Winston did not have a successful term at Harrow School. The Assistant Master wrote Lady Randolph in July that her son was not ‘willfully troublesome; but his forgetfulness, carelessness, unpunctuality, and irregularity in every way, have really been serious” and requested that the matter be discussed at home. Even then, Winston was exhibiting a life-long habit of being “…regular in his irregularity.”
The teachers were, however, impressed by his ability and suggested that he ought to be at the top of his classes, whereas he was often at the bottom.” He is a remarkable boy in many ways, and it would be a thousand pities if such abilities were made useless by habitual negligence.” Winston’s defence was that he was “not lazy and untidy but careless and forgetful.”
His teachers were particularly pleased with his work in history and be was memorizing Macaulay’s Lays of Ancient Rome, and Shakespeare. He loved singing and claimed that he was one of the most prominent trebles in the school: “Of course I am so young that my voice has not yet broke and as trebles are rare I am one of the few.”
He was also “cheeky” in his relationships with his peers. One day he pushed a fellow student into the swimming pool. In retaliation the victim angrily threw him into the deepest part of the pool. On being told that the other student was a Sixth Form boy, Head of his House and a Champion at Gym, Winston apologized with the remark: “I am very sorry. I mistook you for a Fourth Form boy. You are so small.” Noting the boy’s chagrin at that comment, he quickly added: “My father, who is a great man, is also small.” The other boy was Leo Amery, afterwards a Cabinet colleague of Churchill’s.
Lord Randolph’s opposition to some Government policies was still prominent in the news. One focus of his resistance was the proposal to build a tunnel under the English Channel. In a House debate he ridiculed the suggestion that the tunnel could be destroyed in an emergency by the pressing of a button. “Imagine, ” said Lord Randolph, pointing at the Treasury Bench, “a Cabinet Council sitting in the War Office around the button. Fancy the present Cabinet gathered together to decide who should touch the button and when it should be touched.” The laughter in the House made him forget his final remark: “Fancy the Rt. Hon. gentleman, the member for Westminster [W.H. Smith] rising at length in his place with the words, ‘I beg to move that the button be now touched’.”