Illustrated card from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Papa" [Lord Randolph Churchill] in which he reproaches his father for not visiting him when he was in Brighton, describes visiting a museum and asks his father to send more copies of his autograph.

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 [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].

Part of a letter from [Marquis of Breteuil] (Villa Breteuil, Tarbes [France]) to Lady Randolph [Churchill] in which he apologises for not writing to her sooner; describes the poor weather; says that he is looking forward to seeing her [in London]; asks her to give him the name of the hotel next to her house, describes the countryside and recommends that she should visit with her children [WSC and John S Churchill].

Letter from WSC (The Headmaster's, Harrow [School, Middlesex]) to "Jack" [John S Churchill] in which he asks whether Jack has settled down; informs him that he has a "dear little room" which he has decorated; discusses the possibility of visiting Jack and sending him stamps; and informs him that he has swapped 2 coins. Signed manuscript.

Letter from WSC (The Headmaster's, Harrow [School, Middlesex]) to "Jack" [John S Churchill] in which he thanks him for some books and "P.O.O.'s" [Post Office Orders?]; says that he has purchased curtains for the den and instructs Jack to make 2 bunks for them to sleep in; and informs him that he has begun to study Chemistry. Signed manuscript. Typed transcript at CHAR 28/152A/3-4.

Transcript of a letter from WSC (The Headmaster's, Harrow [School, Middlesex]) to "Jack" [John S Churchill] in which he thanks him for some books and "P.O.O.'s" [Post Office Orders?]; says that he has purchased curtains for the den and instructs Jack to make 2 bunks for them to sleep in; and informs him that he has begun to study Chemistry. Typed. 2 copies. Original letter at CHAR 28/152A/2.

Letter from WSC (50 Grosvenor Square [London]) to "Jack" [John S Churchill] in which he promises to send photographs of [Lord Randolph Churchill and Lady Randolph Churchill]; recommends him to write home often as "papa only remembers getting one letter from you and a very unsatisfactory report"; and says that he has wasted 10 pounds "on a lot of old rubbish". Signed manuscript.

Letter from WSC (50 Grosvenor Square [London]) to "Jack" [John S Churchill] in which he describes a cash box which [Lady Randolph Churchill] has purchased for Jack; describes a walk with "Polly" [Adela] Hacket, a meeting with "Sunny" [Charles, 9th Duke of Marlborough] and luncheon with [Lady Randolph] at White's Club; and discusses rumours of [William] Gladstone's resignation. Signed manuscript. Typed transcript at CHAR 28/152A/21-22.

Transcript of a letter from WSC (50 Grosvenor Square [London]) to "Jack" [John S Churchill] in which he describes a cash box which [Lady Randolph Churchill] has purchased for Jack; describes a walk with "Polly" [Adela] Hacket, a meeting with "Sunny" [Charles, 9th Duke of Marlborough] and luncheon with [Lady Randolph] at White's Club; and discusses rumours of [William] Gladstone's resignation. Typed. 2 copies. Original letter at CHAR 28/152A/20.

Letter from WSC (50 Grosvenor Square [London]) to "Jack" [John S Churchill] including: thanks him for his long letter; his illness and the possibility that he may go to Brighton [Sussex]; news of various friends; a new Chemistry notebooks and an alteration in the period of history to be studied for the Sandhurst examination; and a promise to send money. Signed manuscript.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] in which he thanks him for his letter and discusses visiting Harrow at the weekend. Signed manuscript.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] in which he thanks him for his letter; reports that he has visited the 4th Hussars at Aldershot [Surrey] with Colonel [John] Brabazon; discusses "the watch" [WSC had ill treated a gold watch] and reports that "Papa [Lord Randolph Churchill] is now soothed"; discusses their summer holiday and their next meeting; and reports that the typewriter has arrived. Signed manuscript.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] including: a visit to the Empire [theatre, London]; his intention to bring "Molly" [Adela] Hacket to Harrow; a planned visit to the Derby if [Lord Randolph Churchill] gives his permission; and his progress with a typewriter. Typescript signed by WSC.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] including: a visit to the races at Ascot [Surrey] and dinner with Lord Wolverton; his hopes to see Jack; and the comment "Everything is very damneble [sic] except Sandhurst". Typescript signed by WSC.