The Ace of Spies and Other Significant Espionage Figures

39. From Guarding Brothels to Shooting Cannibals

In his youth, Rosenblum’s politics got him in hot waters with the Tsarist police, the Okhrana. So he fled Odessa at age 19, stowing away in a ship bound for Brazil. It was the beginning of years of years of international travel, during which he claimed to have worked as a dockworker; a dishwasher; a whorehouse doorkeeper; a railway engineer in India; and a spy for the Japanese government. While in Brazil, he served as cook for some British explorers, and reportedly saved them from hostile cannibals by grabbing a revolver and shooting several attackers dead.

The grateful explorers invited their cook to return with them to England, and steered him towards British intelligence. He arrived in London in 1895, 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, each bearing a different name.

38. The Master of Disguise

In 1899, Sidney Reilly was given a permanent position with British Naval Intelligence Department (NID). One of his earliest assignments occurred during the Boer War, when Reilly was sent to Holland to gather information about arms shipments being sent to the Boers in South Africa.

Cool-headed, creative, brave, and a natural at disguises with acting chops that allowed him to do just about any persona, Reilly used his talents to present himself as a Russian arms dealer. That got him invited to inspect various Dutch arms factories, and 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.

37. Reilly Riles Up the Far East

After the Boer War, Reilly spent years in the Far East, under cover of working for 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 spying for the Japanese, who were keenly interested in Port Arthur’s defenses.

Early in 1904, shortly before the Russo-Japanese War, Reilly stole the Port Arthur harbor defense plans for the Japanese. That helped the Japanese Navy to navigate through minefields protecting the harbor, and launch a surprise attack on the night of February 8 – 9, 1904, against the Russian Far East Fleet. Although Japan eventually won the war, that opening attack did not go exactly as planned. Still – things could have gone worse for the Japanese Navy if not for Reilly.

36. The Smooth Talking Womanizer

In 1906, Sidney 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 secret police, the Okhrana, whose attentions had caused him to flee his homeland a decade earlier.

Reilly also developed a reputation as a smooth-talking 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“.

35. Infiltrating the Kaiser’s War Machine

Kaiser Wilhelm II’s expansion of Germany’s war machine in the early twentieth century – especially his naval buildup – alarmed the British. However, British intelligence knew precious little about what was going on inside Germany’s war plants. So in 1909, Sidney Reilly was sent to Essen to gather intelligence.

Under the cover name Karl Hahn, he got a job as welder in the Krupp Gun Works, hoping to photograph the plant and the sensitive plans and information in its drawing office. However, the office was too heavily guarded during the day, so he volunteered for the fire brigade during the night shift. Then he strangled the head of the night security detail, knocked out another guard, and got into the drawing room. Seizing the plans before the alarm was raised, he caught a train, then a boat, and made it back to Britain with his valuable intelligence haul.

34. WWI Exploits

Early in World War I, Sidney Reilly was sent to the then-neutral United States – an important source of weapons and munitions for the Entente – and got involved in the lucrative arms business. During 1914 – 1915, he arranged weapons purchase deals for both the Imperial German Army and its enemy, the Imperial Russian Army. While in the US, he might also have conducted some false flag “German sabotage” operations on behalf of the British, to arouse the American government and public against Germany.

In 1917 – 1918, Reilly returned to Europe, and frequently got behind German lines to carry out intelligence gathering missions in occupied Belgium or Germany. Using a variety of disguises and forged identity papers, he sometimes presented himself as a peasant, and other times as a wounded German soldier or officer on sick leave from the front.

33. Battling the Bolsheviks

In April 1918, Britain’s MI6 sent Sidney 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 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, Reilly tried his hand at a variety of schemes, including an abortive plot to bribe Kremlin guards into launching coup, and a plan to assassinate Vladimir Lenin that wounded but failed to kill the Bolshevik leader. Reilly was forced to flee, escaping the country just a step ahead of the Soviet secret police, the Cheka. The Soviets tried him in absentia, and sentenced him to death.

