The story of the Duke and Duchess of Windsor is one of the most romantic of all time: Edward VIII abdicated his throne and gave up an empire so that he could marry the woman he loved, American divorcee Wallis Simpson. But very few people suspected, and even fewer actually knew, that the Duchess subsequently cuckolded him for a playboy twenty years her junior. It was a relationship that baffled and mystified their friends, and entertained their enemies, not least because the object of her affection was gay. She was one of the most famous women in the world, one half of ‘the love story of the century.’ He was a rich, handsome, high school drop-out and mummy’s boy twenty years younger. They were an odd couple in many ways but despite their differences, the Duchess of Windsor and Jimmy Donahue kept gossips and high society on both sides of the Atlantic agog as they fandangoed, flirted, & flitted (That’s enough F’s: Ed) their way from New York to Europe via Palm Beach.
Jimmy was a sparkling part of American post-war cafe society, helped to a large extent by his having been born into a wealthy family. He could fly a plane, speak several languages, play the piano, and tell marvellous jokes. People loved him for his wit, charm and personality. The grandson of millionaire Frank W. Woolworth, Donahue never felt the need to earn a living, and indeed he lived lavishly, travelling the world with a valet in tow and staying at the most expensive hotels. Gay at a time when the homosexual act was still illegal, Jimmy was notorious within America’s upper strata, and loved to shock. Though press agents arranged for him to be seen with female escorts, his pursuits, until he met the Duchess of Windsor, were exclusively homosexual. In 1950 he was thirty-five when befriended by the Duke and Duchess of Windsor. The Duchess was fifty-four, and despite the difference in age, there was an instant attraction. Of course, all British royals are particularly partial to freebies, & the Windsors were no exception. For years it paid off, with Jimmy, his access to millions & with a disregard for the niceties of social convention, giving Wallis a buzz she wasn’t getting at home from her grumpy, frequently hammered & tight-fisted husband.
Donahue and the Windsors had been introduced in the early 1940s when the Duke and Duchess had travelled to Palm Beach from the Bahamas where the Duke was serving as Governor-General. Jimmy’s mother (Jessie Woolworth Donahue) hoped that rubbing shoulders with the royal couple would boost her own social standing, because although she had inherited millions from her father F.W. Woolworth, she was still considered new money to the old guard of Palm Beach society. For their part, the Windsors found America more congenial than Europe, where the Duke’s indiscreet behaviour, like his meeting with Hitler in Germany, embarrassed the Royal Family. Here the Windsor’s were treated like royalty. Jessie Donahue was thrilled when the Windsors attended lunches and dinners at her palatial Cielito Lindo in Palm Beach or at her triplex in New York. As a kid Jimmy had dreamed of being the best friend of the Duke of Windsor when he was still the Prince of Wales, and now here he was sitting having tea in his mother’s living room. The Windsors were equally impressed by the Donahue’s money, houses, servants and impeccable manners.
Everything changed in 1950, when the Duke and Duchess decided to take the RMS Queen Mary from New York to Cherbourg. It was a trip they had taken many times before but this time Jimmy Donahue was on board. He was an old hand at entertaining older women. His mother had often pulled him out of school to accompany her on her travels. At the start of the trip, Jimmy and Wallis were just friends; by the time they disembarked they were lovers. Wallis was bored and vulnerable – it had been 14 years since the Duke had abdicated the English throne for the ‘woman I love’ and maintaining the love affair of the century was stifling. “You have no idea how hard it is to live out a great romance.” Wallis once confided to a friend. The Duke may have once been king but now he was just an ordinary man, needy and childlike, with certain “needs”, that Wallis endured but never entered into with enthusiasm. The Duke not only had a foot fetish but liked to play ‘nanny’ games which infantilized him, wearing a nappy, with Wallis punishing him for his being a ‘naughty boy.’ Wallis herself had also suffered her share of health problems, been diagnosed with cancer, and would soon have to have a hysterectomy. Life seemed to be passing her by; ahead of her was a long, lonely, empty road. Not even making the best-dressed list year after year made up for the slights and snubs from the Royal Family. Her relationship with Jimmy was a diversion from the empty and meaningless life that she had been leading. He was witty and charming, and despite his sexual inclinations, an intense attraction sprang up between them. Jimmy wasn’t raised to have a career; he was raised to be rich. He was also mischievous, loving to shock high society with his pranks – at dinner parties where, according to Aileen Plunket, the Guinness heiress – he’d liven things up by unbuttoning his trousers and laying his membrum virile on his plate among the potatoes and gravy and sauces, “looking like some pink sausage.”
