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 party at Blenheim Palace on 11 August 1908, in a small summer house known as the Temple of Diana. On 12 September 1908, Winston and Clementine were married in St. Margaret's, Westminster, and thereafter made their home in London. They had five children: Diana (1909–1963); Randolph (1911–1968); Sarah (1914–1982); Marigold (1918–1921); and Mary (1922–2014). Only Mary, the youngest, shared their parents' longevity, the others all dying before reaching the age of 70: Marigold died at the age of two, and the other three (Diana, Sarah, and Randolph) all died in their 50s and 60s. The Churchills' marriage was close and