How King Edward VIII's closest friend was once chased out of a brothel without his trousers: But “Fruity” Metcalfe was still best man when the former monarch married Wallis Simpson, writes CHRISTOPHER WILSON

It was a most strange friendship: a future king and emperor and the penniless son of an Irish prison guard who had “no money and no brain”.

And yet the mischievous Edward “Fruity” Metcalfe became the most important man in the life of David, Prince of Wales, who was briefly King Edward VIII.

Their love of long nights, fast horses and even faster women united the couple, and for twenty years they were inseparable – they thought, dressed, ate and spoke alike.

The prince gave Fruity official court status by appointing him his aide-de-camp – “and his family is furious about it,” a friend confided in her diary.

And that was no wonder, because Fruity was constantly getting into trouble.

“Metcalfe visited a house of ill repute, but was unable to pay and was chased out by the lady who had entertained him. He did, however, get his trousers taken from him, which she had stolen,” recalled writer Duff Hart-Davis.

On another occasion, while visiting a New York brothel, Fruity, while drunk, left behind a wallet containing the prince's private letters.

Edward “Fruity” Metcalfe became the most important man in the life of David, Prince of Wales – later King Edward VIII. Above: Metcalfe (left) with the Prince (centre) and Lord Louis Mountbatten dressed as Japanese coolies on board HMS Renown during the King's tour of Japan and the Far East, 1922

Wedding of Lady Alexandra “Baba” Curzon and Major Edward Dudley “Fruity” Metcalfe in the Chapel Royal, St. James's Palace, 1925. Baba was the daughter of Lord Curzon and for a time the mistress of Oswald Mosley

This disgusted the Prince’s aloof private secretary, the outspoken Alan “Tommy” Lascelles.

Fearing that the scandal could become public and ruin the Prince's years of image-building, he called Metcalfe an “absolute villain.”

The result was as unexpected as it was comical: Fruity was fired, but instead of apologizing, he went to Lascelles' house and beat him up.

The fact that no one bothered to tell him what they thought was a sign of how strong his relationship with the prince was.

Fruity is pretty, has a horse and a captivating Irish accent. She never takes no for an answer.

Although he came from relatively humble beginnings, it was only by chance that he entered the illustrious world of royalty – but once he got there, he was determined to hold on to his position.

The women longed for him—such a bad boy!—and at the same time detested him.

Be that as it may, they talked about him – and it wasn’t long before he had landed a rich and aristocratic woman: Lady Alexandra “Baba” Curzon, the daughter of the greatest Viceroy of India of all time, Marquess Curzon.

Fruity later said, “I don't know why she married me – I have no money and no brain.”

But his reputation in the bedroom probably gave a clue as to why a woman 17 years younger than him fell for him.

The royal family hated him. When he married Baba, his close relationship with the Prince of Wales – and Baba's high social standing – allowed him to hold the ceremony in the Chapel Royal at St. James's Palace.

The Prince of Wales with Sir Walter Peacock and Captain Allen “Tommy” Lascelles, the Prince’s private secretary

The wedding party at the wedding of the Duke and Duchess of Windsor, best man was “Fruity” Metcalfe, who stood next to Edward VIII

Major Dudley Metcalfe with his wife Lady Alexandra Curzon in France for the wedding of former King Edward VIII and Wallis Simpson

The Duke and Duchess of Windsor visit Metcalfe's country house at Coleman's Hatch, Ashdown Forest in Sussex in 1939.

“But shockingly, the royal family is not coming to the wedding,” MP Chips Channon wrote in his diary.

“Her hatred for her son's best friend is of fantastic intensity.”

“All the Prince's escapades are due to his influence. Fruity is stupid and weak, the Prince is stupid and determined – and both are very, very charming. But he [Fruity] is to blame.

“The King and Queen sent no gifts and refused to attend the wedding. Rumor has it that His Majesty has forbidden any member of the family to attend.”

The two men met when the prince was on a trip to India in 1922 and the Irishman was serving as an officer in an unknown cavalry regiment, the Skinner's Horse.

“The prince had no other friend [after that]“, says Channon.

For a while, Fruity's official job was to take care of the prince's horses and organize his equestrian life.

But when his boss reluctantly gave up riding, Metcalfe had less to do and more time to cause mischief wherever he could.

It is perhaps no surprise that this long-standing friendship began to crumble when Wallis Simpson arrived on the scene.

The divorced American was jealous of all of her new lover's friends and had a particular dislike for Fruity and his overly masculine behavior. So he was pushed out of his life. That hurt.

But during the abdication crisis of 1936, when Wallis was temporarily separated from the King (as he had been 11 months earlier), Fruity stepped into the breach.

And before the wedding of Wallis and David in 1937, he offered to fly to Enzesfeld Castle in Austria, where the former king resided.

There the new Duke of Windsor walked up and down alone, waiting for his divorce from Wallis.

Wallis didn't like the prospect of Fruity joining her boyfriend at all.

“You cannot be alone with Fruity,” she wrote commandingly. “He is incapable of handling mail, dealing with servants, etc.”

“It is more likely that she feared Fruity's influence over the Duke,” wrote biographer Anne de Courcy.

“They had a history together long before Wallis came on the scene, and a word or phrase could set off uncontrollable schoolboy giggles.”

While she waited to join her future husband, Wallis nagged David on the phone every day about how much time he spent with his old playmate.

Nevertheless, Fruity was invited as best man to their wedding in 1937 – mainly because no member of the royal family was willing to be photographed in their company.

The latter meant that the guest list was very small.

Edward “Fruity” Dudley Metcalfe attends a polo match with the American dancer Irene McLaughlin at the Ranelagh Club, Barne Elms, 1930

Major Metcalfe with his wife Lady Alexandra Metcalfe and Mrs. Cripps

While the new Duke and Duchess of Windsor settled into a life of exile in France, Fruity returned to London.

But the old friends were reunited at the outbreak of war, when David donned an army uniform and was assigned to inspect troops in northern France.

Once again, Fruity became David's aide-de-camp based in Paris.

But when Fruity called the Duke the morning after the German invasion of France, he discovered that the Windsors had fled to Biarritz and left no message.

“Fruity, who had worked for months without pay and done everything he could to support the Duke and make life easier for the Windsors, was abandoned without a single word from the man he considered his best friend,” de Courcy said.

Humiliated and depressed, Fruity wrote to his wife: “After 20 years, I’m done – I despise him!”

“For 20 years I fought for him and supported him even though I knew what a pig he was, but now it's over.”

“He left his job in 1936. Now he has left his country, at a time when every office boy and every cripple is trying to do what he can. This is the end.”

Through selfishness and his disregard for personal loyalty, the former king had lost his only friend.