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Letter from "Jack" John S Churchill (Elstree School) to WSC, asking WSC to send stamp book, and commenting on horse racing.

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Letter from "Jack" John S Churchill to WSC, on the result of The Derby, and asking him to send stamp book.

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Letter from "Jack" John S Churchill to WSC, on Jack's illness.

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Letter from "Jack" John S Churchill (Elstree School) to WSC, on WSC's visit to the Eton v. Harrow cricket match at Lord's and on Jack's new pony.

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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.

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Letter from "Jack" John S Churchill to WSC, on construction of a hammock.

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Letter from "Jack" John S Churchill to WSC, on disappointment that WSC did not visit him at Elstree.

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Letter from "Jack" [John S Churchill] (Elstree School) to WSC, account of meeting of hunt at Elstree, with sketches of huntsman and hounds.

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Letter from "Jack" [John S Churchill] (Elstree School) to WSC, birthday greetings.

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Letter from "Jack" John S Churchill (Canford Manor, Wimborne, [Dorset]) to WSC, on Jack's visit to Canford, with sketch of Lord Randolph Churchill "looking very well, but with a horrid beard".

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Letter from "Jack" [John S Churchill] (Elstree School, Herts) to WSC, on the Harrow Fencing Cup.

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Letter from "Jack" [John S Churchill] (Harrow School) to WSC, on WSC's failure in the Sandhurst entrance examination.

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Letter from "Jack" [John S Churchill] (Harrow School) to WSC, With little to report due to WSC's recent visit, commenting on WSC's good time in London.

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Letter from "Jack" John S Churchill to WSC, on the state of Jack's finances "I am bankrupt".

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Letter from "Jack" [John S Churchill] (Harrow School) to WSC, school news, regretting that WSC would not be visiting, and commenting on report of speech by Lord Randolph Churchill in The Times.

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Letter from "Jack" [John S Churchill] to WSC, asking WSC not to send him a birthday present, and asking him to save his money until they were at home together.

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Letter from "Jack" [John S Churchill] to Lady Randolph Churchill, on outbreak of scarlet fever at Harrow, Jack's birthday, and WSC's visit to Harrow.

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Letter from "Jack" [John S Churchill] to Lady Randolph Churchill, on WSC's typewriter and on report of speech by Lord Randolph Churchill in the Daily Graphic.

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Letter from Lord Randolph Churchill, 2 Connaught Place, London to WSC, thanks for letters containing news of Harrow, also commenting on the death of "poor Daisy" and sending postal order for 21s.

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Letter from Lord Randolph Churchill, 2 Connaught Place, London to WSC, on the need for WSC to return to Harrow a week early to prepare for the Sandhurst entrance examination, with Lord Randolph's reminiscences about his final examinations at Oxford. Also commenting on the death of the Duke of Clarence "one Of the saddest events I have ever known".

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Letter from Lord Randolph Churchill, 2 Connaught Place, London to WSC, complaining about WSC's spending "I think you have got through about £10 this term. This cannot last, & if you are not more careful should you get into the army six months of it will see you in the Bankruptcy Court".

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Letter from Lord Randolph Churchill, 50 Grosvenor Square, London to WSC and John S Churchill, on Lady Randolph's illness and on the death of his brother-in-law, the Duke of Roxburgh.

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Letter from Lord Randolph Churchill, 50 Grosvenor Square, London to WSC, on WSC's visit to London and on Lady Randolph's illness.

Scope and Contents Letter from Lord Randolph Churchill, Kissingen, to WSC, on WSC's disappointing performance in the Sandhurst entrance examination, particularly on WSC's failure to pass well enough to join an infantry regiment, and the extra expense of a commission in the cavalry. Stating that he would not allow him to remain in the Cavalry, and that as soon as possible he would arrange his transfer to an infantry regiment. "I am certain that if you cannot prevent yourself from leading the idle useless...

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Letter from Lord Randolph Churchill, Le Nid, Monte Carlo, Monaco, to WSC, urging him to work hard at Sandhurst - to "keep the standard up & keep raising"...Pull yourself together & keep yourself well abreast & even ahead of those you are competing with..Keep down the smoking, keep down the drink & go to bed as early as you can" With postscript suggesting that he should substitute "father" for "papa" in future letters.