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Gertrude Legendre - The High Life to Spy Life, and Back

Gertrude Legendre - The High Life to Spy Life, and Back
September 2017

“Nazis Seize N.Y. Socialite”—73 years ago this month, newspaper headlines around the world trumpeted the fate of Charleston’s own Gertrude Legendre, the internationally known globetrotter and big-game hunter who was caught behind enemy lines during World War II. But the United States government hesitated to act because she was just “too hot” to handle. Oddly enough, it was probably her high life that got her into the spy life—and gave her the skill to survive it.

Born in 1902 in Aiken, South Carolina horse country (her family owned famous stables there), Gertrude Sanford could boast two Sanfords for parents. Her father, John, was heir to the New York rug manufacturing company Bigelow Sanford and a member of the U.S. House of Representatives. Her mother, Ethel, was the daughter of a Sanford cousin, Henry, who was not only an international diplomat and an associate of Abraham Lincoln, but the founder of the town of Sanford, Florida. The youngest of three children (her sister, Sarah Jane, would marry into Italian society with ties to Mussolini, and brother, Stephen, called “Laddie,” would become one of the best polo players in the country), “Gertie” was reared in the lap of luxury in Amsterdam, New York, and Manhattan and educated at Foxcroft in Middleburg, Virginia, an elite boarding school known for instilling independence and resiliency in its wealthy charges. She made her debut in 1920—just as the Roaring ’20s did, too.

A close family friend was the Philadelphia playwright Philip Barry, whose play Holiday (which would later become the 1938 movie with Katherine Hepburn and Cary Grant) is rumored to be based on Gertie and her siblings. Glimpsed in society columns and photographed by Man Ray in Paris, she enjoyed a charmed life on the French Riviera, along with other glamorous young expats, such as F. Scott and Zelda Fitzgerald and Ernest Hemingway.

Unlike the jaded flappers of her day, the unflappable Gertrude was as much at ease in hunting garb staring down the barrel of a rifle as she was in high heels. With an appetite for adventure and excitement, she traveled the world, sometimes in high style or roughing it on safaris, a habit she would continue her entire life. She financed expeditions to Africa, Indochina, Persia, and Abyssinia in search of exotic prey. Some of her treks were written up by herself and others in journals such as National Geographic. Many of the beasts she felled still populate exhibits in New York City’s American Museum of Natural History.

It was on her first big safari in Ethiopia in 1928 that she bagged handsome young Sidney Legendre, a Princeton man from a well-heeled New Orleans family. Although Gertie wasn’t considered a conventional beauty, as Christopher Dickey wrote in his tribute to her in The Daily Beast, no one could deny her sharp wit, confidence, and zest for life. Sidney surrendered. In September 1929, the couple was married.

At the time, their set was snapping up derelict plantations in the Lowcountry. Sidney and Gertie bought one of the oldest houses in the state, the Dutch-gabled Medway, about 30 miles from Charleston. They restored the property, not as a showplace, but a home where the pets were welcome on the furniture. “I’m not the formal type. I don’t want to worry about where the dogs sit,” Gertie once wrote. With uninterrupted vistas of river, forest, and marsh, the couple used it as a retreat from their whirlwind lives, hosting dozens of friends for morning hunts, afternoon feasts, and other leisurely activities that now included their two young daughters, Landine and Bokara.


Their idyllic life would be halted after Christmas 1941. “Sidney and I knew it was different, with the thunderclouds of war piling up on world horizons...that the pleasant and carefree life we had been enjoying together would soon be disintegrating under the weight of outward forces,” she wrote in her memoir The Sands Ceased to Run (William-Frederick Press, 1947). Sidney enlisted in the Navy and was made lieutenant. Soon thereafter, they left Medway for Washington, D.C., and within the year, Sidney was transferred to Hawaii.

Gertie wanted to do her bit, too, and for months unsuccessfully sought employment with support organizations such as the Red Cross. Then she aimed higher, finally making it into a secret society called the “OSS.” Today, some jokingly say the initials stood for “Oh So Snobby,” but it was really the Office of Strategic Services, the forerunner of the CIA, administered by General William J. “Wild Bill” Donovan.

