When I hosted a conference a year ago on spies in the American Revolution, there was not enough time to talk about each of the known patriot spies, or speculate on the identities of anonymous agents or unproven spies. This feature takes a brief look at ten patriot spies, some who have become famous, others who remain obscure. Each of them has a story and contributed in different, heroic ways. Some were solitary agents—others were part of a ring of spies managed by a military officer.
Enoch Crosby (1750-1835) was a well-known double agent from southeastern New York who, despite his patriot sympathies, enlisted in a Loyalist militia in highly contentious Westchester County. He was able to maintain his cover while working as one of at least several agents employed by John Jay as part of his counterintelligence operations in the lower Hudson River Valley. His cover was maintained by his own cunning and by his being captured several times by patriot soldiers. His accurate, timely information significantly undermined Loyalist efforts in the region.
Author James Fenimore Cooper published his first best-selling novel, The Spy, in 1821. He based his leading character, Harvey Birch, on the exploits of Crosby as told to Cooper in many stories by his friend, John Jay, years after the war. Jay did not disclose Crosby’s name. Once the novel sold so well, Crosby decided to disclose himself. He wrote and published The Spy Unmasked: Or Memoirs of Enoch Crosby, Alias Harvey Birch. Sadly, much like the Cold War and today, the true exploits of this patriot hero did not sell nearly as well as the fictional account by the famous novelist.
Thankfully, Crosby’s house and gravesite both remain and are in excellent condition. The original headstone of Crosby’s grave in the small, rural Gilead Cemetery in Carmel, New York, fell into disrepair over a century ago. It was replaced sometime in the late 1800s with an impressive monument. The Enoch Crosby Chapter of the New York Daughters of the American Revolution helps keep his legacy alive.
Hercules Mulligan (1740-1825) was a native of Ireland who immigrated to New York, eventually opening a tailoring and haberdashery shop. He was an early mentor and landlord of young Alexander Hamilton. Mulligan graduated from King’s College (now Columbia University) and was a member of the New York Sons of Liberty. Hamilton recommended Mulliganas a patriot spy after the Continental Army was forced to withdraw from New York. Mulliganserved a dangerous role as a “stay behind agent” in the British-occupied city. He gathered important information while maintaining his career as a tailor with many British officers and Loyalist civilians as his clients. Mulliganalso received information from his brother, Hugh, a merchant. Mulligan’s primary courier was Cato, his slave, who would slip bravely between the city and patriot contacts. The legendary exploits surrounding Mulliganmake for interesting reading, with some stories more plausible than others. He may have saved General Washington’s life not once but twice, including thwarting a British plot to capture him in Connecticut in 1781. Like his friend Alexander Hamilton, Mulliganlater served as a founding member of the New York Manumission Society in their efforts to end slavery in New York. Appropriately enough, Mulligan is buried only yards from the grave of Hamilton in the southern section of the cemetery of Trinity Church on Broadway Avenue in lower Manhattan.
Sergeant Daniel Bissell
Daniel Bissell (1754-1824) was born into the locally prominent patriot Bissell family of the Windsor, Connecticut area. His cousin, Israel Bissell, was the courier who rode several horses all the way from eastern Massachusetts down to Philadelphia to alert locals and then Congress that British troops had confronted residents and regional militia at Lexington and Concord.
Bissell served in the war as a corporal in the 5th Connecticut Regiment and then as a sergeant in the 2nd Connecticut Regiment in the Continental Army. Under direct orders from General Washington, Bissell posed as a deserter in New York City from August 14, 1781 all the way until September 29, 1782. In order to obtain the key information that Washington desired, he enlisted in the British Army, specifically, the American Legion, the combined infantry and a cavalry unit commanded by Brig. Gen. Benedict Arnold. Bissell’s intelligence proved valuable, and remnants of it include his sketch of a British fort on Staten Island as part of his lengthy debriefing.
For his conspicuous gallantry he received his Badge of Military Merit from General Washington in June 1783, one of only three recipients of this prestigious award. Unfortunately, that “Purple Heart” was lost in his house fire in upstate New York in 1813. No portrait of him exists; he is often confused with a younger relative in Kentucky. Thankfully, his original grave remains at his gravesite in rural Allens Hill Cemetery in upstate Richmond, New York. There is also an adjacent, modern headstone, along with grave markers from five different patriotic organizations including the S.A.R., D.A.R., American Legion and Purple Heart Association.
