Winston Churchill, the emblematic British wartime leader is instantly recognisable by his cigar, hat, trenchcoat, and imposing frame.



Sir Winston Leonard Spencer Churchill was known for his domineering presence, sharp wit, and uncompromising resilience in the face of adversity, when lesser men would falter. His epic speeches, often paraphrased and parodied, rival Shakespeare and Dickens in their cultural resonance in popular perceptions of Britishness exported across the globe. Often a difficult man, his razor-sharp tongue would frequently get him into trouble, particularly amongst political rivals and the opposite sex.

His role in supporting innovative technological military solutions, including the development of the tank and his recognition of the importance of aerial warfare, are well documented by commentators and historians alike.

Perhaps less well known are his American ancestry, his animated primate impressions and his prolific artistic output.

Military History Monthly examines ten obscure Churchill facts, which may shed some light on the twentieth-century figure.

1. British Bulldog?

Churchill, the ‘British Bulldog’ – and symbol of all things British – is in fact half-American. Churchill’s English roots are undisputed; indeed, his paternal ancestry, courtesy of his father Lord Randolph Churchill, can be traced back to the illustrious Dukes of Marlborough. However, his American heritage is equally impressive. His mother, Jennie Jerome, was the daughter of the American millionaire Leonard Jerome.

As The Times has noted, his paternal grandmother was a relative of George Washington. According to one source, his family tree can be linked to George Herbert Walker Bush and son. Further cementing his American ties, Churchill was the first individual ever to be acknowledged as an Honorary Citizen of the United States.

Incidentally, the Churchill family motto is Fiel Pero Desdichado, meaning ‘Faithful but unfortunate’. Whilst seemingly an unusual choice of mantra, Winston appears to have bucked the trend of misfortune.

2. Impeccable timing – in life and death

One of Churchill’s most revered traits – at various stages, both a blessing and a curse – was a determination, bordering on stubbornness, to operate on his own terms. Whilst no doubt a coincidence, it would appear this applied to entrances and exits.

Churchill was born prematurely in a cloakroom at Blenheim Palace, where his expectant mother was attending a party. She was unable to reach a bedroom in time, before labour commenced. He died on the exact same day as his father (only 70 years later) at the age of 90, in January 1965.

3. Churchill the Artist

Churchill was a prolific painter, producing nearly 600 works throughout his lifetime. Sarah Thomas of Sotheby’s has commented “Churchill took up painting very late… He found relief from all the pressures of his work in his painting.” In December 2006, one piece, ‘View of Tinherir’ from 1951, sold at auction for a record £612,800. According to Thomas, however, it took him a while to master his trade: “His work does vary in quality… A lot of his paintings are pretty poor and amateur and full of splodges.”

4. Prisoner of War

In 1899, Churchill escaped a prisoner of war camp whilst a correspondent in South Africa, during the Boer War. The bounty on his head was 25 pounds. He returned home a hero, perhaps a taster of what was to come for the young Churchill.

5. Churchill the Historian

Winnie was a gifted writer, novelist and historian; in his lifetime, he published volume upon volume of works on the history of England and Europe, including A History of the English Speaking Peoples and, not least, his six-part epic collection, The Second World War.

His literary merit was officially recognised when he won the Nobel Prize for Literature in 1953 “for his historical and biographical presentations and for the scintillating oratory in which he has stood forth as a defender of human values.” Incidentally, he is still the only British Prime Minister to have won the prize.

6. Gorilla Warfare

According to his nephew, John Spencer Churchill, Winston did a good gorilla impression. In his 1961 book, Crowded Canvas, John writes “Few people can say they have seen the ex-First Lord of the Admiralty, crouching in the branches of an oak, baring his teeth and pounding his chest.”

7. Man of the Half-Century

Churchill eclipsed Hitler by being named Time Magazine’s ‘Man of the Year’, not once but twice, in 1940 and again in 1949. The title is granted to men (and also women, since Wallis Simpson in 1936) who have significantly influenced the course of history. On his second time receiving the accolade, he was named ‘Man of the Half-Century’.

8. Churchill the Statesman

Churchill served under an impressive six monarchs: Queen Victoria, King Edward VII, King George V, King Edward VIII, King George VI and Queen Elizabeth II. Whilst serving his country, he held at least nine different offices.

9. School of Thought

As a schoolboy, Winston Churchill did not shine academically; he would often find himself in the bottom half of classes and examinations; his rebellious streak ending in numerous beatings. Few would have predicted a successful career in politics, least of all his headmaster at Harrow, who punished the young boy for destroying his beloved straw hat.

Realising university was not an option, and recognising Winston’s childhood love for toy soldiers, Churchill’s father decided to send him to Sandhurst Military Academy. It would, however, take three attempts before Winston passed the entrance examination.

10. Pillow Talk

Churchill was known to enjoy a siesta, a habit he adopted following his time in Cuba with Spanish forces in 1895. In later life, far from simply aiding his recuperation, Churchill’s bed often acted as his preferred location to discuss matters of great state importance.

Senior military advisors Sir Hastings Ismay and General Alan Brooke would invariably be summoned bedside, for a private audience with the Prime Minister. Reports claim a bespoke breakfast table to fit his bed was commissioned especially to accommodate his unusual conferences.

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