The title Duke of Windsor was created in the Peerage of the United Kingdom in 1937 for Prince Edward, the former King Edward VIII, following his abdication in December 1936. The dukedom takes its name from the town where Windsor Castle, a residence of English monarchs since the Norman Conquest, is situated. Windsor had been the house name of the Royal Family since 1917.

Edward had abdicated on 11 December 1936 so that he could marry the American divorcée Wallis Simpson, who became upon their marriage The Duchess of Windsor.

At the time of the abdication there was controversy as to how the ex-King should be titled – other possibilities were the Dukedoms of Cambridge or Connaught, though neither was likely because the Marquessate of Cambridge and the Dukedom of Connaught were both extant at the time. One of George III's younger sons had borne the title Duke of Sussex, but for unknown reasons that specific title has never been resurrected and, so far as is known, no consideration was given to conferring it upon the abdicated king in 1936. Although the Duke of Connaught was also Earl of Sussex, that title was not in active use as his heir Prince Arthur of Connaught was known as that. Nor do other available titles with Royal connections such as Kendal, Ross or Clarence appear to have been considered. One theory is that it was Prime Minister Stanley Baldwin's idea to create the title Duke of Windsor. Another is that the new King George VI brought up the idea of a title just after the abdication instrument was signed, and suggested using "the family name".

Edward VIII (Edward Albert Christian George Andrew Patrick David; later The Duke of Windsor; 23 June 1894 – 28 May 1972) was King of the United Kingdom and the Dominions of the British Commonwealth, and Emperor of India, from 20 January to 11 December 1936.

Before his accession to the throne, Edward was Prince of Wales and Duke of Cornwall and Rothesay. As a young man, he served in the British Armed Forces during the First World War and undertook several foreign tours on behalf of his father, George V. He was associated with a succession of older, married women but remained unmarried until after his abdication as king.

Edward became king when his father died in early 1936. Only months into his reign, he caused a constitutional crisis by proposing marriage to the American socialite Wallis Simpson, who had divorced her first husband and was seeking a divorce from her second. The prime ministers of the United Kingdom and the Dominions opposed the marriage, arguing that the people would never accept a divorced woman with two living ex-husbands as queen. Additionally, such a marriage would have conflicted with Edward's status as head of the Church of England, which opposed the remarriage of divorced people if their former spouses were still alive. Edward knew that the government led by British Prime Minister Stanley Baldwin would resign if the marriage went ahead, which could have dragged the king into a general election and would ruin his status as a politically neutral constitutional monarch. Rather than end his relationship with Simpson, Edward abdicated. He was succeeded by his younger brother Albert, who chose the regnal name George VI. With a reign of 326 days, Edward was one of the shortest-reigning monarchs in British and Commonwealth history. He was never crowned.

Sir Winston Leonard Spencer-Churchill, KG, OM, CH, TD, PC, DL, FRS, Hon. RA (30 November 1874 – 24 January 1965) was a British Conservative politician and statesman known for his leadership of the United Kingdom during the Second World War. Widely regarded as one of the greatest wartime leaders of the century, he served as Prime Minister twice (1940–45 and 1951–55). A noted statesman and orator, Churchill was also an officer in the British Army, a historian, a writer, and an artist. He is the only British prime minister to have received the Nobel Prize in Literature, and was the first person to be made an Honorary Citizen of the United States.

Churchill was born into the aristocratic family of the Dukes of Marlborough. His father, Lord Randolph Churchill, was a charismatic politician who served as Chancellor of the Exchequer; his mother, Jenny Jerome, was an American socialite. As a young army officer, he saw action in British India, the Sudan, and the Second Boer War. He gained fame as a war correspondent and wrote books about his campaigns.