Widely regarded as one of the most iconic photographic portraits of the 20th century, Yousuf Karsh’s 1941 depiction of Sir Winston Churchill has come to embody the indomitable spirit of wartime Britain. Captured moments after Karsh famously removed the cigar from Churchill’s mouth, the resulting expression, defiant, unyielding and charged with resolve, became the defining image of the British Prime Minister and a lasting symbol of Allied perseverance.

While this portrait is held in numerous institutional and private collections, the present photograph is distinguished by an exceptionally rare and historically significant feature: it bears the autograph of Sir Winston Churchill himself. Further enhancing its provenance, this lot is accompanied by a 1956 letter from Churchill’s private secretary, Doreen Pugh, addressed to William Folger Nickle, former MP and MPP for Kingston. A remarkable convergence of two titans, Karsh behind the camera and Churchill before it, this lot represents a museum-worthy rarity that will appeal to collectors of fine photography and political history alike.