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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.

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Letter from Lord Randolph Churchill, 50 Grosvenor Square, London, to WSC, on the success of WSC's riding instruction with Captain C H Burt, and recommending that he should visit Lord Randolph's dentist, Pritchard, of 9 Albemarle St., London.

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Telegram from Lord Randolph Churchill to WSC, asking WSC not to come up to London as Lord and Lady Randolph were going to Tring.

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Letter from Lord Randolph Churchill, 50 Grosvenor Square, London, to WSC, complaining about WSC's frequent visits to London from Sandhurst, forbidding him to come to London more than once a month, and encouraging him to study at weekends.

Scope and Contents Letter from Lord Randolph Churchill, 50 Grosvenor Square, London to WSC, complaining about WSC's "misuse" of the "very valuable watch" which had been given to him by Lord Randolph, stating that he would have to repay the repair costs of £3 17s. "I could not believe you could be such a young stupid. It is clear that you are not to be trusted with a valuable watch. Commenting that his brother Jack was "vastly your superior" "in all qualities of steadiness taking care of his things & never...

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Letter from Lord Randolph Churchill, 50 Grosvenor Square, to WSC, on WSC's visit to Colonel John Brabazon, 4th Hussars, at Aldershot, and his work at Sandhurst, telling him "not to trouble any more about the watch", [which WSC had damaged] as the rough work of Sandhurst was not suitable for a watch made by Dent. Also advising him not to "attend to moneylenders," put their letters into the waste paper basket".

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Letter from Lord Randolph Churchill, 50 Grosvenor Square, London, to WSC, sending cheque to cover WSC's allowance.

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Letter from Lord Randolph Churchill, 50 Grosvenor Square, To WSC, on visit to Lord Roberts at Grove Park, also on forthcoming visit of the Prince of Wales to Harrow School. Advising WSC to take care with his diet, "Eating fast, as you do is a fertile source of indigestion & heated blood, producing boils". Also advising him to address him as "Dear Father" rather than "Papa" in future letters.

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Letter from Lord Randolph Churchill, 50 Grosvenor Square, to WSC, criticising him for addressing him as "Papa" rather than "Father" in letters "This is idiotic".

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Letter from Lord Randolph Churchill to WSC, on the state of WSC's finances, and his "pedantic and overgrown schoolboy style of letter writing, and complaining about his use of a typewriter "an objectionable machine calculated to spoil your handwriting.

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Letter from Lord Randolph Churchill, Bar Harbour Malvern Hotel, Maine, to WSC, on Lord and Lady Randolph's visit to the United States and Canada, and on WSC's proposed visit to Germany.

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Letter from Lord Randolph Churchill, Hotel del Monte, California, to WSC, on WSC's desire to join the cavalry rather than the 60th Rifles, pointing out that the Duke of Cambridge would be extremely angry, and that he would also oppose the change strongly, also on Lord and Lady Randolph's visit to the United States, and forthcoming Voyage to Japan.

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Letter from Frances, Duchess of Marlborough, [WSC's grandmother], 50 Grosvenor Square, to WSC, family news, visit to the Gaiety Theatre to see Ruy Blas by A C Torr, picture of Lord Randolph Churchill in "Punch", and Lord Randolph's Temperance Bill.

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Letter from Frances, Duchess of Marlborough, Woodlands, Uxbridge, to WSC, family news.

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Letter from Frances, Duchess of Marlborough, Ramsey Abbey, Huntingdon to WSC, his success in the Sandhurst Entrance Examination, Lord and Lady Randolph's visit to Germany, and other family news.