HISTORY

The Tragic, Never-Told Love Story of A Gilded Age–Era Romance

While working on a biography of her great-grandmother Gertrude Vanderbilt Whitney, Fiona Donovan unearthed a trove of letters between Gertrude’s daughter, Flora Whitney Miller, and President Theodore Roosevelt’s son, Quentin Roosevelt, that tell a story of one woman’s battle with grief during a time of war.
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Flora and QuentinCourtesy of Fiona Donovan.

A briny breeze blows across the English Channel, throwing me off balance as we traverse the expansive lawn at the American Cemetery and Memorial in Normandy, France. A memorial that contains the graves of 9,389 American servicemen and women who died in World War II, the cemetery sits on a bluff overlooking five-mile-long Omaha Beach, where most lost their lives in the D-Day landings and the perilous aftermath. Our French guide, clad in a formal navy skirt suit, has me sign the visitor’s book and asks more about why we have come.

While working on a biography of my great-grandmother, the sculptor and philanthropist Gertrude Vanderbilt Whitney, I became intrigued by a significant event in her daughter’s life, a tragedy that, as far as I know, she never spoke of with her children or grandchildren. During World War I, my grandmother, Flora Whitney Miller, was deeply in love with and engaged to Quentin Roosevelt, a fighter pilot and son of Teddy Roosevelt. Quentin perished in the war and is buried at the American Cemetery. I wondered how my grandmother moved on after Quentin’s death, marrying twice and spawning a large family, leaving little trace of this love story, apart from letters.

Flora was born into one of the wealthiest families in the United States in 1897, at the height of the Gilded Age. Her father was the entrepreneur and sportsman Harry Payne Whitney; her mother was a Vanderbilt who had a career as a sculptor, winning large public commissions in the United States and Europe. In 1931, Gertrude founded the Whitney Museum of American Art. As president of the Whitney during the 1940s, Flora was instrumental in its survival today.

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Gertrude Vanderbilt Whitney and QuentinCourtesy of Fiona Donovan.

I remember my grandmother’s gracious manner, the way she floated into a room with expectant delight and curiosity. With her colorful pantsuits, coiffed hair, poppy-red nails, and the elegant cigarette holder she nearly always used, she set a standard for genteel warmth and a blithe sense of fun.

Flora and Quentin met as teenagers in 1915, the year before her Newport debut. That summer, Flora’s mother gave her an uncharacteristically stern warning: “Be very careful with the boys. You are older now and you must not be the least immodest or familiar. They will like you all the better for it. Don’t ever let them touch you even jokingly. I know you know them all so well they seem like Sonny [Flora’s younger brother], but you are grown up now and you must have some reserve. This is not intended to be a lecture, but only to remind you of your extreme old age!!”

At 19, Flora was a fetching young woman with a sweet smile. Clad in a simple white satin dress with silver trim, she appeared lanky and graceful as she stood with her mother, greeting their guests at her coming out party in Newport, Rhode Island. Flora spent much of the evening dancing with her escort, Quentin Roosevelt, an ebullient young man her age. Known for his smarts, humor, and boisterous charm, Quentin was the youngest of Teddy’s six children. Among the hundreds of thank-you notes the Whitneys received after the party, Quentin’s letter to Flora’s mother described how it had left him with a “kaleidoscopic impression…accompanied by a pleasant, subdued tinkle, as of ice against the sides of a cocktail shaker.” Quentin asked her to “tell Mr. Whitney that his efforts toward making me comb my hair have been wasted, as I left my comb at Newport. I think of him nervously now, every time I catch a glimpse of myself in the glass.”

A Harvard sophomore in 1916, Quentin called on Flora for a year, leaving cards and sending letters, cables, and postcards, including a chaste Valentine. That fall, Flora declared in her diary: “IT has happened…Took Mamma out in motor and told her…Oh! Ooh!! Oooh!!!” The young couple had fallen hard for each other. At a teatime gathering in New York in November 1916, Flora noted that “Q and I behaved disgracefully—very bad of us. Nice to see him again as I haven’t for so long!!” Were they making out? Spiking the punch? Flirting madly? Maddeningly, my grandmother didn’t say.

