Celia Sandys begins her pursuit of Churchill’s enigmatic private life at Sandhurst Military Academy, which he left in 1894 to begin a journey in search of adventure and danger, and to gain the adulation he craved. She travels to New York and speaks with former Mayor Rudolph Giuliani, who considers Churchill one of his personal heroes. During their conversation, Sandys learns that her grandfather’s leadership of Great Britain during World War II was one of Giuliani’s guiding lights during his own crisis as the leader of New York on September 11. She visits Brooklyn to find the brownstone where Jenny Jerome, Churchill’s American-born mother, lived and discovers that the actual location is something of a historical dispute. Sandys journeys to the battlefields of the Cuban uprising of 1895, where Churchill nearly died, and South Africa, where, after an amazing tale of capture and escape, he finally found the fame that brought him public acclaim. While in Cuba, she takes delight in visiting a cigar factory to see Churchill’s iconic Havanas — made by hand just as they were decades before.