32. The Bolsheviks Get Their Revenge

Sidney Reilly’s efforts to topple the Bolsheviks had failed, but Britain’s MI6 appreciated the effort, and got 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 Reilly decided to wage his own anti-Bolshevik campaign.

Unfortunately for Reilly, he had found his match in the Reds, whose deviousness was equal to his own. Soviet intelligence created an anti-Bolshevik organization known as the Trust, which was actually run by their own secret police, the Cheka. Trust members met Reilly, and lured him to Russia, under the pretext of meeting its anti-Bolshevik leaders. Upon crossing the border in 1925, Reilly was arrested and taken to Moscow’s dreaded Lubyanka prison for interrogation and torture, before he was eventually executed.

31. America’s Greatest Spy

America has probably never had a greater spy than Robert Townsend (1753 – 1838). Using the codename “Samuel Culper, Jr.”, he headed the American Revolution’s most important spy network, The Culper Ring. Townsend’s espionage activities probably had a greater and longer-lasting historical impact than that of any other single clandestine operative from the country’s founding to the present.

For somebody whose actions played such a great role, he is remarkably little known, and does not get anywhere near the recognition his historical contributions warrant. That was how he wanted it. Townsend never sought recognition during the war, insisting that his 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.

30. Working for Washington

George Washington personally spelled out Robert Townsend’s tasks. In a letter with detailed instructions, the Continental Army’s commander in chief ordered Townsend to work out of New York City and: “… 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“.

Washington went on to add that Townsend was to report on the number of troops operating in New York and its environs; identify their units; the defensive fortifications; the security measures in place to protect transports; the state of supplies and provisions; and the morale of the military and civilians.

29. Townsend Surpassed Washington’s Expectations

George Washington closed his instructions to Robert Townsend by noting: “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.

28. The Master Spy Saves the American Economy

Robert Townsend wrote his reports using invisible ink on seemingly blank reams of paper, that were delivered to Culper Ring agent Abraham Woodhull in Setauket, NY. Woodhull delivered the intelligence to his handler, George Washington’s aide in charge of intelligence, Benjamin Tallmadge, who in turn delivered it to Washington. The general read the reports after developing the invisible ink with a chemical agent and often responded to Townsend with invisible ink messages of his own.

Townsend did a lot of valuable legwork gathering intelligence and fulfilling his assigned tasks. He got a gig as a columnist for a Loyalist newspaper, and visited coffeehouses to hobnob with British officers, many of whom opened to him in the hopes of seeing their name in print. That was how Townsend got wind of a British plot to wreck the American economy by flooding the country with counterfeit dollars. His warning enabled the Continental Congress to avert disaster in the nick of time by recalling all bills that were in circulation and issuing new ones.

27. Saving West Point and Unmasking Benedict Arnold

One of Robert Townsend’s greatest coups resulted from the unwelcome, but as it turned out fortuitous, quartering of British officers in the Townsend family home in Oyster Bay. During the British stay, one of Townsend’s sisters overheard a visiting officer, John Andre – Benjamin Tallmadge’s British counterpart in charge of intelligence gathering – discussing 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 unmasking of Benedict Arnold as a traitor. It came in the nick of the time, during the late stages of a plot to betray the important American fortifications at West Point to the British. John Andre was arrested and eventually hanged, and Arnold fled to the British.

26. Saving America’s Allies

Robert Townsend also discovered that the British had learned that the French, who had joined the war on America’s side, were sending a fleet to land French troops 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. Townsend’s timely warning enabled George Washington to bluff the British into staying put in New York, by feeding them false information about a nonexistent plan to attack the city.

As a result, the British prepared to defend New York against an attack that never came, while the French safely landed their troops in Rhode Island. That link up between French and American armies ultimately doomed the British. The allied Franco-American forces ended up deciding and winning the war in 1781, when they trapped a British army in Yorktown, Virginia, and forced its surrender.

25. Fading Into Anonymity

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 espionage. 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. Robert Townsend lived with his sister in Oyster Bay until he died of old age in 1838, taking 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 spymaster “Samuel Culper, Jr.”, that Townsend’s accomplishments came to light.

