Top 10 Most Valuable Winston Churchill Memorabilia

Ten of the most valuable items of Winston Churchill memorabilia ever sold

Winston Churchill is one of the most iconic and influential political leaders of the 20th century. His memorabilia remains highly sought after by collectors and historians alike, ranging from his personal items to drafts of his famous speeches. Here are ten of the most valuable items of Churchill memorabilia ever sold at auction – source and for more information

winston churc hill gold dentures

10) Gold-plated partial dentures

From a young age Winston Churchill suffered from problems with his teeth, and struggled with a speech impediment which affected his pronunciation. For much of his life he wore a special set of dentures which helped to correct his lisp, and made him the celebrated orator capable of inspiring the nation. Churchill had numerous sets of these dentures cast in gold, and he always carried spares in case of emergencies.

This partial gold set, designed by his previous dentist Wilfred Fish, were sent back for repair just months before Churchill’s death in 1965. They remained in the collection of Wallace Stewart Ross, who succeeded Fish as Churchill’s dentist during his later years, and sold at Bonhams in 2011 for £19,200. (Image: Bonhams)

winston churchill harry truman joseph stalin signed potsdam conference dinner program

9) Signed Potsdam Conference dinner seating plan

In July 1945 Churchill met Harry Truman and Joseph Stalin at the Potsdam Conference in Germany, as Allied leaders gathered to decide how to deal with Nazi Germany after its defeat. However, the conference was held in the midst of a British general election and he was accompanied by the leader of the opposition Clement Attlee while the votes were counted.

On July 23 Churchill held a dinner back at 10 Downing Street for the conference attendees, and three days later Attlee replaced him in the negotiations when the Conservatives were voted out of office. This printed seating plan and program of music from the Downing Street dinner, bearing the signatures of Churchill, Truman, Stalin and all the other guests from Potsdam, sold at Bonhams in 2008 for $48,000 (£27,971). (Image: Bonhams)

winston churchill war letter

8) Handwritten letter about the war to Eliot Crawshay-Williams

In May 1940 Churchill became Prime Minister following the resignation of Neville Chamberlain. He was immediately surrounded by a number of dissenting voices, including the foreign secretary Lord Halifax, that claimed Britain should make a deal with Germany in light of their invasion of France.

He even received a letter from his assistant private secretary Eliot Crawshay-Williams, which stated Britain should use its “nuisance value while we have one to get the best peace terms possible. Otherwise, after losing many lives and much money, we shall merely find ourselves in the position of France — or worse. I hope this doesn’t sound defeatist; I’m not that. Only realist”.

Churchill replied with a short handwritten letter which read: “’I am ashamed of you for writing such a letter. I return it to you — to burn & forget”. This letter, along with the original by Crawshaw-Williams, sold at Christie’s in 2010 for £34,850 ($51,264). (Image: Christie’s)

winston churchill marlborough books neville chamberlain

7) Malborough books signed to Neville Chamberlain

Between 1933 and 1938 Churchill wrote a four-volume biography of his ancestor John Churchill, 1st Duke of Marlborough, an English soldier and statesman whose career spanned the reigns of five monarchs. He sent copies of each volume as it was released to British Prime Minister Neville Chamberlain, who was struggling in the face of the growing threat from Nazi Germany.

The final volume, published in September 1938 – just weeks before Chamberlain’s meeting with Adolf Hitler to sign the Munich Agreement – featured the inscription “Perhaps you may like to take refuge in the eighteenth century”. This set of autographed and inscribed first additions, from Churchill to the man he replaced in office, sold at Bonhams in 2012 for £45,650. (Image: Bonhams)

winston churchill newspaper letters

6) Archive of 29 typed letters

This collection of 29 letters illustrated Churchill’s relationship with the British newspaper The News of the World. Until 1948 British MPs received nominal salaries, and Churchill needed money to fund his often extravagant lifestyle.

From the late 19th century until his second term as Prime Minister in 1951, the majority of his earnings came from writing books and columns for a variety of publications. In the 1930s Churchill was contracted to write a series of features for the News of the World on great men from history, ranging from ancient philosophers to people he had personally known. However, towards the end of the decade his letters and columns offered stark warnings about the threat of the German Nazi party and include a wartime letter describing how the Battle of Britain was won.

Dating from 1934 until 1951, the 29 letters were addressed to The News of the World editors Sir Emsley Carr and Major D. Percy Davis and sola at Christie’s in 2011 for $52,500. (Image: Christie’s)

5) Archive of over 60 typed letters and telegrams

The collection of signed letters, memoranda, printed telegrams and other correspondence documented the editing and proofing process of his numerous books, dating from the 1930s to the mid-1950s. These including his extensive six-volume history of the Second World War, collections of his wartime speeches, and even a work entitled ‘Painting as a Pastime’ which documented his love of art.