Judge Joshua Daniel Mersereau
No proper list of patriot spies would be complete without mentioning at least one member of the large Mersereau family spy ring. Joshua and his brother John deserve acknowledgement for their exploits as two teenage boys from Elizabethtown (now the city of Elizabeth), New Jersey. Their spy activities haven been overshadowed by others such as the Culper Ring. Both Joshua and John were born on nearby Staten Island, and provided important intelligence several years before the Culper Ring even existed.
Joshua (1759-1857) and John (1760-1841) were among the five brothers who served different roles in the war, each of them sons of patriot leader Maj. Joshua Mersereau. (The family surname is spelled with either an s or a c, depending on the family member.) Dad’s role as owner of a local stagecoach line operating in New Jersey between Philadelphia and New York, as well as his role as deputy commissary of prisoners under Elias Boudinot, also of Elizabethtown, provided both logistical as well as informational support for the two brave sons.
Maj. Gen. Israel Putnam relied on their intelligence in a later part of 1776, and by December 1776, Joshua and John discovered evidence of British preparations to pursue the retreating Continental Army across the Delaware River. The Mersereau brothers might have played a role in exposing Maj. John Andre as Maj. Gen. Benedict Arnold’s handler because of Andre’s use of the alias, John Anderson. Much of the correspondence between Arnold in Philadelphia and Andre in New York passed through New Jersey, perhaps on the Mersereau stagecoach line.
John’s gravesite is unknown, but Joshua has a well-marked grave in rural Presho Cemetery, along Interstate 99 and the Tioga River in the upstate town of Lindley, New York. Amazingly, Joshua lived to age ninety-seven, dying in 1857. His gravesite includes a large, twentieth-century replacement of his long-gone original headstone.
Colonel Allen McLane
Thanks to the career as well as cogent historical scholarship of regular JAR contributor Ken Daigler, readers can more fully appreciate the important contributions of Allen McLane (1746-1829) in two key roles as intelligence officer (handling spies) and as a spy. According to Daigler, that was a rare combination. Initially, McLane was a Delaware militia officer in 1775 and 1776 before being commissioned a captain in the Continental Army in January of 1777. Daigler describes how McLane juggled overt and covert roles as a cavalry officer who also debriefed his informants. A lengthy letter from General Washington on October 29, 1777 included twenty-seven military intelligence questions for McLane. This demonstrated Washington’s dependence on reliable information from McLane and his paid sources. Most importantly, McLane was later able to warn Washington of British movement towards Washington’s main army encampment at Whitemarsh, Pennsylvania. This allowed Washington to prepare his army for what he hoped would be another large battle with patriots holding the high ground, similar to Bunker Hill.
Later in the war, McLane served as a soldier, intelligence officer and spy in two battles—Stony Point in July 1779 and Paulus Hook a month later. Finally, Washington sent McLane into New York City in the fall of 1781 to meet with James Rivington, the important intelligence agent and Tory newspaper printer.
Following the war, McLane worked as a farmer in Delaware, served as a member and speaker of the Delaware legislature, and in many other civic roles, including judge and collector of the port of Wilmington. He was an avid abolitionist and an original member of the Delaware Society of the Cincinnati. McLane and his wife Rebecca are marked by their original tablestone monument only a few feet from the Asbury Methodist Episcopal Church Cemetery in downtown Wilmington. The lettering on the horizontal stone is difficult to read. Much like Col. Elias Dayton’s (case officer of the Mersereau-Dayton Ring) crypt in downtown Elizabeth, New Jersey, their gravesite is unfortunately not marked with either a U.S. flag or patriot society markers.
The previous five patriots involved in espionage may not be as familiar to readers as the following five patriots, each of whom performed different roles in the long-famous Culper Spy Ring that operated between British-held New York City, Long Island, Connecticut and wherever Washington’s headquarters were as he and his main army moved in the tri-state region.
