Having a friendly relationship with Adolf Hitler, many speculated that the Duke and Duchess of Windsor were involved in a plot to overthrow the British crown during World War II.

When King Edward VIII abdicated the British throne in December 1936 to marry Wallis Simpson, the pair, now styled the Duke and Duchess of Windsor, began a decades-long semi-exile in continental Europe. Their lavish lifestyle, which included friendships with louche characters of dubious distinction, led to criticism by the press and public. But documents, including some only recently declassified, may help bolster an even darker claim — that the couple harbored pro-Nazi sympathies and were involved in a failed plot to overthrow the British crown during World War II.

Edward expressed his early support for Hitler

Up until it was changed to “Windsor” during World War I, the British royal family’s name of Saxe-Coburg-Gotha made clear their strong German origins. The future King Edward VIII, known as David to his friends and family, was particularly close to his German cousins, and strongly embraced German culture. The horrors of World War I left a deep impression on him, and his wartime service, including visits to the front where he witnessed the carnage firsthand, helped form his determination to avoid another global conflict at all costs.

When Adolf Hitler and his Nazi Party began its rise to power in the late 1920s and early 1930s, many in Europe, Edward included, applauded the economic recovery of war-torn Germany. In Britain, support for more far-right political parties increased, leading to the creation of the British Union of Fascists in 1932, led by former MP Sir Oswald Mosely. Groups like the BUF and others embraced these authoritarian positions as a bulwark against what they perceived to be a growing Communist threat.

A strong streak of anti-Semitism ran through these political groups, as well as the British government and royal family. Many were more than willing to overlook the sharp rise of anti-Jewish attacks and legislation in Germany, with Edward purportedly telling a German relative in 1933 that it was “no business of ours to interfere in Germany’s internal affairs either re Jews or re anything else.” He went on to add, “Dictators are very popular these days. We might want one in England before long.”

British intelligence had Edward and Wallis under surveillance

While Edward's strongly pro-German sentiments were shared by others, his outspokenness as heir to the throne made his words potentially dangerous. His support for Mosely and other fascist organizers (many of whom would be imprisoned after Britain went to war with Germany) increases suspicions on his political beliefs.

Another liability was his playboy reputation and his burgeoning affair with a twice-divorced American, Simpson. Although the British public remained in the dark about the affair, it was common knowledge in royal, government and intelligence circles. Rumors about Simpson’s romantic past swirled, with some claiming she had a begun a long-term affair with Nazi official Joseph von Ribbentrop while he served as Germany’s ambassador to Britain in the mid-1930s. Even more salacious were allegations that Simpson had passed along confidential British government secrets gleaned from private dispatches.

The situation came to a head when Edward became king following his father’s death in January 1936. Fearful that the new king (and his relationship) might be a danger to national security, Prime Minister Stanley Baldwin stepped in, ordering Mi5, Britain’s domestic intelligence agency, to begin surveillance of the couple. Their phones were tapped, and members of their Scotland Yard security team were tapped to provide information about the king they were also charged with protecting.

The British weren’t the only ones worried. After war broke out, the FBI began its own massive file on the couple, closely monitoring their visits to the United States. Among its hundreds of pages were several memos sent to President Franklin Roosevelt, warning of the Duke and Duchess of Windsor’s pro-German allegiances.

The Duke of Windsor in Germany with Dr Robert Ley, leader of the German Labour Front and Wallis Simpson

Edward VIII in Germany with Dr. Robert Ley, leader of the German Labour Front (DAF), and Wallis Simpson in 1936

The couple visited Nazi Germany as Hitler’s guests

In October 1937, four months after their marriage — and despite the strenuous objections of the British government — the Duke and Duchess traveled to Germany. While the Duke claimed he was making the trip to inspect housing and working conditions (a long-time passion of his), he likely hoped the trip would burnish his reputation both at home and abroad and possibly improve Anglo-German relations.

His private secretary later wrote that the Duke also planned to use the trip to showcase his new wife, who had not been granted the title of “Her Royal Highness” upon the couple’s wedding, and who had been shunned in royal circles. And the couple were indeed treated like stars during the two-week trip, which took on the trappings of a mock-state visit. They were met by massive, cheering crowds, many of whom greeted the former king with a Nazi salute, which Edward frequently returned. The Duchess, meanwhile, was met with the royal curtsies and bows she had been denied elsewhere.

