Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles congratulates her brother, Theodore Roosevelt, on the recent birth of a grandchild, and hopes that the news from Roosevelt’s son, Ted Roosevelt and Eleanor Butler Roosevelt, is still good. She appreciated getting Roosevelt’s recent letter, and tells him of the efforts of their joint nephew, Theodore Douglas Robinson, to get into politics. Cowles hopes to be able to visit Roosevelt sometime before winter.

Collection

Library of Congress Manuscript Division

Creation Date

1911-08-20

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles tells her brother, Theodore Roosevelt, about a man who would like to meet him and invite him to the opening of a new library. She greatly enjoyed Roosevelt’s recent visit, and hopes to be able to see him at Sagamore Hill sometime soon. Cowles shares some of her opinions on women’s suffrage with him, remarking that many of the best women she knows are against it.

Collection

Library of Congress Manuscript Division

Creation Date

1911-06-28

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles expresses how much she misses Theodore Roosevelt. Cowles describes a recent drive she took and the different aspects of nature she saw. Cowles mentions a book she has recently read and wants to discuss it with Roosevelt. Cowles informs Roosevelt she reads everything about him, and references his recent “interesting trip.” Cowles mentions Corinne Roosevelt Robinson’s account of Roosevelt during their last encounter with Frances Griscom Parsons, and mentions visiting with Eleanor Butler Roosevelt and Theodore Roosevelt Jr.

Collection

Library of Congress Manuscript Division

Creation Date

1911-05-10

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles regards Theodore Roosevelt’s visit to Hartford, Connecticut, as one of the best Christmas gifts. She is grateful it was on one of her better days when she was “not quite as cripply” and so was really able to enjoy their time together. Everyone else also enjoyed his visit. She is sorry William S. Cowles did not get into the legislature and fears it will be a hard winter since he has no work and she is “not as companionable.”

Collection

Library of Congress Manuscript Division

Creation Date

1910-12-20

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles asks Theodore Roosevelt if he can visit her before or after the dinner in New Haven, Connecticut. Otherwise, she will not see him until spring as traveling is difficult. If she wants to remain at her home during the winter, she must stay mostly inside. Her family is well, and William Sheffield Cowles enjoyed his first Boy Scout meeting. Cowles shares a letter from Caroline Drayton about her loyalty to Roosevelt.

Collection

Library of Congress Manuscript Division

Creation Date

1910-12-06

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Although she feels “horribly selfish” for asking, Anna Roosevelt Cowles is grateful that Theodore Roosevelt can visit at the last moment. She will meet him at Hartford at 2:55 in the afternoon. Cowles asks if Roosevelt wants her to invite anyone over.

Collection

Library of Congress Manuscript Division

Creation Date

1910-12-10

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles wishes she could visit with everyone at Sagamore Hill. She comments on the newspapers’ blaming Theodore Roosevelt for the various Democratic majorities. Her family is settling for the winter. William Sheffield Cowles enjoys public school and spending time with his friend Cameron McRae Winslow. Anna is trying to start a Boy Scout group. She reports that politically, Connecticut is “chastened and entangled” with Simeon E. Baldwin for Governor, and the Senatorial fight still rages. 

Collection

Library of Congress Manuscript Division

Creation Date

1910-11-14

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles now realizes what Theodore Roosevelt went through and accomplished since returning from his Western trip. Her family has settled again in New England, and William Sheffield Cowles is enjoying 8th grade at a public school. She gets many letters about Roosevelt and sends one from a young woman with health issues who wrote a story about Indians in the Grand Canyon. Cowles reports that Joseph W. Alsop’s nomination was successful. She admonishes Roosevelt not to respond as she knows he is busy.

Collection

Library of Congress Manuscript Division

Creation Date

1910-10-02

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Collection

Library of Congress Manuscript Division

Creation Date

1910-08-05

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Recipient

Roosevelt, Theodore, 1858-1919

Publication Date

2025-09-18

Anna Roosevelt Cowles asks President Roosevelt to read the enclosed letter from Frances E. Monson, and to have William Loeb write her if he knows of a place that can help her son. She recently visited New York, where she visited Franklin D. and Eleanor Roosevelt, who have moved into their new home and are expecting their third child. She also saw Mr. Mills, who is frail but fondly remembers Edith. She has seen her nephew Ted, and will see him again on Sunday, and expects to see Alice Roosevelt Longworth today.

