The Epic Winston Churchill Story – The Early Years


On 30 November 1874, Churchill was born at his family's ancestral home in Blenheim Palace, Oxfordshire. Here is where he spent most of his childhood, both before he went to school and during the school holidays.

In fact, Blenheim Palace remained one of Churchill’s favorite places and where years later, he proposed to his wife, Clementine.

From the age of eight, Winston spent most of his days away in boarding schools in Ascot, Brighton, and finally Harrow School, a boarding school for boys.

Throughout his childhood, he wasn’t close to his parents and saw very little of them. Instead, Churchill and his younger brother, Jack, were brought up by his nanny, Mrs. Everest. Young Winston was extremely fond of Mrs. Everest, and he was devastated when she died when he was twenty-one years old.

Young Winston Churchill

Despite the fact that he had been born into a lineage of English aristocrat-politicians— starting from the mid 17th century 1st duke of Marlborough, John Churchill—nothing in his childhood suggested he would end up as one of the greatest statesmen of the 20th century. For one, his academic record at Harrow prep school wasn't the least bit impressive. 

In fact, a letter from the assistant master sent to Churchill’s mother, Lady Randolph, in July 1888 detailed many of his academic shortcomings, including forgetfulness, carelessness, and a lack of punctuality. 

But despite this, he possessed a remarkable ability to memories lines(something that served him greatly later in life during his monumental public speeches). He entered a school competition and won a prize for reciting from memory 1,200 lines from Macaulay’s long poem, Lays of Ancient Rome.

Life as a Soldier

He had a collection of some fifteen hundred Napoleonic era toy soldiers, which he marshaled in mock battle. From a young age, it was evident he had a deep interest in the military.  In fact, weeks after joining Harrow, he joined the Harrow Rifle Corps.

In 1892, he completed his education in Harrow, but his parents had already concluded that he wasn’t clever enough to apply to Cambridge or Oxford. Instead, his father instructed him to apply to join the military and Winston readily accepted.

At first, it didn't seem the military was a good choice for Churchill. His first two attempts resulted in failure. He left Harrow in December 1892 to study for a third attempt in London with Captain Walter James of the Royal Engineers, whose profession was to prepare young men for the Sandhurst exam.

Only on the third trial did he manage to pass the exam for the British Royal Military College. He soon found the military college much more suited to him and graduated two years later, twentieth out of a class of one hundred and thirty.

As a soldier, Winston was eager to be posted to ‘where the action was’. He initially had his eyes set on either Egypt or South Africa, but things didn’t go his way. He ended up being posted to India in the Autumn of 1896. However, the uneventful daily military routine in Bangalore soon bored him.

He soon landed a contract as a war correspondent for the Daily Telegraph in the colonial British North West frontier(modern-day Pakistan). This was one of the many examples of the love of adventure which marked Churchill all his life. He was a man who was definitely not afraid of the battlefield. 

His time here later became the subject of his first book, The Story of the Malakand Field Force, published in March 1898. There he wrote, “Bullets are not worth considering… I do not believe the Gods would create so potent a being as myself for so prosaic an ending.” This portrayed Winston for who he truly was— an extremely ambitious man who didn’t leave any room for fear or self-doubt.

Life after the Army

In 1899, Churchill left the Army and worked as a war correspondent for the Morning Post. The contract he negotiated with the newspaper made him the highest-paid war correspondent of the day(a salary of £250 a month plus all expenses).

This is because Churchill was an excellent reporter and understood history, so his analysis was considered insightful and brilliant. While reporting on the Boer War in South Africa, he was taken prisoner by the Boers during a reconnaissance mission in an armored military train.


Two weeks later, while the guards weren’t watching, Churchill scaled the prison fence in the dead of night, made a break for freedom, and safely navigate the 300-mile journey through enemy territory to reach Portuguese East Africa (now Mozambique).

Soon after his daring escape made headlines, and upon his return to Britain, he wrote about his experiences in the book London to Ladysmith via Pretoria (1900). Winston leveraged his newfound celebrity status to launch his political career.

In part two of this series, we will dive into Winston Churchill’s political journey to becoming the prime minister.

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