The Life & Games of Winston Churchill

Eighty years ago, the fate of the world hung in the balance as Britain stood alone against Nazi Germany. It is the legacy of one man that Britain fought on: Winston Churchill. This post will retrace his life from his early days through his deeds in war (World War I and World War II) and peace (the inter-war period and his later years). Unsurprisingly, a man of the historical importance of Churchill has inspired quite a few board games which will be our companions on the way.

Early Life: A Soldier, Writer, Politician

Winston Churchill was born in 1874 into a family of the English high aristocracy. He was the grandson of a duke and the son of a leading member of the Conservative Party in the British parliament. After the common education for sons of his class at several boarding schools, Churchill joined the British Army. He was stationed in India (a country he abhorred), Sudan, and South Africa. No matter where he was, he read and wrote, and began to sell his accounts of the colonial wars to newspapers. During much of his life, writing newspaper articles and books would be Churchill’s main source of income. While in South Africa during the Boer War, Churchill was taken prisoner and escaped his captivity, making him a minor celebrity back home. Despite his experiences fighting the Boers, he advocated for a conciliatory peace with them afterward – another trait that would show often during his life.
Back from South Africa, Churchill launched himself into politics. He was elected a Member of Parliament in 1900 – like his father, as a Conservative. And like his father he became known for his fiery opinions. After four years of increasingly distancing himself from the Conservatives (mostly over free trade, to which they were not as committed as Churchill, and social reforms, which they unlike Churchill eyed with suspicion), Churchill crossed the floor of Parliament and joined the Liberal Party.
When the Liberals came into government in 1905, so did Churchill. He gained a reputation as a social reformer and held increasingly more important positions – from Undersecretary in the Colonial Office to President of the Board of Trade, Home Secretary, and, finally First Lord of the Admiralty. In this capacity, he was responsible for Britain’s naval war effort when World War I broke out in 1914.

World War I: Making the Plans, then the Munitions

Churchill favored an active, offensive conduct of the war. Thus, he not only implemented the naval blockade of Germany, but also had plans prepared to seize the island of Borkum off the German coast and harry the Germans from there (nothing ever came of that), sent submarines to the Baltic Sea to support the Russian Navy, and even diverted Admiralty funds to the development of the tank (decidedly not a naval weapons system!), because he was convinced it might give Britain an advantage. Many of these projects were scrapped or did not produce immediate results. One idea, however, stuck: When the Ottoman Empire joined the Central Powers, Churchill proposed to attack the straits between the Mediterranean Sea and the Black Sea, seize the capital Constantinople, thereby open a sea connection to Russia again (and maybe even knock the Ottomans out of the war entirely).
The campaign did not go well. A purely naval attack in February could not prevail against the naval mines and coastal artillery of the Ottomans. Therefore, the Allies landed ground troops on the Gallipoli peninsula in April. This landing is covered by Gallipoli: Churchill’s Greatest Gamble (Geoffrey Phipps, GMT Games). In this game (as in real history), the landing is wearying, and it is bloody. The Ottomans had prepared strong coastal defense systems, and their troops were determined and competently led. Consequently, the Allied offensive bogged down. When Bulgaria also joined the Central Powers in October 1915 (and thus a land supply line from Germany to the Ottoman Empire became a possibility), the Allies evacuated their beachheads. The Gallipoli operation had failed.

Gallipoli 1915

The conditions in the trenches at Gallipoli were awful – heat, disease, and enemy fire took a heavy toll on both parties. Box cover of Gallipoli, 1915 ©GMT Games.

