10 of the most valuable pieces of Sir Winston Churchill memorabilia sold at auction

Sir Winston Churchill was a British statesman, politician, and writer who served as the Prime Minister of the United Kingdom during World War II.

He was known for his inspiring speeches and leadership during one of the most challenging times in history.

Here are 10 of the most valuable pieces of Sir Winston Churchill memorabilia that have sold at auction:

1. Sir Winston Churchill’s Cigar:

A half-smoked cigar that Sir Winston Churchill had left behind in a hotel room in 1941 sold for £4,500 ($5,000) in 2010. The cigar had been saved by a hotel employee who later gave it to a British airman as a souvenir.

2. Sir Winston Churchill’s Painting:

A painting by Sir Winston Churchill titled “Tower of the Koutoubia Mosque” sold at auction in 2021 for $11.5 million. The painting was completed in 1943 during a meeting with President Roosevelt and is considered one of Churchill’s best works.

3. Sir Winston Churchill’s Bow Tie:

A black bow tie owned and worn by Sir Winston Churchill sold at auction in 2014 for £7,280 ($10,000). The bow tie had been gifted to a British journalist by Churchill himself.

4. Sir Winston Churchill’s Glasses:

A pair of Sir Winston Churchill’s reading glasses sold at auction in 2016 for £6,875 ($8,500). The glasses had been given to a student by Churchill’s doctor after his death.

5. Sir Winston Churchill’s Cane:

A silver-tipped cane that Sir Winston Churchill had used during his final years sold at auction in 2010 for £18,000 ($23,000). The cane had been gifted to his bodyguard and later sold at auction.

6. Sir Winston Churchill’s Signed Books:

A set of books signed by Sir Winston Churchill sold at auction in 2015 for £22,500 ($32,000). The books included a first edition of Churchill’s memoirs “The Second World War”.

7. Sir Winston Churchill’s Speech Manuscripts:

Manuscripts of speeches made by Sir Winston Churchill sold at auction in 2014 for £7,500 ($10,000). The manuscripts included speeches given during World War II and speeches given after the war.

8. Sir Winston Churchill’s Letters:

A handwritten letter by Sir Winston Churchill sold at auction in 2021 for £15,000 ($20,000). The letter was addressed to his friend and fellow politician Lord Beaverbrook and discussed political matters.

9. Sir Winston Churchill’s Chair:

A chair used by Sir Winston Churchill during his time as Prime Minister sold at auction in 2018 for £9,375 ($12,500). The chair had been used in Churchill’s Cabinet War Rooms in London.

10. Sir Winston Churchill’s Watch:

A gold pocket watch owned by Sir Winston Churchill sold at auction in 2017 for £12,500 ($16,500). The watch had been gifted to Churchill by his cousin and was later given to his bodyguard.

Sir Winston Churchill’s personal items have become highly sought-after by collectors around the world.

From his paintings to his speeches and personal belongings, these items offer a glimpse into the life and legacy of one of the most iconic figures in modern history.

About your Author:

Adrian Roose has over 30 years’ experience covering all aspects of the rare stamp & memorabilia industry during which he has sold over £50m of unique items, helping build collections for Royalty, household name celebrities and 1,000s of collectors around the world.

Adrian was previously a Director at Stanley Gibbons, a Board Member of Stampex, and Executive Director of Paul Fraser Collectibles, PFC Auctions and JustCollecting, prior to founding The Memorabilia Club.

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