Washington's Spies

by Alexander Rose

  Little came of it. Washington lost interest in the affairs in New York when it became clear Carleton would not mount a last-ditch defense of the city. For some time, especially in the New Year of 1783, when Washington was notified of the conclusion of the peace treaty in Paris, Woodhull continued to go through the motions of sending letters, but they are only a poor shadow of his previous efforts, being one-page affairs, messily and hurriedly written. No one in Washington’s headquarters cared anymore about his reports of troop movements on Long Island. They were dutifully read—with a sigh of boredom—and filed away. Woodhull’s last “Culper” intelligence report is dated February 21, 1783.58

  The one Culper Washington continued to take an interest in was the indomitable Caleb Brewster, who had been long intent on settling accounts with his old foes, Captains Glover and Hoyt. The whereabouts of Glover were a mystery, though it was known he was in the pay of the British secret service. In March 1781, for instance, he was acting as the conveyor of intelligence reports from Connecticut-based agents to Long Island; in traveling the opposite way across the Sound from Brewster, and essentially doing the same job, Glover was his Loyalist equivalent in the Clinton-Washington spy game.59 Then in June of that year he was collaborating with Captain Nehemiah Marks, another Loyalist whaleboater based at Lloyd’s Neck, keeping an eye on French naval movements for Major De Lancey.60 After that, nothing. Brewster, unfortunately, never caught up with the slippery Glover. As many of the Loyalist whaleboatmen departed for Nova Scotia and New Brunswick at the war’s close (as Marks did), it’s likely Glover, too, sought refuge well away from the likes of Brewster and his Long Island countrymen.

  Brewster would enjoy better luck with Captain Hoyt, who in July 1781 was commanding the obsequiously named Sir Henry Clinton and working with Colonel Upham at the Lloyd’s Neck stronghold. Hoyt, said Upham, was “very serviceable to us.”61 Before Brewster’s showdown, however, Tallmadge had a run-in with him. In the winter of 1781, the latter recalled, Hoyt’s new ship, the Shuldham, was preying heavily on American and British commerce in the Sound. It seems that since July Hoyt had, or so he said, switched patrons, and was now operating under rebel auspices from Norwalk, Connecticut. Unfortunately, he was playing both sides—and in more ways than one, since a “Mr. Hoyt” was also working for British intelligence—and was involved in smuggling goods out of Connecticut to Long Island, and back again.62 Intending to warn Hoyt off the practice, Tallmadge clambered aboard the Shuldham at Norwalk. After saluting the captain, Tallmadge took him below to discuss the matter, whereupon “he flew into a great passion, and first threatened to throw me overboard.” Tallmadge calmly ordered him to obey his commands, but Hoyt “immediately ordered the anchor to be weighed and the sails hoisted, and stood out to sea.” Tallmadge ordered him to return to Norwalk, to which Hoyt snarled that he would throw him overboard before it came to that. “I assured him if he made any such attempt I would certainly take him along with me.” Tallmadge could see that Hoyt was heading for Lloyd’s Neck. Asking him what he intended to do, Hoyt replied, “with an oath,” that he was kidnapping Tallmadge, who informed him, with remarkable cool, “that for such an offense, by our martial law, he exposed himself to the punishment of death.” Hoyt was unmoved, and “professed to care nothing for the consequences,” though Tallmadge sensed his fortitude beginning to waver. Again, Tallmadge said that “I would have him hanged as high as Haman hung, if I ever returned, as I did not doubt I should.” In the distance—they were now more than halfway across the Sound—Tallmadge saw the waiting whaleboat fleet at Lloyd’s Neck. “The time now became critical,” and “I again demanded that he should put his ship about.” Only now did Hoyt hesitate, soon ordering his crew to steer back to Connecticut. As soon as they were back, “the captain went ashore in his boat, and I never saw him again.” Tallmadge determined this Hoyt to be a “man devoid of principle.”63

  Finding himself now persona non grata among the Americans, Hoyt reappeared in British service a short time later. In November 1782—about a year after his initial encounter—Tallmadge was planning a raid on Huntington, where the Seventeenth Light Dragoons were camped. The attack was set for December 5. As the whaleboat crews and their complements of dragoons were waiting at Stamford, hail and rain began to pelt, delaying their departure. It wasn’t for another two days that the weather abated sufficiently to allow them to leave, and it was as his dragoons were boarding that Tallmadge noticed three Loyalist whaleboats sniffing around off the coast. He ordered Brewster to pursue them before they returned to Lloyd’s Neck to sound the alert. The interlopers immediately started running for home, but Brewster’s three boats raised their sails and used their oars to catch up in the middle of the Sound. As he closed with them, Brewster recognized their admiral—the slippery Captain Hoyt.

