Washington's Spies

1. Early Intelligence Failures Highlight Washington's Need

Intelligence is the life of every thing in war.

Washington's early struggles. General George Washington quickly learned the critical importance of timely and accurate intelligence, especially after defeats like the Battle of New York in 1776. His initial attempts to gather information were often haphazard and unsuccessful, relying on unreliable scouts or agents caught quickly behind enemy lines. The disastrous fire in New York City, while beneficial to the American cause by denying the British winter quarters, also highlighted the lack of control and reliable sources within occupied territory.

Nathan Hale's tragic mission. The story of Nathan Hale exemplifies these early failures. Sent on a mission to Long Island just before the British invasion of Manhattan, Hale was ill-suited for espionage, easily recognized, and quickly captured by Robert Rogers, a seasoned British ranger and spy hunter. Hale's execution, while later mythologized, was a tactical failure that yielded no useful intelligence for Washington and underscored the need for better planning, training, and agent selection.

Lessons learned. Hale's death and other early setbacks taught Washington valuable lessons. He realized the need for:

• Agents specifically trained for clandestine work.
• Secure communication channels.
• Permanent agents embedded behind enemy lines.
• Cross-referencing information from multiple sources.

These lessons would lay the groundwork for a more sophisticated intelligence operation.

2. The Genesis of Washington's Secret Service

The advantage of obtaining the earliest and best intelligence of the designs of the enemy... have induced me to entrust the management of this business to your care.

Formalizing intelligence gathering. Recognizing the deficiencies, Washington began to formalize his intelligence efforts in early 1777. He appointed Nathaniel Sackett as his first spymaster, tasking him with recruiting agents and establishing communication lines, particularly in British-occupied New York. Sackett, though ultimately unsuccessful, experimented with innovative tradecraft like using realistic cover stories and attempting to embed agents long-term.

Early agents and methods. Sackett and other officers like General Charles Scott and Major John Clark experimented with various approaches:

• Sending scouts on short reconnaissance missions.
• Recruiting civilians with access to British areas.
• Using seemingly innocuous cover stories (e.g., poultry traders).
• Attempting to infiltrate British circles.

While these early efforts yielded some useful tactical information, they were inconsistent and often compromised, demonstrating the difficulty of operating against a vigilant enemy.

Tallmadge's emergence. Benjamin Tallmadge, a young dragoon officer and friend of Nathan Hale, was initially appointed as Sackett's military liaison. Tallmadge showed a natural aptitude for the work and, after Sackett's departure, began to take a more central role. His vision for a permanent, secure network of agents-in-place would eventually form the core of Washington's most effective spy ring.

3. Forging the Culper Ring: A Network of Trust

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.

Building on local ties. Tallmadge leveraged his deep connections in Setauket, Long Island, to build his network. He recruited Abraham Woodhull ("Samuel Culper Sr."), a local farmer and friend, who, despite initial timidity, was motivated by patriotism and a personal vendetta against the British for the death of his kinsman, General Nathaniel Woodhull. Woodhull's local knowledge and trusted relationships were invaluable.

Key members emerge. The core of the ring solidified with the inclusion of Caleb Brewster, a fearless whaleboatman from Setauket, who provided the crucial link across Long Island Sound. Austin Roe and Jonas Hawkins, also from Setauket and known to Woodhull and Brewster, served as couriers, undertaking the dangerous journey between Long Island and New York City.

Trust as the foundation. Unlike mercenary spies, the Culper members were primarily motivated by patriotism and mutual trust forged over years of shared history and community ties. This deep personal bond was a critical factor in the ring's resilience against British counterintelligence efforts, as they were fiercely loyal to each other and Tallmadge.

4. Developing Essential Spycraft: Ink and Code

Jay’s recipe, however, was revolutionary enough to amaze Washington.

The need for secure communication. As the ring developed, the need for secure communication became paramount. Plaintext letters were too risky, and simple methods like heat-activated invisible inks were easily detected. Washington sought more sophisticated methods to protect his agents and the intelligence they gathered.

The sympathetic stain. Sir James Jay, brother of John Jay, provided Washington with a revolutionary "sympathetic" ink. This ink was invisible when written and could only be developed by applying a specific chemical reagent. Washington was highly impressed, calling it a "sympathetic stain," and it became a cornerstone of the Culper Ring's security, allowing agents to hide secret messages within seemingly innocuous letters.

The Culper Code. To further protect against interception, Tallmadge developed a simple numerical code based on a dictionary. Key words and names were assigned numbers, and a basic substitution cipher was used for other words and letters. While not cryptographically complex by European standards, this code was sufficient to baffle casual readers and provided an additional layer of security when combined with the invisible ink.

5. Recruiting the Key Agent in New York City

He was a man of parts and halves in a time of wholes and absolutes.

The need for a city source. While Woodhull provided valuable information from Long Island, Washington desperately needed a reliable agent embedded in the heart of British operations in New York City. This agent needed access to military and political gossip, shipping movements, and troop deployments.

Robert Townsend joins the Ring. Abraham Woodhull, while staying at Amos Underhill's boardinghouse in New York, cultivated a relationship with Robert Townsend, a merchant from Oyster Bay. Townsend, outwardly a Loyalist collaborator, was inwardly conflicted and increasingly disillusioned with the British occupation due to its corruption and abuses, particularly in his hometown. Woodhull, sensing Townsend's disaffection and trusting his character, recruited him as "Samuel Culper Jr."

Townsend's unique position. Townsend's background and business provided ideal cover:

• His family's Quaker background instilled a degree of discretion.
• His merchant business gave him legitimate reasons to interact with British officers and officials.
• His investment in James Rivington's coffeehouse, a hub for British officers, provided access to valuable gossip.

