A Nazi diplomat, Mayfair car dealer and a bisexual Woolworth heir: Wallis Simpson's extraordinary collection of lovers exposed after spy dossier is finally revealed ... so did she ever truly love the king who gave up his throne for her?

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The passionate infatuation of the Queen’s uncle, Edward VIII, for Wallis Simpson (pictured) has been hailed as ‘the greatest love story of the 20th century’

The passionate infatuation of the Queen’s uncle, Edward VIII, for Wallis Simpson has been hailed as ‘the greatest love story of the 20th century’. But how much of a love story was it?

There is no doubt about Edward’s resolve to marry the twice-divorced American socialite. After all, he abandoned his throne, country and reputation to make her his wife, and was condemned to a life in exile as a result.

But whether Wallis, who was conducting simultaneous affairs with four other men, ever truly loved the besotted monarch in return is debatable. Was it actually the case that she became trapped into marriage with a man she had come privately to despise?

New evidence supporting the latter view is provided in a Scotland Yard dossier that has been unearthed by academics for a Channel 4 documentary series, Spying On The Royals.

It reveals that Edward’s father, George V, asked prime minister Stanley Baldwin to order surveillance of his own son and heir — something that was long suspected but has always been denied.

The King was concerned about the then Prince of Wales’s friendships with Fascists such as Sir Oswald Mosley, as well as his liaison with the allegedly pro-Nazi Wallis Simpson. Both she and her husband, Ernest, were also monitored by Scotland Yard and the intelligence services.

The surveillance involved close scrutiny of Wallis’s sex life. From her teenage years, she seems to have been irresistible to men. ‘Nobody ever called me beautiful or even pretty,’ she wrote in her memoirs, but she had fine eyes, a trim figure and a sense of style, as well as wit and animation that would make her alluring and challenging to men all her life.

After problems in her first marriage to a violent, alcoholic U.S. naval pilot, Earl Winfield Spencer Jr, Wallis travelled to Hong Kong, where Spencer was stationed, to attempt a reconciliation with him. The reunion was short-lived and they separated soon after.

There is no doubt about Edward’s resolve to marry the twice-divorced American socialite. After all, he abandoned his throne, country and reputation to make her his wife, and was condemned to a life in exile as a result

During what she would later describe as her ‘lotus year’ in Shanghai and Beijing, she is said to have been schooled in some of the more specialised sexual techniques of the Far East.

She also had an affair with a handsome young Italian diplomat and Fascist, Count Gian Galeazzo Ciano, then 21 and seven years her junior, who later became Italy’s foreign minister and Mussolini’s son-in-law.

She became pregnant and underwent a botched abortion that left her with gynaecological problems for the rest of her life.

After her divorce from Spencer, Wallis met wealthy Anglo-American businessman Ernest Simpson in London. He became infatuated and divorced his first wife to marry her in 1928. They set up home in London, where they were soon at the centre of a fashionable, well-connected circle.

In January 1931, Wallis and Ernest were invited to a weekend house party at Burrough Court in Leicestershire, the country home of Edward’s mistress, Thelma, Viscountess Furness. The Simpsons were there ostensibly as chaperones to neutralise gossip about Thelma and Edward — but the seeds were being sown for a far more fateful relationship as they were absorbed into the Prince’s circle.

 Edward FitzGerald (left), 7th Duke of Leinster, and the German Ambassador to the UK, Count Joachim von Ribbentrop (right)

Some three years later, it seemed perfectly natural for Thelma, about to leave for America, to ask her friend Wallis to ‘look after [the Prince] while I’m away’. She returned to find that Wallis had supplanted her in the Prince’s affections.

In spite of his reputation as a womaniser and his numerous affairs with married women, the Empire’s Prince Charming was an unsuccessful lover. Sexually inadequate and far from well endowed, he suffered from premature ejaculation, leaving his partners frustrated and unsatisfied.

Wallis, with a sexual repertoire that included techniques variously known as the Baltimore grip, Shanghai squeeze or China clinch, was reputed to be the only woman capable of alleviating this condition.

