Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] concerning [James] Welldon's proposal that WSC should spend part of his holidays in France. WSC says that [Lord Randolph Churchill] considers the plan "utter nonsense" and argues that he should not be made to go to "a filthy den". In a postscript he comments "I feel less keen about the army every day. I think the church would suit me much better" and bids her to ask Count Kinsky about fireworks.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he asks her to write [concerning James Welldon's proposal that WSC should spend part of his holidays in France] and to send him some money, and reports that he has been made a Lance Corporal.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is looking forward to returning home and asks her to make arrangements for shooting at Banstead [Manor, Newmarket, Suffolk].

Letter from WSC ([Blenheim Palace]) to "Papa" [Lord Randolph Churchill] in which he says that he has been to the Lince with "Baby" [John S Churchill] where he picked hyacinths, and that he has seen a snake which [Elizabeth] Everest would not let him kill.

Drawing of WSC as a small child on a red sofa. Includes frame.

Letter from James Welldon ([Harrow School, Middlesex]) to Lady Randolph [Churchill] in which he discusses arrangements concerning WSC and an appointment with [Bernard] Minssen. He observes that WSC must work while he is staying with [Bernard] Minssen to improve his French, and urges that he should only be allowed to see limited numbers of English-speaking people and says that he is determined that WSC should be accepted by Sandhurst.

Letter from James Welldon (Harrow School [Middlesex]) to Lady Randolph [Churchill] in which he suggests that WSC should spend part of his holiday in France.

Letter from James Welldon (Harrow School [Middlesex]) to Lady Randolph [Churchill] suggesting that WSC should be sent to spend part of his holiday with Madame Elmering in Rouen, France and recommending that he should be urged to work hard to increase his chances of being accepted into Sandhurst.

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 John S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he says that "Winny" [WSC] was not allowed to visit him as he had broken a window, reports on his position in his form and says that he is looking forward to returning home for [cricket at] Lords.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] thanking her for allowing "Woom" [Elizabeth Everest] visit him and saying that the doctor has advised him that he should rest and that he would like to come home.

Letter from WSC ([Blenheim Palace]) to "Mamma" [Lady Randolph Churchill] in which he says that he is well and making progress with his lessons and that "Baby" [John S Churchill] is well.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he was surprised that she visited him in such bad weather and suggests that she might like to come to see the assault at arms or the grand concert. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses approval for a play at the Adelphi theatre [London] called "An English Rose" [by George Sims and Robert Buchanan]. Illustrated with a drawing of a Harrow schoolboy surrounded by luggage.

Letter from "Winny" [WSC] (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he asks her to write to him concerning patterns and to send him some "oof" [money].

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he reproaches her for not replying to his last three letters, asks her to make a surgeon's appointment for him, and discusses his intention to sell his bicycle to buy "Dodo", a bull dog.

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 WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] describing the death of [Elizabeth] Everest from peritonitis. He says that he employed a nurse and that he thinks that his visit "made her die happy" and that he visited "Jack" [John S Churchill] and discusses [Elizabeth Everest's] importance to him and Jack.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he gives the dates of the Easter holidays, describes the weather and a dog given to Miss Thomson and says that he is looking forward to going to Birmingham.

Letter from WSC ([Harrow School, Middlesex]) to Leonie [Leslie, formerly Leonie Jerome] in which he says that he has arrived safely, asks her whether she liked Drury Lane and says that "Jack" [John S Churchill] is well.

Letter from WSC ([2 Connaught Place, London]) to [Lady Randolph Churchill] in which he reports that he has received school prizes for English and Scripture, describes Christmas day and an unwelcome invitation to Blenheim Palace from [Frances, Duchess of Marlborough] and says that "it is very dull without you".

Letter from WSC (45 Hill Street, Berkeley Square [London]) to [Lady Randolph Churchill] informing her that [Elizabeth] Everest is ill and that he and "Jack" [John S Churchill] are staying with Dr [Robson] Roose and feel "destitute".

Letter from WSC (46 Grosvenor Square [London]) to [Lady Randolph Churchill] in which he reports that he has been staying with [Frances, Duchess of Marlborough], that [Elizabeth] Everest has recovered and that he has been given a toy theatre. He discusses plans to see her during term time and a visit to the theatre to see "[HMS] Pinafore" The letter is dated to 1887, but internal evidence suggests that it dates to 1888.