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] ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that "Winney" [WSC] is taking "all kinds of medicines" and sends his love.

Letter from [John S Churchill] ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he discusses arrangements to return home and says that "Winney" [WSC] is unwell.

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 (Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] in which he reports that "Winney" [WSC] appears to be enjoying Sandhurst despite a boil on his face and seems to have grown two inches. He also says that a Constitutional Club is to be opened the following week.

Letter from "Jack" [John] S Churchill (Harrow [School, Middlesex]) to "Papa" [Lord Randolph Churchill] including: his intention to stay with "Grandmama" [Frances, Duchess of Marlborough] and WSC at Branksome Dene; his intention to be confirmed the following year and WSC's progress at Sandhurst.

Letter from "Jack" [John] S Churchill (The Deepdene, Dorking [Surrey]) to "Papa" [Lord Randolph Churchill] in which he says that he is staying with Aunt Lily [Lady William Beresford] who is ill, reports that WSC has "come out second" in the riding at Sandhurst and remarks that he is expecting a telegram to hear that he (Lord Randolph) has arrived at Marseilles [France].

Letter from "Jack" [John] S Churchill (Reverend J E C Welldon's, Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] in which he discusses his clothes, asks about her apartment, says that he has been unwell and that WSC has to work hard [at Aldershot].

Letter from "Jack" [John] S Churchill (Reverend J E C Welldon's, Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] asking her whether she will buy him a bicycle and observing that WSC "seems to be in the very height of his pleasure at Aldershot".

Letter from "Jack" [John] S Churchill (Reverend J E C Welldon's, Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] in which he discusses arrangements for his holiday; reports that there is to be a memorial for [6th] Lord Bessborough; describes a paper chase; says that he intends to join the Cyclist Corps and that WSC has been put in charge of a squadron.

Letter from "Jack" [John S Churchill] (Reverend J E C Welldon's, Harrow [School, Middlesex]) to "Mama" [Lady Randolph Churchill] enclosing a letter from "Grandmama" [Frances, Duchess of Marlborough, see CHAR 28/31/21], reporting that WSC visited him and asking after "Pinky Poo" [a pet dog].

Letter from "Jack" [John] S Churchill] (Harrow [School, Middlesex]) to [Lady Randolph Churchill] in which he discusses WSC's enthusiasm at going to [Cuba], asks for a photograph of WSC "in his glory" and says that Dudley Marjoriebanks [later 3rd Lord Tweedmouth] has visited to play football.

Letter from "Jack" [John] S Churchill to "Mama" [Lady Randolph Churchill] thanking her for sending him a letter from WSC, discussing some puppies and asking her to pay a bill from a "haberdasheranian".

Letter from "Jack" [John S Churchill] ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] thanking her for her letter and for sending him money, asking her to buy a copy of the Pall Mall [Gazette] as it contains an article about Sandhurst by WSC and discussing the expulsion of two boys from Harrow.

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 (Erquy, Cotes de Nord [France]) to "Mama" [Lady Randolph Churchill] in which he says that he is ill, comments on the fact that WSC was "too late" [to see the war between Greece and Turkey], and asks her to send him money.

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 ([45 Rue des Missionnaires, Versailles, France]) to "Mama" [Lady Randolph Churchill] in which he says that he likes Robineau; discusses the behaviour of "the Roumanian"; describes the food and wine; comments on WSC's appointment as acting-adjutant and asks her to send him an English newspaper.

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] (35A Great Cumberland Place [London]) to "Mama" [Lady Randolph Churchill] in which he says that Moreton [Frewen] thinks that she should send WSC's letter to be published. Envelope present.

Letter from "Jack" [John S Churchill] (The Deepdene, Dorking [Surrey]) to "Mama" [Lady Randolph Churchill] reporting that Aunt Lily [Lady William Beresford] likes WSC's book and has "all sorts of schemes about it".

Letter from "Jack" [John S Churchill] (35A Great Cumberland Place [London]) to "Mama" [Lady Randolph Churchill] discussing WSC's position as correspondent to the Times, and reflecting on news [of the Battle of Omdurman, Sudan].

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".