Lieutenant Colonel Benjamin Tallmadge
Before the famous Culper Ring could be created at General Washington’s request, it needed a handler or case officer to supervise the spies and couriers as well as filter and transmit their intelligence to General Washington. Benjamin Tallmadge (1754-1835) proved a very capable case officer, recruiting trusted friends from his childhood spent in Setauket, Long Island. His intelligence responsibilities were personally charged, as he had lost his best friend and classmate at Yale, Capt. Nathan Hale, to the dangers of the spy trade. Tallmadge recruited Abraham Woodhull as his initial primary agent or spy.
Tallmadge also created a concise but effective code book that improved the tradecraft, secrecy and plausible deniability of the entire ring, including himself as well as his boss, General Washington. Washington would simply be referred to as 711, while Tallmadge numbered himself 721 and went the extra step for protection by listing himself with the alias “John Bolton” in case any of the three code books should fall into enemy hands. While some historians have attributed more accomplishments to the Culper Ring than they actually performed or achieved, the tradecraft proved fascinating, including the use of aliases, the Tallmadge code book, the occasional use of invisible ink, and the dramatic dynamics of the ring spread over a very large geographic area.
Tallmadge also served as a brave cavalry officer who personally trained the 2nd Continental Light Dragoons on the town green in his temporary hometown of Wethersfield, Connecticut during the early part of 1777. Towards the end of the war, in 1782, he purchased a stately home in rural Litchfield, Connecticut, which was Litchfield County’s center and included the county courthouse. Tallmadge became a prominent local merchant, opening a shop adjacent to his home. He helped create Phoenix Bank down the street, and he later served several terms as a Federalist U.S. Congressman. He was an original member of the Society of the Cincinnati in Connecticut. His children and grandchildren convinced him to write his memoir, which was not published until 1858, thirty-three years after his death. Tallmadge and his wife, Mary Floyd Tallmadge, are buried in the town center’s cemetery just down the hill from his house and the center of town. Each 4th of July their well-maintained gravesite is part of a celebration of the heroic deeds of patriots in the American Revolution. This author held a special ceremony there in September of 2019 as part of his American Revolution Spy Symposium to help celebrate the town of Litchfield’s three hundredth birthday.
Abraham Woodhull (1750-1826) was a childhood neighbor of young Benjamin Tallmadge in the seaside village of Setauket, located on the north shore of Long Island. Tallmadge approached him in August 1778, recruiting him as his primary agent for intelligence on British military planning and operations in and around New York City. Woodhull agreed to serve, and he sent his first dispatch as “Samuel Culper” on October 29, 1778 after he had sworn an oath of loyalty to the British King, which helped maintain his cover as an agent. Tallmadge assigned him the number 722.
Woodhull initially gathered information by traveling into New York City to visit his sister and brother-in-law’s boarding house where British officers often stayed. He could eavesdrop there and at nearby locations while also gathering some needed supplies for his family farm as part of his cover. He would return to Setauket to send the new intelligence by letters using his alias and later included some numerical codes based on Tallmadge’s code system. His dispatches would arrive in Tallmadge’s hands, often in Fairfield, Connecticut, via his couriers Caleb Brewster and, later, Austin Roe.
Woodhull married his friend Mary Smith in 1781 and they had three children together. She died in 1806. He remarried in 1824 to Lydia Terry. He died in Setauket in 1826 and is buried in the Setauket Presbyterian Church and Burial Ground. His original headstone is embedded into one side of the brick facades of a simulated table stone grave marker that was probably constructed in the early twentieth century; the site is well-maintained.
Robert Townsend (1753-1838) was born, raised, and died in Oyster Bay, Long Island, about thirty miles west of Setauket. He was raised like many on Long Island at that time as a Quaker, who were overwhelmingly pacifist. According the Ken Daigler, General Washington waited until the summer of 1779 to allow Tallmadge and Woodhull to add an intelligence agent. Woodhull then recruited his friend Townsend to share in the duties of primary agent. The agreed arrangement added some complexity but generally worked well. Townsend was given the alias of “Culper, Jr.” and the Tallmadge code book number 723, while Woodhull revised his alias to “Culper, Sr.” That alias helped provide some cover, as Townsend and Woodhull were not related.