After President Woodrow Wilson committed US forces to the Great War in April 1917, Quentin grew hell-bent on serving as a fighter pilot. He stayed with his parents at Sagamore Hill and spent long hours flight training at Hazelhurst Field (renamed Roosevelt Field in 1919, in Quentin’s honor). As he crossed to France that summer, Quentin wrote to his father expressing his appreciation for his parents’ care of Flora: “You can’t possibly know how much you and mother mean to her. You see, you are the embodiment of all the things she has never had—all the family life, all the things that you have taught us…which don’t exist with her father and mother.”

Once Quentin left the States, Flora took comfort in the Roosevelts’ stability; to his mother, Quentin expressed his pleasure that “you like her…. I was sure you would…when you…had got past the fact that she was one of the Whitneys, and powdered her nose." In September 1917, Quentin wrote to Flora and formally proposed, theorizing that “if I’m in the spring offensive, I ought to have [a long leave] by the end of next summer—and if I do, will you marry me, then? This is the first real proposal I’ve made to you and please don’t say no!” Flora was over the moon, though initially they kept their engagement under wraps. Teddy and his wife Edith were “much pleased with Quentin’s engagement. He and Flora seem very happy. She is a dear,” Teddy Roosevelt wrote to one of his sons.

At Issoudun, Quentin was put in charge of transportation and equipment, maintaining the outfit’s 52 trucks and other vehicles and making sure they were well stocked with petrol, parts, and all sorts of other things at a time when supply chain issues plagued the American military.

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Theodore Roosevelt with his sons Quentin and Archibald, 1904.Universal History Archive/Getty Images.

Quentin turned 20 that November. For Christmas, he bought Flora two Tiffany amber bracelets; Flora managed to ship Quentin a silver cigarette case and two boxes of Benson & Hedges—a luxury, with cigarettes in such short supply. She had started typing and shorthand lessons to assist the war effort, working in the Navy’s Office of the Aid for Information at the Brooklyn Navy Yard.

Whether too sick or dispirited to write (he had come down with a debilitating case of pneumonia in early 1918), Quentin got a dressing down from his father, along with some romantic counsel. Teddy advised his son that if he expected to hold onto Flora, he must “write her letters—interesting letters, and love letters—at least three times a week. Write no matter how tired you are, no matter how inconvenient it is; write if you’re smashed up in a hospital; write when you are doing your most dangerous stunts…. Write all the time! Write enough letters to allow for half being lost.” Quentin sent Flora countless letters.

Teddy also urged Quentin to write to Flora and her parents to see if they could arrange her passage to France. Quentin’s sister-in-law offered Flora a room in her Paris apartment and an opportunity to work with her at the YMCA there. And his sister Ethel prodded Quentin: “Flora is one of those people who rise up higher by every trial. She has a very valiant spirit and reserves of strength and patience and courage…. She is really an extraordinary person.”

Quentin was assigned his own Nieuport plane that winter, a castoff from the French flying units. It seemed he could be deployed at any moment.

In May 1918, Flora’s father joined Teddy for dinner at Sagamore Hill, afterward telling his son Kermit that the Whitneys had given their blessing for her to marry Quentin as soon as possible. The Whitneys pressed their friend Henry Davison, head of the American Red Cross during the war, to help negotiate Flora’s crossing to France. President Wilson had signed a law limiting citizens from leaving the United States if it wasn’t in the best interests of public safety.

In June, Quentin was assigned to the 95th Aero Squadron of the American First Pursuit Group. He moved to Toul, near the German border, 160 miles from Paris.

In short order, Quentin was reassigned twice, ending up at a base near the town of Touquin, an outfit offering support to Allied ground forces about 30 miles east of Paris. Starting July 5, Quentin was in the air over the German lines every day. The pilots flew in formations of six, doing their best to avoid being chased and taken down by enemy planes or anti-aircraft shrapnel.