Like Wallis, Jimmy was trapped. In his case, it was wealth and the Woolworth name. He was the quintessential ‘poor little rich boy’, kept on a tight leash by his mother Jessie, who alternately smothered and neglected her favourite son. She kept such a tight leash on her money that even after her death Jimmy wouldn’t have inherited the Woolworth millions if he had outlived her. Jimmy often had to borrow money from his wealthier cousin Barbara Hutton to fund his expensive lifestyle. (Fun fact: BH was a niece of Marjorie Hutton – née Merriweather Post – who built & developed the Mar-A-Lago estate in Palm Beach.) But Jessie was quite willing to open the purse strings now that Jimmy was besties with Wallis and the Duke. Jimmy treated Wallis to shopping sprees at Mainbocher and Hattie Carnegie where she splashed the cash on shoes, dresses, and hats. He encouraged her to acquire a substantial wardrobe of furs, which he paid for. The two would lunch together at the Colony and at Le Pavillion, their heads pressed together as they joked and gossiped. At night the trio would hit El Morocco, the Stork Club and ’21 with Jimmy picking up the check. When the three of them went out, it was not uncommon for the Duke to leave Wallis and Jimmy to dance the night away while he went home to bed alone. Jimmy would whisk the couple away on pleasure jaunts, cruising the Mediterranean on a private yacht, treats they would never have been able to afford on their own. There was never a dull moment when he was around…. the world that revolved around the former king, the “woman I love”, & as Noel Coward put it (& he would know) that insane “camp” Jimmy Donahue.
At first the Duke was pleased with Jimmy’s friendship, they would play golf together, but he soon realized that he was becoming the odd man out in the little trio. When the Duke had to return to England for the deaths of his brother King George VI and his mother Queen Mary, Wallis and Jimmy painted the town red in his absence. The Duke would place frantic phone calls trying to reach her only to be told that she was unavailable, or worse there was no answer at all. The poor Duke watched helplessly as his wife slipped away from him. But the idyll couldn’t last. Jimmy was tired of having to address the Duke in a courtly fashion, and Wallis had become too possessive. Behind her back, Jimmy told friends that on the pillow, her face looked like an old sailor. There was also the matter of the Windsors treating Jimmy and his mother like their own personal cash machine. The Windsors gave little in return other than themselves. On Wallis’ side, she began to realize that Jimmy was limited intellectually. She was used to mixing with politicians, ambassadors, and generals. Friends also warned her that her association with Jimmy was trashing the couple’s already tarnished reputation. The end came while the trio were in Baden-Baden. Jimmy was bored, the atmosphere in the spa town too staid for him. At dinner that night, Wallis remarked that Jimmy reeked of garlic. Jimmy, drunk after several pre-dinner cocktails, saw red. Under the table, he kicked Wallis in the shin hard enough to draw blood. After tending to his wife, the Duke turned to Jimmy and said, “We’ve had enough of you….. Jimmy get out.”
With those words, four years of friendship went down the tubes. Jessie Donahue was devastated, but the door was shut tightly in the Donahue’s face. The cold front lasted for almost twelve years. Finally the Windsors consented to attend a lunch with Jessie, and later visited Jimmy’s house on Long Island but there was no renewal of the special bond that had existed. The end of the relationship with Jimmy brought the Duke and Duchess closer together, whilst Jimmy’s drifted on in a never-ending quest to stave off the boredom in his life, coasting from relationship to relationship until his death in 1966.
© 2021 DJM
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