Anna Roosevelt Cowles (1855-1931) was Theodore Roosevelt’s elder sister. Born in the family’s brownstone at 28 East 20th Street in New York City, she was always known as Bye or Bamie. Independent, intelligent, and hardworking, her mother, Martha Bulloch Roosevelt, and father, Theodore Roosevelt, Sr., both depended upon her. To her siblings, Theodore, Elliott, and Corinne, her maturity made her seem like one of the grown-ups when they were all young.
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.
Theodore Roosevelt, Sr., passed away in 1878, and both Martha and Alice died in February 1884. Bye oversaw the disposition of her parents’ estate and took in her grieving brother’s infant daughter. She and the baby, also named Alice, lived very happily together in her home in New York City. She supervised the building of Sagamore Hill. When Theodore married Edith Kermit Carow in 1886, Alice went to live with the newlyweds. Bye, crushed and saddened at the loss, traveled, up and down the East Coast, to Europe, and to California by way of Medora, North Dakota, to see her brother’s Elkhorn Ranch.
In 1893, Bye served on the New York State Women’s Board, assisting with the Women’s Building at the Columbian Exposition in Chicago. Then family duties summoned her again, and she went to England to care for the children of a distant relative, widower James Roosevelt Roosevelt. There she made many friends and fell in love with U.S. naval attaché, Lt. Cmdr. William Sheffield Cowles. They wed in London in November 1895. Two years later, they returned to the United States to live. In October 1898, Bye gave birth to the Cowles’ only child, named for his father but known as Sheffield.
Cowles worked for the U.S. War Department, and the family moved to Washington, D.C. Bye had always been a staunch supporter of Theodore’s political career. In 1901, when he became president of the U.S. after William McKinley’s assassination, Bye’s home became an important second White House for Roosevelt. He met his Cabinet there initially, as Mrs. McKinley had not yet moved out of the executive mansion. At Bye’s he could entertain friends and associates whose moral standards did not meet the new First Lady’s approval. The Cowles home was a private retreat for Theodore Roosevelt where he regularly sought the advice of his sister. Occasionally, Bye helped Edith with White House entertaining. Her own large circle of friends had entrée to presidential entertainments because of her.
When Theodore Roosevelt left the presidency and Will Cowles retired from the Navy, the Cowles family moved to Oldgate, their home in Connecticut. Sheffield graduated from Yale University and married Margaret A. Krech in 1921. Bye was beset by an increasing deafness, devastating arthritis, the failure of her eyesight, and continued backaches. Will’s health declined as well, and he died in 1923. Despite her sorrow and her physical pain, Bye remained at the center of a large circle of family and friends. She died at Oldgate, on August 25, 1931.