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According to those who knew him, Sidney Cotton had only three real interests: flying, money, and women. What decidedly did not interest him was following rules.

In the First World War he repeatedly clashed with his commanders in the Royal Flying Corps until forced to resign his commission in 1917. Over the next several decades he would make and lose a fortune in a restless string of adventurous pursuits—running an airmail operation in Canada; trading oil leases in the Middle East; managing an apple orchard in Tasmania; searching for a team of missing explorers in the Arctic; running guns to India; taking out patents for inventions that included a cold-weather flying suit, camouflage paint, and dehydrated soup— while marrying and divorcing a string of young and attractive women, including a 17-year-old actress, an 18-year-old school girl, and his 25-year-old secretary, who was less than half his age when he married her.

Early in 1939 Cotton had a new venture: the Aeronautical Research and Sales Corporation. Piloting his own Lockheed 12A airliner, Cotton embarked on a series of flights around Europe and the Mediterranean, giving a range of imaginative explanations for showing up in far-flung spots. He flew over Sicily and around North Africa saying he was a film producer scouting locations, or an archaeologist looking for ancient ruins. In Germany he cultivated an influential business associate with whom he proposed to market Dufay-color movie film, a less expensive rival to the Technicolor process, and soon he was palling around with Luftwaffe chief Hermann Göring and other top Nazis.

Invited to attend a flying rally in Frankfurt in August 1939, Cotton flew back to Germany in a new Lockheed 12A, this one equipped with two extra fuel tanks, painted an attractive light blue, and fitted with another one of Cotton’s numerous personal inventions, a teardrop-shaped side window that afforded an unobstructed view of the ground below. When Albert Kesselring, at that time a top Luftwaffe officer, later Hitler’s commander in chief in Italy, asked to take the “Kolossal Lockheed” up for a spin, Cotton graciously assented, even suggesting that Kesselring take the controls while they fly up the Rhine to Mannheim. His maiden aunt had once visited there, he explained, and had always praised the beauty of its scenery.

In the last week of August, on the very eve of war, Cotton flew out of Germany and nosed along the northwest coast home to Britain. His was the last civilian plane permitted to leave the country before Germany’s attack on Poland a few days later.

Had Cotton’s hosts known of some other inventive gadgets installed on Cotton’s plane, he surely would not have been per mitted to leave at all. For under each wing was a close-fitting panel that could be retracted by an electric windshield wiper motor activated by a button concealed beneath the pilot’s seat, and behind each panel was a Leica camera loaded with 250 frames of film. The Aeronautical Research and Sales Corporation was a front for the British Secret Intelligence Service, MI6, and Cotton had been recruited as one of its larger-than-life spies. The images he photographed of airfields, naval bases, and other military facilities—including those he snapped with General Kesselring at the controls—would for some time provide the RAF with the only detailed targeting data it had for planning its bombing raids.

With the outbreak of war, Cotton was placed in charge of the RAF’s newly established photoreconnaissance unit, where he continued his blend of innovation and insubordination. Dissatisfied with the slow Blenheim bombers assigned to the unit, he wangled two Spitfires from Fighter Command, “Cottonised” them by pulling out their guns to increase their speed, and sent them on a series of daring high-speed dashes into the heart of Germany. Photorecon Spitfires would later take crucial low-level images used to plan the D-Day landings and provide the first conclusive evidence of the Nazis’ V-2 rocket program.

But Cotton was by then long gone; the last straw had been his flying the proprietor of the Christian Dior firm out of Paris just before the Nazis marched in— in exchange for a suitcase full of cash.

Cotton had been quickly dismissed, though not without an award of the Order of the British Empire and a letter of congratulations thanking him for “great gifts of imagination and inventive thought which he had brought to bear on the development of aerial photography.” Though he made millions at one point after the war, he died penniless in 1969.


Originally published in the March 2009 issue of World War II. To subscribe, click here