Gertrude Sanford Legendre: The Socialite Spy

by Jane Ahrens Editor’s Note: Gertie Sanford lived on Fishers Island for many decades. She owned today’s Chocomout House overlooking Chocomount Beach. It was sold to the current owners after her death. As mentioned in the New York Times obituary on March 13, 2000, “Gertrude Sanford Legendre, an unlikely debutante of the 1920’s who forsook society to become a big-game hunter and then to work during World War II for the Office of Strategic Services, predecessor of the Central Intelligence Agency, died on Wednesday at Medway, her historic plantation near Charleston, S.C. She was 97 and also had a home on Fishers Island, off Long Island”.

Photo Illustration by the Daily Beast

The Socialite Spy Who Played So Dumb She Outsmarted the Nazis

Big game hunter, legendary French Riviera partier, and a quintessential WASP—Gertrude Sanford was also a vital U.S. spy who managed to outmaneuver the Nazis after being captured.

By Christopher Dickey
September 25, 2016

PARIS—If you’re going to have an obit in The New York Times, it would be hard to have a more intriguing headline than this one from March 2000: “Gertrude Sanford Legendre, 97, Socialite Turned Hunter and Prisoner of War,” unless they’d added, as they should have done, “Spy.”

One might also have said she was spoiled and impetuous and for several months regarded as the greatest potential disaster confronting American intelligence during World War II, or that she was a true heroine who hated being underestimated because she was a woman, but knew the Nazis—even her SS and Gestapo jailors—would do just that, and so survived, and thus kept her secrets.

Gertrude “Gertie” Sanford was born into a very wealthy and well-connected New York family in 1903. Her mother was the daughter of a famous (some would say infamous) diplomat and businessman who founded the town of Sanford, Florida, hoping to make a fortune off of citrus. Her father, a Sanford cousin, manufactured carpets and raced horses in upstate New York.

She was in many respects the quintessence of WASPdom, as most of the American elite was in those days. She went to Foxcroft School in Middleburg, Virginia, where girls were made to sleep on screen porches through the winter, physical education included riding to hounds, and they learned to have an aggressive sense of, at once, entitlement and self-reliance.

It’s easy enough to imagine Gertie as a young woman played by a young Katharine Hepburn, and in fact she was. As that New York Times obit notes, Philip Barry, a family friend, took the Sanford siblings—Gertie, younger sister Jane, and their polo-playing brother Laddie—as models for the central characters in his play “Holiday,” made into a memorable 1938 movie with Hepburn and Cary Grant.

“Try and stop me someone. Oh, please, someone try and stop me!” says Hepburn at the end of the film as she embraces a life of privileged risk and thrilling experience with a man who shares her desires. 

By the time the movie came out, however, Sanford had moved unstoppably on—and on. On her first hunting trip in Wyoming when she was 18 she had decided she wanted to travel the globe in search of big game, wild landscapes and exotic cultures. Other flappers made the photo pages of American papers with bias-cut dresses and bobbed hair, she was pictured with double-barreled guns and dead lions. And when she wasn’t hunting, eventually collecting specimens for the American Museum of Natural History in New York City, she was partying with the most famous party animals of the Roaring Twenties on the French Riviera. 

The summer of 1928 she was invited to Cap d’Antibes by Gerald and Sara Murphy (subjects of the wonderful biography Living Well is the Best Revenge) and she and her sister hung out with the Murphys’ friends Scott and Zelda Fitzgerald, Ernest Hemingway, Harpo Marx and Somerset Maugham, who called them “crazy show-offs.” 

The young women also met two very handsome brothers from New Orleans who’d been studying at Oxford, Morris and Sidney Legendre, who thought it was amusing to surf behind speedboats on what they called “free boards” made to their specifications by a local carpenter.


