Washington's Spies

by Alexander Rose

  Scott soon after bowed out, reporting to Washington on October 29 (in a swipe at Tallmadge) that for certain reasons he had been having trouble fulfilling his duties as a spy manager. His spies were also failing him. One promising recruit, for example, had just returned from a visit to New York, but “he knows nothing and will not tell me any thing at all, I suspect he is a rascal and shall treat him accordingly.” Worse, family issues were weighing him down, so “my unhappy misfortunes make it indispensably necessary that I should leave the army in a few weeks.”31 Washington graciously accepted his mostly welcome resignation, and gave Tallmadge the chance to head his own intelligence network.

  Unlike Brewster’s missives to Scott, which had been written somewhat stiffly with a full formal flourish, his letters to Tallmadge were casually written and signed with his name. Not just comrades in the war, the two were old friends. And so, too, was Abraham Woodhull.

  Tallmadge was from coastal Setauket, in Suffolk County, the small town in which Woodhull still lived and whence Brewster had left in the years before the war. The three of them had grown up together. Setauket, in every other respect, was an entirely unexceptional Long Island settlement. In 1655, six pioneers from Massachusetts purchased land from the Setalcott Indians; within a half-decade, the capable Richard Woodhull—born in England thirty-five years before and emigrating to Massachusetts in 1640—had taken charge, and the town, and those around it, expanded by underhandedly encouraging its new arrivals to “take some likers [liquors] with them” when they went to talk to the Indians about buying property.32 Woodhull’s great-great-grandson was Abraham Woodhull, who lived with his parents on the family farm, a modest tract on Strong’s Neck facing the placid waters of Old Field Bay. The Tallmadge residence was a few minutes’ walk to the south.33

  As for Caleb Brewster’s people, they emigrated from England in the early 1660s, and had found their way to Setauket by the end of the decade. One, the Reverend Nathaniel Brewster, graduated from Harvard, and served as Setauket’s Presbyterian minister between 1665 and 1680.34 Since then, the family, or at least Caleb’s father, had turned to farming and left the ministering of the flock to the able divine, the Reverend Benjamin Tallmadge, a Yale-educated Whig of stout persuasion and one fearsomely learned in the weightiest of Greek and Roman political philosophy, who alternately denounced the idolators, the damned, and the Episcopalians from his Presbyterian pulpit between 1754 and 1785. (Given the robustness of Tallmadge’s convictions, it was hardly surprising that Colonel Hewlett’s vengeful force of damned, idolatrous Episcopalian militiamen desecrated the church, for which they were duly punished by Brewster, among others, during the August 1777 raid.) His son was our Benjamin, who loved his God and General Washington in equal measure (even if he were perpetually disappointed that Washington was never “explicit in his profession of faith in … the finished Atonemont of our glorious Redeemer”).35

  In such an insular and isolated place as eighteenth-century Setauket, everyone knew each other. This complex web of personal relationships, continuing down through generations and concentrated in one compact locality, was key to the Culper Ring’s later success. Its members refused to work with anyone they didn’t know, and insisted on using Tallmadge as their sole channel to Washington. They were one-man dogs.

  They shared not only a common background, but politics, as well. Those who signed a local petition dated June 8, 1775—seven weeks or so after the first shots at Lexington and Concord, and the formation of New York’s radical First Provincial Convention—were Whigs good and true who resolved “never to become slaves” to tyrants, and most could be counted on to support Congress in its struggle against the Crown. The list itself consists of some seventy names, and includes Woodhull, Brewster, and “John Talmadge” (Benjamin Tallmadge’s younger brother).36

  Those of Tallmadge himself and his father are missing from this “List of Associators.” Tallmadge’s absence is easily explicable: At the time he was away “superintend[ing] the High School in Weathers-field”; as for his father, Tallmadge recalled that despite his zealous Whiggery, he was “very reluctant to have me enter the army.” Like many other Americans trapped in the tempest of the mid-1770s, Tallmadge Senior may have happily boycotted Anglophile tradesmen and berated the Tories, but was in the end unwilling to fight the Mother Country. Cheering the bravery of the tea party was one thing; indulging the madness of the war party quite another.