24. Ancient Greece’s Greatest Traitor

Ephialtes of Trachis, or Ephialtes son of Eurydemos, was a member of the Greek Malian tribe, after whom the Malian Gulf in the northwestern Aegean is named. When King Xerxes of Perisa invaded Greece in the 5th century BC, Ephialtes betrayed the Greeks by showing the Persians a path that allowed them to bypass and surround a Spartan-led blocking force that had halted the invaders at Thermopylae.

The invasion came after decades of mounting tensions, spurred by Athens’ support during the reign of Persia’s King Darius I of a failed rebellion by his Ionian Greek subjects in Asia Minor. That led to a Persian punitive expedition against Athens, which was defeated at the Battle of Marathon in 490 BC. In 480 BC, Darius’ son and successor, King Xerxes, gathered forces for a massive campaign to conquer and subdue Greece once and for all.

23. Bottling the Persians at Thermopylae

Faced with the approach of a vast Persian army, the Malians, at the northeastern juncture of the Greek Peninsula with the rest of the Balkans, were among the many Greeks who chose discretion over valor. They “Medised” – that is, submitted to and collaborated with the Persians against other Greeks. Along the Persian army’s route through Malian lands was a narrow pass known as Thermopylae, or “Hot Gates”, situated between mountains to the south and the cliff-lined shore of the Malian Gulf to the north.

A small Spartan-led Greek force, under the command of Sparta’s king Leonidas, occupied and fortified the pass at Thermopylae. The Persians, forced to attack directly up the pass on a narrow front, had their numerical advantage neutralized. They were bested by the more heavily armed and armored Greeks, especially the elite core of superbly trained Spartans. For three days, the Persians launched futile attacks, but could not make the Greeks budge.

22. Unstoppering the Bottle at Thermopylae

The Persians were stuck in front of the Thermopylae pass, until Ephialtes struck. He informed king Xerxes that he knew of a track through the mountains that bypassed Thermopylae, and reemerged to join the road behind the Greek position. In exchange for the promise of rich rewards, Ephialtes showed the Persians the way. Alerted that he was about to be outflanked, Sparta’s King Leonidas sent the rest of the Greeks away. He stayed behind with what remained of a 300-strong contingent of Spartans, who fought to the death until they were wiped out.

Ephialtes’ was reviled, and his name came to mean “nightmare” in Greek. He never collected his reward because the Persians were defeated at Salamis later that year, and at Platea, the following year, and their invasion of Greece collapsed. Ephialtes fled, with a bounty on his head. He was killed ten years later over an unrelated matter, but the Spartans rewarded his killer anyhow.

21. The Criminality of Agent Zigzag

Agent Zigzag, real name Eddie Chapman (1914 – 1997), was a safebreaker, thief, crook, and all-around career criminal, who became the only Englishman ever awarded a German Iron Cross. It was ironic on many levels, because he was also one of history’s most colorful double-crossers, who fed the Germans false information that derailed the effectiveness of their “Vengeance Weapons”, and likely saved the lives of thousands of Londoners.

Chapman was raised in a dysfunctional family and became a delinquent at a young age. He enlisted in the British Army when he was seventeen, but within a few months, he grew bored and deserted. When the military authorities caught up with him, he was sentenced to a prison stint and a dishonorable discharge. After his release, Chapman turned to fraud and crime to support a gambling habit and a taste for fine drinks.

20. Joining the Germans

Chapman was on the lam in the Channel Islands when WWII began. A botched burglary earned him a two-year sentence in a Jersey prison, and that was where the Germans found him when they captured the Channel Islands in 1940. He offered to work for them to get out of jail, and they accepted. Chapman was freed and trained in the use of explosives, sabotage, and other clandestine skills, before he was parachuted into Britain in 1942, tasked with destroying a bomber factory.

He was arrested soon after landing, however, and immediately accepted an offer to become a double agent – an easy choice, considering that the alternative would have been a hangman’s noose. Given the codename “Agent Zigzag”, a plan was concocted to fake the bomber factory’s destruction, which convinced the Germans and raised Chapman high in their esteem. From then on, Chapman’s radio reports, carefully fed him by British intelligence, were treated as gospel by the Germans.

