Many who have read and relied on Winston Churchill's magnificent historical works may be surprised to learn that he once devised an elaborate explanation of how Jeb Stuart prevented World War I. This seemingly far-fetched analysis was the great man's contribution to If, or History Rewritten, a 1931 collection of essays by historians of the day. Each explored a world where events had unfolded contrary to recorded history, with titles such as "If Napoleon Had Escaped to America" and "If the Moors in Spain Had Won." Churchill penned his contribution during his wilderness years, when he was out of office and working the lecture circuit across America. The essay is a playful study of a Civil War counterfactual: what might have happened had Robert E. Lee, with help from Stuart, won at Gettysburg and carried the South to victory in the war. It offers a look at Churchill's lively imagination at work, as well as a few glimpses of his views on race, war, and international politics as the storm clouds of World War II began to gather.
The seeds of Churchill's excursion into alternative history were planted during his trip to North America in 1929. He and his entourage—including his son, Randolph, an undergraduate at Oxford, and his brother, Jack—arrived by boat in Quebec, then took a train across Canada to the Rockies. Entering the United States, he was indignant when customs officers searched his party's bags, which held Prohibition-defying flasks of whiskey and brandy, plus reserves secreted in medicine bottles.
Churchill, who was in his mid-50s, was endlessly interested in America, the land of his mother's birth. In California he admired the redwoods, visited William Randolph Hearst at the newspaper magnate's seafront castle, and toured MGM's studios. In Chicago, he inspected the meatpacking plants that Upton Sinclair had condemned in The Jungle, which Churchill had favorably reviewed on its publication in 1906.