George Washington's Long Island: A History and Tour Guide

INTRODUCTION

A courier meets clandestinely with a merchant in Manhattan. He’s given a report on British troop dispositions written in invisible ink. He hides the document in his saddle, takes a ferry across the East River and then speeds fifty-five miles east to Setauket. There the letter is handed off to a farmer who passes it to a whaleboat captain waiting in a secluded cove. The document is rowed across Long Island Sound and carried by a relay of dispatch riders to General George Washington’s headquarters north of New York City, where it guides the Continental Army’s commander in chief in planning his moves.

That ongoing Revolutionary War scenario may not be as famous or compelling as the one-time ride of Paul Revere and his two Boston compatriots to warn their fellow Patriots of the coming of the redcoats to Lexington and Concord. But it is one of the most critical activities of the American Revolution because the efforts of what has become known as the Culper Spy Ring played an important role in winning independence from Great Britain.

The Patriot commander knew that gaining intelligence of British military actions through a spy network was critical if his underdog army was to have a chance of successfully fighting the largest military power in the world for the colonies’ independence. So when the British gained control of New York City and Long Island after the Battle of Long Island in 1776, Washington began a long and difficult process of creating an espionage operation in the region.

A 1776 map of Long Island. Long Island Studies Institute at Hofstra University .

Historians have long been fascinated by the intelligence efforts undertaken by the patriotic and enthusiastic amateurs. In more than a dozen books, researchers have tried to sort out who was involved and exactly what their roles were. The biggest mystery was the identity of Culper Junior, the chief spy in Manhattan in the later years of the war. Most of the spy ring operatives identified themselves or were identified after the war, but not Culper Junior. So when Suffolk County historian Morton Pennypacker revealed him to have been Robert Townsend of Oyster Bay in 1930 and then proved it with document analysis nine years later, it generated considerable attention.

Interest in the Patriots’ intelligence network soared when the AMC television series Turn: Washington’s Spies aired for four seasons between 2014 and 2017. Unfortunately, it took great liberties with the facts. These included having the ring created in 1776 rather than two years later, depicting Setauket as a neighborhood of stately stone homes rather than wooden structures, having the hamlet occupied by regular army redcoats rather than Loyalist troops wearing green, portraying Abraham Woodhull’s minister father as a Tory socializing with the occupiers rather than showing the reality of him being a Patriot sympathizer badly beaten by soldiers trying to find and arrest his son and, most ludicrously, having Woodhull and the happily married and older Anna Strong engage in a secret affair. But the series did get people reading and talking about espionage during the war.

As with Turn , Pennypacker and many of the authors who have written about the Culper Ring subsequently have strayed from the truth. Pennypacker’s books, which lack footnotes, transformed some anecdotal information and legends into fact. And later writers have often repeated that material without researching or even questioning it. And while they may have sought information from Long Island historians who have spent decades studying the subject, they didn’t always listen to them.

The most prominent writer in that category would be Fox News co-host Brian Kilmeade, who lives on Long Island. In preparing his 2013 bestseller with coauthor Don Yaeger and other writers, he convened gatherings of local historians from Culper-connected locations such as Setauket and Oyster Bay. They provided him with much information, some of which he ignored when it didn’t fit into his narrative. He also strayed into historical fiction by filling the book with invented dialogue without indicating that the words were never spoken by the participants.

Kilmeade’s work is also filled with supposed statements of fact that can be disputed. These start with the title and subtitle of the book: George Washington’s Secret Six: The Spy Ring That Saved the American Revolution. In a volume lacking footnotes and offering only a smattering of sources, the authors state that the spy ring consisted of exactly six individuals. Many more than that played roles in the operation, including couriers and boat captain Caleb Brewster. He played a critical role in carrying the messages across Long Island Sound to get them to George Washington’s headquarters. Without Brewster there is no Culper Spy Ring. They have Robert Townsend playing the central role. While he was certainly important and the main source of information from New York City in the later years, the chief spy who coordinated the espionage throughout the war was Abraham Woodhull of Setauket. Without him, the spy ring never would have been created.

