The Jazz Age Heiress Who Witnessed WWII Up Close

The Life and Times of Gertrude Legendre, No Ordinary Socialite

On the afternoon of September 22nd, 1944, Gertrude Legendre strolled into the bar on the rue Cambon side of the Hôtel Ritz. Outside the street was lined with US Army jeeps, and inside the place was already crowded, mostly with Americans, a mixture of military officers and war correspondents, their volubility rising amid whorls of cigarette smoke. White-jacketed barmen mixed cocktails behind a dark mahogany counter, and the hotel’s patrons consumed the signature drinks in clusters around the small tables. Just one month after the city was liberated from the Nazis, this was the Paris a certain kind of American remembered: exclusive and jolly and alcohol-soaked.

The 42-year-old Legendre—known all her life as Gertie—was perfectly at ease in the legendary watering hole, a magnet over many years for wealthy Americans and Hollywood stars, as well as assorted European aristocrats, diplomats, spies, oligarchs, and, until recently, Nazi grandees. Field Marshal Hermann Göring had taken over the imperial suite after Paris fell to the Germans.

Gertie knew the head barman, Frank Meier, from previous visits to the Ritz, including a stopover in the winter of 1928, when she was 26 and on her way to a big-game hunting expedition in East Africa. Meier, inventor of such cocktails as the bee’s knees, the royal highball, and the sidecar, was still managing the room in 1944, his eyelids and jowls heavier, but with the same slicked, center-parted hair, groomed mustache, and pince-nez. He had worked in the bar during the occupation but surreptitiously helped the Resistance, ensuring that he kept his position after liberation.

The two reminisced about Gertie’s prewar stays at the hotel, and she talked about the 1928–29 hunt in the highlands of Abyssinia. Meier had told Gertie that when she reached Addis Ababa, she should drop in on his friend the head chef to the emperor Haile Selassie; she later dined with the Lion of Judah in his palace and ate a 14-course meal, alternating between European and African dishes, off dinner plates encrusted with gold coins. Gertie recalled that the local honey wine, called tej, was “especially potent. It went straight to my head like champagne.”

In 1944 Paris, Gertie was wearing the uniform of a first lieutenant in the Women’s Army Corps (WAC), though, as she was the first to acknowledge, she was no soldier and couldn’t salute properly. She did, however, know how to dress. After arriving in the city, she had her khakis tailored by Madame Manon, her longtime dressmaker, who “couldn’t wait to fit my uniform properly—taking it in here, and lifting a bit there.” Her helmet, three sizes too big, stayed as is.

“I must send you a picture of me in my Khaki. You would be so amused,” she wrote to her husband, Sidney, who was serving in Hawaii, a navy lieutenant commander in the intelligence center of the U.S. Pacific Fleet. They had not seen each other for two years and expressed their love—and the distress of being apart so long—through their almost daily letters. “Do you ever cry because you miss me?” wrote Gertie. “I do so much. I wonder if time is rubbing off the edge and you are now accustomed to the separation. I find it an incurable heartache, and I don’t suppose I would want it any other way.”

Gertie was a civilian employee of the Office of Strategic Services (OSS), the U.S. spy agency created in 1942 by President Roosevelt and led by William “Wild Bill” Donovan, whose charisma and daring transformed what had been a bureaucratic stepchild—despised by the FBI and sections of the brass into a global organization that won grudging respect from the U.S. military. (J. Edgar Hoover, director of the FBI, never came around.) By war’s end, more than twenty-one thousand men and women would serve in the OSS.

Gertie was wearing the uniform of a first lieutenant in the Women’s Army Corps, though, as she was the first to acknowledge, she was no soldier and couldn’t salute properly.

Gertie had until recently headed the cable desk at the London branch, overseeing the distribution of all top secret communications in and out of a building that ran European operations. The office was a key point of contact for the governments in exile in Britain; it ran agents into occupied Europe, managed relations with the prickly British services, which resented the growing independence of the OSS, and formulated plans for operations against the Reich after D-day.

Communications about many of these matters passed through Gertie’s hands, and she was privy to some of the OSS’s most secret plans and personnel. She was an administrator, not a spy, but her position gave her unusual insight into OSS operations and post-invasion planning. London was at the heart of the agency’s espionage in Europe, and Gertie sat at the center of all communications about that work, giving her an almost accidental font of knowledge about the war effort.

