In July, Winston was unsuccessful in writing an entrance examination for Sandhurst. He stood 390th out of 693 candidates. However, out of 415 candidates who wrote English History he stood eighteenth. Harrow’s Headmaster, the Rev. Welldon, advised him that “…in coming back to school you should be resolved to work not in fits and starts but with persistent industry…” and that the “…grammatical foundation of your languages is so uncertain that you lose marks which other boys gain.” Lord Randolph wrote the Duchess of Marlborough that if the boy failed another examination which he would write in November “I shall think of putting him in business.” When Winston returned to Harrow he was joined by his brother, Jack, who shared a room with him.
The Churchill family was in difficult financial straits and this forced them to give up 2 Connaught Place and move in with the Duchess of Marlborough at 50 Grosvenor Square. The Unionist Government was defeated that summer by the Gladstone Liberals and the Irish Nationalists. Lord Randolph sat in the Opposition backbenches. He commented that he preferred the Liberals and would have become one were it not for Home Rule.
Although Lord Randolph’s friends noted a new irritability in his character, he provided a rare and therefore special moment in his son’s life. In My Early Life, Churchill recalled this event: “Only once do I remember my father having breathed a word of complaint about his fortunes to me … He had reproved me for startling him by firing off a double-barrelled gun at a rabbit which had appeared on the lawn beneath his windows. He had been very angry and disturbed. Understanding at once that I was distressed, he took occasion to reassure me. I then had one of the three or four long intimate conversations with him which are all I can boast. He explained how old people were not always very considerate towards young people, that they were absorbed in their own affairs and might well speak roughly in sudden annoyance. He said he was glad I liked shooting, and that he had arranged for me to shoot on September 1 such partridges as our small property contained. Then he proceeded to talk to me in the most wonderful and captivating manner about school and going into the Army and the grown-up life which lay beyond. I listened spellbound to this sudden complete departure from his usual reserve, amazed at his intimate comprehension of all my affairs.”