Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that he has visited the swimming baths and asks her to send him autographs.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that Miss Thomson thinks that he should not return home to attend the Jubilee and asks her to write to persuade her to the contrary, commenting "I am in a ferment about coming home".

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] begging her to write to Miss Thomson to persuade her to allow him to attend the Jubilee and including his suggestions for the content of her letter Illustrated with drawings of soldiers and a face. Envelope present.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] informing her of his safe arrival, asking her not to let his bad behaviour influence his summer holidays and reporting that he has made good progress with Euclid.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he reports that he is doing well in Euclid, Greek, Latin and swimming and asks her to send him "Jess".

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] thanking her for her letter and reporting that he is going to Bramber [West Sussex] for the "annual treat" and that his Greek has improved and he has made progress with Euclid.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking for money, books and autographs and saying that he hopes she is not intending to employ a tutor and "make my holiday miserable".

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is looking forward to his holidays and asks whether "Bertie" Roose may accompany him and requests books, autographs and money.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mummy" [Lady Randolph Churchill] thanking her for sending him autographs and money, commenting that he "did not enjoy the letter quite so much" and asking her not to force him to work during his holidays.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] informing her of the progress of his school examinations.

Letter from WSC (7 South Grove Terrace, Ventnor, I[sle of] W[ight]) to "Mamma" [Lady Randolph Churchill] informing her of his safe arrival The letter is addressed and dated in the hand of Elizabeth Everest.

Letter from WSC (29 & 30 Brunswick Road [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] informing her of his safe arrival and that Aunt Clara [Clara Frewen, earlier Clara Jerome] had taken him to the [Devil's] Dyke. Envelope present.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] thanking her for sending him a speech by [Lord Randolph Churchill], anticipating that he will be placed near the top of the class in a recent ancient history examination and reporting that he has been placed top in algebra and history.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he says that he has read part of [Lord Randolph Churchill's] speech, reminds her to send him a copy of "She" and details his marks for conduct.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he asks where [Lord Randolph Churchill] is and describes his financial situation and progress at swimming and with Euclid.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he reminds her to send him a copy of "She" and says that he is contemplating writing a play to be performed at Christmas.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lord Randolph Churchill] in which he expresses his pleasure that he is going to Harrow [School] rather than Winchester [School]; discusses his progress with Euclid, arithmetic and Greek; reports that he is to play roles in plays by Moliere and Aristophanes and says that he wished that his father could attend the distribution of prizes.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he reports on his progress with Greek, Euclid and Latin.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] saying that he has written to a boy at Harrow School and obtained information about the school and its entrance examination and describing underwater swimming and a concert at which George Grossmith and Weedon Grossmith performed.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he would like her and [Lord Randolph Churchill] to attend the distribution of prizes, discusses his birthday party and the future examinations, and asks for more of her autographs as "there is rather a demand for them here".

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.

Photograph showing WSC as a toddler standing on a chair leaning against his mother. WSC has long curly hair and is wearing a velvet and lace dress, bead necklace and boots.

Portrait photograph showing John S Churchill and WSC, as young boys, leaning gently on Lady Randolph Churchill (centre).