NINETEEN TWENTY-SIX proved a banner year for Joe Carstairs—yes, she called herself Joe, not Jo—marking her try as a champion speedboat racer and winning the Duke of York trophy, then the most prestigious in speed racing. She was the only woman in a field of nine in the star-studded event, and the excitement had led tens of thousands of fans (one estimate put the figure at a million) to crowd the banks of the Thames. In short order, one contestant after another fell by the wayside, knocked out of the competition by ignition failure, an engine blowing up, collision with a buoy or another boat—or being thrown overboard by the powerful swell of the water.*
By the final heat, only two of the nine boats remained in contention: Herr Krueger, the German entry, and Joe Carstairs, steering her seventeen-foot hydroplane, dramatically painted black, with a white stripe running its length. Approaching the finish line, both finalists ran into trouble. The connecting rod on Krueger’s boat broke, disabling it, while a tangled rope in the gears threatened to stop Carstairs’ boat cold—until she somehow managed to cut it loose with a knife, and raced to victory. That same year of 1926, after winning a number of other major races, Carstairs was awarded the Médaille d’honneur, given annually for the “most meritorious motor-boat performance throughout the year.”

For the next half-dozen years, Carstairs continued to compete, and with remarkable success. But the sport was both dangerous and expensive. Having driven an ambulance in France during World War I, Joe scoffed at the danger, insisting to one reporter that the so-called “threats” involved were better seen as “discomforts”—though she did acknowledge that “floating wreckage at speed can cut a hole through the bottom of the boat like a razor cutting canvas.” She confirmed to the reporter that she’d been “thrown overboard at speed” in one race, leaving her with three broken ribs, though she omitted the fact that she’d refused rescue until her severely injured mechanic had been hoisted to safety. Joe further acknowledged that running into “a head sea could be nasty … you get a jar absolutely right through you … like a terrific electric shock.” Still, she quickly added: “It’s a marvelous sport. At the end of a race you’re filthy, covered with oil, soaked with water most likely, and nearly deaf with the noise, but there’s nothing in the world so satisfying.”
If the danger didn’t dissuade her, neither did the expense. Her American grandfather, Jabez A. Bostwick, was one of nine men who in 1873 comprised the Executive Committee of Standard Oil, was the sixth largest shareholder, and had sweeping power over the affairs of several Standard Oil companies that collectively made up the monopoly. The powerful group of nine not only drafted general policies but controlled all decisions involving the diverse types of oil and refineries, the buying of crude, the purchase of chemicals and lumber, relations with railroads and other shipping entities, and price quotations.
Jabez Bostwick’s daughter Evelyn was Joe’s mother, but a wholly disengaged one. Something of a jaded, volatile troublemaker, Evelyn married four times. Her first husband, Albert Carstairs, is barely mentioned in the surviving documents and seems to have played little role in Evelyn’s life and next to none in his daughter’s. Evelyn’s fourth marriage, on the other hand, was to Serge Voronoff, a surgeon briefly famous in the 1920s for transplanting monkey testicles into male humans as a purported treatment for “rejuvenation.” Joe (rightly) considered him a charlatan, and the two were rarely in each other’s company. Meanwhile, Evelyn Bostwick became increasingly drawn to alcohol and drugs. As an adult, Joe was quoted as saying that she’d “never been frightened of anybody except my mother.”† There was no riddle to their mutual dislike. Joe herself provided the key: “I was never a little girl. I came out of the womb queer.” At age eleven, Evelyn shipped her off to boarding school.

Jabez Bostwick had died in 1892, leaving most of his fortune to his widow Nellie. Joe, meanwhile, bounced from school to school and then from job to dead-end job. After the outbreak of World War I, she became an ambulance driver in France (the male drivers called her “Tommy”), and while still a teenager she shared an apartment in Montparnasse with four other young female drivers. One of them was Dolly Wilde, a niece of Oscar, with whom Joe had her first sexual experience. She sometimes tagged along with Dolly to Natalie Barney’s famous literary salon, but neither she nor the Bohemian crowd could muster up much interest in each other. Joe loved sex, but the sophisticated manners of the literary set were antithetical to her brisk, strenuous style.
