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 in the south of France. Churchill painted at least two portraits of Castlerosse. Following the revival of his political career, in the late 1930s, Churchill ended the relationship. In the late 1950s, Castlerosse's love letters to Churchill were revealed to Clementine. Churchill's relationship with Castlerosse was the subject of a documentary shown on Channel 4, on 4 March 2018. Churchill was christened on December 27, 1874, in the chapel of Blenheim Palace, and was raised in the Church of England; however, his religious beliefs as an adult have been described as agnostic. A scholarly article published in 2013 sums up