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.
In Winston Churchill’s fanciful alternative history, Lee wins at Gettysburg, and Jeb Stuart prevents World War I
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.
From New York, Churchill headed south and spent 10 days as a guest of Virginia governor Harry F. Byrd at the governor’s mansion on Richmond’s Capitol Square. On Churchill’s arrival, according to his granddaughter Celia Sandys, he mistook 14-year-old Harry Byrd Jr. for a servant, sent him out for a newspaper, and tipped him a quarter. When Mrs. Byrd served Virginia ham, he complained that there was no mustard. With his casual, cigar-waving air of entitlement, Churchill seemed unaware that he had offended his hosts. Young Harry, later his father’s successor in the U.S. Senate, recalled that when Churchill left, Mrs. Byrd ordered her husband never to invite that man to her house again.
On most days during Churchill’s stay with the Byrds, Douglas Southall Freeman, editor of the Richmond News Leader, whisked him away for tours of battlefields of the Civil War, which had fascinated the British leader even as a schoolboy. Freeman at the time was working on his Pulitzer Prize–winning biography of Robert E. Lee. The son of a Confederate soldier, he was famously said to have saluted the statue of Lee on the city’s Monument Avenue each morning on his way to work.
Churchill’s service as a young cavalry officer in India, Sudan, and South Africa as well as his brief duty as a World War I battalion commander had taught him that military history couldn’t be learned in the abstract. “No one can understand what happened merely through reading books and studying maps,” he wrote. “You must see the ground, you must cover the distances in person, you must measure the rivers, and see what the swamps were really like.”
Freeman and Churchill tramped among the ghosts of the Seven Days’ Battles and other famous Virginia showdowns. The British leader also toured Gettysburg, which he considered the decisive conflict of the Civil War. Years later he would analyze its events in his legendary A History of the English-Speaking Peoples, and his critique agrees comfortably with Freeman’s. Although Freeman admired Lee as the beau ideal of Virginia chivalry, he did not insist that he was perfection personified. He criticized Lee for mistakes in the field, as did Churchill. Both men wrote that Lee at Gettysburg had too much confidence in his army, based on its performance against a two-to-one superior force in the Chancellorsville campaign two months earlier. While most accounts of Chancellorsville feature Lee’s bold generalship and Stonewall Jackson’s daring flank march, Lee remembered what his outnumbered troops had done after Jackson was mortally wounded—how they drove Major General “Fighting Joe” Hooker’s powerful army back across the Rappahannock River in brutal, slugging combat.
“Lee believed his own army was invincible,” Churchill wrote, “and after Chancellorsville he had begun to regard the Army of the Potomac almost with contempt. He failed to distinguish between bad troops and good troops badly led. Ultimately it was not the army but its commander that had been beaten on the Rappahannock.” In Pennsylvania, however, it was the glum, courageous Major General George G. Meade who commanded the Union army. “It may well be that had Hooker been allowed to retain his command, Lee might have defeated him a second time,” Churchill speculated.
Both Freeman and Churchill thought that Jackson, had he lived, would have changed the outcome at Gettysburg. “I have but to show him my design, and I know that if it can be done it will be done,” Lee had said of Jackson. “Straight as the needle to the pole he advances to the execution of my purpose.”
Lieutenant General James Longstreet, who would play a critical role at Gettysburg, was a proven fighter, but he was not Stonewall Jackson. He had suggested that instead of attacking Meade’s lines on Cemetery Ridge head-on, Lee should swing south to get around the Federal left, placing the Confederates between Meade and Washington and thus forcing Meade to attack. When Lee rejected the idea, Longstreet sulked for the rest of the campaign.
Churchill sided with Lee: “It is not easy to see how Lee could have provisioned his army in such a position,” he asserted. He was appropriately hard on Longstreet, who balked at Lee’s attack orders on the second and third days of the battle: “Longstreet’s recalcitrance had ruined all chance of success at Gettysburg.”
Ultimately, however, Churchill’s analysis of the battle came back to the actions of Jeb Stuart. The flamboyant cavalry officer and his troops left Lee’s forces before the main fighting to pursue what became an ill-advised and ineffectual raid on the rear of the Union army. “Fortune, which had befriended [Lee] at Chancellorsville, now turned against him,” Churchill wrote. “Stuart’s long absence left him blind as to the enemy’s movements at the most critical stage of the campaign….Lee’s military genius did not shine. He was disconcerted by Stuart’s silence, was ‘off his balance.’”
Given Churchill’s dissection of Gettysburg’s actual events, it’s no surprise that he made Stuart a crucial figure in his imaginary account for If. Returning to England after his jaunt through America, he began to work out in his mind just how Lee lost at Gettysburg—and how he might have won. “It always amuses historians and philosophers to pick out the tiny things, the sharp agate points, on which the ponderous balance of destiny turns,” he writes in the essay.
Churchill goes on to attribute the Rebel victory to many small factors that aligned in their favor. “Anything…might have prevented Lee’s magnificent combination from synchronizing,” he writes. Like most historians, he points to the Confederate July 2 assault on Little Round Top as a pivotal moment; in his fictionalized version of events, the Rebels took the hill, depriving Meade of the high ground for his guns.
But ultimately, Churchill concludes that Stuart was the key. His narrative has the cavalry arrive at the Union rear precisely as Major General George Pickett led his infantry charge on Meade’s position on Cemetery Ridge. This helped produce a panic that swept through the whole left of Meade’s army. There could be “no conceivable doubt,” he writes, “that Pickett’s charge would have been defeated if Stuart with his encircling cavalry had not arrived in the rear of the Union position at the supreme moment.”