19. Foiling Hitler’s Vengeance Weapons

Eddie Chapman was recalled and given a hero’s welcome by the Germans. Soon after D-Day, he was awarded an Iron Cross and sent back to Britain to report on the effectiveness of the German V1 and V2 rocket strikes on London. Under British control, Chapman sent the Germans inflated figures about deaths from their rockets, while deceiving them about their actual impact points. That led the Germans to shift their aim points, with the result that they tended to fall on lower population density parts of London, with correspondingly fewer casualties.

After the war, Chapman continued his colorful life. He went into smuggling, moved to the colonies, started a farm, and in violation of the Official Secrets Act, got his exploits published in The Eddie Chapman Story (1953), Free Agent: Further Adventures of Eddie Chapman (1955), and The Real Eddie Chapman Story (1966). Collectively, those books formed the basis of a 1967 movie, Triple Cross.

18. The Mole

CIA officer Aldrich Ames (1941 – ) rose to high rank within the agency’s Soviet and East European division, which afforded him access to Soviet counterintelligence. He turned traitor and sold his services to the KGB as a deep mole, and became one of the Soviet Union’s, and later Russia’s, most effective double agents in the US.

The son of a CIA analyst, Ames’ family connection paved the way for his joining the CIA in 1962. Notwithstanding heavy drinking, alcohol-related problems that included drunken run-ins with cops and drunken brawls in public with foreign diplomats, as well as sloppiness that once led him to forget secret documents in an NYC subway car, he rose steadily through the CIA’s ranks. After a stint in Turkey recruiting Soviet spies in the 1960s, he returned to the US in the 1970s, before getting posted to Mexico in the early 1980s.

17. The Perfect Wife For a Traitor

It was in Mexico that Aldrich Ames met his second wife, Maria del Rosario Casas Dupuy, a Colombian embassy cultural attaché and CIA informant. They wed in 1985, and that same year, the couple began selling secrets to the KGB. During their run of treason, which lasted until they were finally unmasked in 1994, Ames and his wife were paid over $2.7 million by the Soviets, and after 1991, the Russians.

There were warning signs, including conspicuous consumption and extravagant spending. The couple bought a big $520,000 house paid for in cash, went on luxury vacations, had premium credit cards whose minimum monthly payment exceeded his salary, and luxury cars that stood out in the CIA’s parking lot. The kinds of things no honest public servant could afford on government pay. However, no alarm bells were raised for years, and when they were, it took years more, until 1993, before Ames’ bosses took a serious look at his finances and activities.

16. The CIA’s Most Damaging Traitor

Betraying the CIA was a cakewalk for Aldrich Ames, who passed two polygraphs while spying for the KGB. He needed no high-tech means or complicated capers to smuggle out secrets. Ames simply stuffed whatever documents he wanted to give his KGB and FSB handlers in his briefcase or in trash bags, and brazenly carried them out of the CIA headquarters at the end of the workday. Nobody questioned him.

As a result of Ames’ treachery, at least twelve CIA spies within the Soviet Union were captured, and ten of them were executed. By the time he was finally unmasked, Ames and his wife had revealed to the Soviets and Russians the identity of every CIA spy operating in their country. After he was arrested in 1994, he cut a deal with prosecutors that spared him the death penalty, and ensured that his wife got no more than five years’ imprisonment. He is currently serving a life sentence without the possibility of parole.

15. The Spy Who Burrowed Deep Into the Israeli Government

Austrian-born Israeli officer Israel Beer, or Yisrael Bar, (1912 – 1966), rose to prominence as an expert on Israeli military history. That expertise secured him a high-ranking position in the Israeli Ministry of Defense, which commissioned him to write a book on the Israeli War of Independence. It also won him a place in the inner circle of Israeli prime minister David Ben Gurion, whose trusted confidant and advisor he became.