Toward the end of the summer Gertie and her sister Janie had moved into the Villa les Cèdres on the grounds of the Hotel du Cap, as glamorous then as it is now. One night, during a party in the bottom of an empty swimming pool festooned with Japanese lanterns, “someone challenged Morris and me to ride the free boards in our evening clothes,” Gertie wrote years later in an autobiography, The Time of My Life, that mingles preppy reminiscences and flashes of truly elegant prose:

“I removed my white satin high heels before stepping onto the board. By some miracle it worked! There I was standing on the floating board in the moonlight, watching Morris glide back to join me. The moment that the lines were taut, the engines roared and we took off in a sheet of spray and foam, swinging way out to the sides to impress our audience. Little did we know that the goading had been deliberate and that our performance was to be immortalized on film. Suddenly spotlights illuminated the water and people began to applaud. …

“We circled the harbor twice, waving and showering the night with sparkling fans of water until Morris made a sharp turn and fell.” He called her to join him in the water. “Like hell I will!” she said. 

The boat slowed. Gertie was afraid she’d sink and get her dress wet, so she asked the boat to circle again, bringing her near a floating  platform. “I let go of the tow rope at what I hoped was the right moment and glided towards the float where I stepped onto it, bone dry and slightly incredulous. The audience went wild!”

Alas, the film eventually was lost, wrote Gertie, “and we all began to remember the night differently—each memory perfectly true and exactly how it happened, of course.”

Soon afterward, Gertie, who was in love with both Morris and Sidney, invited them along on a hunt for big game in Ethiopia, where they dined with the Emperor Haile Selassie and shot a zoo’s worth of animals. Eventually, Sidney proposed, and they began their life together with a mix of hunting adventures (in Africa, Southeast Asia, Iran) and house restoration after buying the vast but derelict Medway Plantation outside of Charleston, S.C.


Gertrude Sanford Legendre’s face was not beautiful. One can see that in the many images from her archive that were donated to and digitized by The College of Charleston. Man Ray and Harper’s Bazaar glamorized her as best they could. But her charm—her charisma, in fact—comes through most clearly in her writing.

By 1941, Medway was as much of a showplace as the Legendres wanted it to be. (“I’m not the formal type. I don’t want to worry about where the dogs sit.”) They had two daughters and were settled in.

Then the United States entered World War II. Sidney Legendre went into the Navy and was sent to Hawaii. Gertrude Legendre went to Washington, where she started work in the summer of 1942. “My job was to manage the cable desk for the Communications Branch, which was later to be called the Office of Strategic Services—known as the OSS—commanded by General William J. Donovan, known to his friends as ‘Wild Bill.’” After the war, the organization evolved into what we now know as the Central Intelligence Agency.

Gertrude Legendre was 39 years old and this job in Washington was, as nearly as I can tell, the first time in her adventurous life of hunting and exploring, partying and running a plantation, that she’d actually been an employee, working for men and discovering the way most women were, or more often were not, valued.

“All that year, sensitive and top secret war cables came across my desk—pieces of paper that corresponded to men in the field whose lives depended upon accurate information from us,” Legendre wrote in her autobiography, summing up her first year on the job in a single paragraph of her memoir.

It’s only in her private correspondence, in letters to her husband in faraway Pearl Harbor, that we learn how she actually felt. She marveled at the “terrific waste, tremendous lost motion” in the wartime bureaucracy. She wondered why a young man in her office, who was 32 years old and “strong as an ox,” was not at the front. Many women, she knew, could do his job in Washington.

“What really burns me up,” Legendre wrote in October 1941, “is the unbelievable lack of confidence in a woman’s ability. It positively enrages me. Men cannot bear to have their world encroached upon by more efficient women. They hate to give way [to women], they hate to admit they are good, they hate to give them the power. It fairly drives me nuts. Gee I would love to speak my mind on that subject every now and again.”

In all likelihood, she did just that. 

In fact, Legendre had a close ally in David K.E. Bruce, the right hand of Donovan and the first head of SI, the Secret Intelligence branch of the OSS. A patrician Virginian in his early 40s, and a Princeton man like the Legendre brothers, Bruce was married at the time to the daughter of the fabulously rich industrialist and art collector Andrew Mellon and traveled in many of the same circles as the Legendres.

Whether Bruce just had an eye for talent, or was pushed by Gertrude Legendre, or both, he wound up promoting women within the fledgling espionage agency.

