Letter from WSC (4th Hussars, Hounslow [Middlesex]) to "Mamma" [Lady Randolph Churchill] informing her of his decision to go to America and Havana [Cuba] which he anticipates will not cost him more than o90.

Letter from WSC (4th Hussars [Hounslow, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he describes arrangements made by [1st] Lord Wolsey for his visit to Cuba.

Letter from WSC (Bachelors' Club, Hamilton Place [London]) to "Mamma" [Lady Randolph Churchill] informing her that the War Office have given him permission to go to Cuba and that he has been instructed to collect information on the efficacy of a new bullet. He also says that he intends to buy Havana cigars and that he has discussed Cuba with Tito Holden.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses the legal action to be taken over a fraud [perpetrated on them by James Cruickshank], comments on [Henry Dupre] Labouchere and [James] Welldon's opinions [about a scandal in the 4th Hussars in which WSC was implicated], describes his daily routine at Bangalore and says that he is looking forward to a shooting expedition with Hugo [Baring].

Letter from WSC (Bangalore, [India]) to "Mamma" [Lady Randolph Churchill] in which he says that he does not intend to be a professional soldier and therefore would like either to enjoy himself or "see active service" and that he would like further details about the possibility of going to Egypt with [Sir Herbert] Kitchener and expresses his gratitude for his mother's actions on his behalf. He discusses the anniversary of the battle in which he participated in Cuba.

Letter from WSC ("In the train", Sioni [India]) to "Mamma" [Lady Randolph Churchill] in which he says that he and Hugo [Baring] met [Winifred and Victoria] Kennard, Arnold Morley, Sir Francis McLean, Baker Russell; reports that he received her messages from [Lord] Fincastle; comments on the unpopularity of [Victor, 9th Lord] Elgin as Viceroy of India; apologises for his writing and says that he hopes to be able to go to Egypt [to serve under Sir Herbert Kitchener]. Pencil.

Letter from WSC (4th (The Queen's Own) Hussars, Rajankunte Camp, Madras [India]) to "Mamma" [Lady Randolph Churchill] in which he describes the camp and its location; complains of the difficulty of working in the sun; informs her that he has been made acting-adjutant; speculates on the likelihood that he will be sent to Egypt [with Sir Herbert Kitchener]; discusses the difference between Gibbon and Macauley and comments on the "malevolence" of [Frances, Duchess of Marlborough].

Letter from WSC (4th (The Queen's Own) Hussars, Kundarna Camp, Madras [India]) to "Mamma" [Lady Randolph Churchill] in which he describes the hard work which the regiment has undertaken and his responsibility [as acting-adjutant] which he has discharged "not altogether without success".

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] in which he says that he is busy as acting-adjutant, that he finds it difficult to find material for his letters and is losing touch with England, discusses polo and his reading and asks her to find him a source of detailed parliamentary history.

Letter from WSC ("In camp", 4th (The Queen's Own) Hussars, Bangalore, Madras [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses: the likelihood that he may be posted to Egypt, a recommendation made by the colonel, his intention to return to England if he is not quarantined, sufferings from sunburn and his position as brigade major and adjutant about which he comments "responsibility is an exhilarating drink".

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses: his disappointment at not being allowed to play in a polo tournament and the resulting unpopularity of Sir Mansfield Clarke; the work of an adjutant and his enjoyment of the position; his own military career and the possibility that he will stay in the army for two more years; and his gardening and reading.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses: the likelihood that he might be chosen to serve in Egypt; his plan to return to England; his reading; the behaviour of the British government in Crete [Greece]; his own disagreement with the Conservative Party and disapproval of [Arthur] Balfour, George Curzon [later Lord Curzon] and the government's foreign policy and the possibility that "Jack" [John S Churchill] may enter the army.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] including: the postponement of his leave; his decision to visit Sir Herbert Kitchener in Egypt; a request for letters of introduction; discussion of his reasons for wishing to return to England during his leave; financial affairs; reading and his gratitude at receiving copies of the Annual Register.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] informing her of his decision to go to Brindisi [Italy] as a special correspondent on the war between Turkey and Greece. He asks her to use her influence with the King of Greece and to obtain him a position as special correspondent and discusses financial affairs. Includes envelope.