Beer arrived in Palestine in the late 1930s with an impressive martial resume. He had graduated from the Austrian military academy, and served as a commissioned officer in the Austrian army. He then fought in the Spanish Civil War with the International Brigades, where he was known by the nom de guerre “Colonel Jose Gregorio”. In between his martial exploits, Beer found the time to get a doctorate in literature from the University of Vienna. It was all bunk, and the real Israel Beer had died many years earlier.

14. The Uncircumcised Jew

Israel Beer’s swift rise highlighted the difficulty Israeli intelligence faced in spotting infiltrators during a period of mass immigration. Beer was not even a Jew. A cultured, urbane, and Hollywood handsome man, he cut a swath through Israeli society and Tel Aviv’s nightlife as a ladies’ man. It took a long time before anybody made something about the fact that he was uncircumcised. In the meantime, Beer took advantage of his access to Israeli secrets.

He not only photocopied pages from the Prime Minister’s diary, but tore out entire pages from it and passed them on to his handlers. It was not until 1961, when Beer was caught delivering a briefcase stuffed with sensitive materials to the KGB, that the deception fell apart. He never revealed his true identity during interrogations following his arrest. Tried and convicted of espionage, Beer was sentenced to jail, where he died in 1966, taking the secret of his identity to his grave.

13. WWII’s Most Important Spy

No spy had a greater impact on WWII than Juan Pujol Garcia (1912 – 1988). An eccentric Spaniard, Juan Pujol hoaxed the Germans with fictional spying out of a sheer desire for adventure and excitement. That hoax grew into the greatest double-cross operation of the conflict, and played a significant role in ensuring Allied victory on D-Day and in the subsequent Normandy Campaign.

Juan Pujol hated fascists, so when WWII began, he decided to help the Allies “for the good of humanity”. However, when he offered his services to British intelligence, he was rejected. Undeterred, he posed as a Nazi-sympathizing Spanish government official and offered his services to Germany’s military intelligence service, the Abwehr. The Nazis accepted, and ordered him to Britain, where he was to recruit a spy network. Pujol had neither the means nor the desire to do any such thing, so he simply faked it.

12. Fabricating a Spy Network

Instead of going to Britain as instructed by the Abwehr, Juan Pujol went to Lisbon. From there, he made up reports about Britain, using content culled from public sources, embellished and seasoned with his own active imagination, then sent them to his German handlers as if he was writing from Britain. The Germans whose entire spy network in Britain had been arrested in the war’s opening days, were starving for information. So they eagerly swallowed Pujol’s fabrications, and begged for more.

Pujol obliged by inventing a network of fictional sub-agents and used them as sources for additional fictional reports. Intercepting and decoding secret German messages, the British realized that somebody was hoaxing the Germans, and upon discovering it was Pujol acting on his own, they belatedly accepted his offer of services.

11. Agent GARBO, the Nazis’ Favorite Spy

Juan Pujol Garcia was whisked to Britain, given the codename GARBO, and put to work building up his imaginary network to benefit his German handlers. The original hoax was transformed into an elaborate double cross operation that carefully fed the Germans a massive amount of often true but useless information, mixed in with half-truths and falsities.

The flood of reports from Pujol and his steadily growing network of fictional sub-agents transformed him, in German eyes, into their most successful spy in Britain. The moment for cashing in on that trust came during the buildup to D-Day and the subsequent Normandy campaign. The ultimate aim was to convince the Germans that the Normandy landings were just the first in a series of planned invasions, with an even bigger one planned against the Pas de Calais.

10. Cashing in on the Carefully Crafted Double Cross

To cement Juan Pujol Garcia’s credibility with the Abwehr, British intelligence had him send a message alerting the Germans to the invasion a few hours before its commencement. It was a carefully calculated risk, as Pujol’s handlers figured that by the time the warning worked its way from German intelligence to commanders in the field, the invasion would have already taken place. Thus the warning would have done the Germans no actual good on the ground, but still, enhance Pujol’s reputation with his German handlers.

They then went in for the kill: building upon the years of trust, Pujol informed the Germans that the Normandy landings were diversionary. The real blow, he informed them, would fall upon the Pas de Calais a few weeks later.

