7 Winston Churchill Documents to Add to Your Collection: An Illustrated Guide

Winston Churchill came from a long line of English aristocrat-politicians. His father, Lord Randolph Churchill, was descended from the First Duke of Marlborough and was himself a well-known figure in Tory politics in the 1870s and 1880s. Winston was a prominent figure from his youth, serving as a soldier, a war correspondent, a Member of Parliament, a Cabinet Minister, a loud voice in the opposition during the Wilderness Years, and then the Prime Minister. He also wrote 43 books and won the Nobel Prize.

Churchill’s signed documents convey the character of the man during times of trial and leadership. Below is our illustrated guide to collecting Churchill signed letters and documents.

Churchill signed photo
The Stoneman photograph of Winston Churchill as Prime Minister in 1941, signed, for sale with The Raab Collection

Churchill’s Early Years 

After he left Sandhurst, Churchill traveled all around the British Empire as a soldier and journalist. In 1899, the London Morning Post sent him to cover the Boer War in South Africa, but he was captured by enemy soldiers almost as soon as he arrived. (News of Churchill’s daring escape through a bathroom window made him a minor celebrity back home in Britain.) 

In 1910 Churchill became Home Secretary, and in 1911, he took the office of First Lord of the Admiralty. Noting that Germany was growing more and more bellicose, Churchill began to prepare Great Britain for war. He established the Royal Naval Air Service, modernized the British fleet and helped invent one of the earliest tanks. Despite Churchill’s prescience and preparation, World War I came and was a stalemate from the start. Churchill proposed a military campaign that soon dissolved into disaster: the 1915 invasion of the Gallipoli Peninsula in Turkey. Churchill hoped that this offensive would drive Turkey out of the war, but Turkish resistance was much stiffer than he had anticipated. The Allies failed, and Churchill was blamed. 

Churchill Autograph

Churchill as Author

After the Nazis came to power in 1933, Churchill spent a great deal of time warning his countrymen about the perils of German nationalism, but Britons had grown weary of war and reluctant to get involved in international affairs again. Likewise, the British government ignored Churchill’s warnings and did all it could to stay out of Hitler’s way. In 1938, at the Munich conference, Prime Minister Neville Chamberlain even signed an agreement giving Germany a chunk of Czechoslovakia in exchange for a promise of peace. 

Churchill spent his famed Wilderness Years preparing the British people for the war to come. In a signed letter to his editor from 1936, he announces he is nearing completion of his newspaper series “Great Events of Our Time,” which traced the evolution of the British democracy from the feudal ages, the destruction of continental monarchies during the Great War, and the rise of the Bolsheviks, Fascists, and Nazis. One of the articles contains one of his earliest critiques of Adolf Hitler. 

Winston Churchill signed letter on his newspaper series, “Great Events of Our Time,” for sale with The Raab Collection

Three years later, in another letter to his News of the World editor Percy Davies, Churchill discusses an article entitled “Air Raids and the Population,” originally accepted for publication in a U.S. magazine, but, Churchill writes, “It is a very important article, and of course of greater interest here than in America.” As it turned out, Collier’s ran the article on Saturday June 17, 1939, under the title “Bombs Don’t Scare Us Now.” The News of the World ran the article the next day, Sunday June 18, 1939, under the title “Air Bombing Is No Road to World Domination.”   

In the article, Churchill brought up the real possibility of indiscriminate bombing of big-city populations if war should come. He stated flatly that Great Britain would never be beaten by that means, a statement he helped make true just a year later.

Churchill signed letter 1939
Winston Churchill signed letter on his article about air raids, 1939, for sale with The Raab Collection

Churchill as Leader 

After Hitler broke his promise and invaded Poland, Britain and France declared war. Chamberlain was pushed out of office, and Churchill took his place as Prime Minister in May 1940. Between the Dunkirk evacuation, the British War Cabinet crisis, and the beginning of the Battle of Britain, it was a time that challenged Churchill’s leadership in every way. 

From those early, chaotic days, two deeply important and moving mementos have surfaced: a signed letter from the day the Dunkirk operation ended saying he expected Lord Halifax’s cooperation in rebuilding the British Expeditionary Force and a note from the War Cabinet trying to respond to the Nazi assault in real time. Both are annotated by Churchill’s private secretary John Colville.

