Eleonora Sears, Brahmin Bad Girl on the Tennis Courts (and Polo Field and Squash Court…)

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Eleonora Sears pioneered women’s sports in the way only a Boston blueblood could. When she took up long-distance walking from Boston to Newport, R.I., her chauffeur followed at a discreet distance with a thermos and sandwiches.

Eleonora Sears was a model of social decorum in the mansions of the rich. On the athletic field, however, she shattered the rules during the first half of the 20^th century. She rode horses in pants, crashed men-only squash courts and shocked tennis spectators by playing in rolled-up sleeves. During her lifetime, she accumulated 240 trophies.

She succeeded in sports when it wasn’t thought important for women to succeed.  “Sports were never seen as a proving ground for women, but Eleo made it a proving ground,” said her biographer, Peggy Miller Franck.

Multi-Champion

When Eleonora Sears died in 1968 at the age of 86, Boston Globe sportswriter Victor Jones wrote, she ‘was probably the most versatile performer that sports has ever produced — not just the most versatile female performer, but the most versatile, period.’

She was a four-time national tennis champion, the first women’s squash champion and an accomplished horsewoman who in 1909 became the first woman to ride a horse in a major polo match.

She played 19 sports, including tennis, ice skating, horseback riding, yacht racing, rifle shooting, boxing and football.

Off the field she walked, often commuting the 20 miles from her Beacon Hill home to her summer home in Prides Crossing, Mass. In her 50s walked the 42 miles from Fontainebleu to the Ritz Bar in Paris.

She also was one of the first women to race a car, to fight a speeding ticket and to fly an airplane.

Eleonora Sears, Brahmin

Eleonora Sears was a wealthy Boston Brahmin, born on Sept. 28, 1881, the second child and only daughter of Boston real estate and shipping tycoon Frederick Richard Sears and Eleonora Randolph Coolidge Sears.  Her ancestors included Thomas Jefferson (her great-great-grandfather), John Winthrop and Massachusetts Gov. James Sullivan. She was Henry Cabot Lodge’s cousin.

“I began exercising the first time I fell out of my crib,” she said, according to her obituary in the New York Times.

She divided her time between tony Pride’s Crossing in Beverly, Mass., and Palm Beach. Along the way, she used her wealth and social standing to break down barriers for women who lacked that silver spoon at birth.

Her father introduced her to tennis. He was one of the first to play the game in America, with Dr. James Dwight in Nahant, Mass., in 1874. Her uncle Richard Sears was the first U.S. national tennis champion, winning seven straight championships from 1881 to 1887.

Eleonora played tennis with the Astors and befriended the Roosevelts. She sat for a sketch by John Singer Sargent, at his request. “She looked fine in evening clothes, and didn’t look out of place behind a silver tea service,” wrote Jones.

Known as Eleo, she made the best-dressed women’s lists during the early 20th century. “It isn’t my ambition to be the best dressed women in Boston,” she said. “I think that interest in clothes should be perfectly casual.”

Pants and Cigarettes

She attended society balls, weddings and debuts, but she occasionally broke the rules of her social class even off the field. In 1910, she smoked in the lobby of Boston’s Copley Square Hotel because men were allowed to and women weren’t. Police arrested her.

In 1911, newspapers reported her engagement to Harold S. Vanderbilt, and in 1924 she made news by dancing with the Prince of Wales. But she never married and her contemporaries assumed she was gay.

“Her sexual orientation certainly formed her character, and gave her the drive,” Franck told the Windy City Times. “She was tremendously courageous in the way that she was willing to challenge, in a very public way, the very narrow role that woman had.

Her aggressive style of play made her a fan favorite on the tennis courts. She won the U.S. national doubles title four times between 1911 and 1917, and the national mixed doubles championship in 1916.

In 1909, Eleonora shocked people by riding onto the Burlingame Country Club’s polo field wearing pants. Ministers delivered sermons against her wardrobe choice. The California Mother’s Club condemned her as immodest and unbecoming. “Such unconventional trousers and clothes of the masculine sex are contrary to the hard and fast customs of our ancestors,“ the club said in a statement.

Mother of Squash

Eleonora Sears broke through the Harvard Club’s ban on women, and by 1918 she was playing men on its squash courts. She excelled at the game and brought many women into it as president of the U.S. Women’s Squash Racquets Association. She was known as the ‘Mother of Squash.’

As a girl she loved horses, and she bred and rode them until she died. She displayed saddle horses, rode in jumping events, drove harness horses, rode to hounds — and even helped pay for the Boston Police Department’s mounted police unit.

She rode in steeplechases and once, on a bet in 1912, drove a carriage pulled by four horses down Fifth Avenue in New York. That same year she won a quarter horse race in San Diego.

Land and Sea

She also raced yachts and speedboats, and swam the 4-1/2 miles from Bailey’s Beach to First Beach in Newport, R.I. — the first to do so.

Her habit of long-distance walking came from her father. In 1925, she walked the 47 miles from Boston to Providence in 9 hours and 53 minutes. At the age of 46, she competed against Olympic marathoner Bill Agee in a walk from Laurel, Md., to Baltimore. She also once walked the 73 miles from Newport to Boston in 17 hours.

Eleonora Sears died on March 16, 1968 at age 86, four years before the enactment of Title IX, which prohibited discrimination against women in school sports. She was inducted into the Tennis Hall of Fame, the Show Jumping Hall of Fame, the International Women’s Sports Hall of Fame and the United States Squash Hall of Fame.

This story about Eleonora Sears was updated in 2022.