26. George Washington’s Efforts to Establish a Spy Ring in New York
When the British occupied New York in 1776, George Washington realized the importance of intelligence about his enemies’ troop movements and intentions. After he was defeated and forced to evacuate the city in the summer of 1776, Washington directed that a “channel of information” be established on Long Island. It was an ad hoc and poorly run affair, without permanent agents on the ground. It came to grief with the capture of Nathan Hale, a young Continental Army officer who volunteered to gather intelligence behind British lines, only to get caught and hanged as a spy.
The Hale fiasco convinced Washington that civilians would make less conspicuous spies than military officers. So in February of 1777, he requested the aid of a Nathaniel Sackett to spy on the British, and appointed a Major Benjamin Tallmadge (1754 – 1835), a New York native and Yale graduate, as military liaison and point of contact. Sackett’s information was hit and miss, accurate at times, and inaccurate at others. But even the accurate intelligence lacked both the quantity and timeliness to satisfy Washington, so he sacked Sackett.
George Washington was disappointed with other espionage operations established in 1777. His frustration with the inability to set up a reliable intelligence pipeline continued into 1778. Then in August of 1778, a Connecticut lieutenant named Caleb Brewster offered to furnish intelligence from behind enemy lines. By the end of the month, Brewster had sent in accurate reports about British troop movements, as well as the condition of Royal Navy ships after a storm and battles with the French. Encouraged by Brewster’s success, Washington ordered a General Charles Scott to handle the new intelligence pipeline, and assigned him Major Tallmadge as an assistant. General Scott had a full plate, however, and was uninterested in intelligence gathering anyhow, so Tallmadge ended up as the de facto spy master in charge of Brewster’s espionage activities.
Tallmadge’s remit expanded when Washington ordered him to recruit more spies to gather intelligence from New York and its environs. He recruited Abraham Woodhull, a friend and neighbor with whom he had grown up in Setauket, a small community in Long Island. Woodhull would gather the intelligence and deliver it to Brewster, who would then deliver it to Tallmadge and thus to George Washington. Washington, who was exceptionally hands-on for a general when it came to the oversight of espionage activities, gave Woodhull the codename “Samuel Culper” – a play on Culpeper County, Virginia. With its key players in place and its tasks defined, the Culper Ring was now operational and ready to shape events and make history.
Robert Townsend (1753 – 1838) was probably America’s greatest spy, ever. With the alias “Samuel Culper, Jr.” and codename “723”, he became the key player in the Culper Ring. His espionage activities had a greater and longer lasting historical impact than that of any other single clandestine operative from the country’s birth to the present. For somebody whose actions played such a great role, Townsend is remarkably little known, and he does not get anywhere near the recognition that his historical contributions warrant. That was how he wanted it, however. Townsend never sought acclaim, neither in the midst of the American War of Independence nor after. Indeed, he insisted that his real identity be kept secret even from George Washington. After the conflict, the few who knew his identity – whose numbers by then included Washington – respected his wish to remain anonymous.
George Washington personally spelled out Townsend’s tasks in a letter with detailed instructions that directed him to work out of New York City and: “â¦ collect all the useful information he can – to do this he should mix as much as possible among the officers and refugees, visit the coffee houses, and all public places. He is to pay particular attention to the movements by land and water in and about the city especially“. He added that Townsend should send him thorough reports on the number of troops who operated in New York and its environs, identify their units, and tell him what he could about the British defensive fortifications. He also wanted to find out as much as possible about the security measures in place to protect transports, the state of supplies and provisions, and the morale of the military and civilians.
23. The Spy Chain from Robert Townsend to George Washington
George Washington closed his instructions to Robert Townsend thus: “There can be scarcely any need of recommending the greatest caution and secrecy in a business so critical and dangerous. The following seem to be the best general rules: To entrust none but the persons fixed upon to transmit the business. To deliver the dispatches to none upon our side but those who shall be pitched upon for the purpose of receiving them and to transmit them and any intelligence that may be obtained to no one but the Commander-in-Chief“. Little did Washington know just how well Townsend would perform. Nor could the American commander in chief have predicted just how well positioned Townsend was to come across some of the war’s most sensitive information.
