The Ace of Spies and Other Significant Espionage Figures

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 mobilization plans, army orders, ciphers, codes, maps, reports on road and rail conditions, and other secrets. 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 (1967)

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