She was well-rewarded for her expertise. George V was aghast to discover from the surveillance that his son had given his mistress jewels costing £110,000 (£7 million today).

In recently declassified files in the National Archives, Superintendent Albert Canning of Scotland Yard, the man investigating Wallis, reported that the Prince of Wales was ‘frequently’ visiting the Simpsons’ London home at 5 Bryanston Court, Marylebone, and that in addition to his lavish gifts of jewellery and furs, was paying her £6,000 a year (more than £350,000 today).

Covert surveillance at an antique shop in Kensington frequently visited by the Prince and Wallis confirmed that they called each other ‘Darling’. The antique dealer’s opinion was that ‘the lady appeared to have the Prince of Wales completely under her thumb’.

But Canning also reported that Wallis was ‘very fond of the company of men’ and had had ‘many affairs’.

Apart from her husband, Ernest Simpson, with whom she was still living during the royal affair, there were at least four other men in her life.

In the summer of 1935, the security services shadowing Wallis reported: ‘Although she now spends a great deal of time with the Prince of Wales, it is said that she has another secret lover who is kept by her.’

In a Special Branch report dated July 3, 1935, the ‘secret lover’ was identified as a 36-year-old married Mayfair car dealer, Guy Marcus Trundle, who was described as ‘a very charming adventurer, very good-looking, well-bred and an excellent dancer. He [Trundle] is said to boast that every woman falls for him. He meets Mrs Simpson quite openly at informal social gatherings as a personal friend, but secret meetings are made by appointment when intimate relations take place.’

William C. Bullitt (left), the allegedly pro-Nazi American ambassador to France, and Mayfair car dealer, Guy Marcus Trundle (right)

In due course Trundle was interviewed by Special Branch and admitted that he ‘receives money from Mrs Simpson as well as expensive presents’.

A second man intimately involved with Wallis was the German Ambassador to the UK, Count Joachim von Ribbentrop, later Hitler’s foreign minister, who was hanged at Nuremberg in 1946. He was ordered by the Fuhrer to flatter Wallis and become intimate with her as a means of keeping Edward VIII friendly to the Nazi regime. He took to sending her 17 carnations or long-stemmed red roses daily, allegedly to remind her of the number of nights they had spent together.

Wallis was also reported to be in a sexual relationship with William C. Bullitt, the allegedly pro-Nazi American ambassador to France in the years immediately before the war, while the fourth man was someone well-known to me personally. He was Ireland’s premier peer, Edward FitzGerald, 7th Duke of Leinster, whose family trustee I became in the years before his suicide in 1976.

‘Fitz’ Leinster, a close friend of Edward and Wallis both before and after the Abdication, was dubbed ‘the Shy Duke’ by Wallis, who began an intermittent affair with him in 1935, while he was married to his second wife, Rafaelle.

Relations between Fitz and Wallis resumed in 1946, after the Windsors had returned to France from the Bahamas, where the Duke had been Governor. At that time the Duke of Leinster lived in a villa in the South of France with his third wife, former musical comedy star Denise ‘Jo’ Orme.

A charming man and very much a gentleman, Fitz confessed to me that the running in this relationship was made almost entirely by Wallis, but that he found it impossible to resist her advances. Many years later, when I visited the Windsors at their Paris mansion in the Bois de Boulogne in 1971, Wallis’s face lit up when I mentioned Leinster’s name.

‘Oh, the Shy Duke!’ she said. ‘What a dear man! Please send Fitz my love. I have such happy memories of him.’

The popular view of Wallis Simpson was — and to some extent remains — that she was a scheming, ambitious adventuress who hoped to become Queen. But the evidence does not entirely support this.

Lady Diana Cooper, a close observer of Wallis and Edward’s relationship, wrote: ‘The truth is she’s bored stiff by him, and her picking on him and her coldness towards him, far from policy, are irritation and boredom.’

And indeed that may have been true. There was a part of Wallis still in love with her second husband, Ernest.

