Trivia

Grandson of Winston Churchill and Clementine Churchill. Nephew of Diana Churchill, Sarah Churchill, and Lady Mary Soames. Cousin of Celia Sandys and Nicholas Soames.

Son of Randolph Churchill and Pamela Harriman.

Half-brother of Arabella Churchill and Brooke Hayward.

In 2005, a year of significant anniversaries in the UK, Winston holds the unique distinction of having direct ancestral links with no fewer than three of them. The first, the 60th anniversary of the end of World War II is obvious. The other two are through his mother, Pamela Beryl Digby Churchill Hayward Harriman (AKA Pamela Harriman). Her great grandfather's great grandfather was Captain Henry Digby of HMS Africa which played a significant part in the Battle of Trafalgar (200th anniversary) and, in turn, his great grandfather's great grandfather was Sir Everard Digby, one of the conspirators in the Gunpowder Plot (400th anniversary).

Born at Chequers, the official country residence of the Prime Minister, since at the time of his birth, his mother was married to Randolph Churchill, son of the then Prime Minister of The United Kingdom, Sir Winston Churchill.

His grandfather Sir Winston Churchill's papers were purchased by the government of the United Kingdom in 1995, utilizing £12 million (twelve million British Pounds) of National Lottery money. This transaction happened amid huge public controversy, due to the fact that because he (Winston Churchill) was himself a Conservative Member of the UK Parliament at the time. He was the principal beneficiary of Sir Winston Churchill's estate.

Grandfather of Serena Barbara and John (Randolph's children), and Henry (Marina's son).

Father of Randolph Leonard (b. 1965 - named for both his father Randolph Churchill, and his great-grandfather, Lord Randolph Henry Spencer-Churchill), Jennie (b. 1966 - named for his great grandmother, Lady Jennie Jerome Spencer-Churchill), Marina (b. 1967) and John Gerard (b. 1975).