  Battle was joined. Hoyt’s boat had a small cannon that was fired into the side of Brewster’s, though it was too far away to do much damage. Brewster, racing toward Hoyt, held his fire until he came within 120 feet, then launched one broadside, and then another at 60. The two crashed together, throwing everyone off their feet, but Brewster recovered first and led his men over the side into a melee with Hoyt’s. One of Hoyt’s crew, a bulky Irishman, swung his broadsword to and fro, injuring some of the Americans, until Hamilton, a Massachusetts man, snatched the weapon from him and slashed his throat from ear to ear with it. Brewster, meanwhile, had been shot in the shoulder, and was further struck several times by Hoyt in the back with one of the heavy steel rammers used to load the cannon. Thankfully, one of Brewster’s doughty Connecticuters came to the rescue and slew his assailant. The boat was theirs. Only one man aboard Hoyt’s whaler escaped death or injury, while Brewster’s had four wounded, one mortally (Judson Sturges, aged thirty-five, who died five days later). Meanwhile, the second of Hoyt’s boats was blasted by a swivel gun mounted on one of Brewster’s fleet, killing two men instantly and prompting its surrender immediately after. The third escaped unharmed back to its base. Having lost the element of surprise, Tallmadge aborted his raid.64

  Two weeks later, as reward for “the signal gallantry of Captain Caleb Brewster of the 2nd Regiment of Artillery, and the officers and men under his command, in capturing on the Sound two armed boats then in service of the King of Great Britain,” Washington ordered that the proceeds of selling the boats be shared among them.65 Hoyt’s death and Brewster’s little victory earned him Washington’s plaudits—while his wound earned him a pension of seventeen dollars a month for life. Washington also effusively congratulated Tallmadge on his efforts throughout the war, and though this particular operation had not been executed, “I cannot but think your whole conduct in the affair was such as ought to entitle you still more to my confidence and esteem.” Indeed, waxed Washington, “for however it may be the practice of the world … to consider that only as meritorious which is attended with success, I have accustomed myself to judge of human actions very differently, and to appreciate them, by the manner in which they are conducted.”66

  As for the rest of the Culpers, there remained only a toting up of accounts. In July 1783, Woodhull submitted his bill for services rendered. Over the course of the war, Woodhull had spent a total of £500.15.8, of which £375.9.4 had been repaid at various times. The balance he was owed was £125.6.4. Considering that this number had covered the expenses of several individuals over roughly four years, the figure compares favorably with William Heron’s demands for at least £500 during the Hiram Hoax. Still, it couldn’t be called an insignificant sum. Over the course of the war, Washington spent about £1,982 on gaining secret intelligence; that fully a quarter of his budget was devoted to the Culper Ring testifies to its importance.67 Still, Washington’s expenditure paled next to the £1,000 per month Major Beckwith—De Lancey’s newly promoted replacement—was having to pay his sources.68