  Befitting its Presbyterian heritage, therefore, Setauket was a nest of Patriot sentiment. Religion in the American Revolution was enormously important. Indeed, George III once joked that the Revolution was a “Presbyterian War”—and he was largely right. New England, the most thoroughly Patriot region, was two-thirds Congregationalist and Presbyterian. These were not naturally revolutionary, but their core belief that kings must exercise their power righteously or risk rebellion by God’s Chosen compelled in them a natural sympathy for the American cause.

  High Church Anglicans, Low Church Anglicans, the Dutch, the Quakers, Methodists, and Irish Catholics—all doctrinally and historically opposed to the Yankees—populated the Middle Colonies, though in Pennsylvania, Quaker-loathing Ulster Presbyterians emerged as a powerful force. As a result, Long Island was peculiarly divided. Its eastern half, including Setauket, had once been part of Connecticut, and fire-and-brimstone Presbyterianism accordingly dominated. Few Presbyterians lived in its pro-British western half, where Anglicans and their allies predominated. The Quakers there—mostly merchants, professionals, and prosperous farmers—gravitated toward either neutrality or a diluted loyalty toward the Anglican status quo, partly owing to their distaste for Presbyterians, who had developed something of an expertise in persecuting them.

  Despite these social, political, and religious reasons for backing the rebellion, not every resident of Setauket volunteered to risk his life spying for Washington. The Culper spies also had very personal motives. Aside from the profane abuses perpetrated by Colonel Hewlett against his father’s church, Tallmadge held a grudge against the British occupiers for the death of his eldest brother, who had been captured during the Battle of New York and starved in prison.37

  Unlike Tallmadge, Caleb Brewster’s family doesn’t seem to have suffered loss, either of blood or of treasure, by British troops. Brewster was a man who simply relished action, more so if hand-to-hand fighting was involved. His adventuring started early. Born in September 1747, Brewster chafed as a farmhand on his father’s land in Setauket.38 Bored unto death, when he was nineteen he signed on to a Nantucket whaler that voyaged to Greenland, whose chilly, dark waters concealed a ferocious quarry: the sperm whale, whose head contained the clearest and sweetest oil of all the cetaceans. Whaling was a man’s work. For months, crewmen ate nothing but salt pork, rice, beans, and cornmeal dipped in a little molasses, and they knew they would stay way out there in the blue until either the food ran out, the captain fell overboard in a storm, or they hauled in enough oil to make the trip a profitable one.

  Once a whale was spotted, the whaleboats were lowered and the hunt was on. Muscles tore as the men pulled at the oars to bring the high-paid harpooner within range. Once launched, the spear stuck in the beast and pulled the suddenly fragile craft rapidly through the churn of its wake. Should a sailor be careless enough to be entwined in the snarls of a whirring line, he was yanked from the boat, never to be seen again. Then came the most dangerous time. A wounded, and angry, whale could assault the boat with its fluke, or still more terrifyingly, charge it head-on. “She came at our boat,” recalled one oarsman, “& furiously ran over us and oversat us & made a miserable rack of our boat in a moment.”39

  After a few years, having had his fill of whaling and with a nice stash of cash, Brewster joined a merchantman bound for London. Owing to his seafaring experience, Brewster served as a mate, and imbibed a great deal of invaluable nautical knowledge—which would come in useful as he navigated the Sound—the “Devil’s Belt”—in the dark of the wartime night.

  He
was back home by May 1775, when he signed a petition backing Selah Strong for the post of delegate to the Provincial Convention.40 Strong (born 1737) was a kinsman of Abraham Woodhull’s, as well as his neighbor. Demonstrating how intricately Setauket’s families were enmeshed, Strong’s sister would later marry Tallmadge’s father as his second wife, and his wife Anna’s relative, Mary, would marry Woodhull.41

  In December, Brewster joined the Suffolk County militia as second lieutenant, but was promoted to a full lieutenantcy in the spring of 1776 when Strong—now a captain—took command of the Seventh Company. In the confused aftermath of the Battle of New York, the four companies of minutemen disbanded, but those still willing to fight—including Brewster—made their way to New Haven and Rhode Island.42

