The true stories of 'Mad Jack' Churchill, the Second World War officer with a sword and longbow; 'Lord' Timothy Dexter, the barely literate merchant philosopher; and Lady Hester Stanhope, the aristocrat who made a new life in the Middle East.
History is full of people who refused to live as expected. These three stand out: a soldier who went to war with medieval weapons, a merchant whose terrible ideas kept making money, and an aristocrat who swapped London society for the mountains of Lebanon.
"Mad Jack" Churchill (1906 to 1996)
John Malcolm Thorpe Fleming Churchill was a British Army officer who fought in the Second World War carrying a broadsword, a longbow and a set of bagpipes. Before the war, he had left the army for a time, working as a newspaper editor and film extra, and he competed in archery.
During the retreat to Dunkirk in 1940, he is said to have shot a German soldier with an arrow, and he is often described as the only British soldier known to have killed an enemy with a longbow in the war. He later served with the Commandos, leading raids in Norway and fighting in Italy, and was decorated for gallantry.
In 1944, he was captured in Yugoslavia and sent to the Sachsenhausen concentration camp. He escaped with a fellow officer, was recaptured, and later escaped again, walking a long distance before reaching Allied forces. After the war, he served in Palestine, and he later became a keen surfer. He's remembered for his motto that any officer who goes into action without his sword is improperly dressed.
"Lord" Timothy Dexter (1747 to 1806)
Timothy Dexter was a businessman from Massachusetts who became rich through marriage, buying up devalued currency after the American Revolution, and a series of unlikely trades. According to his own accounts, rivals tricked him into shipping goods that seemed useless, such as warming pans to the tropical West Indies, only for the deals to succeed: the warming pans were supposedly sold as ladles for the molasses industry. Some of these stories may have been embellished, by Dexter among others.
Barely literate, he gave himself the title "Lord" and called himself "the greatest philosopher in the known world". He wrote a book, A Pickle for the Knowing Ones, with erratic spelling and almost no punctuation. In the second edition, he added a page of punctuation marks and told readers to add them as they pleased.
Dexter filled his grounds with wooden statues of famous figures, including himself, and reportedly faked his own death to see how people would react, then was angry that his wife didn't seem sad enough.
Lady Hester Stanhope (1776 to 1839)
Lady Hester Stanhope was the niece of Prime Minister William Pitt the Younger and ran his household, acting as his hostess, until his death in 1806. Restless in Britain, she left in 1810 and never returned.
After surviving a shipwreck, she travelled across the Middle East, often dressed in men's clothing, and rode into the ancient city of Palmyra, in what is now Syria, at the head of a caravan. In 1815, using a medieval manuscript she believed described buried treasure, she led a dig at Ashkelon. It is often called one of the first excavations in the region using written sources. No treasure was found, and she had a statue that was uncovered broken up.
She lived her final years in a remote former monastery in what is now Lebanon, where she exercised considerable local influence, took in refugees, and received curious European visitors. She died there in 1839, deeply in debt.
Why they are remembered?
Each refused the life expected of them, and each left records and stories that still surprise. Their legends have also grown in the retelling, so it's worth separating what's documented from what's anecdote.
Sources and further reading
- Wikipedia: Jack Churchill
- Wikipedia: Timothy Dexter
- Wikipedia: Lady Hester Stanhope
- Project Gutenberg: A Pickle for the Knowing Ones
Facts checked on 20 October 2026. Spotted an error? Tell us and we will correct it.