One of the most extraordinary surveillance operations in UK history involved King Edward VIII, at the time better known worldwide as the Playboy Prince.

Edward’s louche lifestyle alarmed government and intelligence circles in the 1930s - so much so, British Prime Minister Stanley Baldwin had him watched by Scotland Yard with the blessing of Edward’s father, King George V, who suspected his son was being blackmailed.

Initially, when the heir to the British throne was under Special Branch surveillance, the spotlight was on Edward’s party-fueled lifestyle dotted with fascist hangers-on, Nazi sympathizers, and an American socialite and divorcee named Wallis Simpson. Edward appeared besotted. He’d given his secret lover £110,000 ($125,000) worth of jewels.

In addition to tracing Wallis’ movements, opening her letters, and monitoring phone calls, Scotland Yard's Special Branch interrogated shop owners and others who came in contact with the couple, according to Rory Cormac’s The Secret Royals: Spying and the Crown: “They concluded that Wallis and Ernest Simpson [her second husband] were simply a pair of professional hustlers, preying on the prince for money.” 

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King Edward VIII & Wallis Simpson: Nazi concerns

When King George V died in 1936, it was time for Edward VIII to ascend the throne and the British Prime Minister soon found himself overseeing a spying operation involving the new monarch and his American lover. With two marriages behind her, Wallis Simpson wasn’t considered a suitable match for Britain’s new King. Their relationship was a courtship of romance and national disgrace.

Worse, her suspected Nazi sympathies triggered concern within the establishment. Was Wallis unduly influencing the new, pro-German King? At the time, some viewed the Nazis as an acceptable - if undesirable - bulwark against what they perceived to be the even greater threat of Soviet Communism.

Downing Street now turned to MI5 for assistance, which is how MI5 Lt. Colonel Thomas ‘Tar’ Robertson found himself creeping around central London’s Green Park one cold evening in 1936, locating the closest telephone junction box to Buckingham Palace so he could place a wiretap and eavesdrop on the King’s conversations.

The MI5 spy overheard Edward tell his brother the astonishing news that Edward was in love with Wallis and planned to abdicate the throne to be with her, which meant George VI - Queen Elizabeth II’s father - would be crowned next. Britain was about to have their third King in a year and potentially a crisis of instability.

“It was not just MI5. In fact, a world of spies was listening in including the French police. A Paris detective later confirmed that his job had been to ‘review the recorded telephone conversations between King Edward and ‘Wally’ Simpson,’” Cormac said.

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Edward VIII’s tour of Nazi Germany

The abdication left Edward free to marry Wallis in 1937, but the crisis was far from over. The newlyweds - now styled the Duke and Duchess of Windsor - decided to tour Germany at the invitation of the Nazis and against the wishes of the British government. 

In Traitor King, author Andrew Lownie makes the case that Edward and Wallis were not naïve dupes of the Germans but knowingly working against British interests. Even Edward’s father feared his son was secretly passing information to the Germans while still a prince, according to the 2017 documentary Spying on the Royals.

However, Philip Ziegler’s biography, King Edward VIII, argues that no German or ardent Nazi sympathizer visited Edward at his home during his reign and that nothing in the German archives indicates that Wallis or anyone else close to Edward passed information to Berlin.

Still, the couple’s visit to Germany and their social circle gave the strong impression that Edward was an advocate of the Nazi cause. Was he plotting with Hitler during a private invitation to have tea with the Führer in 1937? The typed transcript of their private meeting was subsequently lost, possibly destroyed by the Nazi government, according to biography.com.
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Tea with Hitler

Meanwhile, the mood in Britain was tense amid worries about the couple’s loyalties. Edward’s bodyguard, Chief Inspector David Storrier, secretly reported back to London during the couple’s 1937 German tour. “An internal Metropolitan Police memo from 1937 states the bill for spying was ‘paid for by HM’,” author Dean Palmer writes in Tea With Hitler.

If the couple thought they could simply marry in June 1937 and live happily ever after, they were deluded. Britain wasn’t the only country worried. Prominent members of American Jewish organizations protested and the couple’s planned trip to the US was canceled.

An intense surveillance operation was now underway that would include hundreds of spies across four continents and carry on for another decade.
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Edward VIII and Wallis Simpson: The war years

WWII was underway when the German SS tried, and failed, to kidnap Edward in 1940 under a plan known as Operation Willi. The Germans had hoped to induce Edward to work with Hitler on either brokering a peace settlement with Britain to end the war or restoring Edward to the throne after the German conquest of the UK.

British PM Winston Churchill’s government, determined to get Edward away from German influence and off the Continent, eventually ordered Edward to take on the role of Governor of the Bahamas. At the time, the couple were living in Portugal and dragged their heels for a month but Edward was a military man. He served in the Navy in WWI and was appointed Colonel-in-Chief of the 5 regiments of Foot Guards when he acceded to the throne. The threat of a court martial was persuasive.

MI6 warned the government that Edward was moving slowly, however. Had the couple switched sides in favor of Nazi Germany?

Britain’s foreign spy agency soon relayed that, “A new source… has reported as follows: Germans expect assistance from Duke and Duchess of Windsor, latter desiring at any price to become Queen… Germans have been negotiating with her since June 27th. Germans propose to form opposition government under Duke of Windsor.”

Within weeks, the intelligence was being reported by the world’s media. By July 1940, Edward and Wallis accepted that their fate was to ride out the war some 4,000 miles away from the heart of the action in the Bahamas. They were still scheming, but had been outmaneuvered and would effectively live in exile on a desert island for the next five years.

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With the war at an end, Edward and Wallis shuttled between Europe and the US in the ‘50s and ‘60s, living the life of high society celebrities, mainly in France, until the Duke's death in 1972. Wallis, who lived in seclusion as a widow, remained a divisive figure even after her 1986 death.