  His thirst for adventure was temporarily sated when on October 28, 1776, Brewster and thirty-five other men took six whaleboats and three transports across the Sound to “bring off the effects of Colonel [William] Floyd.” Brewster and company instead captured two sloops taking on wood in Setauket bay. They returned to Long Island twice more. On November 6, they engaged a detachment of freshly enlisted troops, killed five or six of them, took twenty-three prisoner, and hauled in seventy-five muskets for the loss of one man, and one wounded. Two days later, they returned for Floyd’s belongings but were interrupted by an especially unlucky band of militiamen. Result: ten Loyalists lying dead and another twenty-three prisoners. The raiders suffered a sergeant killed in the firefight.43

  Later that month, Brewster volunteered as an ensign in the Second Company, Fourth Battalion, of the Fourth New York Regiment.44 He wasn’t long there. Three months later, in early 1777, Brewster, again a lieutenant, had transferred to the Second Continental Artillery, stationed in Connecticut. And there—apart from the time he dealt with Colonel Hewlett in Setauket—he remained until August 1778, when, tired of the land and homesick for the sea, Caleb Brewster wrote his first letter to General Washington.45

  Born in 1750, Abraham Woodhull, conversely, preferred farming the land and was more than happy not to go gallivanting around the world hunting sperm whales. Despite his appearance as a placid man of toil, Woodhull was inwardly a distinctly odd bird, whereas Brewster was a simpler soul. Both men were patriotic, but in no letter of his correspondence did Brewster ever evince much dislike of the British: One gets the feeling that he was partly in the game because it was fun. Woodhull, on the other hand, turned into a fierce, if outwardly circumspect, partisan, often writing how greatly he loathed his overlords. He derived pleasure from tricking and betraying them secretly.

  Aside from a couple of months as a lieutenant in the Suffolk militia in the fall of 1775, where he saw no action but was trained how to shoulder his musket and wheel smartly on command, Woodhull lacked the martial spirit of Brewster and Tallmadge.46 He never volunteered for further service.47 On a practical level, his two older brothers had died in 1768 and 1774, and Abraham was obliged to stay on the farm to keep it running and look after his aged parents.48 And in any case, at least until the Battle of New York, Woodhull was more politically moderate than Brewster or Tallmadge, more loath to join the colors that attracted so many young men. But something happened during that battle that radicalized him, and made his enmity toward the British more visceral than Brewster’s.

  It was his pang to avenge the callous and needless murder of his kinsman General Nathaniel Woodhull (born 1722) that propelled Abraham into Tallmadge’s secret world. Tallmadge, too, had lost a brother (as well as a near brother, Nathan Hale) during that battle, but as a hard-bitten soldier he understood, and had seen, that terrible things happened in war, and could accordingly rationalize their deaths as inevitable sacrifices in a glorious war of liberation. Brewster, as well, had witnessed shipmates sucked into the watery depths and accepted it as the natural course of events. Woodhull was gentler and unaccustomed to brutality. To him, the loss of Nathaniel came as a far more bitter and unfair blow, more so because his older cousin was an exemplar of moderation, not of revolutionary fervor.

  General Woodhull had fought bravely in the French and Indian War, but by 1776 he was better known as a politician with connections in both Tory and Whig camps.49 Woodhull, despite being the president of the Provincial Convention, did not sign New York’s endorsement of the Declaration of Independence, thinking it too radical and aggressive. He, like many others of moderate persuasion who acknowledged that the colonists did have a point, was reluctant to take such a momentous step as declaring war on Britain and sought to reconcile the two sides. That did not stop him being, as the local arch-Loyalist judge Thomas Jones disapprovingly opined, a “flaming republican,” an unfortunate trait he attributed to his being a “rigid Presbyterian.”50

  The general’s death was no ordinary one. In late August 1776, General Woodhull was ordered to burn grain and round up livestock that could be used by the British once they invaded Long Island. On the twenty-eighth, he wrote his last letter, to the Convention, from Jamaica, Long Island, saying that “my men and horses are worn out with fatigue.” He decided to stay the night at Increase Carpenter’s tavern, a place two miles east of the town. That evening the inn was surrounded by men of the Seventeenth Light Dragoons and the Seventy-first Foot; Woodhull, apparently while attempting to escape, was wounded in the head and arm and taken prisoner. That was the official story laid out in the British military record.

