Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that [James] Welldon has given his permission for WSC to go home for Sunday and begging her to let him have additional days at home and not to be angry with his "silly letters".

Letter from WSC ([Versailles, France]) to "Jack" [John S Churchill] thanking him for his letter and refusing his offer of money and describing toy soldiers which he has seen at the "Bon Marche".

Letter from Lord Randolph Churchill (Le Nid, Monte Carlo [Monaco]) to [Lady Randolph Churchill] enclosing a cheque and relating that he has received a letter from "Jack" [John S Churchill] and has written a letter of advice to WSC.

Letter from "Jack" [John] S Churchill (Harrow-on-the-Hill [Middlesex]) to [Lord Randolph Churchill] asking him when he will make the "promised Sunday visit" and informing him that WSC had promised to visit but had not come Covering letter at CHAR 28/12/71.

Letter from WSC (4th (The Queen's Own) Hussars, Bangalore [India]) to "Jack" [John S Churchill] discussing "Jack's" future career in the City [of London] as an "arrogant plutocrat".

Letter from Lord Randolph Churchill to [Lady Randolph Churchill] including: advice about whether she should go to Sandown [Isle of Wight]; the eagerness of [John, 7th Duke of Marlborough] that the quarrel between Lord Randolph and Cornelia [Lady Guest, later Lady Wimborne, earlier Lady Cornelia Churchill] should be resolved; the time of his arrival in London and his pleasure at receiving "such flourishing accounts" of WSC.

Letter from WSC (Balmoral Castle) to "Mamma" [Lady Randolph Churchill] in which he says that he has enjoyed his stay and that King [Edward VII] has treated him "vy kindly" and asks her to send him notes about [Lord Randolph Churchill].

Letter from [John S Churchill] ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] reporting that "Winney" [WSC] is going to take a medical examination and that he is hoping for a quiet day, commenting "I do not get much peace while he is here".

Letter from Lord Randolph Churchill (Tarbes [France]) to [Lady Randolph Churchill] including his impressions of the area, his hope that she may be able to see [Marquis de] Breteuil in Egham [Surrey] at the end of August and a request that she should send his love to [WSC and John S Churchill].

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] thanking her for her "epistle" and reporting that he has seen [Frances, Duchess of Marlborough].

Letter from "Jack" [John] S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he asks her to allow him to see "Winney" [WSC] during the holiday and to write to him.

Letter from "Jack" [John] S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he asks her whether "Winney" [WSC] will have to go to France during the holidays; asks her to let him see him and to send him some money; and discusses arrangements for his return home.

Letter from "Winny" [WSC] ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] describing the extent of an outbreak of measles at school and asking her to allow him to return home, commenting "I should have imagined that as 300 mamas & 300 papas like to have their 'offsprings' home you would like to have me".

Letter from Lord Randolph Churchill (Moulton Paddocks, Newmarket [Suffolk]) to [Lady Randolph Churchill] describing a meeting with [Frances, Duchess of Marlborough] and Henry Fowler and his success at fishing. He says that he hopes to see her in London the following week, speculates on the success of various racehorses, and comments on a "capital letter" sent to him by WSC.

Letter from "Jack" [John S] Churchill (St George's Terrace, Herne Bay [Kent]) to "Mamma" [Lady Randolph Churchill] in which he says that he is well, that he has received a letter from "Winnie" [WSC] and that he misses her.

Letter from "Jack" [John S Churchill] (Versailles [France]) to "Mama" [Lady Randolph Churchill] in which he says that he is glad that WSC will miss the war in Greece as "he will not be able to agitate about it", describes a concert and his progress at the piano and asks her to send him money and musical scores.

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] (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 George [Cornwallis-West](Arthur's, St James' Street [London]) to "Missie" [Lady Randolph Churchill] in which he discusses his forthcoming interview with [Colonel] Arthur Paget; says that he is devising schemes for the defence of London; and that "Jack" [John S Churchill] has "opened his heart" about Pamela [Plowden, later Pamela, Lady Lytton] and WSC.

Letter from George [Cornwallis-West](Invercauld, Ballater, Aberdeenshire [Scotland]) to "Missie" [Lady Randolph Churchill] discussing the possibility that they may marry. He observes that she changes her mind frequently, says that he will not marry her until he has more money, that he has quarrelled with many of his relations and friends and that WSC made "strong arguments" in favour of leaving matters as they are.

Contains accounts and maps of the First Duke of Marlborough's campaigns and general notes on eighteenth and nineteenth century history.