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Eddie Chapman, a professional criminal, was trained as a Nazi spy in occupied France and parachuted into Britain in December 1941. He immediately defected to MI5. With the help of the secret services, he faked the bombing of an aircraft factory to ensure the continued confidence of his German spymasters, and then agreed to work as a double agent: Agent Zigzag.

Colonel Tar Robertson, the head of MI5’s double-agent section, came in person to congratulate Chapman on the success of the fake sabotage operation. “I consider you to be a very brave man,” Tar declared. “Especially in view of the fact that you are prepared to go back to France and carry on working for us.”

Tar then set out the broad lines of his mission. Once Chapman had learnt his cover story, he would be returning to occupied France as a long-term counter-intelligence agent with the principal aim of acquiring information about the Abwehr, the German secret service. He should accept any mission offered to him by the Germans, and then contact Allied intelligence as opportunities arose.

Tar resumed: “We are preparing a cover story as near to the truth as possible so that if you are cross-examined in detail by the Germans, you need only tell them the truth.”

The chief of MI5’s double-agent section had studied German interrogation techniques and had drawn up a checklist of ways to withstand the pressure: “Always speak slowly; create the impression of being vague; do not appear to be observant; give the impression of being bewildered, frightened or stupid; feign drunkenness or tiredness long before they actually occur.” Chapman might well face physical torture, drugs, or anaesthetic, Tar warned, but German interrogators generally preferred to get results by “procuring mental breakdown . . . by making the witness uncertain, uncomfortable, ridiculous or embarrassed, by stripping him naked or dressing him in women’s underwear, making him stand facing the wall, making him sit on a three-legged chair so that it is a constant effort to keep his balance.” Above all, he should stick to his cover story, and never tell an unnecessary lie.

For all his expert advice, Robertson also knew that if Chapman fell into the hands of the Gestapo, and they chose to disbelieve him, they would break him. And then they would kill him.

The first task was to get Chapman back behind enemy lines, but the Abwehr seemed in no hurry to remove him. It was clear, said Ronnie Reed, Chapman’s case officer, that “any attempt to return to occupied territory would have to be made by Zigzag alone”.

Chapman was in the highest of spirits. To his MI5 case officers, he was an enigma: “Zigzag is himself a most absorbing person,” wrote Reed. “Reckless and impetuous, moody and sentimental, he becomes on acquaintance an extraordinarily likeable character. It is difficult for anyone who has been associated with him for any continuous period to describe him in an unbiased and dispassionate way. It was difficult to credit that the man had a despicable past. His crimes of burglary and fraud, his association with ‘moral degenerates’, and his description as a ‘dangerous criminal’ by Scotland Yard is difficult to reconcile with more recent behaviour.”

It was agreed that Chapman would be shipped to neutral Portugal, disguised as a merchant seaman, where he would re-establish contact with the Abwehr. On March 18, 1942, the merchant vessel City of Lancaster steamed into the port of Lisbon. Chapman was aboard, disguised as assistant steward Hugh Anson, equipped with false papers and false information to pass to the Germans, written in secret ink. Portugal was still neutral, and Lisbon was a cauldron of espionage, awash with refugees, smugglers, spies, hustlers, arms dealers, wheeler-dealers, middlemen, deserters, profiteers and prostitutes. It was Chapman’s kind of town. The Allied and Axis powers maintained safe houses, dead drops, fleets of informants and small armies of competing spies, as well as official consulates and embassies, all under the thin veneer of neutrality. The Abwehr even ran its own bars and brothels, for the express purpose of extracting information from sex-starved and drunken British sailors.

On shore, Chapman (alias Anson) joined four of his crewmates at the British Seaman’s Institute in Rua da Moeda, but then slipped away, telling one the ship’s gunners he had “business to attend to” in town with an old acquaintance.