Anna Roosevelt Cowles (January 18, 1855 – August 25, 1931) was an American socialite. She was the older sister of United States President Theodore Roosevelt and an aunt of Eleanor Roosevelt. Her childhood nickname was Bamie /ˈbæmi/, a derivative of bambina (Italian for "baby girl"), but as an adult, her family began calling her Bye because of her tremendous on-the-go energy ("Hi, Bamie! Bye, Bamie!").
Bye suffered from an unexplained deformity of the spine which was painfully curved and produced a slight hump. At age fifteen, she briefly studied at Les Ruches, a private girls’ school in France headed by Marie Souvestre (who would later teach Bye’s nieces Eleanor and Corinne Roosevelt). Bye made her debut in Philadelphia in 1873. Unmarried through her twenties, Bye minded her younger relatives, including Theodore, whose apartment she set up when he left for Harvard College in 1876. Brother and sister enjoyed a close relationship, and Bye was fond of the woman he married in 1882, Alice Hathaway Lee.
Sister of Theodore Roosevelt helped raise his first child, Alice Lee Roosevelt after her mother's death in 1884.
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 a son, William Jr. (1898–1986), who married Margaret Alwyn Krech (1900–1982) in 1920.
Bye was beset by an increasing deafness, devastating arthritis, the failure of her eyesight, and continued backaches. She died at Oldgate, on August 25, 1931. She is buried at Riverside Cemetery , Farmington, Hartford County, Connecticut, USA.
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