Courtney Letts: Adventures in a Man’s World

By the History Center of Lake Forest-Lake Bluff

Part of the appeal of Lake Forest for author F. Scott Fitzgerald when he visited in 1915 and 1916 was its glamour – the enchanting places he frequented, and the sophisticated people he met. Chief among these, of course, was Ginevra King, the Lake Forest girl with whom Fitzgerald embarked on a brief but influential romance. But around King were a circle of other Lake Foresters whose encounters with Fitzgerald may have also had an impact on his future fiction.

King’s collection of friends centered on the Lake Forest young women who attended boarding school with her. Edith Cummings, Margaret “Peg” Carry, and Courtney Letts were King’s closest companions. They had, in a moment of early marketing genius, branded themselves as “the Big Four” and promoted themselves to the point where they became a focus of press coverage for where they went, what they wore, and with whom they socialized.

Courtney Letts enjoyed a lifelong interest in outdoor pursuits.

Courtney Letts (1899-1995) undoubtedly led the most glamorous lifestyle of the Big Four, marrying four times to four very wealthy men and traveling all over the globe. She was the daughter of Frank C. Letts, a wholesale grocery magnate, and Cora Perkins Letts, daughter of a U.S. Senator from Kansas. During World War I, the family let out their Lake Forest estate at 910 North Green Bay and decamped to Washington, D.C., where Frank C. Letts served as director of supplies for the Red Cross. Courtney Letts made her debut among the cosmopolitan circles of the nation’s capital and remained a society leader there on and off for decades.

Letts’s first marriage was her most conventional, to Wellesley H. Stillwell, a Chicagoan and Yale grad who had been an ensign in the Navy in World War I. His father was president of the retailer and wholesale supplier Butler Brothers, and the family resided in a Lake Shore Drive apartment designed by Benjamin Marshall. Stillwell and Letts married on January 10, 1920. Fitzgerald’s lost love Ginevra King Mitchell, by then married herself, served as her friend Courtney’s matron of honor.

In 1923, after the birth of her first two children, Homer Allison Stillwell and Courtney Louise Stillwell, Letts was named by society writer Antoinette Donnelley as one of “The Twelve Most Beautiful Women in America” (alongside, of course, her friend Ginevra King Mitchell).

The portrait of domesticity described in the “Most Beautiful” article was not to last long, however. In 1924, Stillwell and Letts divorced, and the next year she remarried, to “millionaire explorer” John Borden, 20 years her senior. Borden was a scion of an early Chicago family that had struck it rich in Colorado silver mine and then gone into real estate development. In 1927, Letts insisted on accompanying her new husband on a scientific expedition to Alaska on behalf of the Field Museum, where they collected birds and Arctic plants, as well as tracked and hunted polar bears, walrus and seals. Borden thought that she would balk after not being served tea in fancy China cups. But instead, she loved the ruggedness of it all, throughout the five-month trip. The documentary produced of the expedition can be viewed online at: https://archive.org/details/BordenArcticExpedition192735mm118fps

(Caution—some intense hunting scenes of now-endangered species)

Letts authored a book, The Cruise of the Northern Light, about the trip, full of such gems as “One must wear white in stalking Arctic game.” This led to a lifelong interest in outdoor pursuits, documented in a subsequent book, Adventures in A Man’s World (1933).

Tiring of Borden, in 1933 Letts snagged the most eligible bachelor in Washington for her third husband, Argentinian ambassador Felipe de Espil – despite competition from infamous socialite Wallis Simpson, who then consoled herself with the Prince of Wales. Even as she was named “one of the world’s 10 best-dressed women” by Time magazine in 1943, Letts also became embedded in world diplomacy, going on to publish multiple volumes of diplomatic history as she accompanied her husband to Argentina, Spain and Brazil.

Letts and de Espil were married from 1933 until his death in 1972. She returned to the United States and married her fourth husband, Foster Adams, in 1974.

Find out more about Courtney Letts and the other members of “The Big Four” in the History Center’s exhibition “Behind the Glamour: Inside (and Outside) F. Scott Fitzgerald’s Lake Forest,” which also marks the 100th anniversary of Fitzgerald’s renowned novel The Great Gatsby. The exhibit will be open through Oct. 4, 2025. www.lflbhistory.org