Townsend used invisible ink to write his reports on seemingly blank reams of paper that were delivered to Culper Ring spy Abraham Woodhull in Setauket, NY. Woodhull delivered the intelligence to Caleb Brewster, who delivered it to their handler, George Washington’s aide in charge of intelligence, Benjamin Tallmadge, who in turn delivered it to Washington. The general read the reports after he developed the invisible ink with a chemical agent, and often responded to Townsend with invisible ink messages of his own.
To help fulfill his tasks, Robert Townsend got a gig as a columnist for a Loyalist newspaper, and visited coffeehouses to hobnob with British officers. Many of them opened up to the spy, in the hope that they would thus see their name in print. That was how Townsend learned of a British plot to flood America with counterfeit dollars to wreck the economy. His warnings enabled the Continental Congress to avert disaster in the nick of time with a recall and replacement of all bills in circulation. An equally great coup resulted from the unwelcome, but as it turned out fortuitous, quartering of British officers in the Townsend family home in Oyster Bay.
One of Townsend’s sisters overheard an officer, John Andre – Benjamin Tallmadge’s British counterpart in charge of intelligence – mention the defection of a high ranking American hero. She passed that on to her brother, and from there it worked its way through the Culper Ring to Tallmadge. It eventually contributed to the discovery that Patriot hero General Benedict Arnold was a traitor. It came in the nick of the time, in the late stages of a plot to betray the important American fortifications at West Point to the British. Andre was arrested in civilian clothes with incriminating documents and hanged as a spy, while Arnold fled to the British.
21. An Extraordinarily Successful Spy Who Chose to Fade Into Obscurity
Robert Townsend also discovered that the British knew that the French, who had joined the war on America’s side, planned to send a fleet to land soldiers in Rhode Island. The powerful British Royal Navy planned to intercept and capture or sink the French at the sea before they disembarked their troops. Armed with Townsend’s report, George Washington fed the British false information about a nonexistent plan to attack New York City. As a result, the British stayed put in New York and prepared to defend it against an attack that never came, while the French safely landed their forces in Newport, Rhode Island, in 1780. That link up between French and American armies ultimately doomed the British. The allied Franco-American forces won effectively won the war in 1781, when they trapped a British army in Yorktown, Virginia, and forced its surrender.
Robert Townsend never sought recognition, and chose to fade away after the war. His wishes to remain anonymous were respected by those who knew of his exploits as a spy. He wrapped up his business activities in New York City, and returned to the family home in Oyster Bay, Long Island. He never married, although he fathered an illegitimate son upon a housemaid. Townsend lived with his sister in Oyster Bay until he died of old age in 1838, and took his Revolutionary War “Culper” identity to the grave with him. It was not until 1930, when a New York historian finally uncovered the true identity of the wartime spy master “Samuel Culper, Jr.”, that Robert Townsend’s accomplishments finally came to public light.
As to other key members of the Culper spy ring, Abraham Woodhull got married in 1781, as the war wound down. He had three children with his wife before she died in 1806. He remarried late in life, in 1824, and died two years later in Setauket. By then, he had become a man of stature in local politics, and had served as magistrate of Setauket, judge of the Court of Common Pleas, and first judge of Suffolk County. As to Caleb Brewster, he married a woman from Fairfield, Connecticut, after the war, and settled there with her. The couple raised a family of eight children. He worked as a blacksmith and a farmer until 1793, when he joined the United States Revenue Cutter Service – forerunner of today’s Coast Guard. He eventually retired to a farm in Black Rock, Connecticut, and died in 1827.
Benjamin Tallmadge served in the Continental Army until it was disbanded in 1783. He then returned to civilian life, and settled down to raise a family of seven children with his wife in Connecticut. He became an entrepreneur and entered into a variety of business ventures. Among other things, he became a bank president, and speculated in land in Ohio. When George Washington was elected president, he appointed Tallmadge as postmaster for Litchfield, Connecticut. In 1800, Tallmadge was elected to Congress as a Federalist, and served in the House of Representatives until 1817. He died in 1835.
Master spy and adventurer George Sidney Reilly (1874 – 1925), original name Zigmund Markovich Rozenblum, was born in Odessa, in the Russian Empire’s Ukraine. Relatively few details about his background are known with accuracy, and many of the more romanticized facts about his life might have been his own inventions. Details of his early days and education are sketchy. Although Reilly led an extraordinarily adventurous life, he habitually spiced things up with embellishments or outright fabrications to make himself seem even more exciting.
