In the months ahead, two biographies will be published about Gertrude Sanford Legendre, late of Fishers Island, her 6,700-acre plantation near Charleston, S.C., called Medway, and big-game hunting country in Africa, India, Iran and Indochina.

She was a socialite born to vast wealth — she was a descendant of the Sanford family, which manufactured carpets in Amsterdam, N.Y., and raised thoroughbred racehorses — and she was a prisoner of war, armed with World War II secrets from her work at the Office of Strategic Services (OSS) and captured and held by the Nazis for six months.

She was also the mother of Landine Manigault, for many years a resident of Stonington, who declined to talk to me about her mother. For the record, she also declined to talk to the two biographers.

One is Peter Finn, national security editor at the Washington Post and author of the forthcoming “A Guest of the Reich: The Story of American Heiress Gertrude Legendre’s Dramatic Captivity and Escape from Nazi Germany.” It will be published by Pantheon and released in September.

The other biography, “The Fabulous Life of Gertrude Saanford Legendre: Heiress, Hunter, Socialite, Spy,” is by Kathryn Smith, a writer and editor living in Anderson, S.C. Also to be out in September, it is being published by Evening Post Books in Charleston, S.C., co-founded by Pierre Manigault, son of Landine Manigault and grandson of Gertrude Legendre and chairman of the board of Evening Post Industries, publisher of Charleston’s daily newspaper, the Post & Courier.

As a New York Times profile of Legendre’s other daughter, the late Bokara Legendre, published in 2011, says about Gertie, as she was known: “Motherhood did not impinge on her quest for adventure.  ... Bokara says one of her earliest memories is of her governess answering a stranger’s knock at the door. ‘She said, ‘Say hello to your mother, Bo.’ And I thought, ‘Who is this woman?’”

When Gertrude Legendre died, at age 97, in 2000 at her plantation in South Carolina, obituaries mentioned her regal home on Fishers Island, called Chocomount, which overlooked Long Island Sound from the island’s high ground and where she lived for decades and kept as many as eight servants and two gardeners. It was not unusual to find 15 to 20 people gathered for lunch there on any given day.

Gertie’s husband, and father of her daughters, was Sidney Legendre, scion of a prominent New Orleans family. Among the guests at their wedding in New York were Vanderbilts, Harrimans, Astors and Whitneys. Sidney Legendre died of a heart attack in 1948 at age 44.

As for Gertrude Legendre’s now legendary heroics during the war, her daughter, Landine, likes to tell friends in Stonington that her mother went out for a picnic to see the war and was captured by the Germans.

According to Christopher Dickey, a veteran foreign correspondent writing for in September 2016, that’s more or less what happened, with rather more intrigue involved. The headline: “The Socialite Spy Who Played So Dumb She Outsmarted the Nazis.”

To try to keep this brief, Gertie began working for the OSS (precursor to the CIA) in Washington, D.C., in the summer of 1942. One of few women in a man’s world, she worked closely with a top aide to Gen. William J. “Wild Bill” Donovan, head of OSS, and eventually was one of six women transferred to London. “She was assigned to the Central Cable Desk,” wrote Dickey, “handling the communications from agents all over North Africa and Europe, including France and Germany. Few people in the organization saw more information about who was where and what they were learning.”

In September 1944, three months after D-Day, she and several other women were ordered to join OSS operations in Paris. One evening she was in the Ritz Hotel where Ernest Hemingway, among other luminaries, had gathered, and made a plan with OSS officers she knew to try to find Gen. George Patton and the U.S. Third Army somewhere around Luxembourg.

The next day, Legendre and an officer set out in a banged-up Peugeot, met up that night with another officer and his driver, teamed up but ended up motoring on the wrong side of the small town of Wallendorf, Germany. German soldiers fired on the vehicle, wounding two men, and the group surrendered.

OSS leaders were panicked by Legendre’s capture, dubious about her fortitude in keeping secrets,  but the Germans apparently bought her concocted story that she was a Red Cross volunteer merely along for the ride. She was moved around, eventually taken to a 13th-century castle overlooking the town of Dietz. She was interrogated for six weeks, but rather gently, and in fact befriended her interrogator and, after the war, found him, destitute with his family in Germany, a job in South Carolina.

She was moved to Frankfurt and then Berlin, and though still under guard, was treated kindly. In January 1945, wrote Dickey, she was sent to a hotel in a compound near Bonn where she encountered 42 French generals, 75 colonels, several diplomats and the sister of French leader Charles De Gaulle. They were deemed “honor detainees,” and moved again as the Allies advanced. A short time later, after a bit more intrigue, some of it harrowing, she made her escape across the Swiss border.

Now her outsized life story will be told again, in not one, but two biographies.

Steven Slosberg lives in Stonington and was a longtime reporter and columnist. He may be reached at

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