Much more appealing to Joe’s earthy sensibility was the taxi service she and her friends from the ambulance corps put together in London after the armistice. They called themselves the X-Garage, perhaps signaling their noncompliance with social norms, and made themselves available to transport customers as far as Ireland. Joe seems to have thoroughly enjoyed the adventuresome side of the business, but her need for cash came to a halt with the 1920 death of her grandmother, Nellie Bostwick. Knowing her own daughter Evelyn’s capricious ways, Nellie had already set up two separate trust funds for Joe. By 1922, they were yielding her an annual income of some $200,000—roughly 3.5 million in today’s currency. She became still richer when her mother Evelyn died in 1921. After three years of complicated litigation over the will, by 1925 Joe found herself in possession of a considerable fortune.

Without pausing for breath, Joe immediately commissioned the celebrated boat-builders on the Isle of Wight to build her an up-to-the-minute, seventeen-foot hydroplane, and named her Gwen in honor of her friend and sometime lover, the cabaret star Gwen Farrar, then on the verge of fame. From 1921 to ’24, in partnership with Norah Blaney, Gwen appeared regularly at leading variety theaters. Among her standout shows were Pot Luck, with Bea Lillie; Rats, with Gertrude Lawrence; and The Punch Bowl, with Hermione Baddeley.
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Her fortune legally secured by the mid-1920s, Joe closed the X-Garage, and for the next half-dozen years, she devoted her full—and formidable—energy to femmeboat racing, to the sport that perfectly combined her physical daring with her instinctive indifference to “propriety.” Between 1925 and 1931, she participated in most of the prominent powerboat races and won them often enough to cover the top of a good-sized dining room table with trophies. And she did so without apology, explanation, or self-consciousness; she simply accepted herself. The ’20s, to be sure, were a decade more tolerant of gender and sexual nonconformity than any preceding (or several that followed). Doubtless both her wealth and her manner—“this is me; take it or leave it; I couldn’t care less”—played a role in her general acceptance in a decidedly male sport. Whatever the cause, during the ’20s neither her competitors nor the press mocked her, and “society” did not call for her exclusion. In the more conservative 1930s, however, there was something of an uptick of criticism in the press of her “mannish” ways.
Occasionally, too, someone—usually a stranger—would address her as “sir” or “mister.” When that happened, Joe—who couldn’t have cared less about “passing”—seems to have mostly reacted with detachment, choosing to regard the remark as an innocent mistake, or accepting the fact that there will always be people who take offense at any deviation from prevailing gender norms.
What she did not do was attempt to bring her appearance into conformity with standard gender expectations. She wore her hair in a crew cut, had tattoos running up one arm, and wore mostly working-class dungarees or trousers. Her “manly,” even rakish, stride through the world—her gaze assured, her purpose commanding—was performed with apparent disregard for its effect. When in pursuit of a bed partner, she seized the initiative, appropriating her right to take control and steer the course. However, she wasn’t possessive and didn’t demand (or possibly want) lifetime fidelity. Her pattern in love affairs was short-term and serial. Her many partners were invariably young and drop-dead gorgeous—and none of them, as far as is known, was accorded the privilege of spending the night with her in the same bed. She retained a photograph of every woman she bedded down and put them on display under the glass top of a coffee table; the total was well over a hundred.
Joe’s sexual pattern was much more traditionally male than female—or rather, it represented what many men (so we’re told) would regard as ideal, except that Joe, unlike them, was exceedingly generous to her partners, heeding their wishes, showering them with gifts, without asking for exclusivity. Joe “was just completely open,” Alex Stoll, who knew Joe later in life, told me in a 1997 interview. “I think she was a little pissed that everybody kept everything a secret, because she was the one who didn’t. She was just very honest, very down-to-earth, not sentimental or pretentious.”
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At age 34 and facing tax problems in both Britain and the U.S., Joe, with typical audacity, decided in 1934 to buy the barely habitable island of Whale Cay in the Bahamas, nine miles by four, for the sum of $40,000. In doing so, she became in essence the sole ruler and for a time nearly the sole inhabitant. (A single shack existed for a man and his wife who occasionally tended to the lighthouse.) Covered with shrubs and weeds, the island was sold as entirely non-arable. Joe rolled up her legendary sleeves and embarked on an eight-year project that at its close would boast an elegant pseudo-Spanish villa of hand-polished mahogany, a power plant, fifteen miles of paved road, a wireless station, a schoolhouse, and an agricultural enterprise that included homes and a chapel for the several hundred Bahamians who flocked to Whale Cay’s generous salary scale—and produced the largest granary in the Bahamas.