Furthermore, Kilmeade and Yeager include two individuals among their chosen six who are questionable: James Rivington and a mysterious woman named as only Agent 355. Local historians have concluded that Rivington, publisher of a Loyalist newspaper in Manhattan, is unlikely to have served as a spy and was definitely not part of the Culper Ring. They, and other historians, believe there was no Agent 355, as discussed in chapter 5. And while other historians generally agree the Culper network played an important role, no one else goes as far as to say that it saved the American Revolution. Their contention that the spy ring broke the back of the British military is hyperbole.¹

This volume attempts to synthesize the known information on the spy ring while sorting fact from historical fiction, which makes it unique. I’m hoping readers will care about the nuances of where and how Nathan Hale was captured, for example. I wanted to create the definitive account of the spy ring with the help of the local experts who are often overlooked or ignored and set the record straight on stories such as Anna Strong using her clothesline to signal where Caleb Brewster would be coming to pick up and drop off letters as a service to researchers and history buffs.

Now it will be up to the readers to make up their own minds.

Those readers will notice in the following chapters variant spellings of some words, especially place names, in quotations from the letters. In the late eighteenth century, spelling was not yet standardized. In all of the Culper letters cited, irregular spellings have not been corrected, and no editorial [sic ] has been added for misspelled words. Only when abbreviations or misspellings make it difficult to understand what is written will the corrected spelling be inserted in brackets. Capitalization and punctuation also follow the original cited source.

PART I

THE CULPER SPY RING

1

THE BATTLE OF LONG ISLAND

In early June 1776, several British warships appeared off Sandy Hook at the entrance of New York Harbor. General George Washington and his officers suspected an attack on New York was imminent. But they never did anything to fortify either side of the Narrows between Brooklyn and Staten Island to keep the British out of the Upper Bay and away from Manhattan.

As a result, when the rest of the British fleet began to arrive on June 29, there was nothing to stop them. And by the following day, the entire fleet had arrived from Halifax, Nova Scotia, and was gathered in the Lower Bay south of the Narrows. One observer wrote that it looked like something resembling a wood of pine trees.²

On July 2—the day that the delegates at the Continental Congress in Philadelphia would vote to declare independence—the British ships began sailing up through the Narrows. By 9:00 p.m., the redcoats had landed unopposed on Staten Island, where they were welcomed by the mostly Loyalist residents and the local militia.³

More reinforcements would follow until General William Howe had 24,000 soldiers—including 7,800 mercenaries from Hesse (Hessians)—at his command, along with nearly 400 transport ships and smaller landing craft built on Staten Island to move the troops to Long Island. The warships, manned by 10,000 sailors, were commanded by General Howe’s brother, Lord Richard Howe. It was not only the largest and best-equipped expeditionary force ever mounted by the British but also the largest invasion force ever assembled anywhere before D-Day in 1944. The whole Bay was full of the shipping as ever it could be, wrote Continental Army private Daniel McCartin.⁴

Howe’s initial plan was to trap and destroy the Continental Army in a single decisive battle. But the general changed his mind, deciding to force Washington and his troops out of western Long Island and New York City so he could easily take control of the whole region. Subordinates Henry Clinton and William Tryon urged Howe to land north of the city on Manhattan Island to cut off the Patriots from the mainland, but Howe decided to land on Long Island instead.⁵

Howe changed his strategy because western Long Island was Loyalist territory that could supply his army with provisions and timber instead of having to rely on a supply chain that spanned the ocean. The commanding general also reasoned that attacking Manhattan while ignoring Brooklyn could leave his troops subject to fire from batteries in Brooklyn Heights.⁶

New York was clearly undefendable without huge forts at its gateways or overwhelming sea power, and the Patriots had neither. But giving up the city without a fight was politically impossible and would have struck a serious blow to colonists’ morale. Congress strongly instructed the army commander to defend New York. So Washington established a line of fortifications across northwest Brooklyn. At Brooklyn Heights, a line of forts, redoubts and trenches ran one and a half miles from Wallabout Bay—now the site of the Brooklyn Navy Yard—on the north to Gowanus Bay on the south. Several miles southeast of Brooklyn Heights, at the current site of Green-Wood Cemetery, the Continental Army occupied a thickly forested ridge—the terminal moraine left behind by glaciers as high as 190 feet above sea level and called the Heights of Guan, or Gowanus.⁷

