Letter from "Jack" [John] S Churchill (45 Rue des Missionnaires, Versailles [France]) to "Mama" [Lady Randolph Churchill] in which he expresses pleasure at the news of WSC's success, complains about his ears and says that he is looking forward to returning home.

Letter from "Jack" [John S Churchill] (35A Great Cumberland Place [London]) to "Mama" [Lady Randolph Churchill] in which he says that Moreton [Frewen] thinks that she should send WSC's letter to be published. Envelope present.

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.

Letter from [Albert Edward, Prince of Wales](Cercle de la Mediterranee, Nice[France]) to [Lady Randolph Churchill] in which he thanks her for her letter; says that he has seen his brother [the Duke of Connaught and Strathearn]; comments [on her relationship with George Cornwallis-West] "it is a pity that you have got yourself so talked about -& remember you are not 25!"; and refers to WSC's book ["The Story of the Malakand Field Force"]. Envelope present.

Letter from [Albert Edward, Prince of Wales](Mar Lodge, Braemar [Aberdeenshire, Scotland]) to [Lady Randolph Churchill] in which he thanks her for copying out a letter by WSC about his escape [from the Boers] which he describes as "most interesting" and says that he hopes that her ankle is better. Envelope present.

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 Lord Randolph Churchill to [Lady Randolph Churchill] thanking her for her letter and describing the "Ruin" as "out of order". He expresses the hope that [Elizabeth] Everest's friends are "respectable" and asks [Lady Randolph] to instruct [Elizabeth Everest] not to allow WSC to play with other children, and says that he is feeling better.

Letter from Lord Randolph Churchill to [Lady Randolph Churchill] including his lack of success at fishing and a request that she give orders for WSC's hair to be cut short.

Letter from Lord Randolph Churchill (Blenheim Palace) to [Lady Randolph Churchill] thanking her for her letters and remarking on [a letter] from WSC. He also discusses: the future marriage of [Lord] Curzon [later 4th Lord Howe] to "Georgie" [Lady Georgiana Churchill, later Lady Curzon and Lady Howe] which he describes as "brilliant"; his poor health; and his opinion that it would be undesirable for her to have dinner with Mrs Beauclere alone; and arrangements for moving into a house.

Letter from Lord Randolph Churchill (29 St James' Place [London]) to [Lady Randolph Churchill] including: the annoyance of [Frances, Duchess of Marlborough] at [Lady Randolph] attending a ball; his approval of [his new footman] Frederick; a fight between [20th Lord] Shrewsbury [and Talbot] and [Alfred] Mundy; a planned visit to the zoological [society] by Elizabeth Everest, WSC and [John S Churchill]; and Lord Randolph's opinion that WSC is bored of his holiday.

Letter from Lord Randolph Churchill (Villa Carmen, Monte Carlo [Monaco]) to [Lady Randolph Churchill] including: his apologies for forgetting her birthday; arrangements for her journey to Monte Carlo; Annie's position [Duchess of Roxburghe, earlier Lady Anne Churchill and Lady Bowmont] as Mistress of the Robes; observations on the dullness of letters from [Sir Henry Drummond] Wolff; and a request that she should give WSC some money before he returns to school.