They were feted at receptions, dined with several high-ranking Nazi officials, including Hermann Göring and Joseph Goebbels, and even visited a training school for future members of the deadly SS guard. On October 22, the couple traveled to Hitler’s country home in the Bavarian Alps, known as the Berghof. Hitler and the Duke spoke privately for over an hour, while the Duchess met with Deputy Führer Rudolf Hess. Some accounts of the Duke’s conversation claim he criticized Hitler’s policies, while others maintain he may have given his tacit support. The typed transcript of their meeting was subsequently lost, possibly destroyed by the Nazi government. The couple departed following afternoon tea with Hitler, and it was clear to most observers that the pair were awestruck by their host and had succumbed to the flattery and lavish treatment doled out by the Nazis.

The reaction in Great Britain however, was quite different. As feared, the trip heightened fears about the couple’s loyalties, with many horrified by the Duke’s lack of judgment and common sense. A planned trip to the United States was soon scuttled when prominent members of American Jewish organizations protested the couple’s seeming willingness to ignore Germany’s persecution of Jews.

Germany hatched a bizarre plot to reinstate Edward to the throne

In the waning days of World War II, a large cache of files from the German Foreign Ministry were discovered at Marburg Castle. Among the 400 tons of paperwork were a smaller collection of some 60 or so documents and telegrams, which became known as the “Windsor File,” detailing German communication with the Duke and Duchess of Windsor before and during World War II.

The file included details of a secret plan, codenamed “Operation Willi.” In the summer of 1940, the Duke and Duchess fled Nazi-occupied Paris and traveled to neutral Spain and Portugal. German Foreign Minister Joachim von Ribbentrop ordered local Nazi officials to meet with the couple, who, the Windsor File documents claimed, voiced their displeasure with both the British royal family and Winston Churchill’s government.

That July, in an effort to get him out of Europe and away from German influence, Churchill ordered the Duke to take up a new position as the Governor of the Bahamas. Edward was reluctant to go, and von Ribbentrop played on those fears, allegedly feeding false information to the couple that they were in danger of attack or even assassination by British secret operatives. Nazi officials also tried to get the couple to return to Spain, by force if necessary, and lend their support to the German war effort, which, if victorious would see the overthrow of King George VI — with Edward in his place as a puppet king and with Simpson as his queen.

According to the Windsor files, the couple did not dismiss the plan, nor did they inform British authorities of these conversations. They delayed their departure by nearly a month, but despite last-minute efforts by the Nazis, including calling in a false bomb threat on the ship the couple were booked on, the Duke and Duchess finally left Portugal in August, and spent the rest of the war in the Bahamas, where he continued to publicly cast doubt about Britain’s ability to win the war.

Churchill tried to suppress the Windsor File

Initially, British, French and American officials agreed to declassify and release the Marburg papers and hired a team of esteemed historians to sort through the massive trove, a years-long process. But, as British government documents released in 2017 show, Churchill tried to block the Windsor files, including details of Operation Willi, from being published. He went so far as to contact President Dwight D. Eisenhower, who had worked alongside Churchill during World War II. Churchill claimed the documents were biased and unreliable, and likely to cast the former king in the worst possible light. He asked Eisenhower to prevent the public from seeing them for, “at least 10 or 20 years.”

Many in the US intelligence community agreed with Churchill’s assessment, and Eisenhower wrote to Churchill in July 1953 that the documents were “obviously concocted with some idea of promoting German propaganda and weakening western resistance.” Eisenhower permitted the documents from being released in the initial publication, but they were finally leaked in 1957. The Duke of Windsor strenuously denied any involvement in anti-British plots and called the files a “complete fabrication,” while the British Foreign Office stated that the Duke, “never wavered in his loyalty to the British cause.”

In his memoirs, the Duke of Windsor would dismiss Hitler as a “somewhat ridiculous figure, with his theatrical posturings and his bombastic pretensions.” But in private, he claimed that Hitler was “not such a bad chap,” and frequently blamed any number of groups, including the British government, America and even Jews themselves for causing World War II. While most modern historians are in agreement about the Duke’s pro-German beliefs, there is continued debate over whether those sympathies crossed the line into treason, or if the famously weak-willed and easily swayed former king played right into the Nazi’s hands, making him the most high profile of propaganda tools.