Townsend wasted no time in providing helpful intelligence, sending his first dispatch on June 29, 1779. Just two weeks later Culper Junior informed and warned Tallmadge and then Washington of a British double agent posing as a patriot but working for Loyalist New York City Mayor David Mathews. Townsend also informed Tallmadge and Washington of the British seizure of reams of special paper used by U.S. Congress to produce money. This discovery helped prevent British counterfeit money from flooding the U.S. market.
Providing timely intelligence while living as a stay-behind agent inside British-held New York City was particularly dangerous work. Naturally, Loyalists and British alike became suspicious of Townsend, but they never caught him performing any espionage or even discovered his two small glass containers of invisible ink and developer. He did have very close calls while living mostly in what is now South Street Seaport in southeastern Manhattan. The arrest ordered by traitor General Arnold of Hercules Mulligan as a suspected spy for the patriots understandably caused fear for Townsend. He suspended his secret communication to better ensure his safety, resuming his cover correspondence in 1782, sending what was likely his last dispatch on September 19, 1782.
After the war Townsend ended his business in New York and returned to Oyster Bay to lead a quiet life. He never married. A profile sketch in ink of Townsend reading a book survives, as well as his family’s house “Raynham Hall” in Oyster Bay. Just several blocks south of his house is the Townsend Family Cemetery, well marked behind a house with a large “Fort Hill” sign. Much like the modest spy that Townsend was, his small headstone is tucked alongside a fence. The stone is structurally sound and regularly memorialized with flowers, flags and markers from organizations such as the S.A.R.
Anna Smith Strong
This author chose to include Anna Strong (1740-1812) because, despite unproven stories of her role in the Culper Ring, she reminds readers of the likelihood of at least several brave patriot women who served in various espionage roles during the American Revolution, in the New York region and elsewhere. Their mostly undocumented, heroic efforts are lost to history, much like many patriotic efforts of female spies during both World War II and the Cold War.
The popular story that cannot be proven is that Anna, a native of Setauket, would hang her laundry in different patterns to dry—hidden in plain sight as a coded signal known only to Caleb Brewster, primary courier for the Culper Ring, telling which cove in the Setauket area to enter to retrieve the latest dispatches from Woodhull or Townsend.
Proof of Anna’s role in the Culper Ring remains elusive. She and her husband led a quiet life in Setauket and they are buried together in Setauket under a fine, Federal-era monument, marked by the D.A.R., at St. George’s Manor Cemetery, within view of one of the several coves Brewster likely entered during the war.
Captain Caleb Brewster
Caleb Brewster (1747-1827) was born in Setauket and was a friend of the Woodhull and Strong families. He is included on this list of ten spies to remind readers of the importance of the dangerous work of couriers who might not gather intelligence, yet often faced very difficult and perhaps deadly confrontations while transmitting intelligence from one location to another, especially as suspicion and clues mounted for astute observers. Captain Brewster also made his own independent, direct reports to General Washington regarding British naval activities in New York and Long Island Sound, so he also performed as an agent himself. Examples of Brewster’s intelligence reports to Washington between 1778 and 1781 remain in the Washington Papers at the Library of Congress.
Brewster made regular trips between Fairfield, Connecticut and Setauket, Long Island, New York via his whaleboat. He also travelled in his small craft along the coast of Connecticut, sending dispatches from shoreline locations such as Norwalk.
Following the war Brewster married Anne Lewis of the Connecticut coastal town of Fairfield and moved there. The cove where he very likely came and went in his whaleboat to operate as a courier and spy is next to where he lived later in life, and came to be called Brewster Cove. This eastern section of Fairfield, called Black Rock, became part of Bridgeport in 1836.
Brewster would later serve as captain commanding of one of several cutters—small, fast vessels designed for quick intervention—for the U.S. Revenue Cutter Service created in 1791 by Alexander Hamilton. The Cutter Service later became known as the U.S. Coast Guard.
Brewster died at age seventy-nine. He and his wife are buried in a historic cemetery across the street from the childhood home of this author. The Old Burying Ground is located behind the Old Town Hall, near the corner of Beach Road and Old Post Road. His vertical wide headstone is difficult to read but is structurally sound and well-marked and maintained.