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Winston Churchill: Early and Journalist Years (Birth to Age 29)

by Ron Kurtus (updated 19 January 2022)

Winston Churchill (1874-1965) was a fascinating British politician, author and orator. His achievements started when he was a journalist while in his 20s as, continued when he was a politician during his 30s and 40s, and reached their peak when he became the Prime Minister of the United Kingdom, during the Second World War, while in his 60s. He is regarded as the greatest British leader of the 20th Century.

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Birth to 19 years (1874 - 1893)

Winston Churchill's parents were too busy for him after he was born, and he spent his early years in school rebelling. He also vowed to be tough, which resulted in almost getting killed.

1874: Born to prominent family

Winston Leonard Spencer Churchill was born 2 months premature on November 30, 1874 to Lord and Lady Randolph Churchill, at Blenheim Palace, the family's ancestral seat in Oxfordshire. Churchill's ancestry went back to the great English general John Churchill, the 1st Duke of Marlborough, in the 17th century.

He was the oldest son of Lord Randolph Henry Spencer Churchill, a British statesman who rose to be Chancellor of the Exchequer and leader of the House of Commons. His mother was an American, Jennie Jerome, the daughter of a New York financier.

Parents too busy for him

After his birth, Winston wasn't fed by his mother and was turned over to a wet nurse. His mother, Lady Randolph, was too busy with the fashionable social life to have much time for her baby. Lord Randolph was also too deeply involved in politics, as a Conservative leader, to show more than a passing interest in the boy.

Winston was raised by a Mrs. Everest, a nanny hired shortly after his birth. All the love and affection Winston received came from his nanny. He kept a picture of her in his bedroom until the day he died.

Young Winston

Young Winston

1882: Hated prep school

Young Winston attended Harrow School, on the outskirts of London, where he was schooled in the classics. He hated most of his school time at Harrow and had little interest in learning Latin, Greek or mathematics. But he did love poetry, history and writing English essays.

Winston was short in stature and very headstrong and stubborn. During his early school years, Churchill didn't get along well with other students. He recalled how he had to hide behind a tree when some other boys threw cricket balls at him. After this experience, he vowed to be as tough as anybody could be. He also practiced making fierce expressions to try to scare his opponents.

He later entered the Royal Military College at Sandhurst, from which he graduated with honors.

1892: Nearly died

When he was 18 in 1892, he nearly killed himself by jumping from a bridge to avoid being caught by his cousin and brother who were chasing him. He fell 29 feet, ruptured a kidney, was unconscious for 3 days and unable to work for nearly 2 months.

Ages 20 - 29 years (1894 - 1903)

As an adult, Churchill stood 5 foot 6½ inches tall. He had an exciting life while in his 20s. He was an army officer, a journalist, an author of five books, a war hero, and a politician. These achievements gave indication that he was destined for greatness.

1894: Commissioned in army

In 1894, when he was 20 years old, Winston's father died. Shortly afterwards, Churchill was commissioned as a second lieutenant in the 4th Queen's Own Hussars, a regiment of the British army.

1895: Wrote for newspaper

As he turned 21, Churchill spent his first military leave on assignment for a London newspaper. He traveled to Cuba in order to accompany the Spanish army, which was then attempting to stop a rebellion. This seems to be quite a good assignment for a 21-year-old. Churchill's writing ability must have impressed the newspaper publisher. His family connections also probably played a part in the assignment.

Later, after his regiment was sent to India in 1896, he secured a temporary transfer to the turbulent North-West Frontier, where a tribal insurrection was under way.

1896: Had books published

At age 22 in 1896, the Churchill compiled the dispatches he wrote for the Daily Telegraph newspaper into his first book, The Story of the Malakand Field Force. It seems somewhat unusual for an army lieutenant to be reporting to a newspaper while on duty, unless it was his military job or some "special" arrangements were made to allow him to do this.


When he was 23, Churchill went to Egypt attached to the 21st Lancers and took part in the re-conquest of the Sudan. During the Battle of Omdurman, Churchill participated in one of the last cavalry charges in British military history.


The next year, Churchill again wrote a book based on his newspaper dispatches. The River War was the most substantial work he wrote before entering Parliament.

Resigned commission

That year he resigned his army commission so that he could independently pursue his career in journalism without having to apply for transfers or military assignments. He also wanted to go into politics and at 24 ran for a seat in Parliament as a Conservative candidate. He was not elected.

Captured while covering war

Winston then went to South Africa to cover the Boer War as a journalist. The war had just broken out between Britain and the Boers, descendants of Dutch settlers. He was captured by the Boers and imprisoned. He managed to escape from prison and took the railroad into Portuguese East Africa. This feat made him a national hero.

1899: Wrote 2 more books

In 1899, when he was 25, Churchill returned to South Africa to write about the war. His newspaper dispatches were reprinted in two books, London to Ladysmith via Pretoria and Ian Hamilton's March.

1900: Elected to the House of Commons

When Churchill returned to England in 1900, his South African exploits had made him famous, and he was elected to the House of Commons. Though he was a Conservative, he criticized military spending and supported free trade. This soon resulted in a conflict with the Conservative leadership, who supported large military budgets and protective tariffs.

Churchill also continued writing. His political ambition was evident in his sole novel, Savrola which was published in 1900. In the book, the hero leads a democratic revolution in an imaginary country in the Balkans, only to see the revolution escape from his control.


In 1903, at age 29, he changed political parties to take a seat with the Liberal Party.


In his first 29 years, Winston Churchill developed into a prolific journalist and writer, as well as an adventurer. His family connections probably were a large factor in getting good military assignments, be he still showed the talent and drive to succeed at what he did on his own merits.

Use Churchill's life to inspire yourself to greatness

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