Scandalous Love Affairs: Jimmy and the Duchess

(Jimmy Donahue and the Duchess of Windsor at a party in the 1950's)

"You have no idea how hard it is to live out a great romance." the Duchess of Windsor to a friend.

It was a relationship that baffled and mystified their friends, and entertained their enemies. 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 mama's boy twenty years younger, and gay. 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 danced and flirted their way from New York to Palm Beach to Europe. Wallis was so enthralled with her young swain and the lifestyle that he offered her that she actually contemplated leaving the Duke for him.


Jimmy Donahue and the Duchess of Windsor had been introduced in the early 1940's when the Duke and Duchess had traveled to Palm Beach from the Bahamas where the Duke was serving as Governor General. The Duke of Windsor's former Lord-in-Waiting, the Earl of Sefton, suggested her as a hostess to the royal visitors. Jimmy's mother Jessie Woolworth Donahue hoped that rubbing shoulders with the royal couple would boost her own social standing. 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. Her marriage to James Donahue, whose family had made their money from fat rendering, hadn't burnished her pedigree.

For their part, the Windsors found America more congenial than Europe where the Duke's indiscret behavior, 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 lifestyle.

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. It was there, on the high seas, that Wallis fell in love with Jimmy. He was an old hand at entertaining older women. His mother had often pulled him out of school to accompany her on her travels. He was a brilliant gossip, prankster and jokester. At the start of the trip, Jimmy and Wallis were just friends; by the time they disembarked they were lovers. He was thirty-four and she was fifty-four. Friends say that Wallis did the chasing, that the idea would never have occurred to Jimmy to pursue the Duchess.

By the time the Duchess and Jimmy fell in love, they were both at a cross roads in their lives. The Duchess 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. The Duke may have once been King of England but now he was just an ordinary man. He was needy and childlike, his love smothering. Their love life was unsatisfying, the Duke not only had a foot fetish but he liked to play 'nanny' games which infantilized him, wearing a diaper, with the Duchess punishing him for his being a 'naughty boy.' When she wasn't in the room, the Duke would visibly wilt. Wallis 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 which gave him ample time to cater to the Duchesses whims. He was the archetypal postwar playboy; he spoke several languages, could fly a plane, play the piano, and had impeccable manners. He was also mischievous, loving to shock high society with his pranks. For instance, the time he dressed up as a nun, pulled up his habit and squatted in the middle of the road, defecating. And all those grand dinner parties when, according to Aileen Plunket, the Guinness heiress, he'd liven things up by unbuttoning his trousers and laying his private parts 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 his wealth and the Woolworth name. He was the quintessential 'poor little rich boy' Jimmy was kept on a tight leash by his mother Jessie, who alternately smothered and neglected her favorite 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.

But Jessie was quite willing to open the purse strings now that Jimmy was close chums with Wallis and the Duke. Jimmy treated Wallis to shopping sprees at Mainbocher and Hattie Carnegie where she bought dresses and hats as if they were going out of style. 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. But it wasn't just Jimmy's unlimited expense account that kept Wallis happy. According to biographer Christopher Wilson, Jimmy offered Wallis pleasure in the boudoir like she'd never experienced before which boggles the mind.

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 go to England for the deaths of his brother King George VI and his mother The 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 after 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 hobnobing with politicians, ambassadors, and generals. Friends also warned her that her association with Jimmy was ruining 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 was too full for him. At dinner that night, Wallis remarked that Jimmy reeked of garlic. Jimmy drunk after an several pre-dinner cocktails saw red. He kicked Wallis in the shin hard enough to bleed under the table. 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 Donahues 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 relationship with Jimmy in the end brought the Duke and Duchess closer together. In the end, the Duchess realized that she had made her bed and seemed to finally settle into it.

Jimmy's life drifted on in a never ending quest to stave off the boredom in his life, drifting from relationship to relationship until his death in 1966.
Sources:
Wilson, Christopher (2001), Dancing With the Devil: the Windsors and Jimmy Donahue, London: HarperCollins