Every now and then, when I least expect it, I will stumble across a name that for some reason begins to pop up repeatedly, almost uncannily, in the books I’m reading at that moment. Very often it’s a name I am unfamiliar with up until then. Then suddenly there’s no escaping it! Such an occurrence has just happened to me with Emily Vanderbilt, a beautiful and sometimes scandalous figure who crops up in works by or about Thomas Wolfe, E. E. Cummings, F. Scott and Zelda Fitzgerald, Edmund Wilson, Mercedes de Acosta, Dolly Wilde and Dashiell Hammett, all of which I’ve been dipping my nose into recently. It’s almost as if the hand of fate were poking a finger at me, demanding that I take notice. Well, I have taken notice. Emily Vanderbilt is a fascinating and bewildering creature, an enigma who epitomizes the highs and lows of what Gertrude Stein dubbed “the Lost Generation.” (Emily, above and below, by Arnold Genthe.)

During her glamorous, yet often troubled life, Emily Vanderbilt in fact had many names. Her birth name was Emily O’Neill Davies. She was the daughter of Frederick Martin Davies, a New York banker, broker and noted horseman, who raised his family in a large private house at 20 E. 82nd Street. Her mother, also named Emily O’Neill Davies, was the daughter of Daniel O’Neill, the editor and owner of the Pittsburgh Dispatch. When Daniel O’Neill died in 1877, leaving a fortune valued at $8,000,000, his wife Emma (nee Seely) married his brother, Eugene M. O’Neill, who took over the paper. Some reports describe Emily Vanderbilt as the granddaughter of Eugene O’Neill, but she was not. An 1880 census clearly states that her mother was the “stepdaughter” of Eugene. (Not to be confused with the famous playwright of the same name.)

The Frederick Martin Davies family lived in high style at their posh Manhattan manse. In the 1910 census they are shown to have had ten servants: a parlor maid, waitress, cook, kitchen maid, two chambermaids, two nurses, a laundress and a lady’s maid. Young Emily grew up in a rarefied world of wealth and privilege, summering in Southampton, wintering in Palm Beach, weekending in Newport, and gallivanting as a debutante among the glitterati in Manhattan’s upper crust. It was a life of extreme luxury at the height of the gilded age.

Frederick Martin Davies was the cousin of Bradley and Townsend Martin, and best friend of Alfred Gwynne Vanderbilt. Ironically, Davies died the day before Vanderbilt set sail on the ill-fated Lusitania and lost his life. So it seemed a fitting twist of fate that in a fairy-tale wedding at Grace Church in Manhattan in 1923, Davies’ beautiful young daughter Emily would marry Vanderbilt’s son, William Henry Vanderbilt III (below).

That marriage seemed, at least in the society-mad press, to be a storybook romance. But it did not fare well. They moved to Boston and Oakland Farm in Portsmouth, near Newport, which Vanderbilt had inherited in his father’s will along with $5,000,000. A daughter also named Emily was born in 1924. Three years later, William and Emily split up in a divorce that took only six minutes in court to implement. Emily claimed William had failed to provide. He was rumored to be cruel and over-protective. Some have speculated that he hired detectives to follow his wife who may have been having an affair with a handsome young theatre producer named Sigourney Thayer. In the end, Vanderbilt was granted custody of the child, permitting Emily to see her daughter only three months out of the year. William Vanderbilt III later married Anne Colby, started a bus company in Newport, then went on to become a State Senator, and ultimately Governor of Rhode Island. He died in 1981.

On December 7, 1928, Emily wed Sigourney Thayer (above). An Amherst grad, Thayer was a curious figure in New York circles. His father was William Greenough Thayer, headmaster of St. Mark’s, a tony New England prep school. When they wed, Time quipped that he was a “spasmodic theatrical producer, wartime aviator, Atlantic Monthly poet, socially prominent jokesmith.” Thayer dressed like a dandy and had a showy Proustian mustache. The marriage was a surprise to friends who didn’t think she took the affair that seriously, but perhaps she felt that it would be too big a loss to give up her daughter for a mere youthful indiscretion. She gave legitimacy to the relationship, but the marriage didn’t last. Both agreed it was a mistake. They divorced a year later.

