WWII files reveal bizarre case of British cross-dressing spy

Dudley ClarkeBy IAN ALLEN | intelNews.org |
A set of World War II-era British Foreign Office documents detail a highly unusual incident of a senior British spy, who was arrested in Spain for cross-dressing. The files, which were released this week by the National Archives, concern the case of Lieutenant Colonel Dudley Clarke, a senior operative of British intelligence who served with distinction in Europe and the Middle East. In October of 1941, Clarke was traveling though Spain en route to Egypt, by way of the British colony of Gibraltar. His instructions were to maintain a low profile throughout his trip, during which he posed as a foreign correspondent for The London Times. In reality, he was carrying with him key naval intelligence addressed to the British high command in Cairo. However, soon after arriving in Spanish capital Madrid, Clarke was arrested for appearing in a busy street dressed as a woman. A frantic cable sent to the Foreign Office by the British embassy in Madrid mentioned that the intelligence officer had been detained after he had been found “in a main street dressed —down to a brassiere— as a woman’. According to the —now declassified— memoranda complied by the Foreign Office, Clarke had told his Spanish police captors that he was “a novelist” and had dressed as a woman in order to “study the reactions of men to women in the streets”. But the conservative police officials in Francoist Spain did not buy Clarke’s story, and decided to charge him with “engaging in homosexual behavior”. London, meanwhile, was trying frantically to ensure that Clarke was released before either Spanish or German authorities realized that he was a British intelligence officer. The Foreign Office cabled the British embassy in Madrid with direct instructions that “in no circumstances should it be revealed that C[larke] is a British [intelligence] officer”. The significance of this bizarre incident for British intelligence can be seen in the fact that the Foreign Office thought it prudent to notify Britain’s Prime Minister, Winston Churchill, about Clarke’s detention. Several days later, when a British consular official managed to get access to Clarke, the latter told him that he had been transporting clothes to a female friend of his in Gibraltar and had decided to wear them in public “as a form of prank”.  Meanwhile, members of the German intelligence service operating in ostensibly neutral Spain were convinced that Clarke was a spy who had dressed as a woman to avoid detection. However, after relentless British pressure, Spanish authorities denied German intelligence operatives access to Clarke. Two days later, Clarke entered Gibraltar, escorted by a British diplomat.

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6 Responses to WWII files reveal bizarre case of British cross-dressing spy

  1. Pete says:

    The inevitable Wikipedia bio reveals Clarke rose to Brigadier General, was “instrumental in the founding of three famous military units, namely the British Commandos, the Special Air Service and the US Rangers.” and “was known for having beautiful female acquaintances, to whom his friends referred as “Dudley’s Duchesses””.

    A typical upper class Englishmen, who kept everyone guessing. http://en.wikipedia.org/wiki/Dudley_Clarke

  2. mopsie says:

    this is the most positive spy story i’ve seen in ages. most spies today seem like such degenerates.

  3. Anonymous says:

    Finally some truth.

  4. Anonymous says:

    The only problem with this is that Clarke was not an “intelligence operative.” He was a deception officer; the hows and whys of the crossdressing incident in Spain have never been revealed. Holt’s book, The Deceivers, covered this about 10 years ago.

  5. TFH says:

    Talk about thrill-seeker. Intelligence agent was not enough, he had to be a cross dressing spy in a fascist country!

  6. TFH says:

    @mopsie, the lower they go (as long as the controller knows), the lesser chance of compromise.

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