Gertrude wrote to her husband about a man named Schmidt who’d been made head of her department. “He did not know enough to come in out of the rain,” she said. “He never did catch  on to what was going on. He always had to ask Margaret Griggs everything. (She was the efficient girl you met whom we gave a lift to in the car one day.) Schmidt got a commission as a captain and sat there all puffed up in a uniform but had to ask everything of Margaret who had to be at his elbow to answer all questions. It became ludicrous and Helen and others who know David well tipped him off to what was going on, and David after much bickering with the staff managed to shift Schmidt elsewhere and finally allowed Margaret to take over.

“She is doing a marvelous job, but the staff meetings are something!” Gertrude reported. “The Big Shots resent her bitterly. She is the only woman at the meetings and although David backs her 100 percent the men dislike the idea, and remarks that are made about her are relayed back to us, and it just makes me boil. That’s how it is all through.” The rage was heartfelt from a woman who had traveled to some of the most remote corners of the world, and who knew well that female agents were risking their lives in the field. “Men that have never gone anywhere, never traveled outside the U.S., are sent to Africa in preference of a woman. A woman according to them is small fry. It makes me laugh in my particular job. I get $150 per month and John Hayes gets $300 per month. I do all the work and he does all the talk.” 

After a year earning the respect of her colleagues, Legendre was one of six women transferred to London to work in Bruce’s shop there. To get to England she had to take a ship to Lisbon, then fly in a blacked out plane to England. It lost one of its engines over the Irish channel and had to make a forced landing. London was under regular attack by V-1 “buzz bombs,” the jet-powered precursors of cruise missiles. 

She was assigned to the Central Cable Desk, handling the communications from agents all over North Africa and Europe, including those in France and Germany. Few people in the organization saw more information about who was where, and what they were learning. 

The British motto, “Keep Calm and Carry On,” has become a cliché. But in those days it was a matter of amazing stoic heroism: “By February, 1944, the German Luftwaffe was staging short, but sharper blitzes. Overnight, Hyde Park was bristling with anti-aircraft guns,” wrote Legendre. “Fragments of the flak barrage fell like stones on rooftops and pavement. In the dark of night, blades of light crisscrossed the sky like lattice work.” By September 1 of that year, as Bruce wrote in his diary, the British Empire had “lost in Killed, 242,995; Missing, 80,603, Wounded, 311,500; Prisoners, 290,865… Civilian air raid casualties in the United Kingdom total: Killed (or missing, believed killed), 56,195; Injured and detained in hospital, 75,897.

On June 6, D-Day, Gertrude Legendre awoke at 6 a.m. to the sound of airplane engines overhead. “The sound continued all day as formations blackened the sky. The invasion was under way. People stood silently in the streets, making the ‘V’ for victory sign. Many of us went to St. Martin-in-the-Fields and prayed under the roar of engines and the ringing of bells.”

David Bruce, having sailed with the invasion armada, was on the beach in Normandy alongside Wild Bill Donovan on June 7. By August 25, Bruce was in Paris, with Ernest Hemingway and a motley collection of fighters called the Private Army at his side. In some corners of the city the streets erupted in celebration while in others fighting still raged between the remnant German forces and the Resistance, but Bruce and Hemingway and their crew managed to make it to the almost-deserted Ritz Hotel, with its famous bar. The manager, whom they knew well from before the war, agreed they could bunk down there and asked what he could do for them right at that moment, Bruce wrote in his diary. “We answered that we would like 50 martini cocktails.” The Ritz obliged.

Legendre and a handful of other women staffers received their orders to join the OSS operations in France two weeks later. They put on the uniforms of the Women’s Army Corps (WAC)—and Legendre was suddenly a lieutenant without even knowing, as she said, how to salute— but when they flew in they found the OSS headquarters on the Champs-Élysées wasn’t ready. They had several days in which to do more or less nothing. After exploring Paris, which she already knew well, Legendre, too, wound up one evening at the Ritz bar.

It was full of reporters talking about their plans to go find Gen. George Patton and the U.S. Third Army somewhere around Luxembourg, and she envied them. Then she recognized a fellow OSS officer, Lt. Cdr. Robert Jennings of SI, also on leave, and they began plotting how they might travel north as well. 

