Letter from Jack Milbanke (17 Cliveden Place, Eaton Square) to WSC, offering help, and to intercede with Lady Randolph Churchill if he could be of any use.

Letter from "Jack" John S Churchill (Banstead Manor, Newmarket) to WSC, on their "den" which was dirty inside, but had withstood the weather well, and on the health of the animals.

Letter from Lady Randolph Churchill, 2 Connaught Place, London, to WSC, congratulations on obtaining Remove [into the First Division of the Fourth Form at Harrow], hoping that he would continue to work. Asking him to write at least twice a week.

Letter from Lady Randolph Churchill, 2 Connaught Place, London, to WSC, on his "very bad" school report from Harrow Describing his work as an "insult to his intelligence", and contrasting him to his brother Jack "who comes out at the head of his class every week".

Letter from Lady Randolph Churchill, Banstead, to WSC, apologies for not visiting him at Harrow, and advising him not to sell his bicycle and buy a bulldog puppy "a dog is sometimes a nuisance".

Letter from Lady Randolph Churchill, Iwerne Minster House, Blandford, to WSC, on his school report "You must try & have a better one next term as Papa will be back & will expect glowing accounts of yr work." Also commenting on a day's hunting, and "cutting a lovely somersault" at the 3rd fence.

Letter from John Milbanke, Depot, Royal Sussex Regiment, to WSC, on WSC's life at Harrow School, and success in the Army Preliminary Examination, and Milbanke's life in the Royal Sussex Regiment.

Letter from Charlotte Thomson to WSC, on Brunswick Road School, Brighton.

Letter from Louis Moriarty, Army Class Master, Harrow School, to WSC, on WSC's "very creditable" failure in the Sandhurst entrance examination. Stating that if he worked "earnestly and sensibly" he would pass in November.

Letter from Rev. James Welldon, Headmaster, Harrow School, to WSC, on his failure in the Sandhurst entrance examination. Urging him to work "not by fits and starts but with regular persistent industry". Commenting that the grammatical foundation of his language was so uncertain that he lost marks which other boys gained "You therefore have ground to make up as well as new ground to cover".

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she describes an evening with the de Mondys, reports that the baby [WSC] is better but sad that he is away and asks him to send her regards to [Lord] Blandford [later George, 8th Duke of Marlborough].

Letter from [Lady Randolph Churchill](Blenheim Palace) to [Lord Randolph Churchill] in which she expresses concern about the baby's [WSC's] cold; asks about his interview with Paula; informs him that she is to visit Warwick Castle and that [Lady] Rosamund [Churchill, later Lady Fellowes and Lady De Ramsey] is angry that he intends to throw away waistcoats which she made for him with [Lady] Fanny [Churchill, later Fanny, Lady Marjoriebanks and Lady Tweedmouth].

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she discusses household accounts and the servants; asks about the Hague [The Netherlands] and [Lord] Blandford [later George, 8th Duke of Marlborough] and reports that WSC is missing him.

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she says that she has seen Mrs Moulton, describes various items which she would like him to purchase and says that the baby [WSC] has been out for the first time.

Letter from [Lady Randolph Churchill](Blenheim Palace) to [Lord Randolph Churchill] in which she discusses the sale of their house; comments on his family's disapproval of their plan to go abroad; reports that the baby [WSC] looks pale and that she feels "melancholy".

Letter from [Lady Randolph Churchill](Blenheim Palace) to [Lord Randolph Churchill] in which she discusses the sale of a house in Charles Street; reports that "Mama" [Clara Jerome] is to remain in Paris [France] with Clara [Jerome, later Clara Frewen]; discusses plans to travel to Paris with him;and discusses the health of the baby [WSC].

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she says that she approves of his plans to find lodgings for the cook, discusses financial affairs, and reports that [WSC] is well and can walk unaided.

Letter from [Lady Randolph Churchill](Blenheim Palace) to [Lord Randolph Churchill] in which she comments on a visit to Warwick Castle which she describes as "quite my 'ideale' of a castle", says that WSC has a cold and that she is missing him.

Letter from [Lady Randolph Churchill](Paris [France]) to [Lord Randolph Churchill] in which she gives instructions for [Elizabeth] Everest and the care of the baby [WSC]; expresses approval for his letter to [John, 7th] Duke [of Marlborough concerning Lord Blandford, later George, 8th Duke of Marlborough]; comments on the behaviour of [W H] Trafford; discusses financial affairs and the attachment between Clara [Jerome, later Clara Frewen] and Prince de Claremont.

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects. Includes a note that WSC is "a regular 'pickle' in many ways.".

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects.

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects. Includes a comment that WSC "Does not quite understand the meaning of hard work".

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects.

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects. Includes a comment that WSC "is rather greedy at meals".