The Patriots’ fortifications in Brooklyn Heights were initially oriented to protect against an attack from the East River. But eventually, Washington and his generals realized they were vulnerable to attack from the south as well, from the interior of Kings County. Southeast of Brooklyn Heights, newly promoted Major General Nathanael Greene ordered his four thousand men to work on a new chain of forts and trenches that would extend a mile and a half to protect the rear or southern side of the Brooklyn Heights fortifications. Each of the five redoubts was surrounded by a wide ditch, and the breastworks that connected them were also fronted by a ditch.⁸

Washington knew that for the British to attack from interior Brooklyn, they would have to get through one of four passes where roads cut through the Heights of Guan. From west to east the passes were known as Martense Lane, Flatbush, Bedford and Jamaica. The distance between the westernmost and easternmost passes was six and a half miles. General John Sullivan had his men cut down trees for roadblocks and breastworks for artillery at the three westernmost passes and planned to station eight hundred men at each. He did nothing to protect Jamaica Pass, four miles from the Brooklyn Heights fortifications, apparently thinking it was too far east for the British to utilize. To defend New York, Washington had nineteen thousand troops, Continental regulars and militiamen.⁹

A detail from Plan of the attack on the provincial army on Long Island, August 27th 1776. With the draughts of New York Island, Staten Island, and the adjacent part of the continent by John Bowles, 1776. Library of Congress.

Washington desperately needed to know Howe’s troop strength and intentions. But early in the war, the Continental Army had no well-organized intelligence network. There was one operative living on Staten Island, probably John Mersereau, son of a patriotic merchant who was already supplying intelligence to Washington. But for days, Washington had trouble finding someone who could reach Mersereau. It was only on August 20 that a courier named Lawrence Mascoll was able to rendezvous with the agent and return to headquarters by the twenty-second with an accurate description of the British forces. Unfortunately, that was the day the British began moving troops from Staten Island to Long Island.¹⁰

As former Central Intelligence Agency senior case officer Kenneth Daigler wrote, [F]or intelligence to be useful it must also be timely, and in this case, because of the lack of a functioning clandestine communication system, it arrived too late to assist Washington and his defensive preparations. The only information Washington had on the attacking force came from his scouts. And because of the fact that these localized reports could only describe the British presence each scouting party saw, Continental Army commanders had the impression that the attacking forces were only about half the actual British strength.¹¹

As the battle was looming, Patriot Brigadier General Nathaniel Woodhull was given an important task. Woodhull was born into a wealthy landholding family in Mastic in 1722 and later married his neighbor Ruth Floyd, sister of William Floyd, a signer of the Declaration of Independence. At age thirty-six, Woodhull enlisted with the New York provincial militia as a major to fight for the British in the French and Indian War and rose to the rank of colonel. Woodhull had been appointed commander of the combined militias of Suffolk and Queens Counties by the New York Provincial Congress, which he served as president. He had connections with both Loyalist and Patriot factions, and he did not sign the state’s endorsement of the Declaration of Independence because he thought it was too radical a move.¹²

Woodhull was ordered to take 190 militiamen to herd cattle spread across Long Island and drive the livestock east to keep it out of British hands. Although more than half of his men had deserted by late on August 27, five days after the British began their assault in Brooklyn, Woodhull’s troops had driven 1,400 cattle out onto the Hempstead Plains and had 300 more ready to move. The next day, he wrote his final letter to the state convention from Jamaica, stating that my men and horses are worn out with fatigue.¹³

During a severe thunderstorm, the general took refuge for the night in a tavern run by Increase Carpenter about two miles east of Jamaica. After a British cavalry patrol surrounded the tavern, Woodhull was captured and mortally wounded in the head and arm. Various accounts have him caught and wounded while trying to escape over a fence—the official British version—or Woodhull standing his ground and offering his sword in surrender before being slashed by an officer’s saber, or slashed after refusing to surrender his sidearms. According to legend, a British major ordered Woodhull to say God save the king! The Mastic resident instead defiantly proclaimed, God save us all! before being wounded. While it’s unlikely Woodhull uttered those words, he became a martyr and Long Island’s most prominent military casualty of the war.¹⁴

There are also conflicting accounts of what happened to Woodhull after he was wounded. Most authors have him treated by a British surgeon in Jamaica, then sent aboard a prison hulk in New York Harbor and later taken to a hospital in Brooklyn, where his gangrenous arm was amputated before he died. Alexander Rose, author of Washington’s Spies, has Woodhull transported to the Church of New Utrecht in Brooklyn, where he was deprived of medical care and food. All the accounts agree that Woodhull died on September 20 at age fifty-four and was buried at his Mastic home.¹⁵

