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mittens. She had popularized the sport of long-distance walking—regularly striding from Boston to Newport, Rhode Island, a distance of seventy-one miles. As she paced, she was trailed by her chauffeur driving her green Salamanca-bodied 1914 Rolls-Royce Tourer, a thermos and sandwiches on the back seat. She was also followed by a coterie of photographers, who plastered her picture across the newspapers of Boston, Rhode Island, and New York. Equally famous for her equestrian skills, she had won numerous blue ribbons at the National Horse Show. She was one of the first women who switched from sidesaddle to riding astride. Prior to Miss Sears’s time, women competed only in ladies’ classes, riding and even jumping sidesaddle, an absurd feat that, while considered “more ladylike,” was also much more difficult than jumping with both feet planted firmly in the stirrups. In 1958, Miss Sears, the still-handsome woman who’d once been painted by John Singer Sargent, was one of the most formidable doyennes of the horse world.

And Harry de Leyer had done the unthinkable: he had turned down a job working for her, preferring instead to be his own man. And there was nowhere like Piping Rock to show just how difficult it was to be his own man. It is hard to imagine a more closed world, one in which fortunes were more entrenched or traditions more hidebound. The inherited wealth behind Eleo Sears dated back to shipping fortunes and land grants made in the colonial era. The United States was a land of increasing diversity and opportunity, but among the East Coast establishment, there was no sign that change was coming.

But sometimes change doesn’t just come; people need to make it happen. Harry de Leyer was famous for being stubborn. Too stubborn to let a perfectly sound horse go to a glue factory. Too stubborn to take a job working for one of the top horsewomen in America. Too stubborn to accept the fact that he couldn’t ride against anyone he chose to—and to compete on the basis not of birthright but of skill. People might have considered him crazy for turning down a job at Prides Crossing, Eleo Sears’s Massachusetts estate; any rational person would have thought he was nuts to believe that he and his plow horse could compete against horses who had just flown in from Europe in specially equipped equestrian airplanes. Maybe he was nuts. Only time would tell.

Piping Rock was devoted to the concept of amateur sport. In 1913 a New York Times reporter stressed that at Piping Rock, “Any professionals seen were on the outside of the ring.” Amateurs competed for silver trophies only, the reporter noted, adding that the lack of prize money caused “an outpouring of entries from people who competed for the love of the sport.” By the late 1950s, the show had evolved to the point that professionals were allowed to enter, and monetary prizes were awarded. The purses at Piping Rock were generous, attracting the top horses to the yearly event. But the mind-set—that professionals were not on a par with amateurs—continued unabated. “Amateur” was a code word for the privileged class. Like the climbers who claimed victory in the conquest of Mount Everest, hardly mentioning the local Sherpas who climbed along with them and carried their gear, it was the owners and amateur riders who were important at Piping Rock. Pros may have been allowed inside the ring now, but “professional” was still just another name for the hired help.

By 1958, Miss Sears no longer showed, but contented herself as an owner-spectator. Her two horses, Diamant and Ksar d’Esprit (pronounced kiss-AR dess-PREE), fresh from their European triumphs, would be piloted by the two gentlemen stars of the USET who’d posed beside her in the photograph, Bill Steinkraus and Frank Chapot.

In 1958, the press had been abuzz with the exploits of the United States Equestrian Team in Europe over the summer. On July 18, 1958, Hugh Wiley, riding Nautical, had been the first American ever to triumph in the King George V Gold Cup in London—arguably the most prestigious jumping competition in the world. Then,