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 Frederick Churchill Guest Winston Frederick Churchill Guest Winston Frederick Churchill Guest (May 20, 1906 – October 25, 1982), was an Anglo-American polo champion and a member of the Guest family of Britain. Winston Frederick Churchill Guest was born on May 20, 1906, to Frederick Guest (1875–1937), a British politician, and Amy Phipps. His mother was the daughter of Henry Phipps, Jr., an American businessman and philanthropist. His paternal grandfather was Ivor Guest, 1st Baron Wimborne (1835–1914), a Welsh industrialist. His great-grandfather was John Spencer-Churchill, 7th Duke of Marlborough, making him a second cousin of British Prime Minister Winston Churchill. His brother, Raymond R.