At various times, Reilly claimed to have attended prestigious institutes such as Cambridge University, the University of Heidelberg, and the Royal School of Mines. In reality, he had never attended any of them, but he was good enough at chemistry to become a member of the Chemical Society in 1896, and the Institute of Chemistry a year later. He also had a good ear for languages, and mastered English, German, French, Polish, and Russian. Those gifts would serve him well in his espionage career.
18. A Teenaged Russian Exile’s Convoluted Path to British Intelligence
When he was a young man, Zigmund Rozenblum got involved with a revolutionary group known as the Friends of the Enlightenment, and acted as one of its couriers. Enlightenment was the last thing the oppressive Russian government wanted, and such politics got him in hot water with the Tsarist secret police, the Okhrana. So he fled Odessa at age nineteen, and stowed away in a ship bound for Brazil. It was the start of years of international travel in which he claimed to have worked as a dockworker, a dishwasher, a brothel doorkeeper, a railway engineer in India, and a spy for the Japanese government.
While in Brazil, Rozeblum was hired by some British explorers as a cook on an expedition to the Amazon. He reportedly saved them from hostile cannibals when he grabbed a revolver and shot several attackers dead. The grateful explorers invited their cook to return with them to England, saw his potential as a spy, and steered him towards British intelligence. It is possible that such a dramatic story was bunk, invented by the future master spy to hide how he got to London – which was also dramatic, although less heroic. Other accounts indicate that Rozebnblum had ambushed and killed two anarchists in Paris, robbed them of revolutionary funds, then fled France.
Whatever path he took to London, Zigmund Rozenblum arrived in the British capital in 1895. He got married three years later, and in 1899, took out a British passport with the name Sidney George Reilly. Over the years, he would take out eleven different passports, all with different names. In 1899, Sidney Reilly was given a permanent position with the British Naval Intelligence Department (NID). In one of his earliest assignments, made in the midst of the Boer War, Reilly was sent to Holland to gather information about arms shipments that were sent to the Boers in South Africa.
The new British spy was cool headed, creative, brave, a natural at disguises, and had a flair for acting that allowed him to don just about any persona. Reilly used his talents to present himself as a Russian arms dealer, and that got him invited to inspect various Dutch arms factories. He returned to Britain with valuable information that impressed his superiors. Between that and other early successes, Reilly soon earned a reputation as one of the NID’s top agents.
16. The Secret Agent Who Spied on the Russians for Both the British and Japanese
After the Boer War, Sidney Reilly’s spy masters sent him back to Tsarist Russia, from where he reported on Russia’s development of Baku’s oil fields. He also reported on the progress of the Trans-Siberian Railway, and dipped down to Persia to report on oil developments there. Next, he was sent to the Far East, under cover of an employee of a trading company in Russian-controlled Port Arthur, Manchuria. There, Reilly not only spied for the British, but also got a side gig as a double agent and spied for the Japanese, who were keenly interested in Port Arthur’s defenses.
Early in 1904, shortly before the Russo-Japanese War erupted, Reilly reportedly stole the Port Arthur harbor defense plans for the Japanese. That helped the Japanese Navy to navigate through minefields that protected the harbor, and launch a surprise attack on the night of February 8th – 9th, 1904, against the Russian Far East Fleet. Although Japan eventually won the war, that initial attack did not go exactly as planned. Still – things could have gone worse for the Japanese Navy if not for Reilly.
In 1905, Sidney Reilly reportedly disguised himself as a priest in the French Riviera, in order to get close to businessman William Knox D’Arcy. D’Arcy held Persia’s oil concession, and Reilly inveigled him to sell the concession to Britain, despite fierce French competition. A year later, Reilly relocated to St. Petersburg, where he befriended Russian revolutionaries. He reportedly spied on and reported on them to both British intelligence and the Tsarist Okhrana – the selfsame secret police whose unwelcome attentions had forced him to flee his homeland a decade earlier.
The master spy also developed a reputation as a smooth womanizer. As one account put it: “he had a seductive charm, loving women as he loved himself. A string of mistresses would fall under his spell. Monogamy did not come naturally to Reilly and although he was usually fastidious in his choice of women, it did not prevent him from cavorting around London on one of his visits with a common tart named Plugger. How she acquired her nom de travail can only be imagined“.