As Woodhull and the rest of the Patriot commanders prepared for the coming attack, General Howe was ready to move his forces from Staten Island to Brooklyn on August 18. But stormy weather delayed the transfer. It took several days to load fifteen thousand troops onto transports. On the twenty-second, the advance guard of four thousand troops under Clinton and Lord Charles Cornwallis waded ashore from Gravesend Bay north to Denyse’s Ferry—now Fort Hamilton—with more troops to follow as the landing craft were reloaded. With the bay filled with more than four hundred vessels, the Continental Army made no attempt to interfere with the landing, and the British operation moved smoothly. Most of the troops landed in only three hours, from 9:00 a.m. until noon. Landing craft built on Staten Island with ramps that could be lowered at the bow allowed the British to bring forty pieces of artillery with them.¹⁶

The fatal wounding of General Nathaniel Woodhull during his capture while trying to keep livestock out of the hands of the British on Long Island in August 1776. Long Island Studies Institute at Hofstra University.

Skirmishing broke out the next day, the twenty-third. Washington, unsure of where the major British blow would land and concerned that the Brooklyn landing was a feint, remained in Manhattan receiving dispatches. He crossed the East River on the twenty-sixth and spoke to the troops in Brooklyn. The commander in chief warned them that he had given orders that any soldier who attempted to skulk, lay down, or retreat without Orders would be instantly shot down as an example. He added that the enemy have now landed on Long Island, and the hour is fast approaching on which the Honor and Success of this army and the safety of our bleeding Country depend.¹⁷

With almost twenty thousand redcoats and Hessian mercenaries in Brooklyn facing a Continental Army of fewer than nine thousand, the Battle of Long Island—also known as the Battle of Brooklyn—began about 2:00 a.m. on August 27. It would be the largest engagement of the American Revolution.

The fighting started on the western end of the Continental Army line at the intersection of the Gowanus Road and the Martense Lane Pass. British General James Grant had been ordered to make the feint that Washington had feared to distract the Patriots by attacking their right flank. About three hundred redcoats made the initial assault, surprising the defenders who fled up the Gowanus Road. The colonials’ commander, Major James Burd, was captured with some of his men, but not before he managed to dispatch a messenger to General Israel Putnam in Brooklyn Heights.

Putman ordered his soldiers into the fortifications and used signal lights to alert Washington to come from Manhattan. Putman directed General William Alexander, also known as Lord Stirling, to respond to the British attack. He gathered almost two thousand men, including troops from Delaware and Pennsylvania and Colonel William Smallwood’s elite First Maryland Regiment, for a counterattack. It was the first time that the two armies confronted each other in regular battle formation in open terrain. The Continental Army surprised the British by holding its ground against repeated attacks until the true intentions of the redcoats were revealed to the east.¹⁸

General Howe had begrudgingly accepted the suggestion of his chief subordinate, Henry Clinton, to turn the enemy’s left or eastern flank and get behind the bulk of the Continental Army on the higher ground by capturing and marching through the Jamaica Pass. It would require a column to march six miles at night. About 8:00 p.m. on the twenty-sixth, the advance element of about four thousand troops with fourteen cannons stepped out from Flatlands. Clinton covered the movement by leaving a regiment to maintain campfires and make campground sounds. Anyone encountered along the way was taken prisoner to prevent the spreading of an alarm.¹⁹

The first Patriots to learn where the primary attack would strike were five officers on guard just south of the Jamaica Pass about 3:00 a.m. They were taken from behind by the British, who had left the Jamaica Road, which the Patriots were watching, and traveled across fields to the critical spot. Clinton seized the passage at dawn and two hours later was joined by General Howe, who had left Flatlands at midnight at the head of an additional six thousand troops.²⁰

By 8:00 a.m., the British column of 10,000 troops had turned westward and was now behind the 2,500 Patriots defending the three other passes. At 9:00 a.m., Howe had two cannons fired as a signal to the rest of the troops south of the ridge that he was in position. Colonel Samuel Miles, whose 500 Patriot troops had been guarding the area east of the Bedford Pass, had learned about the British movement along the Jamaica Road about 7:00 a.m. and marched his men east through the woods. He ended