Lord Randolph Churchill's political career was meteoric. In 1886, at age thirty-seven, he was Chancellor of the Exchequer, the youngest to hold the office in over a hundred years. In less than six months, he resigned from the Cabinet over a matter of principle - his insistence on reducing defense spending. He never held high office again. "One could not grow up in my father's house... without understanding that there had been a great political disaster," said Winston. By May he was well immersed in the game: “Polo progresses steadily and I am I think improving fast,” he wrote. “It is the finest game in the world and I should almost be content to give up any ambition to play it well and often. But that will no doubt cease to be my view in a short time.”[15] This is an interesting contradiction to what Churchill himself wrote in My Early Life 30 years later. Here he said he had dislocated his shoulder when he first arrived in India. He described how he had grabbed an iron hand-hold ring at the quayside when the boat fell with a surge and he wrenched his shoulder. Thereafter, he wrote, he had to play polo with his arm strapped to his side. My mother always seemed to me a fairy princess: a radiant being possessed of limitless riches and power. Lord D'Abernon has described her as she was in these Irish days in words for which I am grateful. It means what it says. Mensa, a table. Mensa is a noun of the First Declension. There are five declensions. You have learnt the singular of the First Declension.'

Above all, however, Churchill hungered for a seat in Parliament. Here too he had received encouragement; a good response to speeches he’d made while on leave in England. An important friend, the Prince of Wales, told him, “Parliamentary and literary life is what would suit you best as the monotony of military life in an Indian station can have no attraction for you . . .”[31] Churchill had taken the entrance exam for Sandhurst three times before he passed. His final test score was too low for him to be accepted in the Infantry and qualified him only for the Cavalry — a great disappointment to his father, who remarked, 1 ‘In the infantry one has to keep a man; in the cavalry a man and a horse as well.”‘‘Little did he foresee not only one horse, but two official chargers and one or two hunters besides,” Churchill recalled later, “to say nothing of the string of polo ponies!”[6]

As Churchill tried to forge an alliance with the United States, Hitler made him the gift of another powerful ally – the Soviet Union. Despite his intense hatred of the Communists, Churchill had no hesitation in sending aid to Russia and defending Stalin in public. “If Hitler invaded Hell,” he once remarked, “I would at least make a favourable reference to the Devil in the House of Commons.” He describes his program to broaden his education as an officer in India with much spare time on his hands, especially in the heat of midday. His mother shipped books to him, and he read widely in history, philosophy, and ethics, at the moment when he was ready to absorb the information and keep it in his memory. He describes the effect of one incident in travelling by ship to his first posting in India that dislocated his shoulder, an injury that affected him the rest of his life, limiting his activity in sports and a few times in battle. One example of this was his reliance on a pistol instead of his cavalry sword in battle, with at least one situation where his injured shoulder would have led to him being a casualty instead of the victor. Churchill’s enormous reserves of energy and his legendary ability to exist on very little sleep gave him time to pursue a wide variety of interests outside the world of politics.

Churchill took up painting as an antidote to the anguish he felt over the Dardanelles disaster. Painting became a constant solace and preoccupation and he rarely spent a few days away from home without taking his canvas and brushes. Even during his tour of France’s Maginot Line in the middle of August 1939 Churchill managed to snatch a painting holiday with friends near Dreux. In one of these years we paid a visit to Emo Park, the seat of Lord Portarlington, who was explained to me as a sort of uncle. Of this place I can give very clear descriptions, though I have never been there since I was four or four and a half. The central point in my memory is a tall white stone tower which we reached after a considerable drive. I was told it had been blown up by Oliver Cromwell. I understood definitely that he had blown up all sorts of things and was therefore a very great man.The fateful day arrived. My mother took me to the station in a hansom cab. She gave me three half-crowns which I dropped on to the floor of the cab, and we had to scramble about in the straw to find them again. We only just caught the train. If we had missed it, it would have been the end of the world. However, we didn't, and the world went on. Churchill rose swiftly within the Liberal ranks and became a Cabinet Minister in 1908 – President of the Board of Trade. In this capacity and as Home Secretary (1910-11) he helped to lay the foundations of the post-1945 welfare state. However, Churchill could not be kept out of power for long and Lloyd George, anxious to draw on his talents and to spike his critical guns, soon re-appointed him to high office. Their relationship was not always a comfortable one, particularly when Churchill tried to involve Britain in a crusade against the Bolsheviks in Russia after the Great War. For young gentlemen of Winston's social class only certain professions were considered suitable. The university was the gatekeeper to all but the military, and Winston's poor performance at school closed the university's doors to him.