  Woodhull’s invoice sheds some interesting light on how the Culper Ring worked, and who worked for it. Woodhull himself had incurred nearly a third of the total (£15
4.15.10) on travel and boarding in New York, which included keeping, on Tallmadge’s instructions, “a horse at N. York which in about 9 months or a little more cost me £25.” The horse, presumably, provided readily available transport for Woodhull and his couriers. “J.H.”—Jonas Hawkins—came second with £145.2.6, and after him, “A.R.” (or Austin Roe), with £116.16. Townsend racked up £51.9.4, mostly for buying paper, and there is an entry for a mysterious “J.D.,” who cost £18. J.D.’s identity is troublesome: On the 1775 List of Associators in Setauket and its locale, two men—Joseph Davis and Jonas Davis—bear these initials, but there is also a Joshua Davis who served as a whaleboat captain on the Sound. He acted as Brewster’s deputy whenever he was away on other business. An individual known only as “G.S.” spent £4. This stood for George Smith (dubbed “S.G.” by Tallmadge), who helped convey the Culpers’ dispatches for a short time near the end of the war. An “S.S.” is also listed as having expended £4: This was Selah Strong, or more properly, Anna Strong. Lastly, Brewster had spent £6.12.6 on supplies “when here in distress by bad weather.”69 Woodhull, ever respectable, was always concerned with appearances, and explained to Tallmadge that he could not “particularise dates for I only kept the most simple accounts that I possibly could for fear it should betray me,” but was confident that his invoice was “a just one.” He wanted to “assure you I have been as frugal as I possibly could. I desire you would explain to the Genl. the circumstances that attended this lengthy correspondence that he may be satisfied that we have not been extravagant.”70

  Tallmadge in turn forwarded the invoice to Washington, remarking that it was for “monies due S. Culper and others for Secret Services.” He himself had seen “some of the principals in this business,” had verified Woodhull’s receipts, and was “convinced that he has been as attentive to the public interest as his circumstances and peculiar situation would admit.”71

  Washington’s reply contained a note exemplifying the ingratitude that spies, then as now, often experience from their masters once their usefulness has been exhausted. While he did not doubt, “because I suppose S.C. to be an honest man,” that “the monies charged in his account have been expended, and therefore should be paid,” Washington felt that “the services which were rendered by him (however well meant) was by no means adequate to these expenditures.” Absent the requests of Tallmadge and Rochambeau, “I should have discontinued the services of S.C. long before a cessation of hostilities took place, because his communications were never frequent, and always tedious in getting to hand.”72

  Taken as read, this was an unworthy remark—especially considering the praise Washington had heaped upon the Culpers’ heads in years past, and his repeated pleas for them to come back to work—but can be explained by recalling that after 1781, the Culper Ring had declined precipitously in importance. Nearly all of the expenses still owing dated from that time onwards, so Washington was referring to that two-year period, not the Culpers’ service as a whole.

  Tallmadge, of course, never told Woodhull of Washington’s hurtful remarks. His prime concern was “to insure the safety” of his agents, who were, of course, considered by their neighbors “to be of the Tory character,” the better to further their designs. He obtained special permission from Washington to enter New York soon after the signing of the Treaty of Paris on September 3, 1783 (which ended the Revolutionary War) but before the last British troops finally quit the city (which they did on November 25).

  As he rode down Broadway for the first time in seven years, in American uniform and escorted by a few of his dragoons, Tallmadge was alarmed to see he was surrounded by “British troops, tories, cowboys, and traitors,” though he was treated “with great respect and attention” by army and navy officers, and especially well when he dined with General Carleton one convivial evening. “While at New York,” he said, “I saw and secured all who had been friendly to us through the war, and especially our emissaries, so that not one instance occurred of any abuse, after we took possession of the city, where protection was given or engaged.”73

  That may have been true of his “emissaries”—Tallmadge was too polite to use the insulting term “spies”—but not of regular Loyalists, many of whom were dispossessed, abused, and beaten by their angry neighbors and those newly returned exiles who had fled the British invasion in 1776. The more farseeing of New York’s Tories had begun leaving for Britain as early as the summer of 1782, but London wasn’t keen on a sudden influx of penniless refugees and soon proposed a resettlement scheme in Canada. Heads of families were offered five hundred acres of land (bachelors, three hundred), given an allowance of three weeks’ rations, a year’s worth of supplies, clothing, medicine, and arms. Still, relatively few—convinced that Britain had not yet truly begun to fight—took up the offer to start again in the chilly realm of Nova Scotia. It was only after the cessation of hostilities in mid-February 1783 that there was a rush for the door as despairing and desperate Loyalists realized the Mother Country was not going to save them. Expensive china and imported furniture were dumped at whatever prices could be got for them at auction, some Tories going so far as to dismantle their houses to sell the bricks and wood. There were many reported instances of ruined Tories hanging, drowning, and shooting themselves, and waves of Loyalist refugees cleansed by Patriot militiamen from their homes in areas once under British control threatened to cause outbreaks of disease in the city. To his credit, Carleton realized that if he evacuated New York too quickly with his troops, American reprisals against any Loyalists not yet evacuated might well turn into a massacre.

