Letter from "Jack" [John] S Churchill (Reverend J E C Welldon's, Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] in which he discusses arrangements for his holiday; reports that there is to be a memorial for [6th] Lord Bessborough; describes a paper chase; says that he intends to join the Cyclist Corps and that WSC has been put in charge of a squadron.

Letter from "Jack" [John] S Churchill] (Harrow [School, Middlesex]) to [Lady Randolph Churchill] in which he discusses WSC's enthusiasm at going to [Cuba], asks for a photograph of WSC "in his glory" and says that Dudley Marjoriebanks [later 3rd Lord Tweedmouth] has visited to play football.

Letter from "Jack" [John] S Churchill (Erquy, Cotes de Nord [France]) to "Mama" [Lady Randolph Churchill] in which he says that he is ill, comments on the fact that WSC was "too late" [to see the war between Greece and Turkey], and asks her to send him money.

Letter from "Jack" [John] S Churchill ([45 Rue des Missionnaires] Versailles [France]) to "Mama" [Lady Randolph Churchill] in which he discusses Lord Vernon's illness and says that Lord Vernon is "furious with Winston [WSC], who is a millionaire in India". He also mentions the names of other people he has met who include Lord Charles Beresford and asks her to visit him.

Letter from "Jack" [John] S Churchill ([45 Rue des Missionnaires, Versailles, France]) to "Mama" [Lady Randolph Churchill] in which he says that he likes Robineau; discusses the behaviour of "the Roumanian"; describes the food and wine; comments on WSC's appointment as acting-adjutant and asks her to send him an English newspaper.

Letter from WSC to William Darling, message to officers and men attending 9th Scottish Divisison reunion [carbon].

Letter from Edward Marsh, PS to J H Thomas, Dominions Office, to WSC, sending note on the financial arrangements between the United Kingdom and the Irish Free State [later Ireland] Governments.

Cutting from the "Daily Telegraph": reminiscences of Colonel Deneys Reitz of South Africa including story of WSC inadvertently flooding the British front line when he was serving on the Western Front.

Letter from [Violet Pearman] to the editor of the "Daily Telegraph" denying that WSC tried to dam the Cojeul River when serving on the Western Front. Carbon typescript copy.

Hansard report of WSC's speech on the War Situation: subjects covered include fighting in the Ardennes, the Soviet advance in Germany, the campaign in Burma [later Myanmar] and particularly the Civil War in Greece. Annotated in blue crayon.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] describing his arrival and his impressions of the regiment and the "military existence".

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] discussing arrangements for paying for his outfit, reporting that his name has appeared in the Gazette, that he finds the riding school "fearfully severe" and is suffering from stiffness.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he says that he is suffering from stiffness and reports that he had been put in charge of 80 or 90 horses.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] discussing financial affairs and his search for a charger; saying that he had made friends and that Dudley Marjoribanks [later 3rd Lord Tweedmouth] has been sent to Canada because of an "inconvenient desire" for an actress.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] describing the funeral of [Elizabeth] Everest and his sadness at her death. He says that he is looking forward to the time that he has a home, reports that he is "getting on extraordinarily well" and comments on the stigma attached to those who are forced to leave a regiment through unpopularity.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mummy" [Lady Randolph Churchill] in which he expresses his approval of her plan to visit Switzerland; describes the effect of the arrival of a new Inspector General of Cavalry; and makes observations on a speech made by "Sunny" [Charles, 9th Duke of Marlborough], which he thinks would have impressed [Lord Randolph Churchill], and on the "game of politics" and his conviction that the army is not his "metier".

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he expresses his approval of her plan to visit Switzerland with "Jack" [John S Churchill]; describes the "mental stagnation" caused by life in the army, which he alleviates by reading speeches by [Lord Randolph Churchill], his intention to study economics or modern history, and a meeting with [Henry] Norris.

Letter from WSC (4th Hussars, Hounslow [Middlesex]) to "Mamma" [Lady Randolph Churchill] informing her of his decision to go to America and Havana [Cuba] which he anticipates will not cost him more than o90.

Letter from WSC (4th Hussars [Hounslow, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he describes arrangements made by [1st] Lord Wolsey for his visit to Cuba.

Letter from WSC (Bachelors' Club, Hamilton Place [London]) to "Mamma" [Lady Randolph Churchill] informing her that the War Office have given him permission to go to Cuba and that he has been instructed to collect information on the efficacy of a new bullet. He also says that he intends to buy Havana cigars and that he has discussed Cuba with Tito Holden.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses the legal action to be taken over a fraud [perpetrated on them by James Cruickshank], comments on [Henry Dupre] Labouchere and [James] Welldon's opinions [about a scandal in the 4th Hussars in which WSC was implicated], describes his daily routine at Bangalore and says that he is looking forward to a shooting expedition with Hugo [Baring].