Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she discusses the pain of being separated from him, breakfast with [Henry] Standish and [Helene] Standish, reports compliments on her skating from Madame de Sagan and says that she is not lonely with "dear Winston"[WSC].

Part of a letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] including: the announcement of the engagement of [Lady Rosamund Churchill, later Lady Fellowes and Lady De Ramsey to William Fellowes, later 2nd Lord De Ramsey]; a report in the Morning Post about his "remarks"; Lady Castlereagh's [later Lady Londonderry's] comments on the arguments between her family and the Marlboroughs; and WSC's progress.

Part of a letter from [Lady Randolph Churchill] (2 Connaught Place [London]) to [Lord Randolph Churchill] including: a sea crossing in the Calabria and her illness; the possibility that "Mama" [Clara Jerome] may go to the United States and that Clara [Frewen, earlier Clara Jerome] might be alone; a suggestion that he should avoid writing "melancholy" letters to [Frances, Duchess of Marlborough]; progress with the decoration of a studio; and news of "Jack" [John S Churchill] and WSC.

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 "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 [John S Churchill] (Elstree School [Hertfordshire]) to "Mama" [Lady Randolph Churchill] describing a visit from "Winney" [WSC] and asking about her plans for the holiday, commenting "Do let me keep with Winney whatever happens".

Letter from "Jack" [John] S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he asks her to allow him to see "Winney" [WSC] during the holiday and to write to him.

Letter from "Jack" [John] S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he asks her whether "Winney" [WSC] will have to go to France during the holidays; asks her to let him see him and to send him some money; and discusses arrangements for his return home.

Letter from "Jack" [John] S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he describes a fit experienced by Mr Sanderson, one of his schoolmasters, says that he has not heard from "Winney" [WSC] and that "Papa" [Lord Randolph Churchill] is too busy to visit him. Also numbered "70".

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 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.

Letter from George [Cornwallis-West](Invercauld, Ballater, Aberdeenshire [Scotland]) to "Missie" [Lady Randolph Churchill] discussing the possibility that they may marry. He observes that she changes her mind frequently, says that he will not marry her until he has more money, that he has quarrelled with many of his relations and friends and that WSC made "strong arguments" in favour of leaving matters as they are.

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].