“Half-alien and wholly undesirable” was Lady Astor’s assessment of Winston Churchill. For Winston’s father, Randolph Churchill, had taken an American wife, “a dollar princess,” as many cash-strapped members of the English aristocracy did in the late 19th and early 20th centuries. But Lord Randolph, dead at age 46, left no inheritance. Poor Winston had to make his own way in the world.
Though he had little money, he had a wealth of connections that he adroitly used to promote his own ambitions. One of his tutors, noting Winston’s academic mediocrity, remarked, “that lad couldn’t have gone through Harrow, he must have gone under it.” But Churchill, like many men of genius, found that formal schooling interfered with his education. After leaving school, he joined the army.
In Victorian times, the service was a place for adventure; more importantly for Churchill, it was a place to make a name for himself, “the glittering gateway to distinction.”
Lord Salisbury, then prime minister, got Winston early postings in the Sudan and India—wherever the action was. A talented writer, Churchill turned his adventures into two critically acclaimed books on his military experiences while also finding time to write a novel, all before he turned 25. Churchill’s prose still excites today. His book...