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Rare Winston Churchill despatch boxes from Second World War go to auction

All Access London Team by All Access London Team
June 24, 2026
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Rare Winston Churchill despatch boxes from Second World War go to auction
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A collection of four historically significant boxes, each with direct links to Sir Winston Churchill or his offices, is set to go under the hammer next week, with an estimated combined value of up to £215,000. The items will be a highlight of Christie’s Exceptional Sale: Masterworks Across Cultures.

The auction house has described the pieces as offering “a tangible link to the man and the moments that shaped him, his celebrated career and his enduring legacy”. They collectively span pivotal periods of Churchill’s extensive political career, from his early days in government through both World Wars.

Leading the collection is a prime ministerial despatch box, documented as having been used by Sir Winston around 1940, during what is often referred to as Britain’s “darkest hour”.

Embossed with “Prime Minister”, this box is expected to fetch between £70,000 and £100,000. It is believed to have been among those delivered to him daily, containing vital war papers, as well as cabinet, foreign, and commonwealth documents requiring his immediate attention during his premiership from 1940-1945.

Previously held by the Foreign Office, Christie’s notes that such items are exceptionally rare at public auction, representing “an incredibly rare piece of political history”.

Also featured is a humidor, a gift to the wartime prime minister from US president Franklin D Roosevelt. This item, initially presented to Mr Roosevelt by Cuban president Fulgencio Batista, is said by Christie’s to “encapsulate not only the single most important alliance in the Allied victory in the Second World War but also Churchill’s much famed love of cigars”. It carries an estimate of £25,000 to £40,000.

Four boxes with direct provenance to Sir Winston Churchill or his offices are expected to sell for up to £215,000 at auction
Four boxes with direct provenance to Sir Winston Churchill or his offices are expected to sell for up to £215,000 at auction (PA)

The collection further includes a 1915 despatch box, dating from Sir Winston’s tenure as chancellor to the Duchy of Lancaster. This period saw him take personal responsibility for the Gallipoli campaign, before he stepped down to seek active service on the Western Front, returning to politics in 1916. This box is estimated to sell for between £40,000 and £60,000.

Completing the quartet is a tin deed box inscribed with “The Right Honourable Winston S. Churchill, M.P.”, likely dating from between 1907 and 1922. Evidence suggests its continued use into the Second World War and beyond, potentially serving him through both global conflicts and numerous key moments of his career.

Retained by the British Foreign Office until 1970, it is now expected to achieve £10,000 to £15,000.

Sir Winston’s career as a soldier and statesman spanned the reigns of six British monarchs, from Queen Victoria to Queen Elizabeth II. Christie’s underscores the unique nature of the collection, stating: “This remarkable group of items being sold now from a single collection, represent an unparalleled and tangible link to arguably the most celebrated political leader in modern history.”



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Tags: auctionboxesChurchilldespatchrareWarWinstonWorld
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