9. The Double Cross Pays Off

Juan Pujol’s carefully crafted lies, coupled with other Allied deception measures whereby a fictional First US Army Group, under the command of George Patton, was massed across the English Channel opposite the Pas de Calais, worked. The Germans were convinced during the crucial weeks of June, 1944, to keep powerful formations in that region, rather than rush them to Normandy to help destroy the vulnerable Allied beachhead.

By the time the Pas de Calais formations were finally released, it was too late. The Allies had amassed sufficient forces in Normandy to not only defeat German attacks, but to then go on the offensive, break out of the beachhead, and sweep across and liberate France within a few months.

8. Decorated by Both Sides

Juan Pujol Garcia ended up decorated by both sides. He earned an Iron Cross from a grateful Germany, plus a Member of the Order of the British Empire (MBE) from an even more grateful Britain. After the war, fearing reprisals from the Nazis, he faked his death in Angola in 1949, then moved to Venezuela, where he ran a gift shop and book store.

Pujol led an anonymous life until 1984, when he agreed to be interviewed for a book about agent GARBO. When the story of his deeds finally came out, he was received at Buckingham Palace, and was lionized in Britain. On the 40th anniversary of D-Day, he traveled to Normandy to pay his respects to the dead. He died in Caracas, four years later.

7. When the Spy Catcher is a Spy

Austro-Hungarian Alfred Redl (1864 – 1913) rose through that empire’s officer ranks to become chief of counterintelligence from 1900 to 1912. In that capacity, he was in charge of tracking down and rooting out traitors and spies.

In a twist no one at the time saw coming, Redl was himself a traitor and a spy. He betrayed his country and sold its secrets to its main rival and likeliest future enemy, Tsarist Russia, whose chief spy in the Austro-Hungarian Empire he became. It is suspected that he also spied for both the French and Italians in exchange for money.

6. Background of a Traitor

Alfred Redl was the son of a railway clerk, and was born into a poor family in the Galician province of Austria-Hungary, in what is now Ukraine. Wealth and family connections were the usual prerequisites back then for joining the Austro-Hungarian Army’s officer ranks and advancing. Redl had neither, but he had been precocious from an early age and was highly intelligent, which enabled him to secure a commission.

He had a talent for languages, and his facility with Russian got him assigned to the intelligence branch. There, Redl impressed his boss, General von Geislingen, whose protege Redl became. In 1900, Geislingen promoted Redl and made him his deputy, placing him in charge of the Austro-Hungarian Empire’s counterintelligence corps. Redl quickly gained a reputation for innovation in what had been a disorganized and backward branch, streamlining the system, and introducing new technologies such as the use of recording devices and cameras.

5. Entrapment and Blackmail

Alfred Redl had a secret: he was gay, in an era when homosexuality was a taboo fatal to both social standing and career prospects. Russian intelligence learned of Redl’s homosexuality, entrapped him in a compromising position, and caught it on camera. They then blackmailed him into turning traitor, and sweetened the extortion with the offer of money in exchange for secrets. Redl accepted, and in his first major act of treason, handed the Russians Austria-Hungary’s war plans in 1902.

When word reached the Austrians that the Russians had a copy of their war plans, General von Geislingen tasked Redl with finding the traitor. Redl covered his tracks by unmasking minor Russian agents who were fed him by his Tsarist spymasters, and by framing innocent Austro-Hungarian officers with falsified evidence. That enhanced his reputation within the Austro-Hungarian establishment as a brilliant head of counterintelligence.

4. Unmasking and Undoing

Over a period of eleven years, Alfred Redl sold the Russians Austria-Hungary’s secrets including mobilization plans, army orders, ciphers, codes, maps, reports on road and rail conditions. His treason finally came to an end because of sloppiness by his handlers. In 1912, Redl’s mentor, von Geisl, was promoted to head an army corps and took Redl with him as his chief of staff. Postal censors working for Redl’s successor in counterintelligence intercepted envelopes stuffed with cash and nothing else. However, the envelopes had registration receipts tracing back to addresses abroad that were known to be used by Russian and French intelligence.