An upper crust Princetonian who had earned his nickname for his service on the Mexican border, Donovan had been asked by President Franklin D. Roosevelt to start an intelligence gathering agency before the outbreak of war. Donovan first recruited people in his social orbit, those he knew he could trust implicitly. He also did his research into Civil War spying, during which he could have encountered the story of Gertie’s grandfather, who had been in charge of Lincoln’s espionage system. Only a few hundred women would be chosen for a workforce of more than 20,000 OSS employees; those who spoke foreign languages and who had lived abroad were sought first.

Well-traveled and fluent in French, Gertie was given the first job in her life. The 39-year-old worked her way up from file clerk to head of the cable desk, where she stamped the information going through her hands as “Restricted,” “Confidential,” “Secret,” or “Top Secret.” “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,” Gertrude wrote. But the avowed adventurer wanted more—more excitement, more intrigue—that she could perhaps attain as one of the “glamour girls” of the OSS, those who were called to work abroad.

And she got it; with a transfer via her friend Colonel David Bruce, the first head of the Secret Intelligence branch of the OSS, Gertie landed at the Central Cable Desk in London in August 1943. Her steel safes held messages from all over the world. London was under siege; and it was not just Gertie’s safes that were made of steel—her nerves were too. While some men cowered, she could, according to her recollections, tell by the sound of the buzz bombs if she should stop her dinner party or not.

Even with the adrenaline-induced anxiety of the ever-increasing air raids, Gertie was feeling stifled. “The essential difference between my desk job in London and that I had left in Washington was a mere matter of geography. I still commanded battalions of paper. While my work was of vital importance, it was not always very inspiring,” she wrote. She craved more.


Weeks after the D-Day invasion of Normandy and the retaking of Paris by the Allies in 1944, Gertie and several other women in the London office received orders transferring them to Paris. “The prospects delighted me,” she wrote. “The assignment was just what I had been hoping for.” Arriving in Paris with a five-day leave, her first time off in a year, Gertie visited former haunts like the bar at the Ritz, where she and Sidney had met before their first safari.

Serving as headquarters for U.S. Air Transport Command, the swanky hotel swarmed with officers and war correspondents. “All they could talk about was the front,” Gertie wrote. “Each... wanted to see the war firsthand. I envied them.” It was there that she spied Navy Lieutenant Commander Bob Jennings, an acquaintance from London. The two conspired to leave the “paperwork war” behind them, even if just for a few days. Regulations demanded that the OSS women wear Women’s Army Corps (WAC) uniforms; so outfitted, Gertie set out with Jennings on September 23 to try to find the front in Luxembourg, about 40 kilometers away.

They toured the countryside in an unreliable Peugot, eventually abandoning it and hopping into the jeep of Major Max Papurt and his driver, who were headed to Wallendorf, just over the German border. They passed dead animals and bombed houses. As they neared a signpost for the town, bullets began to strafe their vehicle. Papurt and his driver were wounded. Outgunned, they surrendered, holding up a white handkerchief.

It was Gertie who had the cool presence of mind to gather up and burn all their identification cards and other secret documents they were carrying. The group was captured by German soldiers; Gertie was spirited away further into Germany as the Reich crumbled around her, “driving through thunder and lightning with guns booming and flashing,” she wrote, and was first interrogated by an SS officer with “weasel-like eyes.”

The Germans flaunted their catch, announcing by radio from Berlin that the first American woman captured on the Western Front was of New York’s social elite. There was conflicting information as to what she was doing, not just abroad but in enemy territory.

Earlier in the war, Gertie had complained bitterly of the sexist OSS, where smart women got less pay and respect than the dim-witted men who supervised them. Now she played dumb expertly, insisting over and over again that she was just a lowly employee of the American Embassy and had accompanied the soldiers as a translator. Her captors accused her of lying.