During the early 1930s, with construction crews largely in possession of Whale Cay, Joe traveled widely. Even later, she’d periodically shop and visit friends on the Florida mainland and elsewhere, but starting in the mid-’30s, Whale Cay became her chief residence, as it remained for the next forty years. And she made it a comfortable one: she had a private staff of four houseboys, a nurse, a male cook, and several hundred Bahamian workers to maintain the flourishing plants and crops. When guests were in residence in the villa, dinner was served formally at nine o’clock, with the charismatic Joe in a formal naval uniform complete with trousers appearing to dazzling effect as she descended the curved staircase into the dining area. After dinner, drinks (though Joe herself was a teetotaler) and dancing took up some evenings, but card-playing was the leading indoor sport, with onze (a game similar to gin rummy) and poker the favorites. In attendance most of the time was a rotating parade of stunning female guests occasionally accompanied by a male—usually a famous one, such as the Duke of Windsor, who was at that time the governor of the Bahamas. The roster of visiting female celebrities was larger and included at various times the singer Mabel Mercer (regarded by Joe as “a very great lady … [who]had a marvelous voice. She was very proper, you know, just the opposite to me”); the actress Gwen Farrar and her current lover Tallulah Bankhead; and the international celebrity Marlene Dietrich (see the photos of Marlene on Whale Cay).

And there hang several tales. While biographers have shaded the story variously, the weight of evidence leads to the conclusion that Tallulah Bankhead and Joe did have a brief affair. But the relationship between Joe and Marlene is more difficult to characterize. That Marlene did sleep with women (including the notorious Mercedes de Acosta), and that she and Joe became for a time close friends, is indisputable. Both women—tough, down-to-earth, and authentic—were something like natural soul-mates. At one point Dietrich even sought Joe’s opinion on which film roles to accept, and the two cruised the Mediterranean for two seasons in the late ’30s aboard Joe’s French fishing yacht, The Arkel. In Maria Riva’s impressive biography of her mother, Marlene Dietrich, she confirms that Joe “was the only one who ever called Dietrich ‘Babe’ and got away with it.” For her part, Joe was unquestionably enamored of the bewitching Dietrich and—possessing a powerful sense of entitlement—she repetitively offered to build Dietrich a dream house in which she would live like a fairy-tale princess. Still, I go with David Bret, one of the more cogent of Dietrich’s biographers, who concludes that although Joe “hoped for more than a platonic relationship,” Marlene and Joe “never became sexual lovers. Marlene was only interested in … [Joe’s] personality, which was said to have been electrifying [and]… took it all in with accustomed humor.”*
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Joe Carstairs sold Whale Cay in 1975 (it quickly fell to seed) and thereafter moved between her houses in Sag Harbor and Naples, Florida, where she died in 1993 at the age of 93. In old age she remained, as one friend, Ellen “Pucky” Violett, told me: “awfully sweet, but old school “—that is, not at all political. “Joe wouldn’t talk about her own history,” another of her friends added, “but she would talk about being gay.” According to Alexandra Stoll, who knew her well, Joe was never “an old lady”; even when she had to hobble around with the aid of two canes, she maintained a boat in Sag Harbor, “a sort of small yacht, and she did everything, unroped everything … [she]remained vigorous, mentally strong.” She also remained “very down-to-earth, and very, very honest, not pretentious or grandiose or sentimental, but sympathetic”—and, above all, “completely comfortable with herself.”
* This description of Joe Carstairs’ racing career relies heavily on a batch of some two dozen contemporary newspaper clippings given to me by Julie S. Sewell, a close friend of Carstairs. She gave me as well an album of extraordinary photographs, several of which adorn these pages. I’m indebted as well to Alex Stoll, who introduced me to Julie Sewell, who provided her own recollections of Carstairs.
† The quotation is from Kate Summerscale’s The Queen of Whale Cay, Viking, 1998, to which I am indebted for many details.
Martin Duberman’s recent books include Andrea Dworkin: The Feminist as Revolutionary and Has the Gay Movement Failed?