In September 1936, nine months after Edward had become King and less than three months before the Abdication, Wallis wrote to the King. She told him she needed to renounce him and return to Ernest — the man she was due to divorce — with whom she felt ‘so awfully congenial . . . I know Ernest and have the deepest affection and respect for him. I feel I am better with him than with you . . . I am sure you and I would only create disaster together.’

The King responded to this by threatening to slit his throat if she left him. She knew then that she was trapped. In a poignant letter to Ernest, written two days before their divorce hearing at Ipswich Assizes, she ended with the words: ‘I am so lonely.’

Wallis had a midlife fling with the blond, blue-eyed, 35-year-old homosexual playboy James Paul Donahue Jr (left)

Astonishingly, the surveillance by the security services ordered by his father continued after Edward VIII became King.

On the first weekend of December 1936, a 27-year-old MI5 officer, Thomas Robertson, lay crouched in the undergrowth of London’s Green Park, wire-tapping the telephone junction box that served Buckingham Palace.

Listening in on a private conversation between Edward VIII and his brother Bertie, the future George VI, Robertson became the first person outside the Royal Family to learn that the King was about to abdicate to marry Wallis.

Some historians argue that Edward, while infatuated initially with Wallis, had discerned in her a means of escape from the kingly destiny he found intolerable. And when, despite Wallis’s desperate efforts to dissuade him, he announced that he was renouncing the throne for ‘the woman I love’, she was blamed as she knew she would be.

Five months after her marriage in France to the man now known as the Duke of Windsor, an occasion boycotted by every member of the Royal Family, Wallis was still writing loving letters to Ernest Simpson.

‘Ernest dear’, she wrote from Paris on October 30, 1937, ‘What can I say? When I am standing beside the grave of everything that was us, oh my dear, dear Ernest, I can only cry as I say farewell and press your hand very tightly and pray to God. Wallis.’

The new Duchess of Windsor, exiled in France, ostracised by the Royal Family, denied the title of Her Royal Highness and deluged with hate mail, faced a hollow existence with a man she did not love and whose subservient devotion inspired in her only an icy contempt.

Far from being the idyllic romance of popular legend, their life together was disfigured by drunken bickering. Given the Duke’s sexual inadequacy, no children resulted. When she was once asked why this was, the Duchess snapped: ‘My husband isn’t heir-conditioned.’

British Intelligence continued to watch their every move. ‘They are very clearly Fifth Column,’ stated one wartime report, while their banishment to the Bahamas, where the Duke became Governor, led the FBI to suggest that Wallis was sending messages about British official activities to the Germans.

Marriage to the former King-Emperor gave Wallis fame, wealth, fabulous jewels and clothes, and a life of luxury in their mini-palace in the Bois de Boulogne, with scarlet, blue and gold tapestries bearing the former monarch’s personal standard, and a staff of 25 servants attired in the royal livery.

But it was a tinselled wilderness they inhabited, peopled by fawning, second-rate Americans and ill-chosen friends such as Sir Oswald and Lady Mosley, both of whom had been imprisoned in Britain for their support of Hitler.

After the Windsors’ relegation to what the Duchess described as the ‘moron paradise’ of the Bahamas, the Duke was never given another job and their life together in Paris appeared empty, meaningless and purposeless.

In her 50s, exhausted by the need to maintain the fiction of a great love story, Wallis had a midlife fling with the blond, blue-eyed, 35-year-old homosexual playboy James Paul Donahue Jr — known to gossip columnists as ‘Jimmy’ — who had inherited some $15 million from his grandfather, the five-and-dime stores magnate Frank W. Woolworth.

The scandal generated by this relationship, which created rumour and speculation in gossip columns worldwide, broke the Duke’s heart. But his love for his wife stayed steadfast to the end.

Displayed in their mansion, framed on royal stationery and written in his own hand, were these words:

My friend, with thee to live alone

Methinks were better than to own

A crown, a sceptre, and a throne.

For the devoted Duke those words remained true until his very last breath. Not so, perhaps, for Wallis.

• Spying On The Royals is on Channel 4 tomorrow at 8pm.