The Duke of Windsor’s Royal Summer on Long Island

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L.: This majestic French Normandy brick manor home that was formerly the summer retreat of the Duke and Duchess of Windsor is listed for sale at 11 Horse Hollow Rd. in Locust Valley. R.: The Duke of Windsor with his wife, Bessie Wallis Simpson.

He was a wannabe surfer and jazz drummer who personified the Roaring ‘20s, a decadent playboy partying at luxurious Long Island mansions. And this charismatic, fashionable 30-year-old who danced all night and played polo all day was the future King of England. 

The blue blood said, “America meant to me a country in which nothing is impossible,” embracing all things American — especially women. But one woman tamped down his promiscuity: a divorced American socialite he met in 1931 in London. His affair with seductive Bessie Wallis Simpson generated headlines, especially after he became king. 

King Edward VIII, formerly the Prince of Wales, abdicated to marry “the woman I love,” he said. Their marriage and globetrotting were scrutinized, especially as rumors swirled about anti-Semitic, Nazi sympathizer leanings. 

Today, their story may seem tame. But the myths and truths about the disgraced king — Prince Harry’s great-granduncle — are still news: Their summer retreat on the Island’s North Shore in New York is on the market for $5.9 million.


If the LI mansions’ walls could speak, they would spill the salacious secrets of the over-the-top galas honoring the prince. Throughout the 1920s he hobnobbed with the North Shore elite at William R. Grace’s Crossroads estate at Old Westbury: home base was Woodside, iron magnate James Abercrombie Burden’s Syosset country estate. 

“One shindig featured a ballroom on a 600-acre estate with thousands of roses and hundreds of tables with lobsters piled several feet high. Another banquet at the exclusive Piping Rock Club [in Locust Valley] had Will Rogers roasting the prince about his late-night shenanigans and his uninspiring polo playing,” wrote the New York Post’s Braden Keil.

Enamored of the American West, Edward cultivated a friendship with Rogers, bought a horse ranch, learned to lasso, and wished to be a cowboy, far from the stultifying dictates of the family he claimed to despise.

And he loved surfing, which he mastered while visiting Hawaii, and jazz, whether sitting in with Duke Ellington’s orchestra or the Rivers Chambers society quartet in Baltimore (he told the bandleader, “I can play the drums a little”).


The prince gave up his womanizing after falling in love with Simpson; by 1934 they were lovers. He looked away from the raw ambition others saw, did not hear them whispering that she was an opportunistic ladder climber yearning to be queen. But that title was beyond reach: The monarchy shunned her because she was still married to her second husband.  

After his father died, the prince became king in January 1936; in December of that year he abdicated. He wed Simpson in June 1937 in France, after her divorce became final; he was 41, she was 39. Royals were forbidden to attend, no wedding pictures were shown in Britain, and his name was seldom mentioned among his family. He was demoted and named the Duke of Windsor.

As if the abdication-marriage scandal were not enough, he allegedly supported fascist ideology, which valued nation and often race above the individual and supported a dictator-led autocratic government. When the newlyweds honeymooned on the Venice Simplon-Orient express, fascists showered them with flowers. Photos from 1937 show the couple at German Chancellor Adolf Hitler’s mountain retreat, all smiles; the duke reportedly gave Hitler the Nazi fascist salute.

In 1939 England declared war of Nazi Germany. The ex-monarch was appointed governor of the Bahamas in 1940, to keep him away from the front. The Duke and Duchess of Windsor stayed there until 1945, then settled in France, exiles entertaining Elizabeth Taylor and Richard Burton, Aristotle Onassis and Maria Callas, Marlene Dietrich, and other celebrities. 


The socialites traveled frequently to America, often as guests of American presidents including Dwight D. Eisenhower and Richard Nixon. The couple summered in 1948 at Severn, the French Normandy estate at 11 Horse Hollow Road in Lattingtown, surrounded by four acres of climbing roses, walled gardens, and specimen trees, just steps from the exclusive Creek Club.

In 1957, documents allegedly hidden by the British monarchy surfaced, revealing the Nazi dalliances. Pulitzer Prize winner Russell Baker discounted their validity, writing in The New York Times, “…whether they were merely … cocktail party gossip is impossible to tell from the diplomatic reports.” Celebrity biographer Andrew Morton wrote that the prince “thought Hitler was a good fellow and that he’d done a good job in Germany, and he was also anti-Semitic, before, during and after the war.”

History has judged the duke, as Emily Gaudette wrote in Newsweek: … “It feels especially hollow to remember that he simply lived out his life of luxury in France, socially ostracized but not tried for treason.”

After his death from throat cancer in Paris in 1872, Queen Elizabeth II invited his widow to stay at Buckingham Palace.

For more Rear View columns on Long Island history, visit longislandpress.com/category/past-present/rear-view

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