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Dukes, following his graduation from Charterhouse in 1909, went to St. Petersburg to study music at the conservatory and was attached to the famous Marinsky Theatre. In 1915 he was appointed to a position with the Anglo-Russian Commission and carried the passport of a King's Messenger, effectively a diplomatic courier. His job was to study and report on the Russian press. Dukes was appointed to the British Foreign office with an unusual "roving commission" in 1917, the year of the Russian Revolution. At one point in 1917, Dukes who was in Samara ostensibly working for the American YMCA but his duties, other than "training Boy Scouts," were never explained.
Dukes formally became a member of SIS in 1918 as Agent ST-25 much to his delight as one who thought of espionage as "high adventure" and loved intrigue. He was first summoned to London where he met the SIS Chief Commander Cumming who later stated that Dukes was his "top mate" or agent in Russia. After brief training in invisible inks and codes, Dukes returned to Russia. There he travelled throughout the country making great use of his linguistic skills, becoming a master of many disguises and aliases and an expert in the use of forged identification papers. Dukes observed the chaos the revolution had brought and encouraged Britain to side with the White Russian forces attempting to overthrow the fragile Red or Bolsheviks government. Dukes was eventual placed in overall control of all SIS networks inside Russia. He established contact with the National Centre, the organization that represented the interests of the White Russian monarchists who maintained armies in the field against the Bolsheviks. Using money provided by Cumming, often in the form of gold coins, Dukes helped finance widespread espionage, sabotage and insurrection against the Reds.
Much of Dukes activities were directed toward rescuing prominent White Russians from prison and smuggling them out of the country through Finland. Working with SIS Dukes was able to save hundreds of lives. He also worked with Lt Augustus Agar, a RN lieutenant stationed in Finland who operated a squadron of specially modified fast motor torpedo boat stationed at a base near Helsinki. Dukes supplied information on Russian warships to Agar, which allowed him to lead a highly successful attack which resulted in the sinking of several major Russian warships. Meanwhile, using yet more disguises. He managed to join both the Communist Party and the Red Army, while in 1919 Dukes actually obtained an internal passport which showed him as an officer of the Cheka secret police extraordinary feats in themselves. Dukes was able to obtain important political as well as military information for. Double agents operating for the Cheka however, were eventually able to identify the top leaders of the National Centre in 1919 and they arrested its chief, N N Shchepkin on the night of August 28-29,1919. Dozens of other White Russian spies and a courier from Admiral Alexander Kolchak, head of the White Russian armies were also seized. In the following months more than a thousand members of the National Centre were arrested. Shchepkin and sixty-seven others were later executed.
The Cheka had managed to identify Dukes but its officers could not find the elusive spy. He fled to the Finnish border where he attempted to contact Lt Agar, but failed. To avoid detection from spies at the Kronstadt forts, Dukes crossed nearly impossible terrain to reach Lake Luban and then escaped by foot into Latvia.
When he reached Reval, Dukes was compromised when he injudiciously confided in White Russian friends. The Latvian press obtained some of his comments and these were promptly quoted in Finnish and Swedish newspapers, effectively ending his undercover career in the new Soviet Union. Cumming was so elated with Dukes and Agar that he arranged for both men to meet King George V. Agar was awarded the VC, while Dukes award came in 1920 when he was knighted, becoming the only British agent to receive knighthood as a direct reward for espionage. In 1939, just before the onset of World War Two, Dukes was to have another spectacular involvement with British intelligence. He was sent to Germany by the head of SIS, Admiral 'Quex' Sinclair, acting on behalf of a group of London industrialists. His actual mission was to discover the truth about the disappearance of a wealthy Czech businessman, Alfred Obry, on his way from Prague to Switzerland. It was known that the Germans wanted him to sign over to the Nazi state the huge commercial enterprises he controlled and may have discovered his plans to escape using a false passport. Dukes, ever meticulous and resourceful searched local newspaper and noticed the report of the mysterious death of Friedrich Schweiger, a tailor from Prague whose mutilated body was found on a railway line. Suspecting the worst Dukes tricked the local German authorities into exhuming the body, which did indeed turn out to be that of Alfred Obry.
Dukes exact role during World War Two has not been properly recorded, but that he remained in contact with his old service and had at the very least, an advisory role seems certain
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