Groundbreaking Women in the Guestbook: Eleonora Randolph Sears

Since receiving the amazing gift of an original Staatsburgh guestbook in 2017, the site has been researching all of the people who signed its pages. The guestbook covers the years 1899-1908 and includes approximately 150 individuals who visited Staatsburgh. There are many different people who signed the guestbook including relatives, friends, and neighbors of the Mills family as well as politicians, businessmen, sportsmen & women, and even the President’s daughter! This essay will look at one of the remarkable and barrier breaking women who signed the guestbook, Eleonora Randolph Sears (1881-1968).

Eleonora Randolph Sears, circa 1901, Bain News Service

Cover of Staatsburgh's guestbook dating from 1899-1908

Born in 1881 in Boston, Eleonora (known as Eleo) came from a family full of well-known historic figures that were significant during her lifetime and are still remembered today. The family’s most impressive claim to fame was their descent from President Thomas Jefferson who was Eleonora’s great-great-great grandfather. One of her cousins was Colonel Robert Gould Shaw (1837-1863), who famously led the all-Black 54th Massachusetts Regiment during the Civil War. Another cousin was the politician and senator Henry Cabot Lodge (1850-1924). Her paternal uncle, Richard “Dick”Sears, was a champion tennis player who won the US National Tennis Championships in men’s singles the first seven years they were held.

(l-r) Thomas Jefferson, Col. Robert Gould Shaw, Richard Sears

By the time that Eleonora was born in 1881 to parents Frederick Sears and Eleonora “Nora” Coolidge, both sides of her family boasted wealth and privilege.  Her maternal grandfather, Thomas Jefferson Coolidge was named the minster to France in 1893 replacing Whitelaw Reid who had stepped down to run for Vice President on President Benjamin Harrison’s re-election ticket.  Whitelaw Reid was connected to the Mills family via his wife, the former Elizabeth Mills, who was the sister of Ogden Mills.  When Coolidge moved to France, he brought his daughter’s entire family with him including Eleo.  Her youth was full of travel, culture, and school lessons from the same French governess that previously worked with Consuelo Vanderbilt.

Thomas Jefferson Coolidge, circa 1889-1890, photo by Matthew Brady, Library of Congress

Like Ruth Mills, Eleo had both money and pedigree. However, unlike Ruth, Eleo had less interest in following societal norms and entertaining guests. Eleo was part of a new generation of women looking to live outside the roles society had prescribed for her. She was just two years older than the Mills twins so it is possible that her visit to Staatsburgh was due to a connection with Beatrice or Gladys. Similar to Eleo, Gladys Mills was also active in several sports. Eleo signed the guestbook one time on the weekend of November 3-5, 1906, which appears to have been a weekend house party since she was one of 14 signatures that weekend. One of the other names who signed that weekend was Harold S. Vanderbilt, son of Alva & William K. Vanderbilt and rumored paramour of Eleo, but more on that later.

The Ann Arbor News, October 15, 1909

Despite Eleo's Boston Brahmin family and her illustrious ancestry, she was a woman who broke the mold and broke free from the traditional expectations of the way women were supposed to behave. Eleo was an accomplished athlete who was very skilled and found success in many sports including polo, tennis, squash, skating, golf, and horseback riding. She also raced cars and flew in airplanes. Because she came from a privileged background, she had the means to ride horses every day and the abundance of leisure time to devote to practicing sports.

Eleonora Sears on horseback wearing pants and riding astride, Library of Congress

When opportunities for women in sport did not exist, she worked to create them. Eleo rode astride (not sidesaddle) and wore pants while playing polo, which was traditionally a game for men. She helped develop polo leagues for women so that women had an avenue to play since she had previously ruffled feathers by trying to play with the men. In 1912, at the Burlingame Country Club near San Francisco, she rode onto the “men’s only” polo field and asked to practice with the visiting British team. She was denied and was nearly banned from the club. A local mother’s club spoke out against her and her choice to ride astride and wear pants as immodest and unbecoming of a women.

The San Francisco Call & Post, April 7, 1912

At the end of her life, and also posthumously, she was inducted into the International Women’s Sports Hall of Fame as well as the Hall of Fame for tennis, squash, and show jumping. She was a very skilled tennis player who won five doubles national championship titles and played in countless tournaments. She was inducted into the International Tennis Hall of Fame in 1968. Many considered her the founding matriarch of US Squash and she helped organize some of the founding tournaments for women. She was the National Champion in 1928 and later inducted in the Squash Hall of Fame. Eleo’s competitive success and skill on a horse was also recognized posthumously when she was inducted to the US Show Jumping Hall of Fame in 1992.

