Winston Churchill as an MP in 1904

Officer Cadet To Lieutenant Colonel: Winston Churchill In The British Army

Winston Churchill as an MP in 1904

He’s a national icon and hero to many a politician, but much of what people know about Winston Churchill’s life concerns his later years in politics.

In contrast, what follows is a look at Churchill’s earlier military service by historian and writer Jacob F Field, whose book ‘D-Day in Numbers’ featured in our coverage of D-Day 75.

This coincides with the publication of his new book, ‘The Eccentric Mr Churchill’, which you can get here.

Article by Jacob F Field

Winston Churchill’s long involvement with the British Army did not begin well. 

His father had pushed him towards a military career because he believed he was not bright enough to study law. It took Winston three attempts to pass the entrance exam for Sandhurst and when he did pass, in August 1893, he did not get enough marks to qualify for training as an infantry officer, so was placed into the cavalry. 

This irritated his father because cavalry cadets required an additional £200 of kit per year. 

Luckily, as a result of other candidates dropping out, Winston was offered an infantry training place after all and he passed out with honours in December 1894, finishing eighth out of 150 classmates. 

Churchill as a seven-year-old boy
Churchill as a seven-year-old boy © IWM (ZZZ 7555D)

He was supposed to serve in the prestigious 60 Rifles but Winston was more attracted to the glamour of the cavalry, where promotions tended to be quicker and his small status would not be an issue. As such, Winston switched to 4 (Queen’s Own) Hussars, a socially elite regiment based in Aldershot.

However, Winston’s first taste of combat came not as a soldier, but as an observer, during the Cuban War of Independence. 

In November, 1895, Winston travelled across the Atlantic, arriving in Havana via New York and Florida. He was given permission to join the Spanish forces. Officially a ‘guest’, he could only use his weapons in self-defence. 

Winston spent seven weeks in Cuba, and experienced being under enemy fire for the first time, as well as witnessing a pitched battle. 

(In fact, the US and Britain had a brief dispute over the Venezuelan border that year, before the US went to war with Spain in 1898, invading Cuba in the process). 

The next trip abroad would be to India; in October 1896 Winston arrived at Bangalore, the new base for 4 Hussars. 

He was largely restless and unhappy there; his official duties were undemanding, taking only three hours per day and usually completed by 10.30am. His main priorities appeared to be playing polo (he was part of the victorious team in the Inter-Regimental Polo Tournament in Hyderabad), reading, rose-gardening and collecting butterflies (sadly his terrier ate the sixty-five species he had gathered). 

Officers involved in the Inter-Regimental Polo Tournament at Meerut, 1899 - Winston Churchill is second from right
Officers involved in the Inter-Regimental Polo Tournament at Meerut, 1899 - Winston Churchill is second from right at the back © IWM (HU 98777)

Winston was also unhappy about the officers’ mess, complaining it needed new carpet, cleaner tablecloths and better-quality cigarettes. His attitude annoyed many of his fellow officers, and culminated in him being squashed under a sofa in the mess (he escaped.)

Winston would experience some combat, but once again it was not as a soldier. This time it was in the North West Frontier Province, on the border between British India and Afghanistan. 

The region was inhabited by Pashtun tribes who often rebelled against British forces. In July 1897 they attacked the British garrison in Malakand. A field force was dispatched to stamp out the uprising. 

Winston managed to join the Bengal Infantry, which was part of the field force, but he was attached as a journalist. He spent six weeks with them, filing fifteen dispatches for the Daily Telegraph. 

He came under fire ten times, and was mentioned in dispatches for bravery.  

During this time Winston developed a taste for whisky; at the time it was out of fashion in England and on the few occasions he had tried it he had not enjoyed the smoky taste. However, it was the only drink available in Malakand so Winston learned to appreciate it by the end of the campaign, and it became his habitual beverage of choice.

In March, 1898, an Anglo-Egyptian army was sent out to defeat the Sudanese Mahdists, followers of the religious leader Muhammad Ahmad, who proclaimed himself the ‘Mahdi’, a messianic figure who would redeem Islam. 

As Britain had not fought a major war in over decade, every soldier in the Empire wanted to join the expedition. 

Winston was no different. From India, he requested a transfer to a regiment bound for Sudan, 21 Lancers.

This was approved by the War Office but rejected by Herbert Kitchener, the leader of the expedition. 

Winston took leave to return home to lobby for the transfer, arriving in London in June. Friends and family spoke up for him, and even the prime minister supported his appeal. 

Kitchener, the son of an Irish army officer, still refused, possibly because he resented the young aristocrat’s entitlement and social connections. 

Jacob F Field The Eccentric Mr Churchill high res cover image

Winston finally forced his way into 21 Lancers when Sir Evelyn Wood, a high-ranking general in England who had authority over appointments to the regiment, named him as the replacement for an officer who died in Sudan that July. Winston was with his new regiment by August. 

He had arranged to write reports for the Morning Post to finance the trip, as the War Office would not pay his expenses (as well as declining any liability if he was wounded or killed.) 

On 2 September Winston took part in the decisive engagement of the war, the Battle of Omdurman. 

Kitchener’s forces, though outnumbered two-to-one, were armed with modern artillery, rifles and machine guns. These new weapons cut through the Mahdist lines, killing thousands. 

When they retreated, Kitchener sent 21 Lancers, including Winston, to pursue. 

After the battle, wounded Mahdists were left to die or shot and bayoneted where they lay. This was approved by Kitchener, shocking Winston, who criticised the decision in print. 

He returned to London in October before travelling back to India that December. 

