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,
Sarah Churchill (actress) is said that Clementine (despite her disapproval) managed to be polite to both Vic Oliver and Anthony Beauchamp after Sarah had married them, but Winston Churchill remained rather cold and hostile toward both, considering them to be self-centred, superficial types who ultimately did not make his beloved Sarah either happy or fulfilled. Sarah's marriage to Beauchamp in America in 1949 came as a shock to her parents since they had neither been introduced to Beauchamp nor informed of the forthcoming marriage. Despite her stubborn rebellion against the expectations of both parents, Sarah reportedly felt guilty about this for the rest