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 (1940–2010) Defence Association. He was also involved with the National Benevolent Fund for the Aged, as trustee from 1974 and chair from 1995 to 2010. He attempted to be selected as an MEP but was unsuccessful. Churchill was the son of Randolph Churchill (1911–1968), the only son of Sir Winston Churchill, and of Randolph's wife Pamela Digby (1920–1997), later to become famous as Pamela Harriman. His parents divorced in 1945. His father married June Osborne: their daughter was Arabella Churchill (1949–2007). Churchill's first marriage, in July 1964, was to Mary "Minnie" Caroline d'Erlanger, the daughter of the banker Sir Gerard John