Who was the most successful German spy against Great Britain in WWII, from the contemporary German perspective?

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Accepted answer

From the "contemporary German perspective", the answer is doubtless "Alaric", Juan Pujol García, known to the British as "Garbo". He was paid a total of US$340,000 and awarded the Iron Cross, second class, in July 1944 for his contributions to the war effort. He operated a network that grew to 27 sub-agents in all parts of the UK, communicating via post to Lisbon at first, and later by radio.

Unfortunately for the Germans, they never realised that he was a double agent. He'd gone into business for himself, selling the Germans "intelligence" that he simply invented. He had an extraordinary imagination, and they found him quite convincing, in spite of his lack of knowledge of the UK. He'd wanted to work for the British, but they were not interested at first. Later they took him up, moved him to the UK, and provided information for him to send. The sub-agents were all fictional.

There was a structural weakness in the operations of the Abwehr during WWII. It had bases in neutral countries, whose operations were not confined to those countries, so they were in competition with each other. Alaric was handled by the Madrid base: his messages were all sent there. This gave his handlers no motive to suspect that the intelligence was false: discovering that would be very bad for their comfortable positions in Spain, with the Eastern Front and the U-Boats always short of officers. They would, in fact, do better if they promoted the work of their agents, and thus their own, in the continuous competition of the Nazi state.

This was why the Abwehr were so readily deceived by the Double-Cross System operated by the British. They essentially stopped sending agents to the UK after 1942, because they were confident in their sources. The British were operating all of the remaining agents, and the messages they sent by post or via radio to their handlers were often re-sent to Abwehr HQ by radio, using the Enigma machine, providing chosen-plaintext attacks on the Enigma.

The regular reading of Abwehr Enigma enabled the British to be sure that they had all German agents in the UK under control, allowing them much greater scope in misleading the Abwehr. This contributed significantly to the success of the invasion of Normandy, as they were able to convince the Abwehr via "reports from agents" that there were large forces in Kent and Sussex ready to invade in the area of Calais. This compelled the Germans to keep part of their forces in the Calais area, making them unavailable for defending Normandy.

All this amply justified MI5's policy of capturing and turning agents sent by the Germans, as opposed to the FBI's policy of high-profile trials and executions. Most of the agents listed in the question were not sent by the Germans, but people who decided to spy for the Germans of their own accord. Without training, they weren't very successful.

Sources: Masterman The Double-Cross System and Hesketh Operation Fortitude.

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