Esmond Romilly Esmond Marcus David Romilly ( 10 June 1918 – 30 November 1941 ) was a British socialist and anti - fascist , now remembered mainly for his marriage to Jessica Mitford , one of the Mitford sisters . He was born to a family of public service and aristocratic descent , but at a young age became a communist and turned his back on the privileges of his birth . Family . Romilly was born in Huntingdon Park in Herefordshire , the son of Colonel Bertram Romilly , a soldier with a distinguished record in World War I and governor of Galilee in 1919 – 20 , when the country was under British military government , before it came under the British Mandate of Palestine . The Romillys were of Huguenot ( French Protestant ) origin and settled in England in 1701 . Esmond ' s mother was Nellie Hozier , daughter of Colonel Sir Henry Montague Hozier ( 1838 – 1907 ) and Lady Henrietta Blanche Hozier ( 1852 – 1925 ) , eldest daughter of David Graham Drummond Ogilvy , 10th Earl of Airlie . Nellie ' s sister Clementine married Winston Churchill , making Romilly the nephew by marriage of one of Britain ' s most prominent politicians . In 1923 another cousin , Hon . Charles Carnegie , had married Princess Maud , Countess of Southesk , a granddaughter of king Edward VII . It was frequently rumoured that the Hozier children were not fathered by Sir Henry , but rather by one of Henrietta ' s many lovers . Possible candidates for the paternity of Nellie and Clementine Hozier include Wilfrid Scawen Blunt , poet and anti - colonialist , or Capt . William George " Bay " Middleton , a noted horseman — Mary Soames , Clementine ’ s youngest child , takes this view . According to Clementine Churchill ’ s biographer , the father was Lord Redesdale , the husband of Henrietta ' s sister Clementina and grandfather of Esmond Romilly ' s future wife Jessica Mitford . If Redesdale was indeed Nellie Romilly ' s biological father , then Esmond ’ s mother and Jessica ’ s father were half - siblings . Jessica Mitford suggested in more than one letter to her family that Romilly might have been the illegitimate son of Winston Churchill , stating that she thought her late husband had resembled him . School . Educated at Wellington College , Romilly and his brother Giles refused to join the Officers ' Training Corps , distributed pacifist leaflets , and ultimately ran away from school . They published a book about the experience , " Out of Bounds : The Education of Giles and Esmond Romilly " ( 1935 ) . Esmond moved to London , working in a communist bookshop and founding a centre for other boys who had " escaped " from public schools . His activities at such a young age , of turning his back on class privilege so ostentatiously , won the attention of the newspapers , eager to report on the doings of Winston Churchill ' s " red nephew " . Spain . As the political situation across Europe continued to polarise , and with the storm clouds of war becoming ever more visible , Romilly ' s anti - fascism clashed increasingly with his pacifism . The outbreak of Spanish Civil War decided him . He bicycled to Marseille and joined the International Brigades , hoping he would be accepted despite his lack of military training . With a minimum of preparation , he and other ill - assorted British volunteers were thrown into the defence of Madrid as a machine - gun section with the German Thaelmann Battalion . Almost all his companions were killed ; he was invalided out with dysentery , and sent back to Britain to recover . While recuperating , he met and fell in love with his second cousin , Jessica Mitford , all the more ardent an anti - fascist for her elder sisters ' strong Nazi sympathies ( Diana married Oswald Mosley , leader of the British Union of Fascists , and Unity was a friend of Adolf Hitler ) . He had an offer from the " News Chronicle " to return to Spain as their correspondent and they created an elaborate plot that allowed her to accompany him . Romilly took up journalism , sending back war news , along with his friend Philip Toynbee , who later wrote his memoirs . After some legal difficulties , Romilly and Mitford , both 19 , married in Bayonne , France , on 18 May 1937 . He spent his honeymoon writing " Boadilla " , an account of his Spanish experiences . America . They returned to Britain , where Romilly joined the Labour Party and lived in the East End of London , then a poor working - class district . Their first daughter was born there , and died a few months later in a measles epidemic . The grieving couple eventually decided to move to the United States , where Romilly picked up a variety of odd jobs : selling silk stockings door to door , setting up a bar in Miami . They were perpetually short of cash . When Britain declared war on Germany in September 1939 Romilly remained in the USA , before moving in 1940 to Canada to volunteer . He served in the Royal Canadian Air Force and was shot down over the North Sea in 1941 after a bombing raid over Germany . He was 23 . He had two children with Jessica : It was rumoured during his life that Romilly was born of an affair between his mother and Winston Churchill . The news that his plane had gone missing in action was broken to his wife by Churchill personally ; Jessica Mitford took many months to accept that he had died .