CHURCHILL, Winston S. Autograph letter signed ("Winston S. Churchill"), to Elaine, London, 10 October 1903. 1 page, 8vo, 105 Mount Street stationery. A short note about an upcoming legislative battle (most likely the fight over Free Trade which caused Churchill to abandon the Tories and join the Liberals): "The speech is capital: but we shall all have to fight vy hard." -- CHURCHILL. Typed letter signed ("W. S. Churchill") to H. C. Robbins, 31 October 1923. 1 page, 4to, 2 Sussex Square stationery. Marked 'Private and Confidential." Churchill tells Robbins, of The Press Association, that he will "address a meeting in the Free Trade Hall, Manchester, on November 16, under the auspices of the Free Trade Union. I hope you will arrange to report this speech fully. It will be about three columns, and will deal with the new political situation which has so suddenly developed..." This second letter, 20 years later, sees him moving back to the Conservative side of the House. After losing his seat to a Labour candidate in the December 1923 general election, Churchill stood as an ant-Socialist Conservative in the next general election that followed just 10 months later. He won handily, and to his surprise and pleasure, found himself being asked by Prime Minister Stanley Baldwin whether he would like to join the Cabinet as Chancellor of the Exchequer. "I should have liked to have answered, 'Will the bloody duck swim?'" Churchill told his biographer; "but as it was a formal and important conversation I replied, 'This fulfils my ambition. I still have my father's robe as Chancellor. I shall be proud to serve you in this splendid office'" (ODNB, quoting, Churchill and Gilbert, 5:59). Two fine letters on the crucial domestic issue that defined Churchill's early political career. (2)