(Above: Aline Bernstein; E. E. Cummings; Thomas Wolfe; Edmund Wilson)

Emily Vanderbilt Thayer led a gay social life in Paris and was a fixture in literary circles. She aspired to be a writer and critic, and surrounded herself with well-known authors. She knew Gertrude Stein and Alice B. Toklas, and became chummy with dancers from the Ballets Russes. At a party hosted by Muriel Draper, she first encountered E. E. Cummings. He found her, according to one source, “blonde, statuesque, charming and gorgeous.” They had a two-month affair. She soon fell for Thomas Wolfe whom she met through Aline Bernstein. Emily “tried to make him,” according to F. Scott Fitzgerald, who followed her comings and goings with a fascinated eye. She would write Wolfe urgent notes written in a childish scrawl, begging to see him. Wolfe reportedly was astonished by her beauty and seductive charms, but was wary of her insolence and sexually aggressive ways. He found her “fundamentally trivial.” Wolfe’s biographer David H. Donald says he was “disgusted by her systematic and rather dogged experience of the life of degeneracy and refused to join her in smoking opium.” He detested her gigolo Raymonde, “a bad Valentino.” Worse, she paraded Wolfe among her friends as someone “madly in love with her.” He fled to Rouen. Wolfe eventually used Emily as the basis of the character Amy Carlton in his novel You Can’t Go Home Again. Fitzgerald praised his description of her “cracked grey eyes,” and “exactly reproduced speech,” as “simply perfect.”

Emily didn’t limit her affairs to male writers. She was drawn to the lesbian demimonde, dominated by Natalie Barney and Djuna Barnes. According to Zelda Fitzgerald biographer Sally Cline, Emily was most likely bisexual. She was close friends with Dolly Wilde, the notorious niece of Oscar Wilde, as well as Mercedes de Acosta, another social butterfly who achieved fame by her dalliances with great writers and movie stars.  I found a ship record for the two of them traveling together aboard the Olympic from France to New York in 1929. On it, Emily gave her birthday as August 10, 1903. Mercedes claimed to be 30, born in 1899, although she was actually six years older. At the time Emily maintained a home at 176 E. 75th St.

(Above: Djuna Barnes and Natalie Barney; Zelda Fitzgerald; Mercedes de Acosta; Dolly Wilde)

During this period, as the Jazz Age reached a fever pitch before the inevitable plunge, Emily was swept up in the decadence of cafe society, flouncing around with a bunch of Hemingwayesque expatriate socialites who’d come to live it up in Europe. Zelda Fitzgerald said that she “was sorry for her. She seemed so muddled and lost in the grist mill.” Scott, hoping to bolster Zelda’s spirits, who was jealous of Emily’s sophisticated allure, dismissed her in a letter as someone who “could not dance a Brahms waltz, or write a story. She can only gossip and ride in the Bois and have pretty hair curling up instead of thinking.” Scott may have been projecting his own sense of insecurity among the very rich. Thomas Wolfe considered him a social climber. Fitzgerald, despite his misgivings about her, had an affair with Emily in 1930, when Zelda was in Prangins recovering from a breakdown. But it didn’t amount to much. Fitzgerald later wrote that she “was too big a poisson for me.” He remained mesmerized by her, however. Both he and Zelda kept clippings about her in their scrapbooks.

Emily in fact did have higher dreams than just being a transatlantic party girl. She wrote books and articles but never tried to get them published. Asked if she would ever write for publication, she coyly answered: “I will tell you in twenty years.” In 1929 it was announced with fanfare that she would become a reader for the publishing firm Boni & Liveright (one of the foremost houses in publishing at that time). Its founder Horace Liveright was a bon vivant and ladies man who managed to lure the leading lights of the literary firmament to his doors. Eugene O’Neill, T. S. Eliot, Ernest Hemingway and Theodore Dreiser were all published by him. Emily relished her role as reader and used her contacts to aid Liveright. Lillian Hellman first took note of Emily Vanderbilt at the 1934 opening night party of her first play, The Children’s Hour, which was about a lesbian scandal in a girl’s school. Hellman described her as a “a handsome, boyish-looking woman” seen at every literary cocktail party. Judging by photos of Emily taken by Carl Van Vechten in this period (below), she was still striking looking, but perhaps not as innocently radiant as before.

Emily’s interest in literature was serious and well-informed. It might explain her marriage in 1933 to the writer Raoul Whitfield. One of the big names at Black Mask magazine, a pulp that published Dashiell Hammett and Raymond Chandler and defined the “hard-boiled” genre, Whitfield was a former aviator who fought in World War One and claimed to have won the Croix de Guerre for distinguished service, although some critics have suggested that such an honor was more likely a “flight of imagination.” One biographer described him as sporting a “cane, elegant leather gloves and a silk scarf around his neck, looking aloof and imperious. His mustache is carefully trimmed, his dark hair slicked back and parted in the middle. Every inch the gentleman.” (Below, Raoul Whitfield from Argosy).