In the early twentieth century, Kaiser Wilhelm II kicked off a rapid expansion of Germany’s war machine. That – especially his naval buildup – greatly alarmed the British. Their fortunes and national survival depended on the Royal Navy’s command of the sea, so any potential threat to their naval supremacy was bound to alarm the powers that be in London. British intelligence knew precious little about the goings on inside Germany’s war plants, so in 1909, Sidney Reilly’s spy masters sent him to Essen to gather intelligence.
Under the cover name Karl Hann, Reilly got a job as welder in the Krupp Gun Works, where he hoped to photograph the plant and the sensitive plans and information contained in its drawing office. However, the office was too heavily guarded during the day, so he volunteered for the fire brigade that worked the night shift. Then he strangled the head of the night security detail, knocked out another guard, and got into the drawing room. He seized the plans before the alarm was raised, and caught a train, then a boat, and made it back to Britain with his valuable intelligence haul.
While in the US, Reilly might also have conducted some false flag “German sabotage” operations on behalf of the British, to arouse the American government and public against Germany. Reilly’s profits as an equal opportunity arms dealer took a hit in 1917. When the US joined the war on the Entente’s side that year, he was no longer able to sell weapons to Germany, now America’s enemy. Later that year, the Russian Revolution erupted, and the Russians ceased their weapons purchases.
With his business as an arms dealer in decline, Sidney Reilly returned to Europe and his British spy masters. They sent him behind German lines on various missions to carry out espionage in occupied Belgium or Germany. He used a variety of disguises and forged identity papers. He sometimes presented himself as a peasant, and at other times as a wounded German soldier or officer on sick leave from the front. In April 1918, Britain’s MI6 sent Reilly to Russia, whose new Bolshevik government had signed a peace treaty that took the country out of the Entente and out of the war against Germany.
The British hoped to overthrow the Bolsheviks, and replace them with a new and more sympathetic government that might rejoin the war on Britain’s side. To that end, Reilly got involved in a variety of plots intended to destabilize the Reds. That spring and summer, he tried his hand at a variety of failed schemes. They included an abortive plot to bribe Kremlin guards and get them to launch a coup, and a plan to assassinate Vladimir Lenin that wounded but did not kill the Bolshevik leader.
After the failed attempt to assassinate Lenin, Sidney Reilly was forced to flee the USSR, and he made it out of the country just a step ahead of the Soviet secret police, the Cheka. The Reds tried him in absentia, and sentenced him to death. Reilly’s endeavors to topple the Bolsheviks had not met with success, but Britain’s MI6 appreciated the effort and awarded him a Military Medal. However, the failure gnawed at Reilly, whose time in Red Russia had turned him into an implacable anti-Bolshevik, and he begged for an opportunity to have another go at the Soviets. His bosses declined, so the master spy decided to wage his own anti-Bolshevik campaign.
There are not that many people who have lived a life as extraordinary or as impactful as Dusan “Dusko” Popov (1912 – 1981), a Serbian WWII spy and triple agent who was decorated by both the Germans and the British. A mostly unsung and largely unrecognized hero, Popov played an oversized role in the success of the Allied invasion of Normandy. And he did it in style. Popov helped beat the Nazis while he traveled around the world and led a playboy life, as he partied in top notch night clubs and casinos with a bevy of beauties and famous actresses.
He pulled that off because he was blessed with an abundance of natural charm and smoothness, good looks that set hearts aflutter, plus an agreeable presence that just drew people to him. That combination of charisma, coolness, wit and looks did not go unnoticed by a mid-level British intelligence officer named Ian Fleming, who went on after the war to create fiction’s greatest spy, James Bond. Indeed, it is almost a certainty that Fleming, who became acquainted with Popov during the war, modeled much of Agent 007 upon the smooth Serb.
9. One of Fortune’s Favorites, With an Ear for Languages
Dusko Popov was one of fortune’s favorites, and such favor began with his birth in 1912 into a wealthy Serbian family that had been affluent for centuries. His grandfather had been a rich banker and businessman who owned factories, mines, and retail establishments, and his father made the family richer still when he added real estate to its investment portfolio. Popov, an avid outdoorsman and athlete since childhood, thus grew up in the lap of luxury, attended by servants in the family’s numerous villas or while he sailed the seas in one of the family’s numerous yachts.
