Of all those appointed to his cabinet in May 1940, Prime Minister Winston Churchill had known Leo Amery the longest—back to when they were schoolboys. Despite the longevity of their relationship, they were never very close. Rather, as Robert Rhodes James wrote, “there was always a definite restraint, a lack of warmth, a noticeable caution and reserve” between them. Nevertheless, Amery played a notable part in ensuring Churchill’s premiership.