Octavian Report: Of all the world-historical names among political leaders, you’ve said you’d most like like to have dinner with Catherine the Great. Why?
Jay Winik: I would redefine that a little bit. I would say that of all the great leaders in the founding period of the modern world, the 1700’s to the 1790’s, I would most want to have dinner with Catherine the Great. That may seem a surprising choice given that such august leaders walked the stage of the world around that time as Thomas Jefferson, Alexander Hamilton, and George Washington. There were also Louis XVI and Marie Antoinette, the tragic and doomed royal couple that presided over the last monarchy of France. Then there were Robespierre and Danton, the revolutionaries who were the master spirits behind the undoing of the French monarchy and then spearheaded a revolution that swept the entire continent of Europe.
In that mix, we have Catherine: not a democrat or a republican like Washington or Hamilton or Jefferson or John Adams. Not a great royalist like a Louis XVI or Marie Antoinette. Not even a revolutionary like Danton or Robespierre. All of these people, mind you, are just inordinately fascinating. At a dinner party, they would captivate and hold your attention endlessly.
But Catherine above all. What makes her different, what makes her so unique, what makes her so worthy of her appellation is that she was a woman definitely in a man’s world — and she was an autocrat. As she put it, she was the autocrat of all the Russias. She was a great empire builder. She expanded the empire of Russia mightily during her reign. She was a great thinker. She bankrolled some of the great philosophes of the day and was friendly with them. All the French philosophes were in one way or another in her debt. In Denis Diderot’s case, she literally bankrolled his library. She bankrolled his studies. She bankrolled his writings. She even invited him to Russia — as she put it, to have a little chat with her. He stayed there with her for some six to eight months where they discussed revolution as a great idea. They discussed republicanism, the great idea. They discussed autocracy versus revolution and democracy and republicanism.
Another thing about Catherine the Great is she was an architect. She gave us buildings like the Hermitage. She had a remarkable painting collection, one that rivaled anythig one would see in the great Palace of Versailles. She was a real poet. What do I mean she was a poet? She assigned a soldier to do nothing but stand and watch over her palace year round awaiting the first drop of snow of the year. Think of how exciting that is and how poetic that is.
OR: How did she build her empire? What can modern leaders in all fields learn from her?
Winik: Catherine was forward-thinking. She was a modernizer. She was somebody who was looking ahead. Obviously, one of the great fears of the day was a health fear around the terror of smallpox. Catherine was behind finding a cure for it — and it stunned her subjects and it stunned her court and it stunned her lover Potemkin when she was the first person in Russia to undergo actually getting a smallpox vaccination. She was showing all her people that it was safe, it was healthy and it would be great for everyone. She took a great risk in doing it, but she did it nonetheless.
She thought about — I don’t want to say peace — but comity: how nations coexist. She corresponded, and this is remarkable if you think about it, with George Washington and Thomas Jefferson alike. She was helping them with the compilation of a dictionary of universal words. How exciting is that?
Then she did something that history has not given her credit for, but it was one of her grandest and greatest achievements. She, along with the French, helped midwife the Americans’ independence. In France’s case, they helped out with their armies and their munitions and their troops. They were critical at Yorktown. In Catherine’s case, she started the League of Neutrality which helped isolate Britain on the high seas. In doing so, she played a role in, of all things, midwifing a democracy, a republic. This coming from the autocrat of all the Russias. That’s fascinating.
She was a shrewd observer of the events of the day and age. She started out being a proponent of democracy, a proponent of republicanism. Then all that changed when Louis XVI was beheaded. At that point, she harshly turned reactionary and she turned violently against democracy, against republicanism, against the Revolution.
To give you a sense of what an empire builder  she was: she went to war against the Ottoman Empire. She wanted to tame, as she put it, the Muslims. Who was one of her great soldiers in that effort? None other than the heralded Navy man, John Paul Jones, who fought side by side with Prince Potemkin and the rest of the Russian armies.
Imagine, if you will, after she had invited John Paul Jones to come and fight with her. He came to the Royal Court and there he presented her with this audacious document. It was a copy of the Constitution. She took it in good spirit and she said she understood it. Then she waged her war against the Ottomans.