Eleonora Sears on the court, year unknown, Library of Congress

Eleo wearing pants with a horse, circa 1915, Library of Congress

Another one of Eleo’s remarkable interests was taking long walks and hikes.  She gained media attention for often walking between cities such as Providence and Boston and Newport and Boston.  In California she walked from the Burlingame Country Club to the Hotel Del Monte, which was 109 miles and it took her 41 hours.  Even though completing these long-distance walks is quite a feat of perseverance and endurance, she did not do it without some assistance.  Her chauffeur followed her in order to provide water and nourishment when needed.

Holyoke Daily Transcript & Telegram, June 12, 1933

Eleo never married or had children, and while there have been various opinions about her relationships, the truth remains hers alone.  Yet there is no disputing the fact that she left the bulk of her estate to a woman who was her close companion at the end of her life.  However, earlier in her life, she attended events and was a frequent companion of Harold S. Vanderbilt for many years.  She even got a speeding ticket for driving his car too fast.  He was cited many times for speeding, so it seems they had a similar love for fast cars.  Newspapers frequently reported their engagement throughout the years, especially countless times between 1909-1914, but they were never officially engaged.  He eventually married Gertrude Conaway in 1933 when he was nearly 50 years old.

The Salt Lake Tribune, August 27, 1911

Democrat & Chronicle, July 20, 1914

Many of the women Eleo spent time with did have documented relationships with other women, but during Eleo’s lifetime same-sex relationships were usually spoken about only in whispered tones. While these relationships were often well known and understood by family and friends, they were usually not documented in a way that would be part of the historical record today. The newspapers would not have reported Eleo’s potential paramours as anything other than friends. We also cannot know exactly how Eleo identified herself or if she placed a label on her own sexuality. Eleo was friends with many women including Isadora Duncan, Mercedes de Acosta, Tallulah Bankhead, Greta Garbo, Marlene Dietrich, and Eleanor Roosevelt. She had relationships with each of them whether it was platonic or romantic.  The photo below shows Sears watching a tennis match with Isabel Pell(1900-1951) in the 1920s. Pell had several relationships with women and was even exiled from New York after a public affair with a soprano at the Metropolitan Opera. Eleo and Isabel often went out together wearing similar outfits, but their relationship was not long lived.

Isabel Pell & Eleo Sears at a tennis match, circa 1930s

At the very end of her life, Eleo became very close with “Madame” Marie Gendron (1903-2004). Gendron was French and hired through an employment agency to replace Eleo’s personal maid and confidante after her retirement. Newspapers referred to Gendron both as Eleo’s employee and close friend, but a biography entitled Pride’s Crossing: The Unbridled Life and Impatient Times of Eleonora Randolph Sears by Peggy Miller Franck reveals something very different.  Franck was the daughter of Eleo’s business advisor and racing stable manager and her close view into aspects of Eleo’s life led her to write the book.  Franck paints Gendron as an opportunist who took advantage of Eleonora by isolating her from her friends and relatives and eventually taking control of her finances.  The two went to live in Palm Beach and Gendron ultimately become her power of attorney three years before Eleo’s death in 1968.  Sears also changed her will shortly before her death leaving the bulk of the estate to Gendron.  The change scrapped a foundation that Sears planned to create as well as large donations to several hospitals.  The will was strongly contested and Gendron was accused of influencing Sears when she was not of sound mind or body.  In the end, Gendron received half of the estate and the hospitals the other half.  We will never know how Eleo and Marie truly felt about each other, or how they personally defined their relationship, but Eleonora’s last years were spent with her.

The Cleveland Press, February 21, 1969

Despite the fight over her estate, Eleonora Sears was much more than her money, homes, and horses.  Even though she was born into wealth and lived a life of privilege, her athletic accomplishments were unparalleled.  She excelled in many, many sports, and paved the way for future women to succeed with increased sporting opportunities.  Originally from Boston, Eleonora spent much of her time at her country home north of the city called Rock Edge because it was located right on the ocean.  The mansion was located in Beverly, MA in a neighborhood called Prides Crossing.  It was a fitting name for the home of a woman who we recognize during Pride Month for breaking barriers, pushing boundaries and serving as an example of excellence to all women in sport.

Charcoal Sketch of Eleonora Sears by John Singer Sargent, 1921, Private Collection

For further reading about Eleonora Randolph Sears:

Peggy Miller Franck, Pride’s Crossing: The Unbridled Life and Impatient Times of Eleonora Randolph Sears, Commonwealth Editions: Boston, 2009.

OutSmart Magazine