Whitfield’s family traveled abroad when he was young and he was raised partly in the Philippines. His middle name was Falconia but he used the name Raoul Fauconnier Whitfield when describing himself. He was something of a mystery himself, and remains so to his most devoted fans. Throughout his life he held many odd jobs, including fire fighter in the Sierra Madre range, a bond salesman in Pittsburgh, and a newspaper reporter. He even tried his hand at acting in silent films. Widely considered one of the top detective story writers, he was a close friend of Dashiell Hammett’s. Hammett later had an intimate affair with Whitfield’s first wife Prudence Smith after the couple’s divorce.

Emily saw in Raoul a way out of her wayward existence in cafe society. She admired his writing ability and wrote a play with him called Mistral. But the marriage was tempestuous from the start. By this time she was drinking heavily and using sleeping pills at night. She became increasingly moody and difficult. Today she might be diagnosed as suffering from manic depression. Yet at first the marriage seemed successful. They bought a rambling spread in Las Vegas, New Mexico which they called “Dead Horse Ranch.” Here they raised cattle, built a polo field, a golf course and entertained friends from both coasts on a lavish scale. But the union soon devolved into jealous rages and accusations of infidelity. Raoul was allegedly having an affair with a local barmaid named Lois Bell.

The final chapter in Emily’s life reads like the climax of one of Whitfield’s violent novels. Shortly after starting divorce action against Whitfield, Emily was found shot to death in her bedroom at the ranch on May 24, 1935. A hastily assembled coroner’s jury found that she had committed suicide, despite the fact that the gunshot wound was on her lower left side and she was right-handed. The bullet, from a Colt .45, passed through her lungs and hit her heart. The New York Times reported that she had become “despondent after a conference yesterday on a divorce suit.” Her friend Mrs. Virginia Haydon Stone was with her earlier but did not spend the night. Emily retired at 11 PM. “The body, clothed in pajamas and a dressing robe, was found at 7:30 o’clock [the next] morning, on the bed, a revolver clutched in the outflung right hand.” The body was discovered by an employee at the ranch. But almost immediately speculation grew that someone had killed Emily Vanderbilt Whitfield. Lillian Hellman did not mince words when she wrote later: “she was murdered… and neither the mystery story expert nor the police ever found the murderer.” (Below: Lillian Hellman and Dashiell Hammett.)

Whitfield was a prime suspect, even though he had proof that he was in California at the time of Emily’s death. Some suspected he hired someone to kill her. For the rest of his life he lived under a cloud. He inherited a small fortune, then married Lois Bell and moved about constantly, almost frenetically. He went through the money like a dose of salts. Adding to the tragedy was the suicide of Lois Bell, who leaped from a hotel window in San Francisco in 1943. Raoul Whitfield’s health deteriorated. He had tuberculosis. Hammett, in a typically generous gesture, asked Hellman to send him a check for $500. Whitfield died, broke, in a military hospital on January 24, 1945.

Not surprisingly, the story of Emily Vanderbilt Thayer Whitfield has fascinated writers for 75 years. Recently a novel based on the case has been published which delves into the circumstances of her death and offers a very dramatic, yet plausible solution. Written by Walter Satterthwait, the novel is Dead Horse. I won’t give away the ending, but it is utterly convincing. You can read more about it at the author’s website: www.satterthwait.com.

As for Emily’s daughter, she was raised by her father William H. Vanderbilt. Nicknamed “Paddy,” she married Jeptha Wade, an attorney, originally from Cleveland. They lived in Boston. He died a year ago August at 83.  She is a Life Member Emeritus of the MIT Corporation, and President of MITS, Inc.

Emily O’Neill Davies Vanderbilt Thayer Whitfield may have been a character of many names, with three troubled marriages, but she was not easily categorized. As a debutante, she enchanted high society. As an heiress, she married “well” only to find that fairy-tale romances are bittersweet. As a mother, she was devoted to her daughter despite years of separation. But she was also a woman who defied the strictures of her age, became a respected devotee of the finest authors of her day, and ended as an iconoclast who lived and loved on her own terms. Whether tragic muse or literary butterfly, her legacy will haunt us for generations to come.