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Theodore Roosevelt expresses his astonishment and happiness over the news his sister Anna Roosevelt is engaged to William Sheffield Cowles. He is especially happy that Cowles is a naval officer. It pains Roosevelt that he cannot leave his work at this time to celebrate with Anna in London.
1895-07-04
Theodore Roosevelt informs his sister Anna Roosevelt that all anyone can talk about is her engagement to William Sheffield Cowles. It upsets him he cannot be with Anna at this time but his work as Police Commissioner is very important at the moment. They are fighting the saloon keepers and Germans over the enforcement of the ban on Sunday sale of liquor. He gives updates on Kermit and Ethel.
1895-07-07
Theodore Roosevelt advises his sister Anna Roosevelt that she must not marry William Sheffield Cowles yet because his previous marriage may not be entirely annulled. He has people researching the problem, but Cowles may have to return and sue his wife for adultery.
1895-07-19
Theodore Roosevelt informs his sister Anna Roosevelt that it does appear her fiance’s divorce would hold up in court and she can marry him and live in California. He asks if she would like him to see another lawyer about the matter.
1895-07-23
Theodore Roosevelt tells his sister Anna Roosevelt he is unsure of what else to do pertaining to her fiance’s previous marriage and divorce problem. He feels Anna and Cowles should return from London and consult with lawyers. There is a chance Anna’s marriage could be declared invalid.
1895-07-27
Theodore Roosevelt advises his sister Anna Roosevelt to return to America with her fiance, William Sheffield Cowles, in order to settle the matter of the legality of his divorce. He compares their situation to that of Mr. and Mrs. Pellew.
1895-08-01
Theodore Roosevelt does not know how else to advise his sister Anna Roosevelt regarding her fiance’s problems with his divorce. The lawyer Cleveland advises Anna and Cowles not to marry yet and come home to deal with the problem.
1895-08-05
Theodore Roosevelt relates the lawyer Cleveland’s advice to his sister Anna Roosevelt regarding her fiance’s divorce problems. If Anna and Cowles were to marry now, their marriage would be legal in California but not in New York, and a suit could be brought against Cowles for bigamy. It is up to them to decide if they want to take the risk.
1895-08-16
Theodore Roosevelt discusses the issue of sister Anna Roosevelt’s fiance’s divorce and thinks it is good she talked to a lawyer named Tracey. He inquires if they will marry in London or back home.
1895-08-21
Theodore Roosevelt is heartened by the advice from General Tracey regarding William S. Cowles’s divorce. Tracey disagrees with the view of lawyer Cleveland and wonders if Tracey should meet with the lawyer. Roosevelt thanks Anna for the clippings she sent and says that despite all the opposition, he has managed to get the saloons closed on Sundays.
1895-08-26
Theodore Roosevelt hopes his sister Anna Roosevelt will spend her first winter married to William Sheffield Cowles in London. He and wife Edith watched the first cup races from the police patrol boat and is excited about the success he has had as Police Commissioner.
1895-09-08
Theodore Roosevelt informs his sister Anna he will meet with Tracey when he is ready regarding Anna’s fiance’s divorce problem. He also talks of meeting and dining with Howard. Roosevelt describes the first yacht race he and wife Edith witnessed and tells Anna to rent her house without regard to their plans.
1895-09-15
Theodore Roosevelt informs his sister Anna Roosevelt that he met with General Tracey and Tracey concludes that if Anna and William Sheffield Cowles are married in London, their marriage will be legal in New York despite Cowles’s previous divorce. Roosevelt and Tracey agree Anna should stay in London this winter.
1895-10-01
Theodore Roosevelt describes friend Bob’s visit to his sister Anna Roosevelt and how he spent a lot of time with Roosevelt’s wife Edith. In spite of Roosevelt’s success as Police Commissioner he has no real standing with the Republican party. He is happy Anna and her fiance William Sheffield Cowles approve of staying in London for the winter.
1895-10-06
Theodore Roosevelt appreciates his sister Anna Roosevelt’s fiancé William S. Cowles sending him some books; however, he has no time to read as he is so busy at work. He hopes Anna settled the wedding date and regrets that he cannot be with her. He works ten hours a day and speaks every evening.
1895-10-18
Theodore Roosevelt is happy sister Anna Roosevelt’s wedding to William Sheffield Cowles will be on November 25 and that sister Corinne and brother-in-law Douglas will be there. He wishes he and wife Edith could attend. Elections are in two days and Republicans will probably lose in the city. Edith will write that they accept Anna’s offer of taking her house at 689 Madison Ave.
1895-11-03
Theodore Roosevelt appreciates sister Anna Roosevelt’s telegram from Paris and tells her not to worry about his reaction to the Republican losses in the recent election. He expected to be blamed because of the unpopular policies he enforced as Police Commissioner. He finds the books Anna’s fiance William S. Cowles sent him most interesting.
1895-11-10
Theodore Roosevelt wishes he could be with his sister Anna Roosevelt Cowles today on her wedding day. Son Ted is jealous and thinks “Auntie Bye” will not care about him anymore. Senator Lodge recounted his visit with Anna and her husband William Sheffield Cowles.
1895-11-25
Theodore Roosevelt informs his sister Anna Roosevelt Cowles all the children are prepared to love their new Uncle William Sheffield Cowles. Roosevelt continues to work a lot and finish his book.
1895-12-01
Theodore Roosevelt tells his sister Anna Roosevelt Cowles how touched he was by her letters and her new husband William Sheffield Cowles’s note. Sister Corinne also wrote and related the details of the wedding. Edith has written to Mrs. Olney on behalf of Anna to see if Anna can stay six or eight months more in London. Though Roosevelt works a lot, he takes some time for leisure with the family.
1895-12-10