  Different versions soon emerged. A newspaper account said that Woodhull had refused to give over his sidearms, and so was “wounded on the head with a cutlass, and had a bayonet thrust through his arm.” Other sources claimed that Major Baird of the Seventy-first Foot had ordered him to say, “God save the King,” to which Woodhull replied, “God save us all,” whereupon he was assailed by Baird’s broadsword. And still others omitted Baird, and instead blamed one “Lieut. Huzzy” for striking the general, who was saved only by the intervention of “Major [Oliver] De Lancey.” James Fenimore Cooper, the Last of the Mohicans novelist who married into the De Lancey family, recalled in 1849 that Oliver had told him this was the case.

  The Continental Congress continued to investigate this dreadful instance of prisoner abuse into early 1777. Lieutenant Robert Troup, a New York militiaman who had been taken in a separate engagement, testified that having seen the “shocking mangled” Woodhull on board a transport, he approached him and asked “the particulars of his capture.” Woodhull himself said the dragoons—“under the command of Capt. Oliver de Lancey”—had asked whether he wished to surrender. When he replied in the affirmative, but only on condition he was treated as a gentleman, they accepted his sword but then De Lancey knavishly “struck him, and others of the same party imitating his example, did cruelly hack and cut him.” Taken to the Church of New Utrecht, the stricken Woodhull was deprived of medical care and food and died in agony on September 20. Some time later, Dr. Silas Holmes, a prisoner and assistant surgeon who attended the dying Woodhull, confirmed in a letter that “the wounded prisoners … were wallowing in their own filth, and breathed an infected and putrid air” during Woodhull’s time in the hospital. A few days later, Dr. Richard Bailey took over as superintendent and rapidly improved the conditions, though by then it was too late for Woodhull.

  However, John Sloss Hobart, who had been detailed by the Provincial Convention in October 1776 to negotiate for Woodhull’s release, made no specific mention of any ill treatment of the general. He said in his report that “the wound in his arm mortified” and the arm was amputated; Woodhull nevertheless continued to suffer gangrene, which carried him off a few days later. Indeed, “he was attended to in his dying moments by his lady, who was permitted to remove the corpse to his seat, where it was interred” about September 23. The Provincial Convention, summing up the case, also failed to cite mistreatment during his captivity causing his death.51

  It’s an intriguing mystery, to be sure, and we’ll never know whether De Lancey was Woodhull’s savior or his tormentor. Troup could easily have gotten his story mixed up, but the
n so too could have Cooper, seventy-five years after the event. As for the ill treatment of prisoners, this did happen disturbingly often, but then so too did dying after an amputation, especially one carried out in a dirty, jerry-rigged prison. It’s most probable that Woodhull—a general, after all, not a common soldier, though only of militia—received slightly better treatment than other prisoners (which isn’t saying much), but no one bothered to exert himself on a rebel’s behalf.

  For Abraham Woodhull, however, Troup’s account, the reports widely printed in the Patriot press, and the rumor mill all rang truer than the cover-up by the respectable Convention. He believed in the perfidy of De Lancey. And so Woodhull single-mindedly devoted himself to destroying the British, their allies, and all that they stood for by spying the daylights out of them. Thus, he leapt at the chance to serve Tallmadge.

  On October 29, 1778, after having sworn his oath of loyalty to His Majesty, Woodhull dispatched his first “Samuel Culper” letter. Hitherto he had passed on intelligence verbally for fear of incriminating documents falling into the enemy’s hands, so Tallmadge had assured him that none but he and Brewster knew his real name, and that, if captured, they would destroy the letters before surrendering. For safety’s sake, Tallmadge did destroy Woodhull’s original letter after copying it verbatim in his own handwriting and passing that version to headquarters. There was nothing left now to trace it back to Woodhull—though the experience of transcribing Woodhull’s epistles must have bored the busy Tallmadge, and he soon resorted to just sending on the originals—without telling his trusting correspondent.