Witnesses to history: two despatch boxes, a deed box and a humidor that belonged to Winston Churchill

On 30 June 2026 at Christie’s in London, The Exceptional Sale: Masterworks Across Cultures will offer two despatch boxes, a deed box and a humidor that are linked to Winston Churchill at some of the most defining moments of his career. These four extraordinary lots, which come from a single collection, chart the politician’s highs and lows, painting a picture of a life that indelibly shaped the history of Britain and contributed to the preservation of the free world.

A humidor gifted by Franklin D. Roosevelt, circa 1940-45

Following the Imperial Japanese Navy’s attack on the US Naval base at Pearl Harbor on 7 December 1941, America was propelled into the war. The 32nd President of the United States, Franklin D. Roosevelt, formed an alliance with Churchill that would become one of the most consequential partnerships in history. Just over a year later, at the Casablanca Conference, the pair agreed that nothing but the unconditional surrender of the Axis powers would end the war.

By 1944, following the Battle of Midway and the Guadalcanal campaign, the US forces were pushing back the Japanese in the Pacific. And in Europe, Operation Overlord in Normandy saw Allied soldiers retaking France. On 8 May 1945, Germany surrendered and victory was declared on the continent. On 2 September, almost a month after the bombing of Hiroshima and Nagasaki, Japan also formally surrendered.

Measuring about 34 by 47 centimetres, this wooden humidor is representative of the personal bond between Roosevelt and Churchill. It was gifted by the president to the prime minister — presumably filled with cigars — at some point before Roosevelt’s death on 12 April 1945, possibly during one of the decisive conferences held in Tehran in late 1943 or Yalta in early 1945. An inscription on the lid indicates that the humidor was originally given to Roosevelt by Fulgencio Batista, the president of Cuba, probably during his visit to visit to the White House in December 1942.

Churchill’s reign as prime minister also concluded just before the war’s end, on 26 July 1945, following a landslide defeat in a general election. For many, a war-time leader wasn’t suitable for an era of peace. He was re-elected for a second term between 1951 and 1955, however, and won a Nobel Prize in Literature in 1953 for his ‘brilliant oratory in defending exalted human values’. In July 1964, aged 89, he stepped down as an MP and left politics. He died the following January, having smoked up to 10 cigars a day for 70 years.

A leather prime ministerial despatch box, circa 1940

Earlier in his career, between 1924 and 1929, Churchill had served as Chancellor of the Exchequer. But over the following decade, he had become politically isolated for speaking out against the concessions that had been made to Germany’s increasingly aggressive Third Reich, and despite retaining his seat as an MP, he held no ministerial office.

On 1 September 1939, Hitler invaded Poland, and suddenly Churchill found himself vindicated. Two days later, Prime Minister Neville Chamberlain reappointed him First Lord of the Admiralty.

On 10 May the following year, as German forces advanced on Belgium, Luxembourg and the Netherlands, and with confidence in Chamberlain having plummeted, Churchill was selected as the new prime minister. Three days later, during his first address to the Commons, he famously declared that he had ‘nothing to offer but blood, toil, tears and sweat’ in defeating Nazi Germany.

Over the following bleak weeks, France fell to Hitler and more than 300,000 Allied troops were evacuated from Dunkirk. Despite this, Churchill galvanised a fighting spirit in Britain, which would eventually help turn the tide of war and lead to victory in Europe.

During those critical months, this despatch box, embossed with ‘Prime Minister’ and the cypher of George VI, was among those in which Churchill’s vital daily briefings were delivered. Stored safely in its interior were confidential papers relating to the most decisive moments of the war — state secrets requiring the prime minister’s immediate attention, some of which may remain classified even today.

A leather parliamentary despatch box, circa 1915

Churchill’s success as a war-time prime minister would have seemed highly unlikely in May 1915, when his political career looked to be in ruins. The disastrous assault on Ottoman forces at Gallipoli had been the latest in a series of high-profile losses for the Royal Navy, and with questions growing over his competence, he stepped down as First Lord of the Admiralty. It was during this reflective moment, in the summer of 1915, that Churchill took up painting.

He was demoted to Chancellor of the Duchy of Lancaster, a role that kept him in Asquith’s cabinet, but it was little more than an administrative sinecure, and a humiliating loss of power for the MP. This dark blue leather despatch box — with gilt embossed cyphers of King George V and the text ‘The Right Hon. Winston. S Churchill, M.P. / Chancellor of the Duchy of Lancaster’ on the lid — was used during this pivotal period to deliver sensitive state documents. It wasn’t needed for long, however: after just six months, Churchill resigned.

Within days of his departure, Churchill had left London for the Western Front in France, hoping that unmediated experience of trench warfare would help rebuild a reputation in tatters. Serving with the 2nd Battalion, Grenadier Guards, he overcame the reservations of his men about having a failed politician as their new leader. ‘He never fell when a shell went off; he never ducked when a bullet went past with its loud crack,’ one soldier relayed. ‘He used to say, after watching me duck: “It’s no damn use ducking; the bullet has gone a long way past you by now.”’

The horrors of the Western Front laid bare the failings of Whitehall policy. After six months, Churchill returned to Parliament, circulating memorandums that criticised military tactics and the growing number of casualties. In December 1916, Asquith was replaced by David Lloyd George, who recognised Churchill’s resolve. In July 1917, after the Dardanelles Commission largely cleared Churchill’s name in relation to the Gallipoli failures, Lloyd George made him Minister of Munitions. The stage was set for his political rehabilitation and a return to being one of the most powerful figures in the British Empire.

A steel deed box, circa 1907-22

Before entering politics, the young Churchill had spent five years serving in the military and as a war correspondent in Cuba, India and Sudan — as well as gaining celebrity for a daredevil escape from a Boer War prison camp in South Africa. He was elected to Parliament in 1900, aged just 25.

He quickly rose through the ranks, first as Under-Secretary of State for the Colonial Office, then as President of the Board of Trade. In 1908, by the age of 33, he had a seat in the cabinet and immense influence. At 35 he was made Home Secretary.

In October 1911, as the threat of war loomed, Prime Minister Herbert Asquith appointed Churchill First Lord of the Admiralty. With crucial foresight, he spent the next two-and-a-half years readying Britain’s navy for combat.

This black steel deed box was used to organise and store essential paperwork relating to these early ministerial roles. It’s neatly gilded with a single row of lettering, which reads: ‘The Right Honourable Winston S. Churchill, M.P.’ The title ‘Right Honourable’ indicates that it was in use after 1 May 1907, when Churchill was sworn in as a member of the Privy Council — the body appointed to advise the monarch, who at the time was Edward VII.

Membership of the council is a privilege for life, and Churchill’s role would extend across the reigns of three more kings and a queen. However, the fact that this box doesn’t include the post-nominal ‘C.H.’, which he used after being elevated to the Order of the Companions of Honour, suggests it was made before 1922, placing it squarely in these formative years of his political career.

The Exceptional Sale: Masterworks Across Cultures in on view at Christie’s in London, 26-30 June 2026

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