Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] asking her to persuade "Papa" [Lord Randolph Churchill] to give him an allowance and saying that he has been waiting for a letter from his father, who he hopes will be pleased that he [WSC] has got into the infantry at Sandhurst.

Letter from WSC ([Royal Military College, Sandhurst, Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he explains that "Grandmamma" [Frances, Duchess of Marlborough] had not given him any money and that he had been forced to borrow some. He expresses his relief that "Papa" [Lord Randolph Churchill] is pleased that he [WSC] has got into the infantry.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] in which he says that he does "the model 'son' very well", reports that he will probably accept an invitation from [Samuel, 2nd] Lord Hindlip, and that he and "Jack" [John S Churchill] miss her very much and discusses financial arrangements.

Letter from WSC (Royal Military College, Sandhurst, [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he discusses arrangements for a dentist's appointment and comments that "Papa" [Lord Randolph Churchill] has not sent him his allowance and that [Elizabeth] Everest has not received a cheque.

Letter from WSC (Royal Military College, Sandhurst, [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he reports that he is doing well and that he hopes that his examination results will please "Papa" [Lord Randolph Churchill], asks her to send him money and wishes her success with her concert.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he thanks her for sending him a costume, discusses arrangements for her to visit him and asks her to send him money.

Letter from WSC (Hotel du Bar, Grindelwald [Switzerland]) to "Mamma" [Lady Randolph Churchill] describing his impressions of the scenery, reporting that he and "Jack" [John S Churchill] are being economical and that the rules for the Sandhurst entrance examination have been changed. He asks her to write and tell him how "Papa" [Lord Randolph Churchill] is and says that he is looking forward to her return.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] in which he describes his financial situation as "most unsatisfactory" and says that he has been forced to pawn several items; thanks her for sending him photographs of her and "Papa" [Lord Randolph Churchill] in which she says she looks beautiful and describes his plans for Christmas.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he explains the order he placed for her cigarettes and objects to her opinion of steeplechasing as "idiotic" and "fatal", gives details of his anticipated expenses and says that he is looking forward to seeing her in Paris [France].

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] discussing financial affairs and his search for a charger; saying that he had made friends and that Dudley Marjoribanks [later 3rd Lord Tweedmouth] has been sent to Canada because of an "inconvenient desire" for an actress.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] concerning financial affairs in which he details the amounts he has spent and asks her to send him money to buy a charger. He also reports that his leg is improving, that he has ridden in a point to point, comments that he is glad that he has made friends and discusses horse racing and the possibility that a colt may run under his name.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he discusses financial affairs and asks her to send him money, describes the wedding of Duchess Lily [Lady William Beresford, earlier Lilian, Duchess of Marlborough] to [Lord William Beresford] and a visit to Newmarket [Suffolk] where he saw the "Allotment colt".

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] thanking her for sending him a cheque and discussing financial affairs, reporting that he has met Prince Alfred of Cobury and the Duke of Connaught and on progress in buying a charger.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] discussing financial affairs and his embarrassment at not being able to pay his mess bill.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he discusses financial affairs and her possible visit.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he discusses financial affairs, the payment of his allowance and her irritation with him. He informs her that he is attending the levee of [Albert Edward, Prince of Wales] and describes the celebrations for Queen Victoria's birthday which will be attended by "Molly" [Adela] Hacket and his progress at polo.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he discusses financial affairs and his gratitude towards her, and says that he escorted the Duke of Cambridge at entertainments for the Shahzada [Nasrulla Khan] and describes the people he met who included [Albert Edward, Prince of Wales].

Letter from WSC (35a Great Cumberland Place [London]) to "Mamma" [Lady Randolph Churchill] including: discussion of financial affairs; concern at "Jack's" [John S Churchill's] illness; description of a dinner with "all the powers that be" including [Joseph] Chamberlain, Lord Wolseley, [Henry] Chaplin, Lord James and Sir Francis Jeune; observations on South African affairs and Cecil Rhodes' involvement; and a request to borrow money to buy a polo pony.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] including: the postponement of his leave; his decision to visit Sir Herbert Kitchener in Egypt; a request for letters of introduction; discussion of his reasons for wishing to return to England during his leave; financial affairs; reading and his gratitude at receiving copies of the Annual Register.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] informing her of his decision to go to Brindisi [Italy] as a special correspondent on the war between Turkey and Greece. He asks her to use her influence with the King of Greece and to obtain him a position as special correspondent and discusses financial affairs. Includes envelope.

Letter from WSC ("In the train near Dhond" [India] on the notepaper of the 4th Hussars) to "Mamma" [Lady Randolph Churchill] in which he says that he has received a letter from Sir Bindon Blood and is joining the Malakand Field Force as a correspondent. He discusses: his plans; the seriousness of the trouble; his novel ["Savrola"]; his future political career and financial affairs Part of the letter is written in pencil and one section is badly faded. Envelope present.