John F. Kennedy carried on a lifelong love affair with England and the English. From his speaking style to his tastes in art, architecture, theater, music, and clothes, his personality reflected his deep affinity for a certain kind of idealized Englishness. In Union Jack, noted biographer Christopher Sandford tracks Kennedy’s exploits in Great Britain between 1935 and 1963, and looks in-depth at the unique way Britain shaped JFK throughout his adult life and how JFK charmed British society. This mutual affinity took place against a backdrop of some of the twentieth century’s most profound events: The Great Depression, Britain’s appeasement of Hitler, the Second World War, the reconstruction of Western Europe, the development and rapid proliferation of weapons of mass destruction, and the ideological schism between East and West. Based on extensive archival work as well as firsthand accounts from former British acquaintances, including old girlfriends, Union Jack charts two paths in the life of JFK. The first is his deliberate, long-term struggle to escape the shadow of his father, Joseph Kennedy, former U.S. Ambassador to Great Britain. The second is the emergence of a peculiarly American personality whose consistently pro-British, rallying rhetoric was rivaled only by Winston Churchill. By explaining JFK’s special relationship with Great Britain, Union Jack offers a unique and enduring portrait of another side of this historic figure in the centennial year of his birth.