The Churchills at breakfast at Chartwell, Kent ©NT/Anthony Lambert

In his ninety years of life – an incredible span reaching from the autumn of Queen Victoria’s reign in 1874 to the rise of the Rolling Stones in 1965 – Winston Churchill had encounters with the most extraordinary range of people. From Gandhi to Albert Einstein; HG Wells to Charlie Chaplin; Ethel Barrymore to Maria Callas; Harry S Truman to Joseph Stalin to Queen Elizabeth II. Churchill is remembered best as an inspirational war leader and a young army adventurer. But his vividly rich life also encompassed friendships with – among many others – a Bolshevik ambassador, artists like Walter Sickert, actors like Laurence Olivier and poets like Rupert Brooke. Through the eyes and recollections of all these people, one starts to glimpse and understand new depths in Churchill: his character, his passions, his follies –not to mention his amazing propensity for bursting into tears at the slightest provocation!

Sinclair McKay writes for the Daily Telegraph, The Mail on Sunday and The Spectator. He is a literary critic for the Daily Telegraph and The Spectator. He has published extensively on Bletchley Park and codebreakers in his books, The Secret Life of Bletchley Park, The Secret Listeners, and Bletchley Park Brainteasers. Among his other books include Dresden: The Fire and the Darkness (2020) and Meeting Churchill: A Life in 90 Encounters (2023). His upcoming book St. Petersburg: Sacrifice and Redemption in the City That Defied Hitler, is due to be released in October 2025.

Sinclair McKay writes for the Daily Telegraph, The Mail on Sunday and The Spectator. He is a literary critic for the Daily Telegraph and The Spectator. He has published extensively on Bletchley Park and codebreakers in his books, The Secret Life of Bletchley Park, The Secret Listeners, and Bletchley Park Brainteasers. Among his other books include Dresden: The Fire and the Darkness (2020) and Meeting Churchill: A Life in 90 Encounters (2023). His upcoming book St. Petersburg: Sacrifice and Redemption in the City That Defied Hitler, is due to be released in October 2025.

Tickets: $15 members*; $25 non-members
*Membership discount applied automatically when logged into your Royal-Oak.org account