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.

Telegram from WSC to Randolph Churchill wishing him a Happy Christmas from WSC and family. Carbon copy followed by letter from "T L R" [Leslie Rowan, Prime Minister's Private Secretary] to Resident Clerk, Foreign Office, asking for it be despatched, with copy of final telegram sent through Minister of State [Middle East, Oliver Lyttelton, later 1st Lord Chandos].

Telegram from WSC to Oliver Lyttelton [later Lord Chandos, Minister of State in the Middle East] against suggestion that Randolph Churchill act as liaison between Lyttelton and WSC.

Telegram from Oliver Lyttelton [Minister of State, Middle East, later 1st Lord Chandos] to WSC requesting permission to overrule WSC's objections and appoint Randolph Churchill as liaison between themselves.

Telegram from WSC to Minister of State, Middle East [Oliver Lyttelton, later 1st Lord Chandos] rejecting appointment of Randolph Churchill as liaison between them and recommending he return to active service.

Letter from WSC to Jean [Ivan] Maisky [Soviet Ambassador to Britain] thanking him for his enquiry about Randolph Churchill's injury.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, London, to WSC, on the success of WSC's riding instruction with Captain C H Burt, and recommending that he should visit Lord Randolph's dentist, Pritchard, of 9 Albemarle St., London.

Telegram from Lord Randolph Churchill to WSC, asking WSC not to come up to London as Lord and Lady Randolph were going to Tring.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, London, to WSC, complaining about WSC's frequent visits to London from Sandhurst, forbidding him to come to London more than once a month, and encouraging him to study at weekends.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, to WSC, on WSC's visit to Colonel John Brabazon, 4th Hussars, at Aldershot, and his work at Sandhurst, telling him "not to trouble any more about the watch", [which WSC had damaged] as the rough work of Sandhurst was not suitable for a watch made by Dent. Also advising him not to "attend to moneylenders," put their letters into the waste paper basket".

Letter from Lord Randolph Churchill, 50 Grosvenor Square, London, to WSC, sending cheque to cover WSC's allowance.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, To WSC, on visit to Lord Roberts at Grove Park, also on forthcoming visit of the Prince of Wales to Harrow School. Advising WSC to take care with his diet, "Eating fast, as you do is a fertile source of indigestion & heated blood, producing boils". Also advising him to address him as "Dear Father" rather than "Papa" in future letters.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, to WSC, criticising him for addressing him as "Papa" rather than "Father" in letters "This is idiotic".

Letter from Lord Randolph Churchill to WSC, on the state of WSC's finances, and his "pedantic and overgrown schoolboy style of letter writing, and complaining about his use of a typewriter "an objectionable machine calculated to spoil your handwriting.

Letter from Lord Randolph Churchill, Bar Harbour Malvern Hotel, Maine, to WSC, on Lord and Lady Randolph's visit to the United States and Canada, and on WSC's proposed visit to Germany.

Letter from Lord Randolph Churchill, Hotel del Monte, California, to WSC, on WSC's desire to join the cavalry rather than the 60th Rifles, pointing out that the Duke of Cambridge would be extremely angry, and that he would also oppose the change strongly, also on Lord and Lady Randolph's visit to the United States, and forthcoming Voyage to Japan.

Letter from Frances, Duchess of Marlborough, [WSC's grandmother], 50 Grosvenor Square, to WSC, family news, visit to the Gaiety Theatre to see Ruy Blas by A C Torr, picture of Lord Randolph Churchill in "Punch", and Lord Randolph's Temperance Bill.

Letter from Frances, Duchess of Marlborough, Woodlands, Uxbridge, to WSC, family news.