The future spy was set on the playboy path from an early age by an indulgent father, who built his kids a huge seaside villa, and gave them generous allowances that allowed them to host lavish parties there. Although indulgent, Popov’s father did not simply spoil his kids rotten. He made sure that they got as great a top notch education as his considerable wealth could afford. Thus, by the time Popov was a teenager he was fluent in French, German, and Italian, in addition to his native Serbian. Such linguistic skills came in handy down the road.
8. The Nazis Awakened This Dilettante Playboy’s Interest in Politics
After Popov studied in England – where he got expelled from a prestigious prep school – and France, he returned home to study law at the University of Belgrade. When he was twenty two, not long after the Nazis came to power, he headed to Germany to pursue a law doctorate at the University of Freiburg. There, he befriended a rich German student named Johann “Johnny” Jebsen, who had anti-Nazi views. Until then, Popov had simply been a dilettante playboy with no interest in politics. His time in Germany caused him to loathe the Nazis and develop strong political opinions against them.
The young Serb was not discrete about his views, however, and that proved to be a problem in the totalitarian Third Reich. In 1937 he was arrested by the Gestapo, who suspected that he might be a communist, and was tossed into prison. His friend Johnny Jebsen came to his aid and alerted Popov’s father, who in turn got the Yugoslav government involved. After high level contacts between Yugoslavia’s prime minister and Herman Goering, then head of the Gestapo, Popov was released from jail, and expelled from Germany.
Dusko Popov’s experience in Germany did not improve his opinion of the Nazis, and when WWII broke out, he was primed and eager to pay them back if the opportunity presented itself. It presented itself when his friend Jebsen, whose family’s business needed favors from Popov’s, informed him in 1940 that he had joined Germany’s military spy agency, the Abwehr. Popov passed that information to a contact in the British embassy named Clement Hope, along with the observation that Jebsen was not that fond of the Nazis. Jebsen sought to recruit Popov as an Abwehr spy, and when he passed that on the British, they recruited him as an MI6 agent, and urged him to play along with the Germans and join the Abwehr.
Popov was given the codename Ivan by his German handlers, while the British codenamed him Tricycle, because he was in charge of three double agents. Popov eventually turned Jebsen, and recruited his German recruiter into British intelligence as a double agent. Popov also fed information to his native Yugoslavia’s intelligence, which made him a triple agent. He moved to London, and his family’s business activities gave him cover to travel back and forth to neutral Portugal. There, Popov met his Abwehr contacts, and fed them information provided to him by the British service that ranged from harmless truths, to half-truths, to outright lies.
The Abwehr was quite pleased with their spy Dusko Popov. Although some of his German handlers grew suspicious, their suspicions did not make their way up the chain of command. Among other things, an assignment to German military intelligence in Portugal was a cushy gig compared to less attractive ones, such as an assignment to the Eastern Front. Also, many in the Abwehr, from its chief Wilhelm Canaris on down to lower officials such as Johnny Jebsen, disliked the Nazis and did what they could to undermine them.
In 1941, the Abwehr furnished Popov with a small fortune, and sent him to the United States to gather intelligence on American defensive measures. The information sought included an extensive list of questions about the defenses of Pearl Harbor, in which Germany’s Japanese allies were keenly interested. The British worked with the Feds to handle Popov while in the US, but FBI Director J. Edgar Hoover and his G-men lacked the vision and finesse of their British counterparts. Rather than use Popov as a double agent to suss out German intentions and feed them false information, Hoover simply wanted to use him to catch German spies.
J. Edgar Hoover failed to pass on Dusko Popov’s Abwehr questions to American military authorities – particularly the ones that sought information about Pearl Harbor’s defenses. After the Japanese attack wrecked the US fleet there a few months later, Hoover’s oversight should have wrecked his career. However, he buried it so deep that it did not come out until after his death. In the meantime, the prissy FBI Director, whose private life was even more scandalous than the Serb spy, got moralistic about Popov’s promiscuous lifestyle, nightlife escapades, and playboy antics. Hoover even threatened to have Popov arrested under the Mann Act for traveling with a woman across state lines “for immoral purposes”.