Collection

Library of Congress Manuscript Division

Creation Date

1908-11-18

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles celebrates the election of William H. Taft, which was a triumph for President Roosevelt. She was amused to hear that Ambassador Whitelaw Reid and his wife want to stay in London. She discusses the electoral results in Connecticut, where George L. Lilley was elected governor. Walter L. Goodwin and John Q. Tilson also won their elections, while Joseph W. Alsop also did well. She hopes to hear more about the details of her brother’s African trip and heard from his son Ted by telephone when he assured her the he was “all perfectly right.”

Collection

Library of Congress Manuscript Division

Creation Date

1908-11-08

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles wishes her brother, President Roosevelt, a happy birthday. Cowles wishes that she could see him for a “real talk.” She asks him if it would be possible for him to receive Joseph W. Alsop’s cousin, Mary Oliver Alsop Dabney Boreham, with Hubert D. Astley and his wife, Lady Sutton, when Edith Kermit Carow Roosevelt can also be there. Astley is interested in birds. Cowles discusses the political situation in Connecticut, which is not very good. George L. Lilley was chosen in the caucus, but is having a hard time on the ticket, where he is challenged by A. Heaton Robertson. Alsop is struggling in the state senate race. She asks if Roosevelt can have William Loeb telephone her when he is sure about the result of the presidential vote.

Collection

Library of Congress Manuscript Division

Creation Date

1908-10-27

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles writes “many happy returns” for President Roosevelt’s birthday.

Collection

Library of Congress Manuscript Division

Creation Date

1908-10-27

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles asks that William Loeb try to telephone her on election night the moment he thinks he knows how the election has gone. She asks him to telegraph the same message at the same time, in case he cannot get through on the phone. She will be anxiously waiting to hear from him.

Collection

Library of Congress Manuscript Division

Creation Date

1908-10-29

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles says the news about Ohio Senator Joseph Benson Foraker validates President Roosevelt’s feelings, and Justice William H. Moody thinks the situation will help William H. Taft. Ambassador to Brazil Edwin V. Morgan has commented on the recent political involvement of the wealthy. Cowles thinks Seth Low Pierrepont is qualified to enter the diplomatic service and she hopes Roosevelt will speak to him. Joe Alsop’s senate nomination and hard work have pleased Cowles. Mabel Boardman, who Cowles is visiting, is going to Washington for the tuberculosis congress in her usual hardworking spirit. She invites Ted Roosevelt to visit Farmington, though he might find it boring.

Collection

Library of Congress Manuscript Division

Creation Date

1908-09-19

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles has heard that President Roosevelt had a full and busy fourth of July, as usual. She received a letter from Henry Cabot Lodge before he left on his trip saying he was very glad that Roosevelt was satisfied with his speech at the Republican National Convention. Cowles also comments on William H. Taft’s attitude to his nomination by the Republican Party for president.

Collection

Library of Congress Manuscript Division

Creation Date

1908-07-06

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles forwards her brother, President Roosevelt, a letter and asks him if he has any recommendations about how to answer it. Cowles is very interested in Roosevelt’s upcoming trip to Africa, and writes to him about Leigh S. J. Hunt, who Roosevelt might already know, but who is a polarizing figure. Her family is looking forward to an upcoming trip to Sagamore Hill.

Collection

Library of Congress Manuscript Division

Creation Date

1908-07-08

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

President Roosevelt’s sister, Anna Roosevelt Cowles, writes to him expressing her wish that she were at Chicago in person, rather than trying to get news of what was going on from newspapers. She thinks that a stampede for Roosevelt is close. Her visit to Groton has been pleasant, and she enjoyed seeing Kermit Roosevelt while she was there. She thanks Theodore Roosevelt for being good to her “very much better better half,” William S. Cowles, as Roosevelt is making it possible for him to fly his flag again before he retires. Cowles also comments on other political events, including the appointment of someone to the Senate, and mentions upcoming travel plans.

Collection

Library of Congress Manuscript Division

Creation Date

1908-06-16

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles is glad that President Roosevelt has been able to get away from Washington, D.C., for a time to go to Sagamore Hill. Cowles congratulates Roosevelt about something in which she feels that Roosevelt was able to control the flow of events well. She also mentions a humorous comment from Senator Morgan G. Bulkeley.

Collection

Library of Congress Manuscript Division

Creation Date

1908-06-20

Creator(s)

Cowles, Anna Roosevelt, 1855-1931

Anna Roosevelt Cowles writes to her brother, President Roosevelt, about the political situation in Connecticut. In particular, she has recently seen Judge Marcus H. Holcomb, who is satisfied with the action of the state convention, especially in regard to how the Senators were handled. Cowles has joined the Grange, and tells Roosevelt that he would have been amused to see the reaction of the members of her household.

Collection

Library of Congress Manuscript Division

Creation Date

1908-05-30

Creator(s)

Cowles, Anna Roosevelt, 1855-1931