Churchill, naturally, received much of the blame. His political fortunes dwindled when Prime Minister Asquith sounded out a coalition government with the Conservatives – who had not forgotten Churchill’s unfaithfulness to their party and demanded his dismissal from government as a precondition for their entry. Churchill left the Admiralty in November 1915.
After a brief stint back in the army (commanding a battalion on the Western Front), Churchill, who still held his parliamentary seat, focused on politics again. He had seen the downsides of this fickle business, but his star rose again when his fellow Liberal firebrand David Lloyd George became Prime Minister. In July 1917, Churchill was back in government as Minister for Munitions, and one year later, also as Secretary of State for War and Air (in which capacity he greatly aided the creation of the Royal Air Force). He remarked, „Not allowed to make the plans [for the war], I was allowed to make the munitions.“
When the war had been won, Churchill – just like after the Boer War – argued against a peace too harsh. His voice, however, did not carry enough weight, and the heads of government of the big four Allied powers (besides Britain also France, the United States, and Italy) decided otherwise.


While his Prime Minister Lloyd George negotiated the peace to World War I, Churchill pushed the deployment of Allied troops in the Russian Civil War. Event card “Winston Churchill” from Versailles 1919 (Geoff Engelstein/Mark Herman, GMT Games).

In any case, Churchill was less busy with the peace than he was with yet another war (a common occurrence in his life): After the October Revolution in Russia, Britain and some of the other Allies had sent expeditionary corps there to assist the Whites against the Reds in the Russian Civil War. Churchill, an avowed anti-communist, was keen on „strangling Bolshevism in the crib“, as he martially put it. Like Gallipoli, the operation did not meet with success.

Between the Wars: Chancellor of the Exchequer and Wilderness Years

Churchill’s political career took a hit when he was not returned to parliament in the election of 1922 – and did not regain one in the next election just a year later. Churchill used the time to reposition himself. After a short attempt at establishing himself as an independent candidate, Churchill rejoined the Conservative Party in 1924, and with its backing, went back to parliament – and, as the Conservatives had won the election, also to government, now as Chancellor of the Exchequer, possibly the most important government post aftet the Prime Minister. Now overseeing finances, he once more proved his political versatility.
His career came to a halt again when the Conservatives were voted out of government in 1929. Churchill, never one for idleness, searched for a new cause he could take up. Initially, he found one in opposing the process for more self-government – and eventually independence – for India. His views on the country and its people as backwards and in need of guidance of their British colonial masters had not changed since his time as a young Army officer there. (Later, during World War II, Churchill’s dislike of India would contribute to the policies of food exports from India which exacerbated the Bengal Famine that claimed millions of deaths and soured the relationship between Indians and their colonial masters in London, as shown in Gandhi: The Decolonization of India, 1917—1947 (Bruce Mansfield, GMT Games)). However, there were fewer and fewer Britons who shared these views, even in Churchill’s own Conservative Party. He therefore became politically isolated again.

Great Bengal Famine Churchill

The Bengal Famine offered the chance to the British government of India to gain support by appropriate handling of the crisis (top part of the event). As they did not, many Indians previously supportive of the British Raj turned away from it (bottom part of the event). Card “Great Bengal Famine” from Gandhi, ©GMT Games.

This isolation did not decrease when he moved on to the next issue: After the Nazis had taken power in Germany in 1933, Churchill warned against their expansionism and called for a firm hand and military readiness in dealing with them. All matters military were deeply unpopular in Britain at the time, as the country was still scarred by World War I – and the most unpopular of them were rising military expenditures. On the one hand, Britain’s spending was already higher than ever before during peacetime due to the welfare measures implemented after the war. On the other, public revenue had taken a massive hit with the global economic crisis following the crash of 1929. Therefore, his warnings went unheeded.
In any case, Churchill had a lot of time being not in government. He dedicated much of that on writing: He finished his multi-volume treatment of World War I, wrote a large biography of his ancestor John Churchill, the first Duke of Marlborough, some biographical essays on his contemporaries, and an autobiographical book on his early life. And maybe this was also the time when he took up playing the notoriously difficult solitaire variant that goes by his name now: Churchill Solitaire. The game has been released in app form by former US Secretary of Defense Donald Rumsfeld – who had picked it up during his time at the NATO headquarters in Brussels in the 1970s from André de Staercke, who in turn had been taught by Churchill himself when he was Belgian ambassador to the Allied forces in World War II. And to World War II we will now turn our attention.