He had developed a reputation as a daredevil, one who was either extraordinarily brave or took needless risks. According to the decorated pilot Eddie Rickenbacker, who had seen Quentin fly often, “his bravery was so notorious that we all knew that he would either achieve some great, spectacular success or be killed in the attempt.”

On Bastille Day, Quentin’s unit took flight over the German lines. Once airborne, German fighter pilots managed to break up the formation of his squadron. With three German planes on his tail, Quentin was shot and plunged out of control; his Nieuport 28 went down behind enemy lines in the village of Chaméry.

For two days, his unit and his family held out hope that Quentin was alive. On July 16, Teddy made a statement confirming Quentin’s death and called Flora to break the news. Once they discovered Quentin’s identity (established by letters from Flora he carried with him), he was buried in a proper military ceremony.

Lost on Bastille Day, beloved son (the only child of a US president to die in combat), and notably charismatic, the young pilot became a symbol of military courage and honor, the ultimate American casualty of the Great War.

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Flora Whitney Miller with daughter Flora Miller Biddle at the dedication of the new home for The Whitney Museum.

Fairchild Archive/Getty Images.

After Teddy’s announcement, Flora spent several nights at Sagamore. That fall, she confided to Quentin’s sister Ethel: “Everything just hurts nearly all of the whole time. There is no one I can talk to who half understands. It is all so lonely.” Her parents knew that she suffered. Yet in the hundreds of condolence letters to Flora from friends and family and other correspondence from this time, there are none between Flora and her parents that mention Quentin or his family. Despite this, one of the more poignant bronzes her mother made at this time is of Flora, seated quietly in an armchair, the curve of her body and downcast expression manifesting her pensive mood.

Flora and Teddy took solace in each other’s company. Teddy wrote to Flora that fall reminding her that “for as long as I live, I shall love you as if you were my own daughter.” During that time, Flora did some work for Teddy, who she called “the Colonel,” taking dictation and typing letters and other documents. In January 1919, Roosevelt died of an embolism. His death plunged Flora further into grief.

After that, Flora lived for a time with Quentin’s half-sister, the fiercely independent Alice Roosevelt Longworth, in Washington, DC, volunteering at the Women’s Republican Committee in the office of former congressman Ruth McCormick. In the summer of 1919, Flora’s parents urged her to go to France with her aunt Dorothy Whitney, who had lost her husband, Willard Straight, in the influenza pandemic.

There the women visited Chaméry, where Quentin was buried. Flora’s grief came flooding back. Paris, though, lit up with post-war joie de vivre, was the perfect antidote. The women shopped on the rue de la Paix, heard Tosca at the Tuileries, and walked in the Bois. The days flew by until they sailed home from Southampton a month later. Flora felt a brimming lightness, her sprightly grin restored, a new swing in her step. Theodore Roosevelt was onto something when he wrote to his daughter-in-law Belle the summer before that “there is nothing to comfort Flora at the moment, but she is young. I most earnestly hope that time will be merciful to her and, in a few years, she will keep Quentin as only a memory of her golden youth…and that she will find happiness with another good and fine man.”

Our American Cemetery guide escorts us along a sea of marble headstones to Quentin’s grave. He is buried next to his oldest brother, Brigadier General Theodore Roosevelt Jr., who died of a heart attack in France at the end of World War II. Quentin is the only World War I pilot interred there, his remains moved in 1955 at the request of his family. Once we reach the grave, our guide attends to the noble task performed by volunteers for visiting family members and every year on the anniversary of D-Day. With a sponge, she rubs Omaha Beach sand over and into the incised letters on Quentin’s headstone. She carefully wipes off all but the sand impressed into the channels of his name, rank, unit, home state, and date of death, highlighting them. As a gentle fog rolls in from the Channel, bathing the cemetery in a soft haze, she plants two flags—one American, one French—on either side of the grave.

The American Cemetery’s unsettling serenity reminds one that freedom comes with responsibility and at a tremendous cost. Appalled by the barbarity of battle evoked in the sites I visited around Normandy’s beaches, I left awed at the courage of Quentin and Flora, and all those caught up in the war’s unpredictable forces.