The collection chiefly compiles Lady Onslow's personal letters written to her parents and sister "Jim" from her travels in Churchill's service. They provide first hand evidence of her experiences and include lively recollections of Churchill, descriptions of her work and colleagues, and descriptions of journeys, accommodation and surroundings. The letters are supplemented by a small number of photographs and other mementos.

Letter from WSC (S S Britannia, In the Indian Ocean) to "Mamma" [Lady Randolph Churchill] in which he says that he is looking forward to reaching India and describes sailing through the [Suez] canal and his intention to continue playing chess. He also reports that he spoke in a "Breach of Promise" case and was surprised by his success and that his speech impediment did not interfere with his speech, and comments on a fraud [perpetrated on them by James Cruickshank].

Letter from WSC (Bradford [Yorkshire] on the notepaper of 35a Great Cumberland Place) to "Mamma" [Lady Randolph Churchill] describing the success of his speech at Bradford, his hopes that he may be able to contest the Central Division, his pleasure at "rousing and amusing" his audience and that his [speech] impediment was not a hindrance. He also informs her that he has definitely decided to resign his [army] commission.

Letter from WSC (35a Great Cumberland Place [London]) to "Mamma" [Lady Randolph Churchill] in which he says that he has been working hard at his speeches, describes a dinner at which he met Morbely Bell, informs her that a letter of his has been published in the W[estminster] G[azette] and that [Alfred] Harmsworth [later Lord Northcliffe] will publish a speech that WSC is to give at Dover [Kent].

Letter from WSC (35a Great Cumberland Place [London]) to "Mamma" [Lady Randolph Churchill] in which he says that his speech at Dover [Kent] was successful despite a pause when he lost his train of thought.

Letter from WSC (Savoy Hotel, Cairo [Egypt) to "Mamma" [Lady Randolph Churchill] in which he informs her that he has decided to stay in Egypt to research ["The River War"]; discusses his portrayal of the Sirdar [Sir Herbert Kitchener] and [Charles] Gordon; the expenses of conquest in Egypt; the progress of her magazine ["The Anglo-Saxon Review"] and his future speech at the Albert Hall Signed typescript.

Letter from WSC ( [Oldham, Lancashire] on the notepaper of 35A Great Cumberland Place [London]) to "Mamma" [Lady Randolph Churchill] in which he discusses the certainty of his success in winning [the Oldham election] and asks whether she and Pamela [Plowden, later Lady Lytton] will attend his opening address. He notes that his speech was enthusiastically received and that "There is practically no local society - only multitudes of workers".

Letter from WSC (105 Mount Street [London]) to "Mamma" [Lady Randolph Churchill] in which he expresses concern for "Jack's" [John S Churchill] involvement in fighting in South Africa and sorrow at the death of Albert Savory and encloses a report [not present] of his speech in Beverley [Yorkshire] about which he comments as "the best platform effect I have ever produced".

Letter from WSC (105 Mount Street, Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] in which he informs her of his decision to accept an invitation to speak to the Institute of Journalists; arrangements for his speaking tour; the future general election and Oldham [Lancashire] where "the situation...will be much complicated by the great depression and struggle in the cotton trade". Signed typescript with manuscript corrections.

Letter from WSC (105 Mount Street [London]) to "Mamma" [Lady Randolph Churchill] concerning arrangements for his lecture tour. He says that he hopes that [16th] Lord Derby will chair the Liverpool meeting, reports on the success of his lecture at Harrow [School, Middlesex] and details financial assistance provided for his election costs by "Sunny" [Charles, 9th Duke of Marlborough].