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".

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] (Bachelors' Club, Piccadilly [London]) to "Mama" [Lady Randolph Churchill] in which he discusses financial affairs, including WSC's loan, reports that he has been talking about the City with [Ernest] Cassel, that he hopes to hear news of WSC and learn shorthand and that he has received an invitation from [5th Lord] Rosebery.

Letter from "Jack" [John S Churchill] (Savoy Hotel, Cairo [Egypt]) to "Mama" [Lady Randolph Churchill] in which he gives the names of the people he has met; makes observations about Caryl [Ramsden?]; says that he appreciates her letters and reports that the Sirdar [Sir Herbert Kitchener] has ordered that WSC is not to be given any information.

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 (Ladysmith [South Africa]) to "Mama" [Lady Randolph Churchill] including a description of the unpleasantness and monotony of camp life; the news that WSC has gone to join [1st] Lord Roberts; a request that she should pay a bill on his behalf; the news that she received a great reception in Cape Town; conditions [on the hospital ship] Maine and the reaction to WSC's telegrams about the treatment of the Boers.

Letter from "Jack" [John S Churchill] (Standerton [South Africa]) to "Mama" [Lady Randolph Churchill] in which he says that despite skirmishes with the Boers and the Free Staters the regiment is "very bored and tired", reports that Olive Guthrie saw some fighting at Blomfontein, and comments on WSC's escape.

Letter from "Jack" [John S Churchill] (Standerton [South Africa]) to WSC in which he says that he has decided to remain in South Africa until the [Boer War] is over; discusses dissatisfaction with the lack of coverage of the actions of the Natal Field Force and lack of credit given to [Redvers] Buller; describes the action against the Boers in which the SALH [South African Light Horse] have participated and comments on the popularity of WSC's book.

Letter from "Jack" [John S Churchill] (Helvetia, Second Cavalry Brigade [South Africa]) to "Mama" [Lady Randolph Churchill] including: [1st] Lord Roberts' kindness towards him; a meeting with a man who helped WSC escape; the fighting which he had witnessed; the terrible sight of the wounded and the dead and his hopes that the war is almost at an end. Four typed copies of the letter at end of file.

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 "Jack" [John S Churchill] (4 Moorgate Street [London]) to "Mama" [Lady Randolph Churchill] discussing financial affairs and the possibility that "G" [George Cornwallis-West] may be declared bankrupt. He also says that WSC has been working hard on Cabinet business.

Copy of a letter from John Colville [pilot, RAFVR, former Private Secretary to WSC] to CSC with impressions of South Africa and criticisms of the Empire Air Training Scheme; with correspondence between WSC, Sir Archibald Sinclair [Secretary of State for Air, later 1st Lord Thurso] and 1st Lord Cherwell [Personal Assistant to WSC, earlier F A Lindemann] enquiring about the efficiency of the scheme, and Colville's progress.

Correspondence on John Colville [former Private Secretary to WSC] being found unfit for a pilot's commission; includes letters between John Martin [Private Secretary to WSC], WSC, Sir Archibald Sinclair [Secretary of State for Air, later 1st Lord Thurso] and Ronald Melville [Private Secretary to Sinclair] on the inconvenience to WSC of releasing Colville, his progress in training, and the limitations of training in South Africa.

Correspondence between Francis Brown [Private Secretary to WSC], WSC, Lieutenant-General Bernard Paget [Commander-in-Chief, Home Forces] and "Bert" [10th Duke of Marlborough, earlier Lord Blandford] on arrangements for Marlborough to be Liaison Officer to General Hugh Ellis, Regional Commissioner, Southern Command and also on the defences of [?] Chequers [Buckinghamshire].

Notes by Anthony Bevir and John Martin [Private Secretaries to WSC] on contacting Sir Charles Wilson [President, Royal College of Physicians, later 1st Lord Moran]; includes correspondence between Bevir and Wilson.

Correspondence between Alfred Clark, Chairman of the Gramophone Company Limited, Anthony Bevir [Private Secretary to WSC] and WSC on recordings of speeches by WSC and Field Marshal Jan Smuts [Prime Minister of South Africa] and correspondence between Bevir, Rutherford Tippetts [Principal Private Secretary to Minister of Supply] and Bernard Sendall [Principal Private Secretary to Minister of Information] about provision of paper or woodpulp in making the album of speeches.

Correspondence between Commander Charles Thompson [Personal Assistant to WSC], Colonel [? Denys Hicks], 1st Anti-Aircraft Division, and Major A McGrath [? Military Assistant] to the Commander-in-Chief, Home Forces, on defence and security arrangements for Chartwell [Kent].

Letter from Robert Barrington-Ward, Editor of the Times, to Brendan Bracken [Minister of Information] on the foresight of WSC's Romanes Lecture ["Parliamentary Government and the Economic Problem", 19 June 1930], with covering note from Bernard Sendall [Principal Private Secretary to Bracken] to John Martin [Private Secretary to WSC].

Letter from Alfred Townsend, Editor of Export, to WSC on the role of Export as journal of the Institute of Export and requesting permission to quote from WSC's 1930 Romanes Lecture ["Parliamentary Government and the Economic Problem", 19 June 1930] following up on an article on the Atlantic Charter in Export [June 1942; copy enclosed]; also includes reply by John Peck [Assistant Private Secretary to WSC].

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.

Note from Francis Brown [Private Secretary to WSC] to Randolph Churchill enclosing a War Cabinet report on foreign propaganda broadcasts: report includes undermining of WSC with a quote from Randolph Churchill on WSC keeping his money safely in the United States, and the suggestion that Sir Stafford Cripps, Lord Privy Seal, is a Bolshevist sympathiser and possible agent.

Telegrams between General Sir Claude Auchinleck, Commander-in- Chief, Middle East, Sir James Grigg, Secretary of State for War and WSC on Major Randolph Churchill being ordered to remain in Britain, the false position he has been placed in, and Auchinleck's request that he should be returned to the Middle East; includes covering correspondence between Sydney Redman [Principal Private Secretary to Grigg], Leslie Rowan and Francis Brown [Private Secretaries to WSC].