Letter from [Leonard Jerome] to Jennie [Lady Randolph Churchill] in which he says that he would increase the amount of money that he gives her from o2,000 if "I could feel that it would do you and [Lord] Randolph [Churchill] the slightest particle of good". He speaks of rearrangements to the Club House; financial arrangements connected with the lease of the Club; asks after WSC and asks Randolph to send him plans of stands for race courses.

Letter from Lord Randolph Churchill (Bedford Hotel, Brighton [East Sussex]) to [Lady Randolph Churchill] expressing his distress that WSC's fever has returned, enclosing a telegram [not present] and including directions for [Dr Robson] Roose as to where he is staying.

Letter from Lord Randolph Churchill (House of Commons) to [Lady Randolph Churchill] reporting that all their friends are glad to hear good news of WSC['s recovery from pneumonia], anticipating the resignation of "Joe" [Joseph Chamberlain], and comments that the political events with which he was involved have gone awry during his absence.

Letter from Lord Randolph Churchill (Novar, Evanton, Ross-shire [Ross and Cromarty, Scotland]) to [Lady Randolph Churchill] thanking her for her letters to him and requesting that she should thank WSC for his letter, approving of her decision to send "Jack" [John S Churchill] to Brighton [East Sussex] and predicting that [Sir] Charles Legard's letter [to the newspapers] will not harm him.

Letter from Lord Randolph Churchill (2 Connaught Place [London]) to [Lady Randolph Churchill] including the end of excitement in the French Chamber at the election of the new president; a meeting about the unemployed in [South] Paddington [London] which resulted in the establishment of a relief fund; his intention to see WSC when he visits Brighton [East Sussex] and an outline of his planned itinerary.

Letter from Lord Randolph Churchill (Tarbes [France]) to [Lady Randolph Churchill] including: his impressions of Tarbes, [the Marquis de] Breteuil's unease at the possible effect of the arrival of Jeanne Granier, a French actress, on the local electorate; his desire that WSC should read during his school holidays and his outrage at the marriage of the Duke of Montrose.

Letter from Lord Randolph Churchill (Tarbes [France]) to [Lady Randolph Churchill] including his impressions of the area, his hope that she may be able to see [Marquis de] Breteuil in Egham [Surrey] at the end of August and a request that she should send his love to [WSC and John S Churchill].

Letter from Lord Randolph Churchill (2 Connaught Place [London]) to [Lady Randolph Churchill] informing her that he intends to travel to Newmarket [Suffolk] that afternoon, advising her not to spend her money on a new brougham commenting "you seem rather like Winston [WSC] about money", and describing those he has met in London who include "Natty" [1st Lord Rothschild] and [Count Charles Kinsky].

Letter from Lord Randolph Churchill (Moulton Paddocks, Newmarket [Suffolk]) to [Lady Randolph Churchill] thanking her for her letter, describing his success at the races where he has "cleared a monkey [o500]", relating the friendliness of [Albert Edward] Prince of Wales returning a letter [not present] from WSC.

Letter from Lord Randolph Churchill (Royal Station Hotel, York) to [Lady Randolph Churchill] in which he tells her that he is down o300 through losses at the races; discusses the possibility that Sir [?] Jatton may buy his racehorse the Abbesse for o3,000 and enclosing a bill [not present] for WSC.

Letter from Lord Randolph Churchill (Moulton Paddocks, Newmarket [Suffolk]) to [Lady Randolph Churchill] describing a meeting with [Frances, Duchess of Marlborough] and Henry Fowler and his success at fishing. He says that he hopes to see her in London the following week, speculates on the success of various racehorses, and comments on a "capital letter" sent to him by WSC.

Letter from Lord Randolph Churchill (Banstead Manor, Newmarket [Suffolk]) to [Lady Randolph Churchill] reporting that [WSC and John S Churchill] have been good and that WSC rides well. He also relates his anger about arrangements for racing [his racehorse] Inverness and that WSC has made friends with the servants and is "full of local gossip".

Letter from Lord Randolph Churchill (Banstead Manor, Newmarket [Suffolk]) to [Lady Randolph Churchill] discussing financial affairs and his pleasure with a bay pony he has purchased, reporting that [Frances, Duchess of Marlborough, WSC and John S Churchill] are leaving to go to Cliefden [Cliveden, Buckinghamshire] where he will join them and enclosing newspaper cuttings [not present].

Letter from Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] reporting his safe arrival at Cliveden; describing an evening spent at Moulton [Paddocks, Newmarket, Suffolk] where "Lady G" was amusing about her lovers and his success at the races at Windsor [Berkshire]; and commenting that [WSC and John S Churchill] are well and "permit us to lead a fairly tranquil existence".

Letter from Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] discussing financial matters and asking her to be more careful; describing an expedition to Oxford with [Lady] Sarah [Churchill, later Sarah Wilson], WSC and "Jack" [John S Churchill] and "Jack's" first ride on his pony and discussing arrangements for her to come to Cliveden.

Letter from Lord Randolph Churchill (Le Grand Hotel, Monte Carlo [Monaco]) to [Lady Randolph Churchill] in which he describes the leisurely way he spends his days and a visit to Nice [France]; speculates on the likelihood of a dissolution of Parliament and asks her to wish WSC a happy birthday on his behalf.

Letter from Lord Randolph Churchill (Hotel Bristol, Rome [Italy]) to [Lady Randolph Churchill] in which he expresses his admiration for [Charles] Parnell's manifesto and speculates on the future of the Home Rule alliance and the likelihood of a dissolution of parliament. He describes an evening spent with [1st Lord] Dufferin [and Ava] and says that he has received a letter from WSC "giving a glowing account of himself".

Letter from Lord Randolph Churchill (Minich, "On the Nile" [Egypt]) to [Lady Randolph Churchill] describing his travels on the Nile and the boat he is travelling in. He asks her to thank Moreton [Frewen] for his telegram regarding the [gold crushing] "machine" and to wish [WSC and John S Churchill] a happy Christmas and asks about the results of WSC's examination.

Letter from Lord Randolph Churchill (Johannesburg [South Africa]) to [Lady Randolph Churchill] including: descriptions of his activities at game hunting, letters to the Daily Graphic, travel plans and details of his investments; his relief at not being involved with the Tories; and his pleasure at a "capital letter" he has received from WSC.