Winston Churchill signed notes 1940
A surviving page of the famous letter from Churchill to Lord Halifax on June 3, 1940 for sale with The Raab Collection

Churchill During World War II

Just as Churchill predicted, the road to victory was long and difficult. France fell to the Nazis in June 1940. From July to September 1940, all waited tensely for the German invasion of Britain to begin, as the Battle of Britain was fought to secure air supremacy. By mid-September it was clear that the Royal Air Force had denied the Luftwaffe the control the Germans needed to cross the English Channel, and the Nazi leaders decided to concentrate instead on bombing cities to pound the British people into submission. German fighter planes began bombing British civilians in what came to be known as the Blitz.

Though the future looked grim, Churchill did all he could to keep British spirits high. He persuaded U.S. President Franklin D. Roosevelt to provide war supplies – ammunition, guns, tanks, and planes – to the Allies, a program known as Lend-Lease, before the Americans even entered the war. 

By 1942, when Operation Torch, the Allied invasion of North Africa, commenced, the Americans had joined the British. It was the first great Allied operation of the war, and Churchill declared its success in this signed letter from November of that year. 

Churchill signed letter on Operation Torch
Winston Churchill signed letter declaring Operation Torch a victory, for sale with The Raab Collection

Churchill the Victor

More victories were to come, at an immense cost. Finally, on May 7, 1945, Germany surrendered unconditionally. The work of Churchill, and the British people, in Europe was done. Letters poured in congratulating Churchill on the winning of the war. These included letters from school children, adults, municipalities, and organizations of all kinds. Churchill sent a now famous reply

Below is the original of Churchill’s famous signed letter congratulating the British people on their victory in the war, written later that month. It is on paper marked with the official stamp of the Prime Minister and the address of 10 Downing Street. Churchill writes: “I have been deeply touched by all the messages of good will which have reached me at this time. Thank you so much.” 

Churchill signed letter 1945
Churchill’s original 1945 letter of thanks to a triumphant English people, signed, for sale with The Raab Collection

As the Daily Mail recently reported of this letter, it was the work of a man who “has been praised by many historians for refusing to do a peace deal with Hitler when one was offered in 1940” and then “helped to maintain British morale” throughout the war. 

In our view, it is a treasure from the end of World War II in Europe, one of a kind. 

Winston Churchill’s Speeches

It was said of Churchill during World War II that he “mobilized the English language and sent it into battle,” such was the force and persuasive nature of his speeches. His words rallied a nation behind the war effort and those speeches – delivered in his idiosyncratic, croaky bulldog style – are still famous today.

As Churchill declared, “We have before us many, many long months of struggle and of suffering. You ask, what is our policy? I can say: It is to wage war, by sea, land and air, with all our might and with all the strength that God can give us; to wage war against a monstrous tyranny, never surpassed in the dark, lamentable catalogue of human crime. That is our policy. You ask, what is our aim? I can answer in one word: It is victory, victory at all costs, victory in spite of all terror, victory, however long and hard the road may be; for without victory, there is no survival.” 

Churchill often spoke to Parliament on matters of importance. In this rare, hand-held reading copy of an actual speech he gave, Churchill advocates a stronger navy. “So there is no enemy against which to match the strength of the British fleet…”

Churchill speech 1948
Churchill’s hand held reading copy of a great postwar speech to parliament, for sale with The Raab Collection

Churchill in the Post-War Years

After WWII, in a speech in Fulton, Missouri, in 1946, Churchill declared that an anti-democratic “Iron Curtain,” had descended across Europe. His speech was the first time anyone had used that now-common phrase to describe the Communist threat. In 1951, 77-year-old Winston Churchill became Prime Minister for the second time. He spent most of this term working (unsuccessfully) to build a sustainable détente between the East and the West. He retired from the post in 1955.

Churchill was one of the first to realize and highlight the dangers of Nazism, and he refused to waver during the 1930s when many sought to appease Hitler’s Germany. Instead, he galvanized the opposition to fascism. Ultimately Britain backed his utter determination to fight the Nazis to the end despite the enormous sacrifice involved.

Buying Churchill Signed Documents

Some of Raab’s most prestigious acquisitions of Winston Churchill autographs and documents over the past few decades have included signed speech notes of Churchill for delivery to Parliament, Churchill documents invoking Hitler and his menace by name, and Churchill signed letters calling on the bravery of the English during the war. To learn more, visit our dedicated Churchill page

Nathan Raab, president of The Raab Collection, has also written an article for Forbes  about how he authenticates autographs of Winston Churchill

More From the Newswire

Join Us

Stay informed about new historical documents, historical discoveries, and information for the educated collector.

Collect. Be Inspired.