Letter from WSC (Chicago [United States] on the notepaper of 105 Mount Street) to George [Cornwallis-West] expressing pleasure at the news that George is to leave the army and describing the disadvantages of a career in the army. He comments on the lack of success of his lecture tour from which he has made o1,600 and on the fact that "Jack" [John S Churchill] is to continue living at 35A [Great Cumberland Place, London].

Letter from "Winny" [WSC] ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he describes his bicycle accident, asks her to visit him and to allow [Elizabeth] Everest to visit as he is bored.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] asking her to send him money.

Card from WSC (Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] informing her of his safe arrival and that he is sharing a room with Count Eric Steenbock [Stenbock, the son of a Swedish-Norwegian Minister] and is not spending his money rashly.

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 (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 (Reverend James Welldon's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that Welldon is determined that WSC should get his remove and that he hopes that he will be allowed to take a holiday on his birthday. Envelope present.

Letter from WSC ([Harrow]) to "Mama" [Lady Randolph Churchill] describing the contents of an examination he has taken and his hopes that he has passed. He lists the essay questions which were set and comments on his luck that he had revised the map of New Zealand. Envelope present.

Letter from WSC (Wady Halfa [Sudan]) to "Mamma" [Lady Randolph Churchill] including: the battle of Omdurman and his opinion that the British forces should have made a charge and made the "performance historic"; the names of his friends who were killed in action; and complaint at the publication of his letters in the Morning Post and Oliver Borthwick's alterations to them.

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 (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 "Jack" [John] S Churchill (Andermatt [Switzerland) to "Mama" [Lady Randolph Churchill] describing his journey and climbing Pilatus. He also reports that "Winney" [WSC] "went nearly mad" at the news that he had passed the Sandhurst examination and is writing to "Papa" [Lord Randolph Churchill].

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he likes his school, that he has purchased a "frouster", asks her to send him food and money and says that he wishes to learn gymnastics. Envelope present.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to make arrangements for someone to attend speech day.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses pleasure that he is not going abroad for his holidays, describes arrangements for a camp and asks her to give him money and to buy him a pair of butcher boots. He encloses the camp regulations [not present] and suggests that she might approach officers at Aldershot [Hampshire] to introduce themselves to him.

Letter from WSC ([Cliveden, Buckinghamshire]) to "Mummy" [Lady Randolph Churchill] in which he informs her that he is well, describes a punting trip with [Lady Sarah Churchill, later Sarah Wilson] and a visit to Newmarket [Suffolk].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] reproaching her for not replying to his last three letters, commenting "If [Elizabeth] Everest did not write to me I should hardly imagine that there was such a place as Banstead [Manor, Newmarket, Suffolk], and asking her to contact him about a [surgeon's] appointment.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he informs her that he has joined the "Army class" and that he is learning French and geometrical drawing and studying for the Shakespeare prize. Envelope present.