They set off next day in a battered Peugeot that broke down constantly, and after spending the night at a little hotel, met yet another OSS officer, Maj. Maxwell Papurt of X-2, the OSS counterintelligence branch, who had controlled important enemy agent operations in Italy. He had a jeep driven by a young private named Doyle “Dick” Dickson.  All four drove together in search of the front line (as others, including David Bruce, were doing that day), but as they approached the little town of Wallendorf, Germany, they suddenly found themselves on the wrong side of it. 

German soldiers opened up on the jeep, badly wounding Pvt. Dickson and Maj. Papurt. As they lay “in a slime of blood, mud and oil,” Legendre remembered, they realized their situation was hopeless. Jennings “pulled a white handkerchief from his pocket and tied it to the end of Papurt’s rifle.”

So began an ordeal for all of them. Jennings would survive in a prison camp. Dickson appears to have died from his wounds, and Papurt was killed when the Allies bombed the hospital where he was taken.  The men who ran OSS had confidence that the men taken prisoner wouldn’t break. But as Douglas Waller writes in his authoritative biography of Wild Bill Donovan, “Panic swept through the OSS over Gertrude Legendre’s capture.” 

In early October, German radio proclaimed her “the first American woman to be made a prisoner of war on the Western Front.” The broadcast brought some relief, in fact. The Germans seemed to believe the cover story Legendre had concocted on the spot, that she was nothing but a Red Cross volunteer along for the ride to translate for Jennings. After all, she was just a woman.

American newspapers ate up the story: a New York socialite was a Nazi prisoner. They bought the cover story the Germans had broadcast, as well, and Donovan had the War Department confirm it. But she was, in his eyes, like the concierge who has the keys to all the apartments in the building. Legendre had “a tremendous fund of information concerning the OSS operation in the European theater,” he warned the War Department. “Any discovery by the Germans that she possesses such information would have grave consequences not only for her personally but also for the organization.” A top secret OSS memo warned the staff of Gen. Dwight Eisenhower, commander of all Allied forces, this could be “one of the disasters of the war.”

The decision was made by Donovan that no rescue mission or exchange would be attempted, lest it endanger other agents and Legendre herself.

She was on her own.

There are many facets to the spy business. One is uncovering secrets. Another, every bit as important, is keeping them. 

After several days being moved around, Legendre was taken to the 13th-century castle overlooking the town of Dietz and locked in cell number 38, where she would remain for six weeks. 

Every evening a German SS officer, Lt. William Gosewich, came to interrogate her, and every evening she repeated her story word for word until she came to believe it herself as she talked about Edna and Sarah in the State Department filing office.

She was lucky in the Germans’ choice of interrogator. Soon she was learning as much about him as he thought he was learning about her. He said he had lived in the United States for 18 years, where he ran a lunch counter. He’d married an American girl and had two American children. And “after a while,” Legendre wrote, “our evening meetings became more social chats than rigorous interrogations. Sometimes we’d share a little wine or Nescafe and talk about the outcome of the war.” Lt. Gosewich was now “Bill.”

But after six weeks, Gosewich was called to the front, and the Gestapo moved in. Legendre was taken to Frankfurt, then to Berlin, a city in ruins. “We walked through the deserted streets and stopped in front of 8, Prinz Albert Strasse. I knew the address because I had seen it on many OSS reports. It was Gestapo headquarters.” From there she was driven to a building under Himmler’s Central Security Office, which she also knew. It “had a practice of issuing blank murder orders at whim.”

Legendre spent the next two months there under constant surveillance by two tough women guards, who eventually were joined by an interpreter named Ursula. And again, Legendre got lucky. Ursula “was young, impressionable, and interested in the outside world. … I told her that the German people were being told lies and that Jews in Germany were being murdered. At first, she wouldn’t believe me, but, in the end, she believed that I was telling the truth and risked her life many times by standing guard at the head of the kitchen stairway while I frantically tried to tune in the BBC on a radio.”

There may have been several things that contributed to Legendre’s luck. She was something of a prize as the “first American woman to be made a prisoner of war” by the GermansIndeed, one of her guards in Berlin told her she might even be taken to meet Hitler—and flew into a rage when Legendre said she’d rather not.

Legendre also took advantage, at first, and when it suited, of the way men underestimate women. Even though she was captured with two OSS officers, her interrogators continued to assume she had just been along for the ride.

