John Singer Sargent and Eleonora Sears are both favorites of mine, and so I was delighted to discover their paths crossed in 1921, when Sargent wrote to Sears asking her if she would sit for a drawing, and she accepted. Ethel Barrymore, the actress, wrote of her friend Eleo, “She has more charm than anybody I ever met and a devastating smile that Sargent caught so marvelously in his drawing of her.”

Sargent had sketched Barrymore as well, and she described the session: “He was delightful, humming around the room while he worked. He would sit down occasionally while in the midst of the drawing and play little snatches on the piano and then come back to his work again.”

Sargent was a great artist and a lucky guy. Eleonora Randolph Sears was a fitting subject and a remarkable person.

She came into the world in 1881, the daughter of a shipping and real estate tycoon. Born into wealth and the highest strata of society, she could pretty much do whatever she wanted to do, and she did a great many things that others felt she should not do.

She rode, bred and trained show horses all her life. She rode in steeplechases. On a bet one winter’s morning in 1912, she drove a four-in-hand coach down Fifth Avenue, shocking the fraternity of coachmen. During a 1912 stay in California, she won a quarter horse race in San Diego and fielded a women’s polo team at the Hotel Del Monte on the Monterey peninsula.

At the Burlingame Country Club, south of San Francisco, she rode out onto the “men only” polo field and asked if she could join in a practice session with the visiting British international team; she was rebuffed, and almost lost her membership because of this outrage. And because she was wearing breeches and riding astride at the time, a local mother’s club passed a stern resolution: “Such unconventional trousers and clothes of the masculine sex are contrary to the hard and fast customs of our ancestors. It is immodest and wholly unbecoming a woman, having a bad effect on the sensibilities of our boys and girls.”

On the water, Miss Sears skippered a yacht that raced Alfred Vanderbilt’s Walthra, and won. She also raced speedboats. In the water, she was the first person of either gender to swim from Bailey’s Beach to First Beach in Newport, Rhode Island, a distance of 41/2 miles.

With two different partners, she won the U. S. women’s doubles tennis championships in 1911, 1915, 1916 and 1917. She won the mixed doubles title in 1916. It is said that she scandalized the crowd every time she rolled up her sleeves to play.

In 1928, at the age of 46, she won the first national women’s squash title. (The first time she ever picked up a squash racquet, in 1918, she beat the “ablest male player in Rye, New York.”)

She was an excellent golfer. She played baseball. She played football (as the fullback). An accomplished skater, she played hockey. She also tried boxing, and was one of New England’s best trap shooters.

She was one of the first women to fly in a plane (in 1910 with pilot Claude Grahame-White) and to race a car. In the summer of 1913, she was summoned to appear in court for driving a “high-power roadster” on the roads of Massachusetts. The police presented the summons at Miss Sears’ home, presumably because they could not catch her on the open road.

One might think, given this recitation of athletic prowess, and her more than 240 sporting trophies, that Miss Sears was a tomboy, or even a tad mannish, but in fact, she was a great beauty and, after dark, every inch the socialite. She was unfailingly popular among the elite of Boston and New York, and frequently topped the Best Dressed list. (In 1909, she was known as “the best-gowned woman in America.”) During a visit to Boston in 1924, the Prince of Wales was so charmed by Sears that he spent most of the night as her dancing partner.

Ethel Barrymore wrote about visiting with Eleo. “In the evenings at Beverly Farms when I had to stay indoors and play the piano for Mr. and Mrs. Sears, Eleo would be on the porch with a beau. I never knew anybody who had so many beaux and such nice ones, but she never married anybody.”

Some have suggested that she preferred the company of women, but one must consider the possibility that she simply never met a man who could keep up.

Along that line, she was known for her walks. Her “customary walk” was from Providence to Boston, a distance of 44 miles, which she covered in about 10 hours. She once walked from Newport to Boston, 73 miles, in 17 hours. During her California visit of 1912, she walked from the Burlingame Country Club to the Hotel Del Monte, 109 miles, in 41 hours. In France, she walked 42 miles from Fontainebleu to the Ritz Bar in Paris in about 8 hours. In 1934, in her fifties, she walked 35 miles to call on one friend, and 23 miles to call on another.

In a memoir of his boyhood, The Worcester Account, writer S.N. Behrman included a chapter entitled “My Romance with Eleonora Sears.” He wrote about clipping newspaper photos of her when he was a boy, and identifying with her as one who walked long distances. (In Behrman’s case, it was to save trolley fare.) Then, years later, he was suddenly invited to tea at her home by a mutual friend. He accepted, and wrote of meeting her for the first and last time:

“I found myself in Miss Sears’ drawing room, and there she was coming toward me to greet me. Her pedestrianism, as she crossed the room, met all my expectations; it was still elastic and lively. She was slim, tweedy, and, although her hair was gray, the whole impression she conveyed was youthful. Her eyes were very blue and very clear. She said that she was glad to see me. I told her at once that during my childhood in Worcester I had been, like her, a pedestrian. Miss Sears mistook, somehow, a past avocation for a present one.

“‘What was your last walk?’ she asked, without beating around the bush.

“I had just come from the Pacific Coast. I don’t know what made me say it, unless I thought it would make Miss Sears smile. ‘Los Angeles to San Francisco,’ I told her.

“‘I’ve done it,’ said Miss Sears crisply. ‘How long did it take you?’”

I have suggested that no man could keep up with her, but there was an exception. Usually when she walked, she was followed by her chauffeur, who drove along behind with a thermos and sandwiches.

Eleonora Sears died in 1968. She could have lived a life of pampered indolence, but she would have none of it. She blazed a trail for women in sports; she epitomized the spirit of independence.

John Singer Sargent’s sketch of Eleo, charcoal on paperboard, survives her. In 2005, it sold at auction for $96,000. What a steal.