TR’s Sister Anna Roosevelt Cowles

Anna Roosevelt Cowles (1855-1931) was closer to Theodore Roosevelt than anyone.  And he respected her more than anyone.

  Anna Roosevelt:  A First-Born Syndrome


Anna Roosevelt Cowles was Theodore Roosevelt’s older sister, and a remarkable woman in her own right. Despite physical infirmity, she maintained a fashionable political salon in Washington.

Anna Roosevelt, nicknamed “Bamie” was the eldest of four remarkable Roosevelt children born to Theodore (Sr.) and his wife Martha Bulloch.

Afflicted in early childhood with an illness that affected her spinal cord, she would wear a metal brace throughout her youth, and her physical growth would become one of obvious deformity.   Despite her health issues, Bamie had the oversized Rooseveltian intelligence, personality and energy that so marked her younger brother – himself a sickly asthmatic child.

It would be easy to claim that Bamie was prematurely mature: middle-aged from the time she was a child, and obviously destined to remain single.  There would never be a family crisis, when she wasn’t summoned to provide her uncommon common sense, leadership, and active assistance. She would become the dependable go-to person that her siblings, and even the second generation would rely on for the rest of her life

Home-schooled through the early years, then broadly educated at the Allenswood School in Paris and London, she had a fine and receptive mind, despite her frail body .  Her upbringing would provide the foundation for becoming one of the best known salon hostesses in high governmental circles.  She kept the aches and pains of her physical shortcomings it to herself and presented an image to the world at large that far surpassed any handicaps.  She would always have many friends and admirers.

Alice’s “Auntie Bye

On February 14, 1884, Theodore Roosevelt endured the most tragic day of his life.  His mother died of typhoid fever.  In another room of the same house, Alice Lee, his young wife of only three years, died having given birth the previous day.

The twenty-five year old new father was overwhelmed with grief, incapable of caring for an infant daughter, name Alice for her deceased mother.  Instead, TR entrusted the baby’s care to his older sister, who was delighted to be foster-mother.  Alice would live with Auntie Bye (her siblings called her “Bamie;” the second generation called her “Bye”) until she was three, but the bond between them would be lifelong.

baby lee roosevelt

“Baby Lee” as Alice Roosevelt was called, was raised by “Auntie Bye” for the first three years of her life. They would always remain close.

Three years later, Theodore Roosevelt married Edith Carow, a childhood friend of the family.  TR had decided to have Bamie formally adopt “Baby Lee” as he called her, but Edith would not hear of it.  She is reported to have said, “She is your daughter, and now she will our daughter, and sister to whatever children we have.”  “Baby Lee” would now be called “Sister” in the family circle, and would prove to be a fine one to the five more Roosevelts who came along.

Alice Roosevelt had inherited her late mother’s good looks and her father’s rambunctious temperament.  Even as a child, she was a handful.  With Edith occupied with five more rambunctious Roosevelts, if Alice became too difficult, she would be packed off to Auntie Bye, who could balance both love and discipline.  She would also receive a subliminal education in sophistication and style that she would perfect in her mature years.  As a teenager, Alice packed herself off periodically.  She did not have to vie for attention with Auntie Bye.

Eleanor’s Auntie Bye

Alice was undoubtedly the niece nearest to Anna Roosevelt’s heart, but Eleanor Roosevelt was the niece who truly needed an Auntie the most.  She was the daughter of Theodore’s younger brother Elliott, whose alcoholism and morphine addition led to his early death when Eleanor was ten.

Eleanor’s mother, the beautiful Anna Hall, died of diphtheria when Eleanor was eight.  Thereafter she was raised by her somewhat eccentric Grandmother Hall and an assortment of equally dotty Hall aunts and uncles.

Auntie Bye would have her visit from time to time, as would Uncle Theodore.  Eleanor did not inherit her mother’s beauty, and was painfully shy and awkward, with none of the graces and verve of her cousin Alice, even though they were born only months apart.  The glitter of her aunt’s hosting and social skills did not make an impression.

young eleanor

At Auntie Bye’s suggestion, orphaned Eleanor Roosevelt was sent to the Allenswood School in London when she was in her mid-teens. It was a seminal experience for the young woman.

Perhaps the most important contribution Anna Roosevelt Cowles made to Eleanor’s life however, was the recommendation that she attend the Allenswood School – the same one she had attended – and run by the same redoubtable Mlle. Souvestre.  The English school was an awakening for the lonely and affection-starved Eleanor, and would be a seminal experience of her youth.

Mrs. Anna Roosevelt Cowles:  Hostess and Presidential Confidante

Anna Roosevelt was forty when she surprised herself (and everyone else) by falling in love and marrying Lt. Commander William Sheffield Cowles.   Two years later, she surprised everyone even further by having a baby.

The couple moved to Washington, DC, and their townhouse became a center for the movers and shaker of political life.  Her brother Theodore had emerged on the national scene, first as a Civil Service Commissioner, and later as Assistant Secretary of the Navy.  Mrs. Cowles was happy to open her home to her brother for both socializing and private conversation.

When TR was named Vice President under William McKinley in 1900, his sister’s house became his pied-a-terre, since The Vice Presidency did not warrant a physical move to the capital.  Six months later Theodore Roosevelt became President following McKinley’s assassination.   By virtue of her close kinship to the President as well as her formidable social skills, Anna Roosevelt Cowles was acknowledged as the premier hostess whose elegant “small table” was a mecca for the highest levels of political society.

Anna Cowles: The Later Years

Despite her infirmities, Anna Cowles lived to be past seventy-five, outliving her brother Theodore by more than a decade.  Arthritis further crippled her weakened bones.  She developed cataracts and severe hearing loss.  Nevertheless, her remarkable intellect, her buoyant spirit and unflagging energies remained.

In her advanced age she was faced with divisive family ties between the Republican Theodore Roosevelt side of the family (including Alice) and the up-and-coming Democrat side, headed by Franklin Delano Roosevelt, who had married his fifth cousin, Eleanor.

It would be Alice Roosevelt Longworth who would inherit her aunt’s mantle as Washington premier power broker.  Eleanor, of course, would emerge as First Lady and a political powerhouse in her own right.




·         Caroli, Betty Boyd – The Roosevelt Women – Basic Books, 1998

·         Cordery, Stacy A. – Alice Roosevelt Longworth – Viking, 2007

About Feather Schwartz Foster

Feather Schwartz Foster is an author-historian who has made more than 500 appearances discussing presidential history. She teaches adult education at the Christopher Wren Association (affiliated with William and; Mary College), and adult Education programs at Christopher Newport University. She has been a guest on the C-SPAN "First Ladies" program. She has written five books.
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5 Responses to TR’s Sister Anna Roosevelt Cowles

  1. nerdtrips says:

    I appreciate that you called Theodore Roosevelt “TR.” When we visited his birthplace, the rangers were insistent that he did not like the nickname “Teddy.”

  2. energywriter says:

    Another top-notch story. Those Roosevelt women were made of tough stuff. sd

  3. Marilyn Greene says:

    Thank you for your article! I am curious if you have any information about Bamie’s actual date of birth. I most often see the date of January 18th, 1855, as being her birthday. However, in both The Roosevelt Women, 1998, (page 37) and Theodore Roosevelt: Volume I – The Formative Years, 1958 by Carleton Putnam (page 21), the date of birth is given as January 7th, 1855. Why the discrepancy?

  4. K says:

    ER wrote in her autobiography that she absolutely was affected by and impressed with Bye’s hostess and social skills.

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