Now she was among the flocks of Americans descending on Paris to set up shop behind the advancing Allied armies. Everyone entering the European theater of operations fell under General Dwight D. Eisenhower’s command, so Gertie, unlike in her previous posting, was required to wear a WAC uniform. In Paris, it carried the mark of the liberator, a feather that had yet to lose its plume among the French. It also got you into U.S. mess halls.

*

Gertie wasn’t classically beautiful, describing herself unkindly as a “moon-faced, buxom girl.” But she radiated confidence and resolve, and her brown eyes and laughing smile were immediately winning. Her grandfather nicknamed her Spunky, and the moniker captured something essential about the girl, and later the woman, with the sometimes fierce mien. Her face, quicksilver in its expressiveness, could open in sparkling enthusiasm or crease in sour distaste. When she was five or six and her governess swept her hair up in a blue taffeta bow that held a corkscrew curl over her forehead, Gertie cut off the twirl of hair with scissors, infuriating the household.

Gertie was self-possessed, impatient, charming, and courageous and appeared to those who met her in London and Paris to be an archetypal American woman endowed with a kind of bullying certainty, as if she had just strolled, cigarette in hand, out of a celluloid frame. “When Gertrude felt strongly about anything all opposition died a quick if not graceful death,” her husband said. Another less forgiving observer said, “I have to leave my personality at the door. There’s no one in the room but her. She fills up all the space.”

She was, in fact, the inspiration for the character Katharine Hepburn played in the movie Holiday, based on the 1928 Broadway play by Gertie’s friend Philip Barry. Hepburn’s character is an amusing, cocky, sometimes abrasive society girl who wants to escape the confining expectations of her family’s fabulous wealth. The play, with a light, comic touch, captured some of the undercurrents of dissatisfaction with the materialism of the Jazz Age just before the crash, but without ever probing the theme too deeply.

Gertie’s desire for escape, too, was more intuitive than the result of any great introspection. “I look ahead. I always have,” Gertie said. “I don’t contemplate life; I live it.” It was a philosophy that would steer her and others toward tragedy.

Just a couple of weeks before her visit to the Ritz bar, Gertie got her orders to leave England and join the new office the OSS was opening on the Champs-Élysées, where she would also run the communications office. She also agreed to take on the added, volunteer duty of helping to organize a Paris club for the Supreme Headquarters Allied Expeditionary Force (SHAEF), the command of General Eisenhower.

The club was to be located in Paris’s Grand Hotel, with a cafeteria, a dancing hall, a bar, and an information bureau. She was to serve as the American representative on the organizing committee with the wives of Anthony Eden, the British foreign secretary, and Marie-Pierre Koenig, military governor of Paris.

Since D-day on June 6th, Gertie had been pining to get across the channel because London seemed “dead as a doornail.”

“Life has moved to Normandy, and it makes me want to go too,” she said. Gertie felt overlooked because many of her male colleagues, including the head of the London branch, Colonel David K. E. Bruce, had already made it to France. “I only wish I could be jeeping my way in on their cloud of dust,” she said, complaining that “a female civilian is the worst thing you can be in a war.”

There was lots to envy. Bruce entered Paris, still occupied by some German forces, in the company of Ernest Hemingway and his band of irregulars. “Everyone thrust drinks at us that they had been hoarding for this occasion,” Bruce wrote in his diary. “It was impossible to refuse them, but the combination was enough to wreck one’s constitution. In the course of the afternoon, we had beer, cider, white and red Bordeaux, white and red Burgundy, champagne, rum, whiskey, cognac, armagnac, and Calvados.”

Gertie’s boss and Hemingway raced through side streets until they emerged behind the Arc de Triomphe, which they ascended at the invitation of the French captain guarding it. They looked out over “the golden dome of the Invalides, the green roof of the Madelaine, Sacre-Coeur.” The air shook with the sound of tank fire, and the arch itself was under attack from snipers, but the view “was breathtaking.”

