Letter from WSC (35A Great Cumberland Place [London]) to "Mamma" [Lady Randolph Churchill] in which he asks her to keep his secrets and those of others, not to bet or play cards as it will bring "the most terrible misery" and to organise a political dinner for him.

Letter from WSC (Ladysmith, South Africa) to "Mamma" [Lady Randolph Churchill] enclosing a letter [not present] and asking her to negotiate financial terms for a visit to the United States, commenting "o5,000 is not too much for such a labour and for making myself so cheap.".

Letter from WSC (105 Mount Street [London]) to "Mamma" [Lady Randolph Churchill] concerning arrangements for his lecture tour. He says that he hopes that [16th] Lord Derby will chair the Liverpool meeting, reports on the success of his lecture at Harrow [School, Middlesex] and details financial assistance provided for his election costs by "Sunny" [Charles, 9th Duke of Marlborough].

Letter from WSC (Chicago [United States] on the notepaper of 105 Mount Street) to George [Cornwallis-West] expressing pleasure at the news that George is to leave the army and describing the disadvantages of a career in the army. He comments on the lack of success of his lecture tour from which he has made o1,600 and on the fact that "Jack" [John S Churchill] is to continue living at 35A [Great Cumberland Place, London].

Letter from WSC (105 Mount Street [London]) to "Mama" [Lady Randolph Churchill] in which he explains that he has not been able to come and see her in Bournemouth as he has been invited to contest the Birmingham Central Division. He expresses concern for her health and for their finances.

Letter from WSC (Salisbury Hall, St Albans [Hertfordshire]) to "Mama" [Lady Randolph Churchill] marked "private" informing her of his decision not to leave for Scotland because of his progress with [his biography of Lord Randolph Churchill] and commenting on J[ohn] M[orley]'s encouragement with the book and his hopes to make 8-10,000 pounds from it.

Letter from WSC (Dalmeny House Edinburgh [Scotland]) to "Mama" [Lady Randolph Churchill] in which he says that he is glad she enjoyed herself at Sandringham, reports on the success of his speech in Glasgow [Lanarkshire, Scotland] and discusses financial affairs. Annotated "Five years since the armoured train!".

Letter from WSC (105 Mount Street [London]) to "Mama" [Lady Randolph Churchill] including: the success of his speech in Glasgow [Lanarkshire, Scotland]; financial affairs and his plans to see her before going to Manchester. Manuscript in the hand of Annette Anning signed by WSC.

Letter from WSC (105 Mount Street [London]) to "Mama" [Lady Randolph Churchill] in which he says that he has discussed her affairs with "Sunny" [Charles, 9th Duke of Marlborough] and asks her to write a letter authorising him to investigate the matter with Lumley, the solicitor. Manuscript in the hand of Annette Anning signed by WSC.

Letter from WSC (105 Mount Street [London]) to "Mamma" [Lady Randolph Churchill] in which he informs her that he will conduct the "Inquisition" [into her affairs] on 7 and 8 February and asks her to read the Manchester Guardian for reports of him and says that [5th Lord] Spencer has invited him to Althorp [Northamptonshire]. Manuscript in the hand of Annette Anning signed by WSC.

Letter from WSC (Blenheim Palace) to "Mama" [Lady Randolph Churchill] marked "private" inviting her to a meeting in Manchester at the Free Trade Hall at which Sir Edward Grey and Lord Durham are to speak and saying that he hopes to make a great deal of money [from his biography of Lord Randolph Churchill]. Envelope present.

Letter from Lord Randolph Churchill (Le Nid [Monte Carlo, Monaco]) to [Lady Randolph Churchill] describing a trip to Nice [France] and the people he has met who include "Ronny" [Ronald] Greville and attempts by the Duchess of Montrose to "take the Nid by storm". He also discusses WSC's riding expenses and asks her to draw WSC's attention to "expressions of authority".

Letter from Lord Randolph Churchill (Royal Station Hotel, York) to [Lady Randolph Churchill] in which he tells her that he is down o300 through losses at the races; discusses the possibility that Sir [?] Jatton may buy his racehorse the Abbesse for o3,000 and enclosing a bill [not present] for WSC.

Letter from Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] discussing financial matters and asking her to be more careful; describing an expedition to Oxford with [Lady] Sarah [Churchill, later Sarah Wilson], WSC and "Jack" [John S Churchill] and "Jack's" first ride on his pony and discussing arrangements for her to come to Cliveden.

Letter from WSC (29 [& 30] Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he asks for money as he has been "very extravagant" and has bought stamps and a stamp book.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking for a postal order of 10 shillings, relating the success of the second run of the school play and discussing arrangements for his return (which include a maid being turned out of his room).

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking her to send him a postal order and discussing the start of examinations and arrangements for his return home.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he reports that he has been unable to cash a postal order, describes an agricultural show and asks her to visit him.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] enclosing a photograph [not present] of himself and asking for money.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] asking her whether she will allow him to learn the violincello instead of the piano, speculating on the Conservatives electoral prospects and asking for money as he is "bankrupt".

Letter from "Winny" [WSC] (Prospects House, Skegness [Lincolnshire]) to "Mamma" [Lady Randolph Churchill] apologising for not writing previously and asking for money. Annotated with a note in the hand of Elizabeth Everest that "Master Winston" is continually requesting money which he wastes and advising that he should not be given any more money. Envelope present.