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Churchill served under six monarchs - Queen Victoria, King Edward VII, King George V, King Edward VIII, King George VI and Queen Elizabeth II.
- Churchill took up cigar smoking in 1895 while accompanying Spanish forces in Cuba, where he had gone both as a military observer and journalist. It was in Cuba that he also acquired the habit of taking a daily siesta.
- Churchill was a prolific author and journalist. His first book, The Story of the Malakand Field Force 1897, about his experiences on the Northwest Frontier of India, was published in 1898, one of forty titles published in over sixty volumes during his lifetime. Churchill was awarded the Nobel Prize for Literature in 1953.
- Churchill was not the natural successor to Chamberlain as Prime Minister in May 1940. Lord Halifax, the Foreign Secretary, was the preferred choice of the Conservative Party, the King and Queen and Chamberlain himself. But Halifax recognised that he lacked the necessary qualities to lead Britain in war. Churchill was the only possibility once Halifax had ruled himself out.
- Within fifty years of Churchill's life there were radical changes in the technology of war. Churchill took part in the last great cavalry charge at the Battle of Omdurman on 2 September 1898 during the Sudan campaign. During the Second World War, as Prime Minister, he set Britain on the road to becoming a nuclear power.
- Churchill would regularly wake at about 8.30am, have a cigar in bed and then hold court sitting propped up in bed. He would read all the major daily newspapers, study the papers in his Prime Ministerial box, give dictation to his secretaries and hold discussions with senior military advisors such as Sir Hastings Ismay and General Alan Brooke. A breakfast table which was specially made to fit over Churchill's bed can be seen in the Cabinet War Rooms.
- Meal times were seldom changed and both lunch and dinner would routinely be accompanied by champagne. A mid-afternoon nap, followed by a bath were part of his daily regime, and undoubtedly gave Churchill his legendary ability to work until 3 or 4am, totally oblivious to the hunger or fatigue of those around him. He would often hold meetings at midnight and was in the habit of venturing up on to the roof of what is now the Treasury building to watch the enemy bombers attacking London.
- In December 1931, Churchill, while on a lecture tour of the United States, was hit by a car in New York and was nearly killed.
- Churchill contested twenty-one election campaigns from 1899 to 1959. He won sixteen of them. He served under thirteen Prime Ministers and was Prime Minister himself 1940-1945 and 1951-1955.
- Churchill helped lay the foundations of the welfare state as President of the Board of Trade 1908-1910 in Asquith's Liberal government. He advocated a minimum wage, state run industry and compulsory education, as well as the introduction of labour exchanges.