Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he reports that he has received a letter from "Papa" [Lord Randolph Churchill] about his [gold] watch and that his father seems "very cross". He also thanks her for her letter saying "You are the best and sweetest mummy in all the world".

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he discusses his plans to visit [London] at the weekend and asks her to write to inform him whether "Papa" [Lord Randolph Churchill] is still angry with him.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he says that he was "very low" at her departure, that he hopes that she is cheerful and that "Papa" [Lord Randolph Churchill] is better. He informs her that he has been working for his examinations and that he hopes to persuade [Lord Randolph] to allow him to enter the cavalry and says that he would like a letter from her.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] in which he describes his financial situation as "most unsatisfactory" and says that he has been forced to pawn several items; thanks her for sending him photographs of her and "Papa" [Lord Randolph Churchill] in which she says she looks beautiful and describes his plans for Christmas.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] in which he says that [Elizabeth] Everest has broken her arm; that he is getting on well with "Grandmamma" [Frances, Duchess of Marlborough], although he is depressed at having to go into the infantry; that he has seen [Adela] Hacket often. He reports that "Jack" [John S Churchill] is keen on photography and that he is looking forward to receiving news of her and "Papa" [Lord Randolph Churchill].

Letter from WSC (Royal Military College [Sandhurst, Camberley, Surrey] on the notepaper of 50 Grosvenor Square) to "Mamma" [Lady Randolph Churchill] in which he expresses his concern about a report on the health of his father [Lord Randolph Churchill], asks her to write to him "unreservedly" on the subject, and says that he worries about the effect of anxiety and travelling on her.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] expressing shock at a telegram from Madras [India] reporting the deterioration of [Lord Randolph Churchill's] health, and his intention to see his father with "Jack" [John S Churchill]. He bids her to "keep your pluck and strength up" and to write to him.

Letter from WSC (Royal Military College, Sandhurst, Camberley, Surrey]) to [Lord Randolph Churchill] in which he says that he is looking forward to his father's return, describes the honour of competing for the riding prize at Sandhurst in which he was awarded second place, reports that he is working hard for the examinations and hopes that his father will be pleased with him.

Letter from WSC (The Deepdene, Dorking [Surrey]) to "Mummy" [Lady Randolph Churchill] in which he details his and Jack's [John S Churchill] plans, comments on the kindness of Duchess Lily [Lilian, Duchess of Marlborough, later Lady William Beresford], describes shooting and the examinations at Sandhurst and his determination not to go to Germany.

Letter from WSC (Blenheim Palace) to "Mamma" [Lady Randolph Churchill] describing his stay and the kindness of Sunny [Charles, 9th Duke of Marlborough] and [Albertha] Lady Blandford and wishing her a happy Christmas.

Letter from WSC (4th Hussars, East Cavalry Barracks, Aldershot [Hampshire]) to "Mummy" [Lady Randolph Churchill] in which he says that he is no longer suffering from stiffness, reports that [Lilian, Duchess of Marlborough, later Lady William Beresford] has given him "carte blanche" to get a charger, that he has seen [Frances, Duchess of Marlborough whom he describes as "not particularly malevolent" and that he has declined an invitation to speak to the electors of Barnesbury.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] expressing concern at the news of "Grandmamma" [Clara Jerome] and at the sad time experienced by his mother and asking her to write to him with information.

Letter from WSC (Admiralty, Whitehall) to "Mamma" [Lady Randolph Churchill] about the naval estimates which he describes as "past the danger point". He informs her that he has written to Sir E[dward] Grey about a consulship for "Hugh", and that Lady Blanche [Hozier] is better and that the children are well. In a postscript he makes comments on the poor health of [5th Lord] Rosebery. Envelope present.

Letter from John S Churchill (Elstree School [Hertfordshire]) to "Mama" [Lady Randolph Churchill] in which he says that he is waiting to receive a letter from "Winey" [WSC] to hear that he has taken Sandhurst by storm.

Letter from "Jack" [John S] Churchill (St George's Terrace, Herne Bay [Kent]) to "Mamma" [Lady Randolph Churchill] in which he says that he is well, that he has received a letter from "Winnie" [WSC] and that he misses her.

Letter from WSC (4th Hussars [Bangalore] India) to "Mamma" [Lady Randolph Churchill] discussing financial affairs, his acceptance of liability for a loan provided the amount is shared with "Jack" [John S Churchill], and her extravagance. Envelope present.

Letter from WSC (Peshawar [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses financial affairs, expresses relief that "Jack" [John S Churchill] will be jointly liable for a loan which she is taking, asks her to reply to his letters, and makes observations on relations with the tribes which make it likely that there will be no fighting. Includes envelope.

Letter from WSC (4th (The Queen's Own) Hussars, Bangalore [India]) to "Jack" [John S Churchill] discussing "Jack's" future career in the City [of London] as an "arrogant plutocrat".