Photograph of Frances, Duchess of Marlborough.

Photograph of John S Churchill in uniform.

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].

Letter from [Lady Randolph Churchill] to "R" [Lord Randolph Churchill] including: the engagement of [Lady] Rosamund [Churchill, later Lady Fellowes and Lady De Ramsey] to [William] Fellowes [later 2nd Lord De Ramsey]; her concern about the attitude of [Frances, Duchess of Marlborough] to the engagement; the behaviour of the Duke of Connaught [and Strathearn]; and discussion about servants.

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.

Letter from [Lady Randolph Churchill](Carton, Maynooth [County Kiladre, Ireland]) to [Lord Randolph Churchill] in which she gives the names of those present at the party who include Captain Rochford and his wife, [Henry] Guinness and [Emelina] Guinness and comments on [Frances, Duchess of Marlborough's] opinion about the engagement of [Lady Rosamund Churchill, later Lady Fellowes and Lady De Ramsey] to [William Fellowes, later 2nd Lord De Ramsey].

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 John S [Churchill] ([Elstree School, Hertfordshire]) to "Mummy" [Lady Randolph Churchill] in which he discusses plans to see her and "Papa" [Lord Randolph Churchill] as he says that he has not seen his father for a long time.

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] ([Elstree School, Hertfordshire]) to "Mama" [Lady Randolph Churchill] in which he says that he was very disappointed that he was not allowed home and "still more disappointed" that she did not visit him.

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] to "Mama" [Lady Randolph Churchill] in which he says that he is sorry to have missed her, reports that [Edmund] Wheater [George Cornwallis-West's business partner] is "very bitter at George [Cornwallis-West] leaving him to face the music" and asks her to write to "Goonie" [Lady Gwendeline Churchill, formerly Lady Gwendeline Bertie].

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].