The night time the Prince of Wales’s chum, Edward Dudley ‘Fruity’ Metcalfe

It was the oddest friendship: a future king-emperor, and the penniless son of an Irish prison official with ‘no money and no brain.’ 

Yet the rascally Edward ‘Fruity’ Metcalfe was to become the most important man in the life of David, Prince of Wales, who would go on to briefly be King Edward VIII.

Drawn together by their love of late nights, fast horses and faster women, for twenty years the pair were inseparable – they thought, dressed, ate, and talked alike. 

The Prince gave Fruity official Court status by appointing him his aide de camp – ‘and his family are furious about it,’ a friend confided to her diary.

And no wonder. Fruity was constantly getting into hot water.

‘Metcalfe visited a house of ill repute but, finding himself unable to pay, was chased from the premises by the lady who had been entertaining him, minus his trousers, which she had stolen,’ recalled the writer Duff Hart-Davis.

On another occasion, visiting a New York bordello, Fruity drunkenly left behind a wallet containing private letters from the Prince.

This disgusted the Prince’s prim private secretary, the forthright Alan ‘Tommy’ Lascelles.

Fearing that the scandal would become public and ruin the product of years of burnishing the Prince’s image, he denounced Metcalfe as ‘an absolute bounder’.

The result was as unexpected as it was comical – Fruity was fired, but instead of apologising, went round to Lascelles’ house and floored him. 

It was a measure of the strength of his relationship with the Prince that nobody bothered to tell him off.

Handsome, horsy, with a beguiling Irish brogue, Fruity would never take no for an answer. 

From relatively humble beginnings, he entered the rarefied world of royalty only by a freak of chance – but was determined once he got there to hang on to his position.

Women both craved him – such a bad boy! – and loathed him. 

Either way, they talked about him – and before too long he’d landed himself a rich and aristocratic wife, Lady Alexandra ‘Baba’ Curzon, daughter of the grandest-ever Viceroy of India, Marquess Curzon.

Later Fruity was to say, ‘I don’t know why she married me – I’ve got no money and I’ve got no brain.’ 

But his reputation in the bedroom probably offered a clue as to why a woman 17 years his junior fell under his spell.

The Royal Family hated him. When he married Baba, his close bond with the Prince of Wales – and Baba’s elevated position in society – meant they were allowed to hold the ceremony in the Chapel Royal at St James’s Palace.

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

‘Their hatred of this, their son’s greatest friend, is fantastic in its intensity.

‘All the prince’s escapades are down to his influence. Fruity is stupid and weak, the Prince is stupid and determined – and both are quite, quite charming. But he [Fruity] is to blame.

‘The King and Queen sent no presents and refused to come to the wedding, and rumour has it His Majesty forbade any member of the family to attend.’

The two men met when the Prince toured India in 1922 and the Irishman was serving as an officer in an obscure cavalry regiment, the Skinner’s Horse. 

‘No other friend did the prince have [after that]’, according to Channon.

For a time, Fruity’s official job was to look after the Prince’s horses and organise his equestrian life. 

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

Perhaps unsurprisingly, this long-established friendship started to wane around the time Wallis Simpson came on the scene. 

Jealous of all her new lover’s friends, the American divorcee had a particular dislike of Fruity and his excessively masculine ways. So he found himself being squeezed out. It hurt.

However, during the 1936 Abdication crisis, while Wallis was temporarily separated from the King (as he had become 11 months earlier), Fruity stepped into the breach. 

And prior to Wallis and David’s wedding in 1937, he offered to fly out to the Schloss Enzesfeld in Austria – where the former King was staying.

There, the new Duke of Windsor paced the floor, alone, waiting for Wallis’s divorce to come through. 

Wallis didn’t like the prospect of Fruity joining her beau one bit. 

‘You cannot be alone with Fruity,’ she wrote commandingly. ‘He is not capable of handling the mail and dealing with servants, etc.’

‘It’s more likely that she feared Fruity’s influence with the Duke,’ wrote the biographer Anne de Courcy. 

‘They had shared a past long before Wallis came on the scene, and a word or phrase could set them off into uncontrollable schoolboy giggles.’

As she waited to join her future husband, Wallis nagged David daily over the telephone about spending so much time with his old playmate. 

Nevertheless, it was Fruity who was invited to be best man at their 1937 wedding – mainly because no royal was prepared to be photographed in their company.

The latter fact meant that the guest-list was tiny.

So 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 on the outbreak of war, when David donned Army uniform and was given the job of inspecting the troops in northern France.

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

But the morning after the Germans invaded France, Fruity telephoned the Duke only to discover the Windsors had fled to Biarritz, leaving no message.

‘Fruity, who’d worked for months with no pay, doing everything he could to support the Duke and make the lives of the Windsors easier, found himself abandoned, without a single word from the man he considered his best friend,’ said de Courcy.

Humiliated and depressed, Fruity wrote to his wife: ‘After 20 years I am through – I despise him! 

‘I’ve fought and backed him up, knowing what a swine he was, for 20 years, but now it is finished.

‘He deserted his job in 1936. Now he’s deserted his country, at a time when every office boy and cripple is trying to do what he can. It is the end.’

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