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 (Cavalier) Winston Churchill (Cavalier) Sir Winston Churchill, MP FRS (18 April 1620 – 26 March 1688), known as the "Cavalier Colonel", was an English soldier, nobleman, historian, and politician. He was the father of John Churchill, 1st Duke of Marlborough, as well as an ancestor of his 20th-century namesake, Prime Minister Sir Winston Churchill. Churchill was the son of Sir John Churchill of Dorset, a lawyer and politician, and his wife Sarah Winston, daughter of Sir Henry Winston. Churchill was educated at St John's College, Oxford, but he left university without taking a degree. The main reason of it was the