Anna Roosevelt Cowles (January 18, 1855 – August 25, 1931) was the older sister of United States President Theodore Roosevelt and the aunt of Eleanor Roosevelt. Her childhood nickname was Bamie, a derivative of bambina, but as an adult, her family began calling her "Bye" because of her tremendous on-the-go energy - (Hi Bamie, bye Bamie). Throughout the life of her brother, Theodore, she remained a constant source of emotional support and practical advice. On the child-bed death of her brother Theodore's young wife Alice, Bamie took custody of the child, assuming parental responsibility for TR's first daughter, Alice Lee Roosevelt.
Anna was born in a brownstone home at 28 East 20th Street in New York City on January 18, 1855. Her parents were Martha and Theodore Roosevelt. Her other siblings were Elliott Roosevelt and Corinne Roosevelt. Anna was afflicted by a spinal ailment that led to her being partially crippled and confined by corrective steel braces as a child.
TR's daughter, Alice Roosevelt Longworth, once remarked that had Bamie, with her incredible intelligence and energy, been born a 19th Century man, without the social restrictions that the era placed on women, she would have been president instead of her brother. Bamie's niece, Eleanor Roosevelt, stated in her autobiography that Bamie had "an able man's mind." Although she was not a stunningly gorgeous woman like her mother, Mittie or her sisters-in-law, her natural intelligence and energy was magnetic to both men and women. She remained an emotional pillar of strength for all the Roosevelts.
Because Bamie's mother, Mittie, was often distracted by illness or by her grand social life, Bamie increasingly took a central role in running the Roosevelt household, particularly after the premature death of her father, Theodore Roosevelt, Sr. In fact, TR's first daughter, Alice, remarked that Bamie almost seemed to be born into middle age, so significant were the adult responsibilities put into her hands from childhood. Unlike many children in a similar situation, Bamie had the natural maturity, judgement and wisdom to "hold the family together," Alice said.
When TR's first wife, Alice, died suddenly following childbirth, most probably of kidney failure (Bright's Disease), Bamie took custody of her infant, Alice. Because her grieving father would not call her by his late wife's name, Alice was called "Baby Lee" for her mother's family, the Lees of Boston. Alice would say of Bamie that she was the most influential person in her entire life. When the young and vivacious Alice became more than her stepmother, Edith Roosevelt, or her father could handle, they would send her up to Auntie Bye for a dose of discipline and to give her the structure that the Roosevelts in the White House were not able to exert.
Bamie's other sister-in-law, Anna Roosevelt, wife of Elliott, had wished for Bamie to have custody of her children Eleanor, Elliott Jr. and Hall upon her death. She was separated from her husband, and died young of diphtheria. Custody of the children was not immediately possible because Elliott was still alive—though exiled by the family because of his alcoholism—and could not be bypassed in the event of litigation. Bamie considered a custody suit but realized that Mary Hall, Eleanor's maternal grandmother would not be willing to give the children into Bamie's care. She did open her home to Eleanor, who was a welcome visitor and made extended stays. Bamie was successful, though, in getting Eleanor out of the oppressive and harrowing home situation by demanding that she be sent to Allenswood school for girls in England where Eleanor developed socially and emotionally. During Eleanor and Alice's childhood, Bamie kept them informed of each other's activities, helping to maintain something of a relationship between the two, though it was a vexing relationship, ranging from sometimes being very close and often a bitter and competitive relationship. She was close to both girls and contributed greatly to their development.
Throughout his life, Bamie's brother Theodore often turned to her for counsel in letters and personal conversations. In fact, it was said by their niece Eleanor that TR made few important significant political decisions and even fewer personal decisions without getting the input of his sister. She remained a trusted confidante for his entire career. As president, he would walk down to her residence at 18th and I in Washington so often that Bamie's house was sometimes called the "other White House." As she became more infirm, TR turned more and more to his daughter, Alice, for advice and to act as a go-between in delicate political situations.
In 1895 at age 40, Anna Roosevelt married US Navy Lt. Commander (later Rear Admiral) William Sheffield Cowles (1846—1923), a divorcé who was 49. They had one child, William Sheffield Cowles, Jr. (1898 - 1986), who married Margaret Alwyn Krech (1900 - 1982) in 1920.
When her niece Eleanor Roosevelt campaigned against Eleanor's first cousin and Bamie's nephew Theodore Roosevelt, Jr., she publicly broke with her niece after the ordeal. In a letter to her son, Bamie wrote of Eleanor:
Bamie's niece and TR's daughter, Alice Roosevelt Longworth, also broke with Eleanor over this highly distasteful (to Theodore's family) political activity that included Eleanor riding up to Ted, Jr's speaking engagements with a teapot on her car to remind voters of Ted's supposed (but later disproved) connections to the Teapot Dome Scandal. Eleanor dismissed Bamie's criticisms by referring to her as an "aged woman." Despite all these intra-family discords, long after Bamie's death, Alice and Eleanor would later reconcile after Eleanor wrote Alice a comforting letter upon the death of Alice's daughter, Paulina Longworth.
Bamie and her niece, Eleanor Roosevelt, eventually reconciled, and in an article in the Ladies Home Journal, "How to Take Criticism," Eleanor referred to her aunt Bamie, saying, "I can honestly say that I hate no one, and perhaps the best advice I can give to anyone who suffers from criticism and yet must be in the public eye, would be contained in the words of my aunt, Mrs. William Sheffield Cowles. She was President Theodore Roosevelt's sister and the aunt to whom many of the young people in the family went for advice. I had asked her whether I should do something which at that time would have caused a great deal of criticism, and her answer was: "Do not be bothered by what people say as long as you are sure that you are doing what seems right to you, but be sure that you face yourself honestly." 
Alice and Eleanor's warmest link to their fathers' generation died on the night of August 25, 1931, aged 76. Her last words, "Never mind, it's all right," were reportedly spoken to her friend Sara Roosevelt, Franklin Delano Roosevelt's mother, before Bamie slipped into a coma and died.