But the willful Gertie stuck to her guns—as she faced the threat of literal ones—so much so that she ended up believing her fabrications. “My imaginary life as an embassy clerk was real,” she reminisced years later. “I could see the room, the steel filing cases, a table littered with requests for typewriters, drawers and drawers of manila folders, lettered alphabetically. Even my women colleagues I invented began to assume a personality of their own.”

As she was transported from one prison to another, from cells infested with fleas to a locked room in an ancient castle, and once almost to Gestapo headquarters, OSS leaders panicked, knowing that if she broke down, Gertie could single-handedly undermine the growing French underground resistance to the German army. (When held captive with the sister of Charles De Gaulle, the leader of the Free French, she had to keep her lips sealed as to what she knew about his activities.) But they obviously did not know Gertie. As she played the socialite and dropped the names of the generals, diplomats, and ambassadors she knew, the attitude towards her changed. Maybe, her captors thought, this flighty society woman could be used as a negotiating chip.

One of her jailers was undone by her charm, manners, and empathy. SS Lieutenant William Gosewich had lived in New York City for 18 years and was caught in Germany during a visit home as war broke out. Conscripted by the Reich, Gosewich was now second-in-command at the castle in Dietz in which Gertrude was imprisoned. “After a while, our evening meetings became more social chats than rigorous interrogations,” Gertie wrote. He even promised to help have her case resolved and keep her from the Gestapo. On November 3, she was removed to the Berlin suburb of Wansee, where the final solution of the Holocaust had been planned.

Gertie didn’t crack and was eventually transferred to Kronsberg, where through an intermediary she was put back in touch with Gosewich, who, she believed, helped her escape. On March 22, 1945, after six months of captivity, she was driven through devastated Frankfurt. She boarded a train to Switzerland and hid until the Swiss border station loomed within sight. When the train suddenly stopped short of the border, she slipped into the night and ran.

As German soldiers shouted for her to stop, she expected shots. “American passport,” she screamed to the Swiss guard while ducking under the raising arm of the gate. “I still don’t know why he didn’t shoot me,” she later wrote.

Ever the professional, Gertie stuck to her story of being an American Embassy file clerk once she was turned over to the American legation. That did not check out, of course, and now the Americans wondered if she were not a spy for Germany. But higher-ups stepped in. Almost immediately she was a house guest of Allen Dulles, an OSS operative in Switzerland, who would later head the CIA under Presidents Eisenhower and Kennedy. After her debriefing, one wonders if they chatted about mutual friends; the Dulles family was originally from Charleston.

Dulles told Sidney, still in Hawaii, of his wife’s release; Gertie was back in Paris by March 29 to celebrate her 42nd birthday.


Just a few years later, Gertie had to show her mettle again when her beloved Sidney died of a heart attack in 1948. She remarried briefly and financed more expeditions, including some to Africa, where she met humanitarian Albert Schweitzer. She helped found the Medway Plan, enabling Americans to send food and medicine to beleaguered Allied countries. (The City of Charleston will place a plaque on Adger’s Wharf commemorating it in the coming months.) In 1950, proving that a lady never forgets a kindness, Gertie did one better, bringing Lieutenant Gosewich and his family to South Carolina, finding him a job and a way out of impoverished post-war Germany.

The circle was closed; she was having adventures still, living life to the fullest, but perhaps not as dangerously. She published two autobiographies, The Sands Ceased to Run in 1947 and The Time of My Life (Wyrick & Co.) 40 years later. Throughout that era, she was a fixture in Charleston social, philanthropic, and cultural circles. Her New Year’s Eve costume parties at Medway were the hottest ticket in town.

And no wonder, for who but Gertie had mastered the art of masquerade (even duping the Nazis) or had embraced the enjoyment of life more fully? Life was a party for her—and living well was not as much a luxury as it was a necessity.

Gertrude Sanford Legendre died March 8, 2000 at Medway and was buried there next to Sidney, the love of her life.


Photographs courtesy of College of Charleston Addlestone Library’s Special Collections & Lowcountry Digital Library