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 St Helier. Churchill found himself seated beside Clementine, and they soon began a lifelong romance. He proposed to Clementine during a house party at Blenheim Palace on 11 August 1908, in a small summer house known as the Temple of Diana. On 12 September 1908, he and Clementine were married in St. Margaret's, Westminster. A. G. Edwards, the Bishop of St Asaph, conducted the service. Their first child, Diana, was born in London on 11 July 1909. After the pregnancy, Clementine moved to Sussex to recover, while Diana stayed in London with her nanny. On 28 May 1911, their second