This insightful portrait of Winston Churchill delves beyond well-known political moments, incorporating perspectives from various individuals who encountered him throughout his life. From Bletchley Park codebreakers and Hollywood stars such as Charlie Chaplin, through writers as varied as H. G. Wells and P. G. Wodehouse, to the likes of Harold Wilson, Mahatma Gandhi and Queen Elizabeth II, these lesser-known interactions reveal glimpses of the man behind the legend. We meet Churchill the exuberant schoolboy thug with an early mania for bull-dogs, and Churchill the elder statesman shedding a tear in the House of Commons smoking room. Other incidents include a young journalist rudely dismissing a call from Churchill as a prank, and a visiting Dwight D. Eisenhower dreaming of being strangled, only to awake entangled in Churchill’s borrowed nightshirt. The book showcases the profound transformations during Churchill’s lifetime, which ran from Benjamin Disraeli’s premiership to the release of the Rolling Stones’ ‘Route 66’, and the shift from steam to atomic power. Examining controversial aspects of his legacy, this multifaceted portrait challenges preconceived notions, inviting readers to reconsider the complexities of Churchill.