Today I will keep this short as it is still finals time and I have papers to grade.
Of all the quixotic pastimes, asking “what if” is perhaps the one most associated with history. Perhaps the first serious work in the genre is Tirant lo Blanc, a Catalan epic written by Joanot Martorell and Martí Joan de Galba. It is an adventure story that is most famous for the main character Tirant the White, a Breton knight who goes on a quest to save Constantinople in 1453 and stop the Ottoman conquest. It was written in 1490, before Columbus sailed the ocean blue two years later. What might have been if Constantinople had held out is a topic that 20th-century writers would return to.
Speculation can be for romantic regret, like the loss of a great imperial legacy; it could be simple literary enjoyment; or it can seek to make a point about the present by playing with the past.
In 1930, Winston Leonard Spencer Churchill wrote a short satire titled “If Lee Had Not Won the Battle of Gettysburg.” A perfect title for a cheeky, funny short story. In it, Churchill opens with a bang where his narrator remarks on how great things were for Kaiser Wilhelm II in the alternative 1930 and how it might not have been so grand if old Robert E. Lee had not won Gettysburg and split the United States into two separate countries.
The quaint conceit of imagining what would have happened if some important or unimportant event had settled itself differently has become so fashionable that I am encouraged to enter upon an absurd speculation.
—Sir Winston Churchill, If Lee Had Not Won the Battle of Gettysburg published in Scribner’s Magazine, December 1930
For a short story that was originally only ten pages, Churchill makes the gag work as well as one could imagine for a story that has Lee capturing Washington and then unilaterally freeing all the slaves by military diktat, leaving Jefferson Davis and the whole Confederacy no choice but to bow to Lee’s will.
It is hard to read it without laughing.
Churchill is playing with history in an unserious manner in order to make a sly argument that an association of the English-speaking peoples, meaning the British Empire and the USA, would be great for the stability of the world. To do this, he needs the rebel Confederacy to win, then for the UK to back them after winning the battle, but that means slavery has to go away or the UK would be backing slavery, and this allows the defeat of the Union to not be a loss for civilization but simply the fate of nations in a contest of arms. With that done, Churchill can get on with his crazy tale of how the English-speaking peoples worked everything out among themselves and by 1914 are strong enough to tell the continental powers of Europe to knock it off so World War One does not happen.
Churchill’s narrator is a historian in an alternate 1930 who is lecturing us about how small changes can lead to bigger changes, and why the British imperial system is so much better than American liberalism on issues such as race and civil rights.
It is wild to think that Winston Churchill wrote such a thing, and how much authors like Harry Turtledove have basically taken Churchill’s plot way too seriously, to the point that I cannot read the crazy Southern-focused plots without thinking of them as derivative of Churchill.
However, the American Civil War aka the War of the Rebellion, has been a classic playground for the speculative-history genre. “What if Lee had won at Antietam?” is almost a cliché turning point by now. But the twentieth century shocked our imaginations. The Second World War, the war where Churchill was the leader, is now the biggest “what if.” Our bookstores are full of works of non-fiction and fiction that speculate about Churchill and his struggle against Hitler. The runaway success of Amazon’s Man in the High Castle confirmed it. At the time Amazon had a “pilot season” program that let viewers watch various pilot episodes and provide feedback and ratings so Amazon could decide what shows to produce and what to turn down. Man in the High Castle crushed its competitors, while a Civil War series offered at the same time was dismissed by most viewers. It is hard to top the A-bomb, D-Day and Pearl Harbor.
The Second World War touches so much. The rise of China. The Civil Rights Movement. The American Century. The reordering of the Middle East. The Cold War and the Space Race. What if indeed.
In fiction as well as non-fiction, WWII is the champion. Which makes sense because we still question aspects of that war, eighty years after it ended. And yet, sometimes, the questions we ask, the ones that are most interesting, are the ones that history does not provide answers for, and we must engage our imaginations. But also the author as an artist may find that the canvas they need is an alternative world that is real, but altered, and there history can provide scenarios that are more enticing or haunting than pure fantasy can manage: The dark mirrors of our pasts. I think Winston would approve.

