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".

Letter from "Jack" [John] S Churchill ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] in which he says that "Winney" [WSC] is looking after him, discusses arrangements to have his watch sent to Dent's and says that he prefers [Harrow] to Elstree [his previous school].

Letter from "Jack" [John] S Churchill ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that "Winney" [WSC] is looking after him, that he has passed the arithmetic exam and that he has been given a nice room.

Letter from [John S Churchill] ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] reporting that "Winney" [WSC] is going to take a medical examination and that he is hoping for a quiet day, commenting "I do not get much peace while he is here".

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 "Jack" [John S Churchill] (Erquy [France]) to "Mama" [Lady Randolph Churchill] in which he reports that she has made an impression on Robineau and comments that a letter from WSC was "decidedly hot and his writing was melting".

Letter from "Jack" [John] S Churchill ([45 Rue des Missionnaires] Versailles [France]) to "Mama" [Lady Randolph Churchill] in which he discusses Lord Vernon's illness and says that Lord Vernon is "furious with Winston [WSC], who is a millionaire in India". He also mentions the names of other people he has met who include Lord Charles Beresford and asks her to visit him.

Letter from "Jack" [John S Churchill] (Versailles [France]) to "Mama" [Lady Randolph Churchill] in which he says that he is glad that WSC will miss the war in Greece as "he will not be able to agitate about it", describes a concert and his progress at the piano and asks her to send him money and musical scores.

Letter from "Jack" [John] S Churchill (45 Rue des Missionnaires, Versailles [France]) to "Mama" [Lady Randolph Churchill] in which he expresses pleasure at the news of WSC's success, complains about his ears and says that he is looking forward to returning home.

Letter from "Jack" [John] S Churchill (31 Throgmorton Street, London) to "Mama" [Lady Randolph Churchill] in which he says that he has seen WSC who he describes as "as usual trying to do everything at once".

Letter from "Jack" [John S Churchill] (Bachelors' Club, Piccadilly [London]) to "Mama" [Lady Randolph Churchill] discussing WSC. He comments that WSC "will always try and go one better", and that if he abuses the Sirdar [Sir Herbert Kitchener] he will "find himself in the wrong box". He also discusses an insurance policy.

Letter from "Jack" [John S Churchill] (Presles [Belgium]) to "Mama" [Lady Randolph Churchill] concerning his future career. He says that he is going to enter the City although he was "built heart and soul for the army" because she asked him to give it up. He also says that he was attracted to study at Oxford because of the idea "of going where Winston [WSC] had not been", discusses financial affairs and says that he would like to come home.

Letter from "Jack" [John S Churchill](41 Cromwell Road [London]) to "Mama" [Lady Randolph Churchill] discussing the legal implications of the terms of "Papa's" [Lord Randolph Churchill's] will and its' effect on her financial situation and on his and WSC's wives and children. He begs her to live within her means and says that he has not heard from "G" [George Cornwallis-West].

Letter from Clara Jerome (Paris [France]) to [Frances] Duchess [of Marlborough] thanking her for her letter, saying that she was disappointed at not being able to be with [Lady Randolph Churchill] for the birth of WSC and that she hopes to receive daily reports from [Lord] Randolph [Churchill].

Letter from [Frances, Duchess of Marlborough] (50 Grosvenor Square [London]) to Jennie [Lady Randolph Churchill] in which she discusses the health of [Lord Randolph Churchill] and the high expenses of their travels, she suggests that Jennie should consider cutting down on the number of servants, reports on the wedding of Frances [Wimborne] and gives news of WSC and says that she has been obliged to check him as he needs a "firm hand".

Letter from [Frances, Duchess of Marlborough] to Jennie [Lady Randolph Churchill] in which she discusses the difficulty of persuading "R" [Lord Randolph Churchill] not to travel; gives news of "Jack" [John S Churchill] and WSC whom she has "lectured freely"; and comments on the marriage of Miss M Wilson to Lord Willoughby.

Letter from [Frances, Duchess of Marlborough] (Canford [Wimborne, Dorset]) to Jennie [Lady Randolph Churchill] in which she discusses the health of "R" [Lord Randolph Churchill] and says that she hopes that he will be "prudent & docile"; gives news of "Jack" [John S Churchill] and WSC; discusses financial affairs and a bill from the Munro Club and the abscondment of Healy, a servant.

Letter from [Frances, Duchess of Marlborough] (B Dene, Bournemouth [Hampshire]) to Jennie [Lady Randolph Churchill] in which she asks her to read the letter which she has written to "R" [Lord Randolph Churchill], says that it is useless to talk of her feelings, and that she would like support in her advice that "Jack" [John S Churchill] and WSC should not be allowed to travel to meet them.

Letter from [Frances, Duchess of Marlborough] (50 Grosvenor Square [London]) to Jennie [Lady Randolph Churchill] in which she discusses the sorrow caused by the death of "the poor little [?] Win"; the letting of a house; her fear of "Georgie" [Lady Howe, earlier Lady Curzon and Lady Georgiana Churchill] having an accident while riding; and says that she has been reading "Sea Wolves" and "Under Sealed Orders" and that WSC has written her a nice letter.

Letter from [Frances, Duchess of Marlborough] (Ramsey Abbey, Huntingdon) to Jennie [Lady Randolph Churchill] in which she says that "Jack" [John S Churchill] is well and that she has not heard from WSC, that she has visited Leominster [Herefordshire] and is not satisfied with Escott's book [about Lord Randolph Churchill]. She also discusses [5th] Lord Rosebery's loss of nerve and speaks of the "dreadful ending" to Randolph's life.

Letter from [Frances, Duchess of Marlborough] (Ramsey [Abbey, Huntingdon) to Jennie [Lady Randolph Churchill] in which she discusses the letters she has received from "Jack" [John S Churchill] and WSC, the death of Sir Samuel Wilson, the possibility of a dissolution of parliament. She also comments on Jennie's financial situation and the expense of renting a house in Portman Square [London].

Letter from George [Cornwallis-West](Arthur's, St James' Street [London]) to "Missie" [Lady Randolph Churchill] in which he discusses his forthcoming interview with [Colonel] Arthur Paget; says that he is devising schemes for the defence of London; and that "Jack" [John S Churchill] has "opened his heart" about Pamela [Plowden, later Pamela, Lady Lytton] and WSC.