Cuttings of the following articles by WSC from "My Life": "Taken Prisoner by the Boers" on WSC as a war correspondent in South Africa; "My Escape from Pretoria"; "My Entry into Politics" on writing Lord Randolph Churchill's autobiography and the Free Trade issue; "Changing the Political Camp" on going over to the Liberals, South Africa and the Board of Trade; Looking Back on Sixty Years" on WSC's childhood, education and time at Sandhurst.

Letters from Elizabeth Everest [Churchill family Nanny] to 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 Jack Milbanke (17 Cliveden Place, Eaton Square) to WSC, offering help, and to intercede with Lady Randolph Churchill if he could be of any use.

Letter from "Jack" John S Churchill (Banstead Manor, Newmarket) to WSC, on their "den" which was dirty inside, but had withstood the weather well, and on the health of the animals.

Letter from "Jack" [John S Churchill] (Elstree School, Herts) to WSC, on the Harrow Fencing Cup.

Letter from "Jack" [John S Churchill] (Harrow School) to WSC, With little to report due to WSC's recent visit, commenting on WSC's good time in London.

Letter from Lady Randolph Churchill, 2 Connaught Place, London, to WSC, on his "very bad" school report from Harrow Describing his work as an "insult to his intelligence", and contrasting him to his brother Jack "who comes out at the head of his class every week".

Letter from Lady Randolph Churchill, Banstead, to WSC, apologies for not visiting him at Harrow, and advising him not to sell his bicycle and buy a bulldog puppy "a dog is sometimes a nuisance".

Letter from Lady Randolph Churchill, Iwerne Minster House, Blandford, to WSC, on his school report "You must try & have a better one next term as Papa will be back & will expect glowing accounts of yr work." Also commenting on a day's hunting, and "cutting a lovely somersault" at the 3rd fence.