Diana Churchill Diana Churchill Diana Spencer-Churchill (11 July 1909 – 20 October 1963) was the eldest daughter of British statesman Sir Winston Churchill and Clementine Churchill, Baroness Spencer-Churchill (née Hozier). She attended the Royal Academy of Dramatic Art, where she spent five terms, without any real intention to become an actress. On 12 December 1932, she married John Milner Bailey (15 June 1900 East Grinstead – 13 February 1946 Cape Town, South Africa) (became the Bailey baronet Sir John Milner Bailey, 2nd Bt), but the marriage was unsuccessful and they divorced in 1935. On 16 September 1935, she married the Conservative politician,
Winston Churchill as writer and at least two film scripts. John Gunther in 1939 estimated that he earned $100,000 a year ($ in ) from writing and lecturing, but that "of this he spends plenty". In 1899 Churchill became aware of the American novelist of the same name. He wrote to his American contemporary and offered to sign his own works "Winston Spencer Churchill", adding the first half of his full surname, Spencer-Churchill, which he did not otherwise use. In practice the middle name was turned into an initial, and his pen name subsequently appeared as "Winston S. Churchill". The two men met in