Shortly afterwards the British Army instituted a regulation forbidding serving officers from simultaneously working as war correspondents. This contributed to Winston resigning his commission so he could pursue writing, as well as politics. 

Winston left India for the final time in March 1899; that July he stood as a Conservative candidate in the Oldham by-election but was unsuccessful.

In October, 1899, war erupted in South Africa between Britain and the independent Boer Republics of Orange Free State and Transvaal. 

Winston would cover the conflict for the Morning Post but his journalistic enterprises were interrupted on 15 November, when his train was ambushed and derailed by the Boers. Winston was captured and held at a POW camp in Pretoria, the capital of Transvaal. 

On 12 December, he scaled the walls and escaped, stowing away on a freight train. 

Winston Churchill doing a backwards victory sign
Churchill doing a backwards victory sign in December 1942 © IWM (H 25966)

Without any supplies, he disembarked at the mining town of Witbank to look for food. By this time he was wanted dead or alive and there was a £25 bounty on his head. 

Fortunately, Winston came across the home of an English mine manager who agreed to feed and shelter him. 

He was hidden first down a mine, then in an office, and, after six days, was placed aboard a train hidden in a consignment of wool bound for Portuguese East Africa (modern Mozambique), where he arrived on 21 December. 

Winston then sailed to Durban and joined the South African Light Horse regiment as a lieutenant. He took part in the Relief of Ladysmith before joining in the capture of Pretoria. 

After the fall of Pretoria, the war transitioned to a guerrilla conflict between Boer commandos and British and Commonwealth forces that went on until May 1902. 

Meanwhile, Winston had left South Africa and on 20 July 1900 arrived home. 

Reports of his escape had made him a national celebrity, helping him to be elected MP for Oldham that October. 

Whilst pursuing his career as a politician and writer, Churchill decided to volunteer for a yeomanry regiment, and in January, 1902, Winston joined the Queen’s Own Oxfordshire Hussars (QOOH), as a captain. In 1905 Winston became a major in the regiment, and until 1913 commanded its Henley-on-Thames squadron.

In September, 1906, whilst still a junior minister, Winston travelled to Silesia (a region now mostly in Poland, but then part of Germany) and spent a week observing the manoeuvres of the German Imperial Army. 

He stayed in Breslau (now Wrocław) and with other guests and officials and was taken by train out to the countryside to view the assembled ranks of 50,000 soldiers going through their exercises. 

The evenings were spent at official banquets. Winston would even meet Kaiser Wilhelm II

He reported that the Germans were very well-organised and disciplined, although he noted that Wilhelm had little conception of the power of modern weaponry. 

Winston Churchill as an MP in 1904
Churchill as an MP in 1904 © IWM (Q 42037)

The next year, Winston attended the manoeuvres of the French Army; he adored their bright uniforms and the pageantry of the occasion. 

It made him a firm believer in the recently-established Entente Cordiale, an alliance that would hold steady throughout World War I, which broke out in 1914. By this time, Winston was First Lord of the Admiralty.

He still played close attention to his reserve regiment, the QOOH. Shortly after the war started he intervened to ensure they would be sent to serve on the Western Front

The regular army did not hold them in high regard, nicknaming them the ‘Queer Objects On Horseback’ or ‘Agricultural Cavalry’. 

Winston fell from power following the disaster of the Gallipoli Campaign, which he had been a major supporter of, he was forced out of the position in May 1915, and was demoted to being Chancellor of the Duchy of Lancaster, a post with no real power or influence. 

That November, Winston resigned from government and returned to the Army, hoping to play a role in the fighting. 

In December, Winston went to the Western Front for one month of training with the Grenadier Guards infantry regiment. 

By the new year he was a (temporary) lieutenant-colonel commanding 6 Royal Scots Fusiliers, an infantry regiment posted at Ploegsteert (known as ‘Plug Street’ by the British) in Flanders, a fairly quiet sector at the time. 

He made sure he was well-provisioned, taking with him food boxes from Fortnum & Mason, corned beef, stilton, cream, ham, sardines, dried fruit, steak pie, peach brandy and other liqueurs. He also brought a gramophone to put in the officers’ mess, as well as a portable bath.

Winston Churchill with French officers in Belgium during the First World War
Churchill with French officers in Belgium during the First World War © HU 55578

Winston’s first major initiative was a campaign of delousing, as well as encouraging sports days and singing while marching. He then focused on building and repairing the trenches his battalion was stationed at. He proved to be popular with his men; attentive to wounded soldiers but perhaps over-lenient on disciplinary matters. 

In total, Winston made thirty-six forays into No Man’s Land, often placing himself at some risk. However, with little chance of a promotion or a transfer to a more active sector Winston returned home in March. 

He eventually returned to government in July 1917, serving as Minister of Munitions (a post formerly held by then PM David Lloyd George) and playing an important role in securing victory for the Allies.

Winston would carry on serving as a reserve officer until 1924, when he resigned from the Territorial Army.  

By this time, the QOOH had converted into an artillery force. For much of World War II they served in England and Northern Ireland, until in October 1944 Winston, by now Prime Minister, personally requested they be sent to fight in France. 

He was the regiment’s Honorary Colonel until his death, and left instructions they be given a place of distinction in the procession at his state funeral, immediately in front of his coffin.

That procession would take place on January 30, 1965, six days after Winston’s death.

For more on ‘The Eccentric Mr Churchill’, including his time in the military, read Jacob F Field’s book.

The Queen’s Own Oxford Hussars were present at Churchill’s funeral parade, though they are most likely ahead of the camera in this footage

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