Churchill Solitaire 1

Churchill Solitaire as an app. ©WSC Solitaire.

World War II: His Finest Hour

Churchill’s Cassandran warnings of Nazi expansionism had fallen on deaf ears. The British government had tried to appease Nazi appetites by agreeing to their rearmament, the occupation of the demilitarized Rhineland, the unification of Germany and Austria, and the annexation of the German-speaking Sudetenland in Czechoslovakia. But when Germany annexed then the entirety of Czechia on top, even Chamberlain had to admit that the time for appeasement was over. When Hitler made his next land grab in Poland, Britain (and France) demanded the German forces leave Poland. When this ultimatum expired on September 3, 1940, they declared war on Germany.
Now, of course, Churchill was back in political demand. British Prime Minister Neville Chamberlain asked him to join his War Cabinet – once more, as First Lord of the Admiralty. As in World War I, he pushed for an active conduct of the war – very much in opposition to the „Phoney War“ on the Western Front where German and Allied troops just observed each other. For that end, he eyed Norway. Much of Germany’s iron ore supplies came from mines in northern Sweden, and when the Baltic Sea was frozen in winter, it could only be brought to Germany via the Norwegian port of Narvik. Churchill approved of a plan to mine the Norwegian coastal waters to stop these transports (Operation Wilfred). A German response was expected, and Britain would answer it with the invasion of northern Norway and Sweden (Plan R 4). Wilfred was to go into effect on April 8.
The plans, however, were overtaken by other events: Only one day after ships of the Royal Navy had set out for Wilfred, Germany invaded Denmark and Norway. The south of Norway fell soon, but the small German invasion force in Narvik was counter-attacked by Norwegian and Allied forces and had to withdraw into the mountains. Overall, the Norwegian campaign is an interesting intersection between land battles at the major ports (roughly evenly matched with slight advantages for the Germans), naval warfare to transport troops and supplies and deny these transports to the enemy (in which the Allies had a clear advantage), and air operations to support the ground battles and interdict naval forces (in which the Germans had a clear advantage). One game that captures this three-way nature of the land-sea-air struggle is Invasion: Norway (Kevin Boylan, GMT Games).

Invasion Norway

German soldiers in a small boat make their cautious way towards a fjord – overlaid with the Narvik Shield, a medal given by Nazi Germany to the soldiers who had fought at this critical port in northern Norway. Note that the medal is shown with the swastika (whose display is forbidden in modern Germany except for education purposes) – during the mid-90s, publisher GMT was obviously not yet aiming for the German market. Box cover of Invasion: Norway ©GMT Games.

Churchill’s Royal Navy performed well in the battle for Norway and sunk a staggering number of German ships. However, the campaign was an overall failure for the Allies; and the British government came under attack for their conduct of the war – even from some of the Conservative Members of Parliament on whom it rested. It became clear to Prime Minister Chamberlain that he needed to broaden his base of support. However, Labour, the largest opposition party in Parliament, indicated that they would not support a government led by him. Chamberlain resigned. Churchill was elected as his successor on May 10, 1940. On the same day, Germany invaded France and the Low Countries.
The first weeks of Churchill’s time as Prime Minister were therefore full of failures. The German forces went through the Allied defenses in the West like a hot knife through butter. By late June 1940, France had surrendered, the last Allied soldiers had left Norway (including Narvik), Italy had joined the war and threatened the British position in Africa, and the greatest success so far was that not the entirety of British forces had been defeated in France (made possible by the much-storied Dunkirk evacuation). Churchill’s task was to mitigate these disasters – and breathe the fighting spirit back into his government and his people, many of whom were inclined to seek a negotiated settlement in the face of a possible German invasion of the United Kingdom. There could have been no better person for the job than Churchill. His oratory, always acknowledged by friends and opponents alike as powerful, albeit a bit old-fashioned, rose to its peak. It is testament to the power of Churchill’s four great speeches of summer 1940 that the main phrase of each of them is still a household quote, and two even had wargames named after them:

  • Three days after having been elected Prime Minister, on May 13, Churchill laid out his political program and prepared his people for the coming hardships: „I have nothing to offer but blood, toil, tears, and sweat.“
  • On June 4, when the Dunkirk evacuation was successfully concluded, but France’s ability to fight on was questionable, Churchill warned his compatriots that „wars are not won by evacuations“ and made clear that the United Kingdom was willing to fight on, even in case of an invasion: „we shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall fight in the hills; we shall never surrender“. Fight on the Beaches (John Lambshead/Robert Sandell, World Wide Wargames) takes on the first few days of a hypothetical invasion of southeast England.
  • Two weeks later, on June 18, the fall of France was imminent. Churchill called on the British to realize their potential in the face of history (surely also thinking about himself): „Let us therefore brace ourselves to our duties, and so bear ourselves, that if the British Empire and its Commonwealth[e] last for a thousand years, men will still say, ‚This was their finest hour.‘“ Their Finest Hour (Rich Banner/Frank Chadwick/Marc W. Miller, Game Designers‘ Workshop) zooms a bit out in comparison to Fight on the Beaches and gives players the entirety of the Battle of Britain and a possible German invasion to play out.
  • Early during the Battle of Britain, on August 20, Churchill gave the last of the four great 1940 speeches. As the air combat raged over Britain, it all came down to the performance of the Royal Air Force, and among them, to just a few thousand fighter pilots: „Never in the field of human conflict was so much owed by so many to so few.“

The British, Commonwealth, and Allied pilots prevailed. Germany never dared an invasion, and, in 1941, turned eastward. Churchill had strengthened the morale of the enemies of fascism and bought time for its defeat. After Britain had stood alone for a year (from June 1940 to June 1941), the fascist powers attacked the Soviet Union. Of course that was an opportunity for Britain to gain a powerful ally, and one which, unlike themselves, could immediately bring a large number of land forces to bear on Germany. But could Churchill reconcile this with his avowed anti-communism? – He could. Ideology never blinded his eye for opportunities: „If Hitler invaded hell I would make at least a favourable reference to the devil in the House of Commons.“ And so he flew to Moscow and struck a deal with Stalin. Later the same year, Britain gained another ally, and this time, one more to his liking: When Japan attacked the United States at Pearl Harbor and the British possessions in Southeast Asia, and Hitler then also declared war on the United States, the wealthiest and potentially most powerful democracy in the world joined the fight.
With these new allies, Britain’s relative weight decreased. And so one of Churchill’s main tasks during the later years was to preserve Britain’s interests in this coalition of the Big Three (which, as the war went on, became more and more the Big Two Plus Britain). These inter-allied negotiations form the heart of Churchill (Mark Herman, GMT Games).


Of the big three, Churchill had the least hard power at his disposal. For many years, he made up for it with his determination and persuasion. Box cover of Churchill ©GMT Games.

On the other hand, these powerful new allies made victory – at least in Churchill’s ever-confident mind – almost a certainty. Over the next years, the Allies made their slow progress through Africa, the Atlantic, the Pacific, and Europe, until finally Germany and Japan were defeated. Churchill saw the first event as Prime Minister, but not the second: In the election of 1945, the British voting public had decided they had enough of him. He was revered for his wartime feats, but for the coming peace, they felt they needed someone else. Churchill’s successor, his erstwhile Labour deputy Clement Attlee, delivered on that and laid the foundations for the British welfare state, including an ambitious council housing program and the foundation of the National Health Service.

Later Life: The Setting of the Sun

Churchill was now the leader of the opposition in the United Kingdom. However, he took liberties with this office and spent much of his time travelling Europe and North America, giving speeches on world politics. In one of these, in Fulton, Missouri, he popularized the term „Iron Curtain“ for the beginning division of Europe in a liberal-capitalist West and an authoritarian-communist East – another phrase so catchy that it has been adopted as the title of a board game (on the Cold War, of course) – Iron Curtain (Asger Harding Granerud/Daniel Skjold Pedersen, Ultra Pro). In another speech, he called for the unification of (continental) Europe among the ruins of the war – the „United States of Europe“, as he called it. He is therefore considered a spiritual founding father of the European Union.