  A particularly tricky problem was posed by the situation of the many thousands of blacks freed by the British during the war whose former, and unforgiving, American masters were intent on re-enslaving them. Carleton, writing that “I had no right to deprive them of that liberty I found them possessed of,” decided to allow them to embark upon the Canada-bound ships but compiled a registry in case their former owners sued the British government for compensation. The preliminary articles of the peace agreement, however, forbade the conveyance of “American property,” which of course included slaves, from American shores. To this end, Washington, at the behest of Congress, complained mightily to Carleton about this theft of valuable people, but the latter casually referred him to his registry and said that should his policy later be found to violate the peace treaty, the Crown would compensate their ex-masters. (Even so, old, sick, or “troublesome” blacks would have been exceptionally fortunate to land a berth aboard one of the transports.) By mid-November 1783, thanks to Carleton’s go-slow policy, the transition had been more or less peaceable: Some twenty-nine thousand Loyalists had been shipped out, their vacated houses and stores gradually filled by incoming Patriots. On November 25, there remained only a core force of British troops, who began marching down the Bowery to the East River wharves at eight in the morning.

  As the British boarded the transports for the Atlantic crossing, American soldiers paraded down Queen Street before turning west on Wall Street to Broadway. At the foot of the street, they could see the royal ensign fluttering from the flagpole at Fort George. An infantry and artillery detachment were sent to haul it down and replace it with the stars and stripes. Unfortunately, in one last parting prank, some redcoats had mischievously greased the pole, cut away the halyards, and removed the cleats. It took a sailor four attempts, aided by the tallest ladder available, to clamber up high enough to nail sufficient cleats to reach the top and tear down the offending flag.74

  A little later, Tallmadge went home to Setauket to see his father, Woodhull, Roe, Hawkins, the Strongs, and Brewster. Much of the town congregated on the public green to celebrate their emancipation “from their severe bondage” by roasting an entire ox. Tallmadge was invited to serve as master of ceremonies, and “after a blessing from the God of Battles had been invoked by my honored father,” he “began to carve, dissect, and distribute” the “noble animal” to “the multitude around me.”75


  With the war over, the British had packed their bags, but not all of them left town. Closet Tories everywhere abounded, many of them willing to pass on snippets, and many former agents went underground, poised for reactivation. The secret service itself relocated, along with thousands of Loyalist refugees, to Canada, where it kept a beady eye on American developments. There might still be a use for the spies.

  For the cabinet in London, the war had finished, but not yet the struggle. Washington’s government was weak and suffered an economic and diplomatic embargo. In the west, Indian confederations attacked settlers, while separatist movements arose on the Vermont, Maine, Kentucky, and Tennessee frontiers. In the years to come, predicted thoughtful observers, the newfangled United States might collapse, necessitating British intervention. Perhaps the rebellious colonists—as some in London persisted in regarding them—might even call upon British arms to save them from themselves—or the French or the Spanish. If that happened, an efficient spy service could quickly be resurrected.

  From 1786, Lord Dorchester (the former Sir Guy Carleton, now elevated to the peerage) ran intelligence operations from his perch in Quebec. Carleton retained the services of another old America hand, George Beckwith, aged thirty-four. New York, however, had declined in importance, at least in terms of espionage, though Beckwith did report on anti-congressional sentiment among the merchants and their desire to create an American monarchy with Washington as their sovereign. For the most part, Beckwith focused on finding assets in such potentially troublesome areas as Vermont, the Florida border, Kentucky, Tennessee, and the new western Appalachian territories. For the next few years, Beckwith fomented problems wherever he could, but by the early 1790s, British troublemaking was the least of Washington’s worries. (Beckwith himself went on to glittering things, becoming governor of Bermuda in 1797, a knight in 1808, and a general in 1814.)