Master of deception: Dudley was arrested in Madrid dressed as a woman

The secret war of a wolf in chic clothing

Dudley Clarke had his fingers in many of the most interesting pies of covert operations in World War II


This article is taken from the June 2024 issue of The Critic. To get the full magazine why not subscribe? Right now we’re offering five issues for just £10.

If you’ve ever read anything much about British intelligence and special operations in the Second World War, the name Dudley Clarke will have popped up. He was one of the earliest protagonists of “Commando” units and was then involved in deception operations in the Middle East. But the thing everyone remembers about him is that, on 17 October 1941, he was arrested by General Franco’s police in Madrid dressed in women’s clothing, “brassière and all”.

This rather undersells the man because, as Robert Hutton’s excellent and entertaining new book makes clear, Clarke had his fingers in many of the most interesting pies of covert operations in World War II and was also one of the progenitors of the “information war” which has been swirling around us ever since.

Clarke was born in Johannesburg, South Africa, in 1899, the son of a successful English businessman. After being trapped at the Siege of Ladysmith, the family returned to England. When the First World War broke out, Clarke was attending Charterhouse’s cadet corps summer camp. Desperate for action, but still too young, he struggled to join the military until the weight of losses persuaded the army that it needed to expand its intake of young officers.

The Illusionist: The True Story of the Man Who Fooled Hitler, Robert Hutton (Weidenfeld & Nicolson, £25)

Commissioned in the Royal Artillery, then trained as a Royal Flying Corps pilot, Clarke never reached the Front, but opted to stay in the army after the Armistice. In the 1920s and 30s he followed a moderately successful path of appointments at home and in the Empire, earning himself a reputation as an intelligent, creative, likeable and reliable staff officer with an adventurous, even rebellious streak. In the late thirties, he served in Palestine as a staff officer alongside Orde Wingate, where his unconventional thinking attracted the attention, first of Sir John Dill, and then Archibald Wavell.

When the Second World War broke out, Clarke undertook sensitive missions to Ireland and Norway, but it was his appointment as military assistant to Dill, Chief of the Imperial General Staff, which led him to make his first significant impact. Contemplating the defeat of the British Expeditionary Force in France in May 1940, Clarke mused on how the army could regain its “offensive spirit”: his solution was to form units to conduct quick “butcher and bolt” raids. Dill agreed, as did Winston Churchill, newly installed as Prime Minister. Using a term from his South African childhood, Clarke christened these new units “Commandos”.

He accompanied the first commando operation, a raid on the French coast near Boulogne, during which Clarke managed to be the only participant to be wounded — a stray German bullet to the ear — but his active involvement was brief. He soon took on the role for which he is celebrated: head of deception operations in the Middle East, first for Wavell, then Auchinleck and finally Montgomery.

Hutton’s description of how Clarke approached this task is masterly. Clarke was a highly competent staff officer, but his approach to deception was ahead of his time. First he worked out what he wanted the Germans to do, then constructed a story from snippets of information and short narratives, delivered through a multiplicity of different channels; once German intelligence pieced it all together, it would, brilliantly, persuade them to do it.

To achieve his objectives, Clarke assembled a collection of disparate characters, including an Oscar-winning film director and Jasper Maskelyne, a magician who specialised in camouflage and concealment (and whose subsequent tall tales about these operations Hutton dismisses). But his work was taken seriously and quickly integrated into the planning of operations. 

In the autumn of 1941, Clarke was indoctrinated into the “Double Cross” system, with the intention that the German spy network in Britain, entirely controlled by MI5, could conduct deception at the strategic level. Then the Madrid arrest took place. Had Clarke faced a hostile interrogation, it is quite possible that he could have blown the secret of Double Cross: fortunately he didn’t, and strategic deception — conducted according to Clarke’s principles and often under his supervision — went on to fight another day.

The Illusionist really is popular history at its best. Hutton writes with a light and humorous touch but the book is well researched and tells a fascinating story about an intriguing man. Too much Second World War history claims that this or that operation was the “most important” or “most successful” of the war. Hutton avoids this by placing Clarke and deception properly in context and in a way that is eminently readable. I couldn’t recommend the book more highly. 

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