Perhaps Churchill’s adventurous service as a cavalryman inspired him to assign the decisive role to the dashing Stuart and his horsemen. For him, the battle was tipped not by the collision of masses of infantry, but by the hard-riding cavalry that moved on the fringes of the central ground.
Students of Churchill’s strategic leadership on a much bigger stage have seen that he often proposed roundabout approaches rather than direct confrontation. He did so in 1915, when as First Lord of the Admiralty he urged the disastrous Gallipoli landing in Turkey. Not long after, he must have been moved by the waste of lives he witnessed in his three months of service in France, where he became commander of the 6th Battalion, Royal Scots Fusiliers.
But Churchill doesn’t credit Stuart simply with saving the battle for Lee; he claims the cavalryman’s raid was exactly one of those “sharp agate points” that changes destiny. In his alternative history, Lee and his Army of Northern Virginia took Washington within three days of Gettysburg. Lee then declared the end of slavery in the South—a “master stroke,” Churchill wrote, that swung British opinion behind an alliance with the Confederacy. Faced with such a formidable combination, and with the moral issue of slavery removed, President Abraham Lincoln agreed to peace that September in the Treaty of Harpers Ferry, which gave all slaves their freedom and established the South as an independent nation.
Churchill’s imagination didn’t stop there. When tensions arose between the North and the South, he wrote, Lee created a diversion by sending the Confederate army to conquer Mexico in three years of bloody guerrilla war. At the turn of the 20th century, affairs beyond the oceans began to present graver threats. In his fable, Churchill explains how Prime Minister Arthur Balfour and President Theodore Roosevelt met to discuss a moral and psychological union. Once President Woodrow Wilson of the Confederacy joined the effort, “this august triumvirate” agreed to the Covenant of the English-Speaking Association on Christmas Day 1905.
The association adopted peace and international disarmament as its cause. But its voice was unheeded as the European powers began to mobilize for war in 1914. Calling for peace, it urged all nations to halt their armies at least 10 miles from their borders. If they did not, the association would consider itself “ipso facto at war with any power…whose troops invaded the territory of its neighbor.”
The combined influence of Britain and America brought breathing space to Europe. The armies backed away. Thus World War I—which “might well have led to the loss of many millions of lives, and to the destruction of capital that twenty years of toil, thrift and privation could not have replaced”—never came to pass.
And that, in Winston Churchill’s whimsical fantasy, is how Jeb Stuart prevented World War I. Amusing as it is, Churchill’s fictional account also suggests that, although he was out of Parliament, his mind was still busy with the political issues of the day, particularly race. Since he and Freeman were used to publishing their opinions on tender subjects, they may have discussed racial matters as they drove to and from the battlefields.
Freeman was moderate by the standards of the time, less of a hardliner than Governor Byrd, for example, who decades later as a U.S. Senator led Virginia’s campaign of “massive resistance” to school desegregation.
But moderation was not in Churchill’s makeup. In his If essay, he wrote derisively about what might have followed a Union victory in the war: “Let us only think what would have happened supposing the liberation of slaves had been followed by some idiotic assertion of racial equality, and even by attempts to graft white democratic institutions upon the simple, docile, gifted African race belonging to a much earlier chapter in human history.”
Churchill was not simply critiquing what happened in the postwar South. He was also underscoring his strong objection to what was happening in England’s colonial holdings. Mahatma Gandhi was crusading for the independence of India, and Churchill vehemently opposed the liberation movement throughout his career, correctly anticipating that it would lead to the breakup of Britain’s far-flung, mostly dark-skinned empire. He was a champion of liberty, but not too much of it, not for everyone.
Reading between the lines of Churchill’s alternative history, we also find signs of what Churchill valued in war. As military historian Max Hastings and others have noted, the British in World War II liked minor operations, while the Americans did not. “The mushroom growth of British special forces,” Hastings writes in Winston’s War, “reflected the prime minister’s conviction that war should, as far as possible, entertain its participants and showcase feats of daring to entertain the populace.” Hastings was speaking of Churchill’s enthusiasm for commando raids like those at Saint-Nazaire and Dieppe in 1942, and later for thrusting into the soft underbelly of Nazi-held Europe by attacking Crete and giving priority to the Italian campaign—campaigns with strong echoes of those of the gallant Stuart and his cavalrymen
Given that Churchill’s public life was so long and full, it’s hard to say how his study of the Civil War influenced his thinking in World War II. But it is obvious that to the end of his days, he was fascinated by this chapter of American history. He returned often to Gettysburg. He was there again in 1943 as the guest of Franklin Roosevelt during a wartime visit to the president’s Catoctin Mountain retreat of Shangri-la (later Camp David), a few miles south of the battlefield. (He is said to have corrected Roosevelt when the president mistakenly said that the battle had been fought in 1864.) And in 1959, when he was 84 years old, he took a presidential helicopter tour of the battlefield with Dwight Eisenhower, whose farm was nearby.
Since Churchill’s time, the alternative-history genre has thrived, with many books about the Civil War and at least one about Gettysburg. There is also a computer game, taking off from the moment in 1931 when Churchill looked the wrong way in New York and stepped off the curb into the path of an oncoming automobile. The game deals with what would have happened to the world if that accident had proved fatal. Some ifs are terrible to contemplate.