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,
Clementine Churchill eighteen. Clementine first met Winston in 1904 at a ball in Crewe House, home of the Earl and Countess of Crewe. In March 1908, they met again when seated side by side at a dinner party hosted by Lady St Helier, a distant relative of Clementine's. On their first brief encounter, Winston had recognised Clementine's beauty and distinction; now, after an evening spent in her company, he realised she was a girl of lively intelligence and great character. After five months of meeting each other at social events, as well as frequent correspondence, Winston proposed to Clementine during a house