Back on the street, where they hid behind a tank during a gun battle, a man dove in beside Bruce, asked if the Americans would like to drink some champagne, and led the group through a confusion of gunfire—“every side street seemed enfiladed”—to several iced magnums at his luxurious apartment on the avenue Foch.

The ultimate goal, especially for Hemingway, was the Ritz, which was almost completely deserted when the writer’s ragtag group of fighters strode through its doors on the Place Vendôme. Claude Auzello, the “elegantly unruffled” manager, asked what he could do for them. “We answered we would like 50 martini cocktails,” Bruce wrote in his diary. “They were not very good, as the bartender had disappeared, but they were followed by a superb dinner”—soup, creamed spinach, raspberries in liqueur, and Perrier-Jouët champagne.

The France that greeted Gertie was a vista of flattened villages, toppled spires, and fields pitted by shells.

Gertie feared that the adventures would all end before she could witness the U.S. Army on the march. “Her obsession was to see the battle,” recalled a friend, who described her as “completely fearless” and with “the vitality of ten men.”

Gertie finally took off from Croydon in south London on September 17th, with seven other OSS employees transferring to France. It was a country she knew well from before the war, remembering, apart from the Ritz, “summers in Biarritz, St. Jean de Luz, and Cap Antibes, the color and odor of Riviera flowers and the deep blue of the Mediterranean.” They flew low over the countryside, and the France that greeted her was a vista of flattened villages, toppled spires, and fields pitted by shells.

Outside her port window, a formation of B-17 Flying Fortress bombers swept by, heading back to England after another mission in the relentless pounding of Germany. The pilot came in low over the Paris rooftops, circling the city center to allow a view of the iconic and intact landmarks, before descending to Orly Airport, where a newly repaired runway was still a gouge of red dust.

Gertie had arranged to stay with a friend from their days in London, Marian Hall, who worked with the Red Cross and had recently rented a flat on the rue François Ier, near the Champs-Élysées. Gertie also planned to volunteer with the Red Cross, as she had in the United States right after Pearl Harbor.

Electricity, heat, and food were all in short supply, but Paris crackled with a “great gaiety of spirit.”

“I am getting used to cold baths, candles and no heat,” she wrote to her husband.

The OSS building was still being renovated, so the arrivals from London were free to roam. “During the day, I walked around Paris, amazed at how beautiful it still was,” Gertie recalled. “The Parisians looked exhausted, although less shabby than Londoners. Always alert to fashion, young girls were painting their wooden heels to match the hue of their lips. Pedestrians and cyclists filled the streets.” The shops, although largely empty of goods, were decorated with red, white, and blue flags and ribbons. “It’s really gay and stimulating and I’m sure the GIs love it.”

As she walked down the Champs-Élysées, an approaching American, also in uniform, saluted her. “I looked around to see who was behind me,” Gertie recalled. “Then it dawned on me—the uniform.” Everything was a little disconcerting. With almost no cars on the streets, Paris seemed strangely serene, as if it were awakening, not yet restored to its old noisy bustle.

Gertie checked in each day with the OSS, but the renovations were slow going, and her boss decided to give some of the staff a formal five-day leave. It was her first official break in more than a year, and she “decided to chance luck to turn up something interesting to do” with the free time.

That Friday afternoon in September, her first stop was the Ritz, where she soon found herself in the company of a group of American reporters. They were leaving the next day for Luxembourg, near where elements of the Third Army under General George Patton were headquartered. Gertie knew Patton from London and they had had dinner and attended the theater together. “It is always fun to meet the guys who run the war, and though less attractive than some, we had a good evening,” she recalled.

The chattering reporters prompted a stab of envy. “I wanted so desperately to see troops on the move, to actually feel the urgency of war, and to know more of what it really meant,” Gertie said.

She could not get that feeling in Paris. The city, now well behind the front lines, was a playground for officers and GIs. Eisenhower, at first, had considered leaving Paris in German hands for the short term, concerned about bloody street fighting and then feeding a vast civilian population when his troops could be better deployed chasing the retreating Germans across northern France. Better, the military initially calculated, to “bypass and encircle it, then await the inevitable capitulation of the isolated garrison.”

