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 sent five paintings by her late husband to auction. Only after her death was it discovered she had destroyed the famous Graham Sutherland portrait of her husband because Winston had not liked it. Lady Spencer-Churchill died at her London home, at 7 Princes Gate, Knightsbridge, of a heart attack on 12 December 1977. She was 92 years old and had outlived her husband by almost 13 years, as well as three of her five children. She is buried with her husband and children (with the exception of Marigold who is interred in Kensal Green Cemetery in London) at St Martin's