A sting operation was set up, the envelopes were delivered under surveillance, and Redl showed up to claim them. Arrested, he confessed to treason, and requested that he be left alone with a revolver. His request was granted, and after writing brief letters to his brother and to von Geisl, he committed suicide.

3. The Triple Agent

English jailbird Harold Cole (1906 – 1946) served in the British Army during WWII, then in the French Resistance, before he betrayed both by working as a double agent for the Germans. During his extraordinary wartime career, he lied and conned his way across France, joined the Nazis, and spied and snitched on the Resistance, resulting in the arrest and execution of many.

Cole was a dirt bag from early on. By his teens, he was already a burglar and check forger. He was no criminal mastermind, however, and kept getting caught: by 1939, Cole had served multiple stints in prison. When WWII began, he lied about his criminal history to enlist in the British Army, and was sent to France. Promoted to sergeant, he was arrested for stealing money from the Sergeants’ Mess to splurge on prostitutes. He became a POW in May, 1940 when the Germans captured the guardhouse where he was jailed.

2. Joining and Betraying the French Resistance

Harold Cole escaped German captivity and made his way to Lille, where he got in touch with the French Resistance. He convinced them that he was a British intelligence agent sent to organize escape lines to get stranded and fleeing British military personnel back home. At first, Cole actually helped the Allied cause, escorting escaped personnel across Nazi-occupied territory to the relative safety of Vichy France, from which they slipped into Spain and a ship back home.

He also embezzled from the funds intended to finance those operations to pay for a high society lifestyle of nightclubs, pricey restaurants, expensive champagne, fast cars, and faster girls. When his thefts came to light in 1941, the Resistance arrested and locked him up. While they deliberated what to do about him, Cole escaped. On the run from the Resistance, he turned himself in to the Germans, gave them 30 pages of Resistance member names and addresses, and became an agent of the SS’ Sicherheitdienst, or SD.

1. Triple Cross

Over 150 Resistance members were arrested because of the information that Harold Cole gave the Nazis. At least 50 were executed, and Cole was present during the interrogation and torture of many of his former colleagues. When the Allies liberated France in 1944, Cole fled in a Gestapo uniform. He turned up in southern Germany in June 1945, claiming to be a British undercover agent, and offered his services to the American occupation forces. Triple crossing, he turned against the Nazis, hunting and flushing them out of hiding, and murdering at least one of them.

The British eventually arrested Cole, but he escaped while awaiting court martial and fled to France. There, French police received a tip-off revealing his whereabouts in a central Paris apartment. On January 8^th, 1946, they crept up a staircase to seize him, but their heavy tread gave them away. Cole met them at the doorway, pistol in hand, and was killed in the ensuing shootout.

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Where Did We Find This Stuff? Some Sources and Further Reading

BBC News Magazine, January 8^th, 2014 – The Woman Who Tracked Down a CIA Mole

Daily Mail, June 30^th, 2017 – The Worst Traitor of All: How an East End Jailbird Lied and Cheated His Way Across France, Joined the Nazis and Condemned 150 Resistance Fighters to Death

Encyclopedia Britannica – Alfred Redl, Austrian Military Officer

Lockhart, Robert Bruce – Ace of Spies (1984)

Macintyre, Ben – Agent Zigzag: The True Wartime Story of Eddie Chapman, Lover, Betrayer, Hero, Spy (2007)

Macintyre, Ben – Double Cross: The True Story of the D-Day Spies (2012)

New York Times, January 27^th, 1995 – How the FBI Finally Caught Aldrich Ames

Rose, Alexander – Washington’s Spies (2006)

Sadler, John – Spy of the Century: Alfred Redl and the Betrayal of Austria-Hungary

Seaman, Mark – Garbo: The Spy Who Saved D-Day (2004)

Spartacus Educational – Sidney Reilly

Spence, Richard B. – Trust No One: The Secret World of Sidney Reilly (2003)

Wikipedia – Harold Cole

Wikipedia – Israel Beer