General Charles de Gaulle, the leader of the Free French Forces, objected strenuously and argued that Paris would be razed by vengeful Nazis, which had happened in Warsaw earlier that month as Soviet troops stood by on the opposite bank of the Vistula River. There must be no such cold-bloodedness by the Allies. Through his characteristic hauteur and bluster, de Gaulle got his way. Eisenhower moved up the attack on the city, which swiftly fell.

At the liberated Ritz, Gertie spotted Bob Jennings, a wiry, sandy-haired navy officer and World War I aviator. He was a friend of her husband’s; Gertie also knew him from London, where they had met socially several times at cocktail parties. Originally from Michigan’s Upper Peninsula, the 49-year-old Cornell graduate had prospered in the Texas oil industry and in investment banking during the interwar years. His security background check for the OSS noted that he had “accumulated a comfortable fortune in the oil business and is worth four or five hundred thousand dollars.”

After Pearl Harbor, Jennings reenlisted and served in the Aleutians, the Alaska islands seized by the Japanese in June 1942 and retaken by the United States after some bitter fighting the following year. Jennings, a lieutenant commander, had been transferred in 1943 to the London branch of the OSS. His assignment was to help the spy service with its air operations; OSS relations with the U.S. Army Air Forces were often strained as the spies battled to secure planes to conduct their work.

Jennings was also at loose ends. He was scheduled to leave for London early the following week and from there to return to the United States. He had promised his mother he would be able to spend Christmas with her. Listening to the reporters, he, too, was soon infatuated with the idea of getting closer to the western front, though one of the reporters also discussed the risks.

Bill Hearst of the International News Service, the agency founded by his father, William Randolph Hearst, told Jennings that three correspondents had recently been captured. Edward W. Beattie Jr. of the United Press, John Mecklin of The Chicago Sun, and Wright Bryan of NBC and The Atlanta Journal had stumbled into German hands while driving near the French city of Chaumont. The front lines were dangerously fluid.

Jennings, undaunted, said he could borrow an old Peugeot convertible, originally German property but now with “USA” tags and an American flag sticker on its bumper. The car was a little dilapidated, Jennings confessed, but it would get them there and back. Gertie said she could possibly arrange for them to say hello to Patton at his headquarters near Luxembourg.

At the last minute, the trip became all the more urgent for Gertie. She had gotten a letter from her husband, Sidney, telling her that he had finally been granted permission to travel home from Hawaii for a break—the first leave he had received since he was commissioned after Pearl Harbor. “The impossible has happened,” he told her, “a months duty on the mainland and a months leave, making a total of two months on the mainland . . . It will be such heaven to pick up our lives again.”

He said he would leave Oahu on October 1st and suggested they meet in New York City, where their two young children, Landine, eleven, and Bokara, four, had been in the care of their longtime nanny. Gertie and Sidney both missed their girls, but with none of the fervor they felt for each other. Children, in their milieu, were to be enjoyed, but in small doses; the quotidian work of parenting was best left to maids and governesses. “Watching their lives,” their youngest daughter commented, “was like looking at a movie in installments—most of which I never saw.”

Gertie now knew that the trip to Luxembourg might well be her last chance to get close to the front in order “to smell the fighting.” She could get up and back for one last adventure before flying home to Sidney; she felt sure Bruce would sanction her reassignment.

“Just received this minute the great news about your return to the States on leave. Hooray! Hooray! How marvelous,” Gertie wrote back to her husband. “Of course I can return and will . . . beat it home in all speed . . . a little shooting, a bit of sea and sun life and Oh what fun together. [Here’s] to our happy future darling—I too can’t wait.”

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From A Guest of the Reich by Peter Finn. Copyright © 2019 by Peter Finn. Reprinted by permission of Pantheon Books, an imprint of the Knopf Doubleday Publishing Group, a division of Penguin Random House LLC.

Peter Finn
Peter Finn
Peter Finn is the national security editor at The Washington Post and the co-author (with Petra Couveé) of The Zhivago Affair: The Kremlin, the CIA, and the Battle over a Forbidden Book, which was a finalist for the National Book Critics Circle Award for non-fiction. His latest book is A Guest of the Reich: The Story of American Heiress Gertrude Legendre's Dramatic Captivity and Escape from Nazi Germany.





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