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 affectionate despite the stresses of public life. During World War I, Clementine Churchill organised canteens for munitions workers on behalf of the Young Men's Christian Association (YMCA) in the North East Metropolitan Area of London, for which she was appointed a Commander of the Order of the British Empire (CBE) in 1918. In the 1930s, Clementine travelled without Winston aboard Lord Moyne's yacht, the "Rosaura", to exotic islands: Borneo, Celebes, the Moluccas, New Caledonia, and the New Hebrides. During this trip, many believe that she had an affair with Terence Philip, a wealthy art dealer seven years her junior. However,