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.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] thanking him for a present, discussing arrangements to visit Harrow, and informing him that [Lord Randolph Churchill and Lady Randolph Churchill] are returning [from Japan] to Monte Carlo as [Lord Randolph] has been advised to have "perfect quiet". Signed manuscript. Typed transcripts at CHAR 28/152A/32-33.

Transcript of a letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] thanking him for a present, discussing arrangements to visit Harrow, and informing him that [Lord Randolph Churchill and Lady Randolph Churchill] are returning [from Japan] to Monte Carlo as [Lord Randolph] has been advised to have "perfect quiet". Typed. 2 copies. Original letter at CHAR 28/152A/31.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] informing him that [Lord Randolph Churchill and Lady Randolph Churchill] are returning [from Japan] to Monte Carlo and commenting on [Lord Randolph's] health "if he keeps perfectly quiet he may yet get well- though he will never be able to go into Politics." Signed manuscript. Typed transcripts at CHAR 28/152A/35-36.

Transcript of letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] informing him that [Lord Randolph Churchill and Lady Randolph Churchill] are returning [from Japan] to Monte Carlo and commenting on [Lord Randolph's] health "if he keeps perfectly quiet he may yet get well- though he will never be able to go into Politics." Typed. 2 copies. Original letter at CHAR 28/152A/34.

Letter from WSC (35a, Great Cumberland Place [London]) to "Jack" [John S Churchill] in which he discusses the route of the P & O express and says that he will not see him until he returns from India; discusses his speech; and asks him to write often. Signed manuscript.

Part of a letter from WSC (4th (The Queen's Own) Hussars, Bangalore, India) to "Jack" [John S Churchill] in which he expresses sorrow that "Mamma" [Lady Randolph Churchill] has not written to him, asks Jack to find out why she is "so unkind", and says that the mistakes in ["The Malakand Field Force"] have caused him "acute pain". Manuscript.

Letter to WSC and CSC from Gladys Gough, enclosing a cutting from the New York Times on Mary Churchill [later Mary Soames] being spanked by a United States soldier at an ATS [Auxiliary Territorial Service] party; also includes press transcripts and notes by John Martin [Private Secretary to WSC] and D Parker-Bowles, Duty Officer, Ministry of Information, on whether the incident should be prevented from appearing in British newspapers.

Correspondence between Randolph Churchill and William Connor, "Cassandra" of the Daily Mirror, on Randolph Churchill's recent unopposed election success at Preston [Lancashire] and his criticism of Admiral of the Fleet 1st Lord Chatfield but not Lord Halifax [earlier Edward Wood and Lord Irwin] and Sir Kingsley Wood as former advocates of appeasement; includes covering notes by Lilian Buck, Secretary to Randolph Churchill and John Martin [Private Secretary to WSC].

Correspondence between WSC, and Major Randolph Churchill on the latter's new posting to the Middle East; includes covering correspondence between Edmond Armstrong, War Cabinet Office and John Martin and Francis Brown [Private Secretaries to WSC] and a note from Martin to Pamela Churchill [earlier Pamela Digby, later Pamela Harriman].

Minute from Lieutenant-General Sir Hastings Ismay [Chief of Staff to WSC] to WSC on a proposed appointment for Randolph Churchill as Intelligence Officer to the Commando Brigade.

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] (Elstree School, Herts) to WSC, on activities at school.

Letter from "Jack" [John S Churchill] (Elstree School, Herts) to WSC, on WSC's visit to Elstree.

Letter from "Jack" John S Churchill to WSC, (Elstree School) on WSC's visit to Elstree, contains sketch of cricket match and "white pony".

Letter from "Jack" John S Churchill (Elstree School) to WSC, asking WSC to send stamp book, and commenting on horse racing.