomy with it. If Continental money can be made to answer the purpose in part, it will be a very desirable circumstance, as it will facilitate the necessary supplies.”88 Be that as it may, replied Woodhull on January 22, 1779, quite sensibly if a touch testily, “Continental money will not serve me; It is much lower here.”89 Washington’s remark about using “great oeconomy,” however, continued to rankle his spy, who reminded the commander-in-chief that “I have not an independent fortune,” but that “I can assure you … I have had nothing else in view. And in one word a sufficiency for … support.”90 To which Washington, hoping to soothe a ruffled amour propre, clarified, it was “the difficulty of furnishing specie, not the mere matter of expense which I had in view when I recommended oeconomy.”91

  Mollified, and good and faithful servant that he was, Woodhull continued to do his master’s bidding.

  Winter was traditionally a quiet time for armies, summer being the accepted and most civilized season to recommence killing the enemy. For Tallmadge, however, the winter of 1778–79 offered no respite and he was instead kept exceptionally busy by his spy ring. Washington had directed him to find a faster method of conveying Culper’s letters to headquarters, and to this task he devoted himself.

  There were two bottlenecks. Since Woodhull was now doing much of his spying work in the city at Amos Underhill’s house, messages were delayed between there and Caleb Brewster’s pick-up spot fifty-five miles away in one of the quieter bays just outside Setauket where the surrounding woods concealed these illicit goings-on from prying eyes. Assuming Brewster’s crew were available, he could transport the letters across the Sound in just a few hours. The second bottleneck was on the Connecticut side, where it was proving onerous for Tallmadge both to rendezvous with Brewster and then ride to Washington’s headquarters.


  The latter was easily fixed. At Washington’s suggestion, Tallmadge stationed a dragoon officer at Danbury who relayed the letters up the line to camp “without his knowing the person from whom they came,” as the general put it.1 By January 2, 1779, this single officer was replaced by a chain of “regular expresses established between Danbury and the headquarters of the army” who were given special permits to ride through American checkpoints.2 Even so, there was the occasional delay: A Culper letter of mid-January was days late owing to a dragoon’s lame horse and his need to “get some repairs to his accoutrements.”3

  The New York–Long Island stretch was trickier. Just before Christmas 1778, Tallmadge brought Jonas Hawkins into the Ring to courier the letters to Setauket. He didn’t omit to assure Washington that Hawkins was sound.4 Hawkins officially began work in mid-January. Little is known of him apart from his family’s longtime presence in Setauket—a Zachariah Hawkins arrived in the town two years after its founding—that he owned a tavern and store, that (like Woodhull and Brewster) he signed the List of Associators in 1775, and that he served in the militia after the war for a short time. He was some years younger than Woodhull, Brewster, and Tallmadge, and had known them as the “older boys” since his childhood.5 Like Amos Underhill, he was never, however, a full-time operative of the Ring, and soon began splitting his courier duties with Austin Roe, another signatory to the Associators’ list. The latter, born in 1749, was also of an old Setauket family (related to Hawkins) and he owned a tavern—about fifty yards from the house where Caleb Brewster had grown up—on the short road between Setauket and Port Jefferson. Roe had bought it from the Woodhulls.6 At this stage, the growing cell was recruiting solely from the ranks of men its members knew they could trust implicitly, men who shared their religion, blood, class, and creed.7

  With Hawkins and Roe undertaking the hazardous trip between Woodhull in New York and Brewster waiting off Setauket, the new system quickly demonstrated its superiority. At the end of January 1779, the Ring managed to convey a letter from New York to Washington in a week, at least half the time it had previously taken.8 Information could also travel in a more regular fashion, as Washington happily noticed when he received two Culper letters—one from Woodhull, the other, Brewster—in late February.

  Brewster’s was a short report on a visit he’d paid to Long Island, and was mostly concerned with naval matters, such as his observation that “they are repairing all their flat bottom boats in New York and building a number at the ship yards”—indicating that the enemy was gearing for a landing somewhere, probably Connecticut. There was also a tip that “the inhabitants [are] fitting a number of privateers out in the City,” so allowing American commanders to warn merchantmen to be on the alert.9

  Any intelligence of privateer-building activity was bound to be worrisome. New York’s geographical position between Canada, Europe, and the Caribbean had long allowed privateering—the practice of allowing armed, private ships to attack those owned by the enemy and take their cargoes as prizes—to flourish on the side, but during the war, when it was impossible to obtain certain goods on the open market, it turned into a cross between an indispensable lifeline and a speculative thrill. (One such venture was the Royal Charlotte, a vessel owned by a consortium of New York high-society ladies patriotically intended “to assist in humbling the pride and perfidy of France, and in chastising the rebels of America” while also turning a sweet profit for its proprietors.)10

  For Americans, over the course of the war their fleet of congressionally approved privateers—which varied between 73 (in 1777) and 449 (1781)—brought in 3,100 merchant vessels, of which 900 were eventually recaptured or ransomed to their owners. Though British global trade was mostly undisrupted by these losses (the premiums at Lloyd’s of London, the maritime insurers, rose but not so much as to stifle commerce), the money generated by Continental privateering helped nourish the sinews of the war on land.11