Including correspondence with his proof reader C.C Wood, and his editors William Deakin and Denis Kelly, the archive of material sold at Christie’s in 2012 for $52,500. (Image: Christie’s)

winston churchill letter t.e lawrence

4) Handwritten letter to T.E Lawrence

T.E Lawrence was a celebrated British military officer whose life and exploits during WWI inspired the nickname ‘Lawrence of Arabia’. Lawrence’s own account of his adventures was published in 1922 in the book ‘Seven Pillars of Wisdom’, which became a best-seller and captured the imagination of readers around the world.

In May 1927 Churchill sent Lawrence a letter expressing his admiration for the book: “The impression it produced was overpowering…I think your book will live with Gulliver’s Travels & Robinson Crusoe. The copy which you gave me, with its inscription, is in every sense one of my most valuable possessions.” The four-page hand-written letter sold at Christie’s in New York in 2004 for $59,750. (Image: Christie’s)

winston churchill signed photo to stalin

3) Signed photograph to Joseph Stalin

The Soviet Union, under the lead of Joseph Stalin, suffered the greatest number of casualties during WWII with approximately 20 million men killed in action. Having previously entered into a non-aggression pact with Nazi Germany, the Soviets found themselves repelling a German invasion in June 1941 and Stalin was forced to join with the Allies. In 1943 he met with Churchill and U.S President Theodore Roosevelt at the Tehran Conference, where the three leaders set out a plan for defeating Germany and the future of Europe after the war.

In September 1944, following Soviet victories throughout Eastern Europe, Churchill inscribed a photograph of himself to Stalin: “From his Friend Winston S. Churchill, September 1944 To Marshal & Premier Stalin who at the head of the Russian Armies & of the Soviet Government broke the main strength of the German military machine & helped us all to open paths to Peace, Justice & Freedom”.

However, finding that the frame for the photograph obscured the inscription he re-wrote it on another and gave the first to his assistant private secretary Sir John Colville. It remained in the personal collection of Colville and his descendents until 2011, when it sold at a Christie’s auction in London for £73,250 ($114,050). (Image: Christie’s)

winston churchill letter

2) Handwritten love letter to Pamela Plowden

In September 1896 Churchill and his regiment set sail for India, where they would be stationed until March 1899. However, Churchill’s ambition would see him travel to Egypt and South Africa during that period, as both a soldier on the front line and a celebrated war correspondent.

During this time Churchill was also besotted by the society beauty Pamela Plowden, described as the “first great love of his life”, with whom many believe he was informally engaged. However, his lack of money put pay to his plans of marriage and his frustrations were illustrated by a letter written whilst in Calcutta in 1899:

“I have lived all my life seeing the most beautiful women London produces… Never have I seen one for whom I would forego the business of life. Then I met you… Were I a dreamer of dreams, I would say… “Marry me – and I will conquer the world and lay it at your feet.” For marriage two conditions are necessary – money and the consent of both parties. One certainly, both probably are absent. And this is all such an old story…”

Just two years later Plowden would marry Victor, Earl of Lytton, the son of a Viceroy of India, and Churchill went on to marry his wife Clementine in 1908. But the hand-written love letter survived, and in 2003 it sold at Christie’s for £77,675 ($133,368), three-times its high estimate of £25,000. (Image: Christie’s)

winston churchill battle of britain speech

1) Battle of Britain speech typescript

On August 20, 1940, Churchill gave one of the greatest speeches of the 20th century known as ‘The Few’. It was given during the Battle of Britain, the air campaign waged by the German Luftwaffe against the United Kingdom from July to October that year, which claimed around 90,000 civilian casualties and killed 544 air-crew.

The speech included the now-immortal live “Never in the field of human conflict was so much owed by so many to so few.” This described the contribution of the Allied Airmen of the Royal Air Force, comprised of almost 3,000 men from who had fought the Germans in the skies above Britain, in particular the Fighter Command who engaged in aerial dogfights. The speech inspired the British people during one of the toughest periods of the war on home soil, and spoke of a growing allegiance with the United States which would

The only-known draft of the speech, complete with Churchill’s hand-written amendments, was sold at Christie’s in June 2008. Originating from the personal collection of Sir John Colville, the speech had spent years on loan to Chequers, the official country residence of British Prime Ministers where Churchill had originally written it. It realized £139,250 ($272,234), establishing a new record for Churchill memorabilia. (Image: Christie’s)

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