Bamie Roosevelt

Anna Roosevelt Cowles was born on January 18, 1855, in New York City, at the family's residence located at 28 East 20th Street. She was the oldest child of Theodore Roosevelt, a businessman and philanthropist, and Martha Stewart Bulloch, a socialite. Her siblings included Theodore Roosevelt Jr., Elliott Roosevelt, and Corinne Roosevelt.

During her childhood, Anna was known by the nickname "Bamie," a diminutive of the Italian word "bambina," meaning "baby girl." As she grew older, her family also referred to her as "Bye" due to her energetic nature. She experienced health issues in childhood, possibly polio or Pott's disease, which resulted in partial disability and the use of corrective steel braces.

Her education details are not extensively documented, but her intelligence and energy were noted by family members and biographers. Her niece, Eleanor Roosevelt, described her as possessing an "able man's mind." While not traditionally considered physically attractive compared to her mother or sisters-in-law, she was recognized for her intellectual abilities and her magnetic personality.

Following the death of her father in 1878 and her mother's passing in 1884, Anna assumed increased responsibilities within the Roosevelt household. She played a central role in managing household affairs, especially as her mother was often preoccupied with social obligations and health issues.

After the early death of Theodore Roosevelt’s first wife, Alice Hathaway Lee, in childbirth, Anna took custody of their daughter, Alice Lee Roosevelt, providing her with care and guidance during her formative years. Anna’s influence on Alice Lee was significant; Alice later recalled her aunt as an influential figure in her life.

Anna Roosevelt Cowles also served as a guardian and caretaker for Eleanor Roosevelt. Following her aunt's death of diphtheria, Anna considered but did not pursue legal custody of Eleanor’s siblings due to family and legal considerations. Nevertheless, she opened her home to Eleanor and facilitated her educational placement at Allenswood School in England, which contributed to Eleanor's social and emotional development. Despite occasional tensions, Anna and Eleanor maintained a relationship with moments of closeness and rivalry.

In 1895, Anna Roosevelt married William Sheffield Cowles, a United States Navy Lieutenant Commander, who later became a Rear Admiral. She was 40 years old at the time of marriage; William Cowles was born in 1846 and died in 1923. They had one son, William Sheffield Cowles Jr., born in 1898, who married Margaret Alwyn Krech in 1920.

Throughout her life, Anna Roosevelt Cowles maintained a close relationship with her brother Theodore Roosevelt, often serving as his confidante. During Theodore Roosevelt’s presidency, her home at 18th and I Streets in Washington served as a semi-official venue for political discussions, earning it the nickname "the other White House."

In her later years, Anna Roosevelt Cowles engaged in family conflicts, notably criticizing Eleanor Roosevelt during her campaign against Theodore Roosevelt III, her nephew. Despite familial disagreements, Eleanor Roosevelt expressed admiration for her aunt’s advice on handling criticism.

Anna Roosevelt Cowles died on August 25, 1931, in Farmington, Connecticut, at the age of 76.