  On the British side, however, privateering was a much bigger business, employing up to six thousand New York seamen.12 Blacks comprised a disproportionate number of these. Privateers were color-blind, and their captains could count on black crewmen—most former slaves freed by the British—not to surrender at the first whiff of American grapeshot. The consequences of capture, for them, were too dreadful not to put up a fight. In April 1782, for instance, when a Continental privateer captured the frigate Alert, it found that eleven out of its forty-six men were blacks, nine of whom were subsequently sold in a Trenton tavern.13 For whites, so attractive were the business’s rewards that the Royal Navy found its own ships undermanned because potential recruits were signing on to privateers. Notwithstanding the public complaints about the degenerate practice of sailing for profit instead of fighting for glory, even high-ranking officers, such as Admiral Howe, took cuts from commerce raiders, and navy captains themselves turned privateer if a juicy Continental plum crossed their path.14 And with good reason: A good take could double, or even triple, a sailor’s annual wages.15

  A privateer who made a living mugging merchantmen often found itself a tempting target preyed on by larger craft: On September 30, 1776, the Industry, an American raider of twenty-six guns, was jumped by the Emerald, a frigate, and suffered thirteen killed and twenty-nine wounded.16 Yet privateers on both sides still found the risk worthwhile. Three enterprising Continental captains, for instance, sailed their sloops into New York harbor and hijacked a fully laden merchantman right from under the nose of the Russell, a mammoth seventy-four-gunner, which failed to do anything to stop it, much to the fury of the New York merchants who could see their stolen property vanishing over the horizon.17

  The British alone authorized some two hundred New York–based privateers to prowl the seas.18 And they did. Roaming as far south as Virginia and the West Indies, and as far north as New England, between September 1776 and March 1779, these hunters brought into port no fewer than 165 prizes worth a staggering £600,000.19 Small wonder that Washington found Brewster’s information most useful, and not a little alarming.

  The second letter in the February package, Woodhull’s, was more substantive, and was the longest dispatch he ever wrote—a full seven dense pages. Now relieved of the burden of traveling back and forth from Setauket, he’d been assiduously touring the British positions. As Woodhull says, explaining his absence over the past weeks, “I have been for some time engaged to find out the true state of the enemy.” Which was: “The 44, 57, 63 [regiments], Colls. Robinson’s and Emmerick with three German regiments all commanded by Governor Tryon, are cantoned [at] King’s Bridge.… From these posts to and within the city are two battalions of Guards, 28 Regm. Welch Fusiliers, the Volunteers of Ireland … and four German Regm. Also in the city are Genls. Clinton, Jones, Mathews, De Lancey, Knyphausen.” He computed “the whole force of the enemy to be thirty four battalions, equal to two hundred and fifty in a battalion.” Rather sweetly, in the margin he calculated the sums for Washington, arriving at 8,500 men. He also independently confirmed Brewster’s report of shipyard activity: “I frequently see General Clinton amongst the carpenters [at the shipyard], in particular viewing the boats.”20

  The importance of Brewster and Woodhull’s early warnings that the British were building flat-bottomed transports and that there were significant numbers of soldiers at King’s Bridge at the northern tip of Manhattan would soon become apparent. At the time, the “royal governor” of New York, William Tryon, had been urging Clinton to authorize the use of “desolation warfare” upon the enemy. For Tryon and other Loyalist hard-liners, Clinton’s reluctance to countenance attacks on pro-Patriot civilians was evidence of namby-pambyism; only by punishing popular support for the rebel regime could Americans be wooed back into the monarchical fold. Though he and Tryon had once been close, Clinton dismissed his comrade’s schemes as mad and immoral. In an attempt to quiet him, at the end of February he allowed Tryon to march from King’s Bridge at the head of his regiments to West Greenwich (more often known as Horsenec
k), some thirty miles away, his objective being to destroy American military stockpiles. Tryon’s raid was a successful one (his men also managed to scuttle three docked vessels), even if he was harried on the way back by Connecticut militiamen.

  Clinton had in the meantime begun musing on a plan that would use Tryon as bait. Come the summer, he would give Tryon command of a small fleet to transport 2,600 troops to the Connecticut coast. That armada was now secretly under construction, explaining Clinton’s interest in visiting the shipyards to inspect progress. The task of Tryon’s expeditionary force was to create a diversion that would lure Washington and the eight-thousand-man army southeast from his main camp near West Point on the upper Hudson. Once he had left his secure defensive redoubts to deal with Tryon’s raiders, Clinton would march rapidly with the main army from New York, capture Washington’s supply depots in New Jersey, and threaten his strongholds on the Hudson. Washington would be forced to rush back to save his rear, thereby allowing Clinton an opportunity to meet him on the field of battle and inflict a decisive defeat.21

  The latest Culper intelligence—Clinton building transports in the midst of winter and Tryon instigating raids on Connecticut—bemused Tallmadge and Washington. Perhaps the two were linked, and Tryon’s next attack would be waterborne; if that were the case, the Connecticut coastline would have to be the target. As Clinton would never stay put in New York during the crucial summer months, what would he do while Tryon was unleashed on Connecticut?

  If Clinton was up to something, Washington wanted to know about it before it happened, and he urged Tallmadge to improve the timeliness of the Culper letters by finding a quicker route. Tallmadge, however, was equally, if not more, concerned with strengthening security. Written as they were openly in black ink, all it would take would be one overly curious trooper on patrol to find the incriminating documents and disaster would befall the Ring.