June 27, 2025

The World of Churchill Collectables

By BRIAN KRAPF

On 30 June 1943, Prime Minister Winston Churchill was awarded the Freedom of the City of London, which is a high recognition dating back to 1237. In medieval times, being a “freeman” meant being free from feudal control and having the right to engage in commerce and trade. In more modern times, the Freedom recognizes people for their contributions to the fields of business, arts, sports and public life. 

While Churchill’s ceremony was held per tradition at Guildhall, it was also held under strict secrecy due to prevailing wartime conditions. Invited guests were warned not to divulge the time or place of the ceremony. This rare set of confidential passes belonged to Paul Bossier, the headmaster of Harrow School, which Churchill attended in his youth.

Interestingly, the passes shown here on the left and the right both give the Prime Minister’s name as “Spencer-Churchill,” which was the family’s legal name and that under which Winston was listed while attending Harrow. The pass shown in the middle gives the Prime Minister’s name as it became after he dropped the use of the hyphen as a young adult.

2025 International Churchill Conference

Join us for the 42nd International Churchill Conference. Washington, DC | October 9-11, 2025

2025 International Churchill Conference

Brian Krapf’s book A Churchill Treasury: Sir Winston’s Public Service through Memorabilia was published in 2024 and is available in the UK and North America.