Iron Curtain

In his later years, Churchill was as eminently quotable as ever – with the phrase “Iron Curtain” one of his most memorable. Box cover of Iron Curtain, ©Ultra Pro/Jolly Roger Games.

One more time in his life Churchill would stand at the political center of attention. His Conservatives won the 1951 election, and he became Prime Minister for the second time. His tenure was marked by the dissolution of the British Empire and the Cold War. Regarding the former, Churchill faced anti-colonial uprisings in Kenya (the Mau Mau uprising) and Malaya (a colonial war euphemistically called the Malayan Emergency). Churchill, in keeping with his traditional imperialism and his disdain for the colonial peoples, called for military solutions – with mixed results. The Cold War, on the other hand, was close to turning hot when Churchill entered office – the United Kingdom was part of the western/United Nations coalition formed against the North Korean (and Chinese-/Soviet-backed) invasion of South Korea. Churchill adopted a tough stance against everything smacking of communism. Thus, he supported the CIA-backed coup against the democratically elected Iranian Prime Minister Mossadegh after Mossadegh had begun nationalizing the petroleum industry of the country.[1] However, after Stalin’s death and the end of the Korean War, Churchill sought to overcome the simmering conflict between East and West by means of a summit – just like the conferences between the Big Three during the war. It was not to happen during his time in office, as Churchill, having been plagued by several strokes, resigned in 1955. Later American-Soviet summits, however, marked important milestones in the development of superpower détente, and, finally, the end of the Cold War. Churchill would not live to see it. Until his death in 1965, he had remained a Member of Parliament for the southern English constituency of Epping.

Games Referenced

Churchill’s Greatest Gamble (Geoffrey Phipps, GMT Games)
Versailles 1919 (Geoff Engelstein/Mark Herman, GMT Games)
Gandhi: The Decolonization of India, 1917—1947 (Bruce Mansfield, GMT Games)
Churchill Solitaire
Invasion: Norway (Kevin Boylan, GMT Games)
Fight on the Beaches (John Lambshead/Robert Sandell, World Wide Wargames)
Their Finest Hour (Rich Banner/Frank Chadwick/Marc W. Miller, Game Designers‘ Workshop)
Churchill (Mark Herman, GMT Games)
Iron Curtain (Asger Harding Granerud/Daniel Skjold Pedersen, Ultra Pro)
Twilight Struggle (Ananda Gupta/Jason Matthews, GMT Games)

Further Reading

A good start on Churchill – and, despite the somewhat grandiose title, no hagiography – is Best, Geoffrey: Churchill. A Study in Greatness, Hambledon and London, London 2001.
Of course, Churchill’s own writings are of great interest to anyone reading on his times, especially his Nobel Prize for Literature-winning The Second World War, six volumes (also published as an abridged one-volume version), Cassell, London 1948—1953.
You can find Churchill’s 1940 speeches, among the finest examples of oratory in the history of mankind, on the website of the International Churchill Society.


1. Ironically, after the immense success of Twilight Struggle (Ananda Gupta/Jason Matthews, GMT Games), most gamers will now regard the „Iran coup“ as a classic Soviet opening to the Cold War instead of the Western move it was in real history.

7 thoughts on “The Life & Games of Winston Churchill

    1. cliosboardgames Post author

      Thanks, Pete!
      I’m sure there are quite some other candidates – I’ve done a two-part Napoleon biography (narrative part: ; analytical part: and a two-part double-biography of Hannibal and Scipio Africanus ( and And my posts on the Reformation are not quite a biography of Luther, but pretty close: and Maybe some of those are of interest to you!

      Liked by 1 person

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