Townsend became the primary source of intelligence from within New York City, providing crucial insights into British plans and movements.

6. Challenges and Tensions Within the Ring

Security and timeliness were incompatible virtues—there would always be a trade-off between them.

Balancing speed and safety. The Culper Ring constantly struggled with the inherent tension between getting intelligence quickly to Washington and ensuring the safety of its members. Woodhull, in particular, was highly cautious and often delayed sending messages if he perceived a risk, frustrating Washington's desire for speed.

Internal conflicts. Tensions arose within the ring, notably between Woodhull and Townsend. Townsend, initially hesitant and later unnerved by close calls, sometimes refused to write reports or insisted on specific, difficult-to-arrange rendezvous. Woodhull, as the cell leader, had to manage these issues, often feeling the pressure from both Washington and his agents.

Financial strain. Despite their patriotic motives, the agents incurred significant expenses for travel, lodging, and supplies. Washington, often short on hard currency, struggled to reimburse them promptly, causing frustration and adding to the agents' anxieties about their financial security after the war.

7. Delivering Crucial Intelligence to Washington

What Roe brought back was explosive.

The communication chain. The established route for intelligence was complex: Townsend gathered information in New York, passed it verbally or in invisible ink to a courier (Austin Roe or Jonas Hawkins), who rode to Setauket. Woodhull received the message, added his own observations, and signaled Caleb Brewster, who crossed Long Island Sound by whaleboat to meet Tallmadge in Connecticut. Tallmadge developed the ink, deciphered the code, added his analysis, and sent the package via express riders to Washington's headquarters.

Key intelligence successes. Despite the challenges, the Culper Ring delivered vital intelligence:

• Warnings of British troop movements and naval preparations (e.g., before Tryon's raids on Connecticut).
• Details on British fortifications and troop strength in and around New York.
• Information on British plans to undermine American currency through counterfeiting.
• Crucially, a timely warning of British plans to ambush Rochambeau's arriving French fleet at Rhode Island.

This last piece of intelligence, delivered just in time, allowed Washington to warn Rochambeau and potentially averted a major disaster for the American cause.

8. British Counterintelligence and Arnold's Betrayal

His betrayal poleaxed Washington.

British efforts to uncover the Ring. British intelligence, particularly under Major Oliver De Lancey and Captain John André, was aware of a leak operating out of Setauket and New York. They increased patrols, cultivated informers, and sought to identify the source, but the Culpers' security measures and tight-knit trust made penetration difficult.

Benedict Arnold's impact. General Benedict Arnold's defection in September 1780 was a severe blow. As Washington's spy chief at West Point, Arnold had been privy to information about American intelligence operations, including the existence of agents in New York and the fact that Tallmadge was running a network. While Arnold didn't know the Culpers' identities, his betrayal heightened British suspicions and led to increased pressure on potential American sympathizers in occupied territory.

Close calls and fear. Arnold's defection and the subsequent British crackdown caused significant anxiety within the Ring. Townsend, in particular, was deeply unnerved and temporarily ceased writing reports after the arrest of Hercules Mulligan, a known American sympathizer and acquaintance, who was briefly imprisoned on suspicion of espionage. The fear of exposure was a constant threat.

9. The Dangerous World of the Whaleboat War

For the course of the Revolution, a low-intensity guerrilla conflict raged in the Sound that was colloquially known as the “Whaleboat War”.

Conflict on Long Island Sound. The waters and shores of Long Island Sound were a constant battleground between Patriot and Loyalist whaleboatmen. Initially commissioned to gather supplies and harass the enemy, these operations often devolved into brutal piracy and plundering, targeting civilians on both sides, regardless of their political allegiance.

Impact on the Culper Ring. The Whaleboat War directly affected the Culper Ring's operations:

• Brewster, the whaleboatman, was frequently engaged in skirmishes, sometimes delaying message delivery.
• Both Patriot and Loyalist raiders posed a threat to couriers and agents traveling on Long Island.
• The violence and lawlessness added another layer of risk and anxiety for the Culpers and their contacts.

Tallmadge and Washington recognized the detrimental impact of this lawlessness on intelligence gathering and civilian morale, but efforts to curb it were largely unsuccessful until late in the war.

10. The Ring's Decline and Lasting Legacy

The Culper Ring’s day was almost over, and that of the professional, the cynic, and the mercenary was dawning.

Winding down operations. As the war drew to a close after the victory at Yorktown in 1781, the Culper Ring's activities gradually decreased. Washington's focus shifted, and the urgency for intelligence from New York diminished as British defeat became increasingly likely. Agents like Woodhull and Townsend, exhausted and seeking to rebuild their lives, became less active.

Post-war lives and obscurity. After the war, the Culper members returned to their civilian lives, maintaining strict secrecy about their wartime service. They did not seek public recognition or compensation beyond reimbursement of expenses, embodying a quiet patriotism. Figures like Woodhull, Townsend, Brewster, and Roe lived out their lives in relative obscurity, their vital contributions unknown to the public.

A different kind of espionage. The book contrasts the Culpers' amateur, trust-based network with the emerging professional espionage of figures like William Heron, a double agent motivated by profit and self-preservation. This shift marked the transition to a more cynical era of intelligence, where loyalty was often secondary to financial gain.

Tallmadge's defense of their honor. Years later, Benjamin Tallmadge broke his silence to defend the honor of his agents and the integrity of their service, particularly against those who profited from the war through less honorable means. His efforts helped ensure that the story of the Culper Ring, a testament to patriotic sacrifice and ingenuity, was not lost to history.

Last updated: June 27, 2025