And finally, it was clear to most people in Germany by the winter of 1944-45 that the war was being lost. So it’s safe to assume that Ursula and Lt. Grosewich thought they could use a friend in America, if Legendre ever got back there.

In the first days of January 1945, Legendre was moved to a hotel surrounded by barbed wire in a compound near Bonn, where she encountered a scene worthy of a film by Jean Renoir: she was among 42 French generals, 75 colonels, seven civilian diplomats and one woman, Mme. Caillau, the sister of Free French leader Charles De Gaulle. These distinguished prisoners, who had been there for eight months, maintained their dignity through rigid protocols and seating arrangements. They passed their time learning and teaching bookbinding. They waited. And perhaps they appreciated how lucky they were. When Monsieur Callou finally was brought to join them, after a year in a concentration camp, his wife at first did not recognize him.  “He had lost so much weight and his voice had so completely changed that she just stared at him.”

As the Allied armies advanced, the “honor detainees” were moved and Legendre eventually was taken away by herself, and placed with a family almost as if she were a boarder. “They made me feel welcome and insisted that the guards at the door were unnecessary.” But as Patton’s forces closed in, the family got nervous. Legendre suggested they get in touch with Lt. Bill Grosewich, who had visited her at the compound near Bonn, and ask him to bring Red Cross packages for them. He did, accompanied by his commanding officer, and they all had a glass of cognac together.

Two days later a small car pulled up to the house and the driver said he had orders to take Legendre to the Swiss border. For hours they drove through the ruins of Frankfurt and Ulm. They were turned back when they reached Konstanz, but the SS driver put Legendre in a safe house. 

She waited until dark, then made her way to the train station, noticing a man in light-colored coat on the platform who seemed to be waiting for something, she wasn’t sure what. Legendre climbed aboard the train. She crouched on the floor, then hid in the toilet. The train rolled forward, and onward, and then jerked to a halt. “I spotted the white gates in the moonlight. It was the frontier, but the train had stopped short of it.” She climbed down and started making her way forward in the shadow of some freight cars. Then she realized the man in the light coat was almost next to her. She froze. “Run!” he said.

A German border guard was after her now, bellowing with rage, but she scrambled into Switzerland, and he pulled up short.

“I still don’t know why he didn’t shoot me,” she wrote more than 40 years later. “Perhaps something had been arranged. I’ll never know. Freedom was enough.”

Legendre left the OSS after she was debriefed in Switzerland, and returned to the United States. She was asked to give no interviews until the war was long over. Her husband, Sidney, died in 1948, but she lived on at Medway.

Elizabeth P. McIntosh, an OSS veteran who interviewed her for the 1998 book Sisterhood of Spies, reports that “it wasn’t until 1950 that Legendre was able to help her German friend, Lieutenant Gosewisch [Gosewich]. She said she found him and his family destitute, as were many in postwar Germany. She was able to get them to South Carolina, where he was given a job working for her [second] husband. They often met and exchanged reminiscences, and he always sent her red roses on holidays. William Gosewisch died the day before the Berlin Wall came down, a historic incident Legendre knew he would have loved to witness.” But it seems he never did tell Legendre how her escape had been arranged, or what part he might have played in it.

Gertrude Sanford Legendre, as The New York Times reported, died in 2000.

On Saturday I asked her grandson, Pierre Manigault, chairman of the board of Evening Post Industries (The Charleston Post and Courier) and co-founder of Garden & Gun magazine, how he thinks Gertie managed to keep so many secrets so effectively for so long.

“She was as tough as she could possibly be,” he said on the phone from Charleston. “And I can imagine that in no circumstances would she give anything up. But she was a very social, very gregarious person, and she charmed everybody. She was very good at making people feel at ease.”

Gertie and Sidney with springer 'Clippy'.
Gertie and Sidney with ‘Clippy’.

Christopher Dickey, a veteran foreign correspondent, is The Daily Beast’s World News Editor. He is the author of seven books, including Securing the City and, most recently, Our Man in Charleston: Britain’s Secret Agent in the Civil War South.

Note: The books mentioned in this article may be found at the Fishers Island Library, through Live-brary and online.

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