Anna “Bamie” Roosevelt Cowles was born on January 18, 1855. She was the oldest child of Theodore and Martha “Mittie” Bulloch Roosevelt, and sister to Theodore Roosevelt.
Anna went by many names including “Bamie” (short for bambina) given to her by her mother, and Bye which she was called by her siblings and many nieces and nephews. As a young woman, Anna dutifully helped her parents entertain and was a role model for her family, even though she was only four years older than her closest sibling Theodore. She was classified as an adult in her siblings’ eyes and in his childhood diary Theodore wrote, “when I put ‘big people’ I mean Papa Mama and Bamie.” Anna suffered from a spine condition which limited her physically, but she had a quick wit and welcoming personality. In her youth, she attended Marie Souvestre’s school in France and then tutored her siblings in French. As an adult, she continued to entertain in the Roosevelt house and acted as a confidante for her siblings, especially for Theodore.
Throughout her entire life, Anna provided support to her family. Beginning in 1878, when her father died, she took on many of his roles. She traveled with her mother and entertained in their house. She also wrote letters to her siblings advising them when they faced hardships.
In 1884, when Theodore’s first wife, Alice Hathaway Lee passed away, Anna managed his Sagamore Hill estate and raised his baby daughter Alice while he tended to his ranch in the Dakota Territory. Anna oversaw the construction of Sagamore Hill as well as furnished the home. After Theodore remarried Edith Carow in 1886, Alice was placed in their care, but Anna and Alice stayed close. Since Anna had shared a special bond with her own father, she wanted the same for Alice, even though it broke her heart to be away from her.
Anna also supported her cousin James Roosevelt “Rosy” Roosevelt. When James’ first wife Helen Astor died in 1893 Anna moved to London, where James was living, to take care of him and his two teenaged children. During her stay with James, she met Rear Admiral William Cowles and they were married in 1895. Together, they had one son, Sheffield. Yet, even with her own family, Anna remained a mainstay in the lives of her siblings, nieces, and nephews. In Alice Lee Roosevelt Longworth’s later years, she called Anna, “her greatest influence.”
Throughout Theodore’s career and especially during his White House years, Anna entertained highly respected residents of Washington D.C. on her brother’s behalf in her own home in the capitol city. During this time her home was considered “the other White House” as it was used often for special meetings and parties. In 1904, Anna advised him when two battleships, Illinois and Missouri collided. Wanting another opinion on the situation, Theodore asked Anna to look over the reports and share her thoughts. She wrote him back saying that the decisions made in the reports were rational and suggested to proceed as usual. Considering Anna’s diplomatic personality and efficiency, Alice Roosevelt Longworth once said, “If Auntie Bye [Anna] had been a man, she would have been president.”
Anna Roosevelt Cowles was an incredibly smart, supportive, and welcoming woman. Her entire life she had been devoted and dedicated to helping her family, and many of her accomplishments are seen in her family’s successes.
She died on August 25, 1931 in Farmington, CT at the age of 76. She is buried at Riverside Cementry in Farmington, CT.