The British assigned a naval intelligence officer named Ian Fleming to watch Popov’s every move in the US. The future author of James of Bond followed Popov around as he made the rounds of American night clubs and casinos, womanized, splurged the cash furnished him by the Abwehr, and made a killing on the roulette tables. The style and panache left an impression that found expression years later in Agent 007. Indeed, some famous scenes from Casino Royale were based on Fleming’s observations of Popov in American casinos.
Eventually, Dusko Popov’s relationship with the FBI grew toxic, and as J. Edgar Hoover stewed over the double agent’s antics, things threatened to get worse. So British intelligence recalled their spy to London, where he continued to feed the Abwehr false information. His biggest contribution to the eventual downfall of the Nazis came in the intricate Allied deception plans, collectively known as Operation Bodyguard. Their ultimate aim was to mislead the Germans about the planned invasion of France, scheduled for the summer of 1944.
Operation Bodyguard had three goals. First, conceal the actual date and time of the invasion. Second, convince the Germans after the Allies landed in Normandy that those landings were just diversions intended to juke the Germans out of the Pas de Calais, where the real Allied invasion would land soon thereafter. Third, convince the Germans after the Normandy landings to maintain a strong defense in the Pas de Calais for at least two weeks, rather than send its defenders to reinforce Normandy. Popov played a key role in a sub-plan of Bodyguard, known as Operation Fortitude, which revolved around a fictitious First US Army Group (FUSAG) in southeast England under the command of General George S. Patton.
Dusko Popov passed on to the Abwehr made up details about FUSAG’s units, strength, and organization. His German handlers swallowed his misinformation hook, line, and sinker. Their faith in Popov’s information was reinforced when they eavesdropped on fake radio traffic between fictitious FUSAG formations. To further reinforce the deception, German reconnaissance planes were allowed to fly over and photograph concentrations of FUSAG tanks and transports that were actually inflatable dummies. A spanner was thrown in the works, however, when the Germans arrested Popov’s friend Johnny Jebsen, the Abwehr agent who had “recruited” him to spy for the Nazis.
2. A Double Agent’s Key Contribution to the Allies’ Success in Normandy
When British intelligence learned that Johnny Jebsen had been arrested by the Germans, they feared that he would reveal that Dusko Popov had actually worked for the Allies all along. They thought it was all over for their Agent Tricycle, and suspended his activities and those of his network. Despite torture, however, Jebsen did not let slip that Popov, Agent Ivan to the Germans, was a British spy. When British intelligence realized that the Abwehr still trusted Popov, they put him back to work to continue the deception. He and Operation Fortitude paid off for the Allies in a big way.
After D-Day, the Germans were convinced that the Normandy invasion was not the main event, but only the first in a series of landings. So instead of rush all available reinforcements to contest the Allies in Normandy, they kept powerful formations in the Pas de Calais, to defend it from the “main invasion” by the fictitious FUSAG. Popov’s British handlers had hoped to convince the Germans to keep the Pas de Calais formations in place for two weeks after D-Day. Things worked out better than their wildest hopes: instead of two weeks, the Nazis kept their units there for seven weeks. By the time the Pas de Calais defenders were finally released, it was too late for the Germans.
The Allies took advantage of the breather afforded them by the success of the Operation Bodyguard and Operation Fortitude deceptions to build a powerful beachhead in Normandy. From there, they eventually broke out to liberate France and Western Europe. After Paris was freed from the Nazi yoke, Dusko Popov was sent to the French capital to help establish a British intelligence network. When Yugoslavia turned communist after the war, there was no future for the playboy Popov back in his home country, so he decided to stay put in the West.
Popov was awarded the Order of the British Empire for his wartime exploits – a nice accompaniment to the medals given him by the Germans during the conflict – and eventually became a British citizen. He prospered as a businessman, and had no intention to reveal his wartime activities. In 1972, however, John Masterman published The Double Cross System in the War of 1939 to 1945, a deep dive in British wartime intelligence. That convinced Popov to write up his own account, and in 1974 his autobiography, titled Spy Counter-Spy, was published. A playboy to the end, he died in 1981, after years of heavy smoking and drinking, and many, many, women.
Where Did We Find This Stuff? Some Sources and Further Reading