What can modern leaders learn from her? That’s a tough question because she was not a democrat. She was not a republican. She isn’t something we would want to see in today’s leaders because we value and cherish the rights of democracy and self-determination for people. But as a leader per se, she has much to commend her. She has to commend her a steadiness of purpose. She has to commend to her, at least on one level, her expansion of Russia. When Putin went in and took the Crimea recently,  he was doing nothing more than trying to replicate what Catherine the Great was doing. She was able to conduct diplomacy with foreign leaders and she knew when to be soft, as when she conducted diplomacy with the Americans or when she corresponded with George Washington or Jefferson. She knew when to be tough as well. She wrote to Louis XVI as he was facing the revolutionaries. She said, “I would pay attention to them the way I would pay attention to a dog baying at the moon.” Then she said something else quite prophetic. She said, “Give me 20,000 Cossacks and I will tame this revolution in a matter of weeks.” I have no doubt that she would have.
One other point I want to make about Catherine is about her turning harshly against republicanism. One has to remember that one of the crowning philosophies of the age was that a democracy could not exist in a large land mass.
If anything, that was the great contribution that the young American republic made, because even a number of the states were considered way too large for democracy to exist. It just seemed to be heresy for a democracy to exist in something as massive and extensive and vast as all of the Russias.
Catherine did not turn against the idea of republicanism because she was against self-determination of the people. She went on frequent trips across her country in which she would let her people see her and in which she listened to her people. She tried to come up with ideas and solutions to better their lot and better the way they lived. She was not a dictator. She was not a tyrant. She was an autocrat and she tried to make autocracy work for the greatest amount of people. She believed that deep somewhere in the Russian soul they were not built for a democracy. 
Does she have something to say for women in today’s world? Absolutely. Here she was, this woman, occupying this man’s world. For that, she was called a number of names. Not unlike Marie Antoinette. Yet Catherine felt that, not unlike some of the great queens of England, she could preside over the empire. She did it in a very tough and steely way. She came to power after a coup deposed her husband. She was tough as could be, but on the other hand, she was a great lover. She had this passionate love affair with Prince Potemkin.
Another one of her contributions to the social life and the social condition would be if one were to read her love letters between her and Potemkin. It’s passionate. It’s exciting. It’s fun. It’s whimsical. Everything about her was exciting and interesting.
OR: What was it that allowed her to do all this?
Winik: I think more than anything else is she understood somewhere in her bones and in her being that Russia was, in many ways, a great power but a backward power. She wanted to modernize and to pull it into the modern world so that it would be every bit the equal of France, which was this glittering monarchy. Every bit the equal of England, which was too a glittering monarchy. Every bit the equal of this young republic, America.
That’s why she built a palace, a Winter Palace, that was as grand and as gorgeous as Versailles. She understood that only by conversing with, conducting diplomacy with and being a part of the great leaders of the day and age could she make Russia a power that would be worthy of the modern world and make her a leader worthy of heading up a great power in that same world. That’s why she was friendly with the Americans. That’s why she was friendly with the European monarchs. That’s why she carefully bankrolled the philosophes. She was irrepressible and, in many ways, she was unstoppable.
OR: What is the episode that most shows her at her best as a leader?
Winik: I think it would really be two things. The first would be her understanding of the different philosophies of governance and governing that were becoming part of the modern world. She thought long and hard about how government should work and how to provide for the needs of one’s people.
At one point she engaged in what one might call a listening tour where she went all around Russia listening to her people. More than that, she even assembled — this was before the Americans did it, before the French did it — a congress of people from all different walks of life to give her guidance on how Russia should take care of the Russian people.
Then there was the warrior side of her. She knew — again, it’s very different from today’s world where we frown upon imperialism and warfare for warfare’s sake — that by making Russia a great power and by taming other powers, therein would lie the greatness of her country and of her nation. It was those two, the yin and the yang, the diplomacy and the warfare, that I think really where the hallmarks of etching her in history.
Catherine had the toughness of a George Washington. She had the forward-looking vision of a Thomas Jefferson or of an Alexander Hamilton. She had the love of culture and a love of social ideas of the philosophers of the day and of the great kings of the day.
She combined all this in one package. That’s, I think, what at the end of the day so pulls us to her and so marks her place as a great historical figure. Not only in her age, but I think in every age.
OR: Do you see any resonances between the rise of Russia under Catherine and the rise of the U.S.?
Winik: The American example is just in so many ways as really generous as the Russian example is. What we see in the American example, at the time that Catherine the Great was walking the earth, is a small group of what we call the Founding Fathers. They had studied the French, studied the English theorists. They had this radical notion that they could somehow create this democracy.
They didn’t call it democracy then, they called it republicanism. It was representative government and they had this notion that they could make it work. First in a small landmass and then in a large landmass. They solved the puzzle, a problem that nobody else had solved philosophically and theoretically. They figured out how there could be state government, a local government that would serve the needs of the people, while at the same time having a federal government which would knit everything together.
That was a great experiment. That was something that even the British couldn’t figure out. Certainly the French, as they tinkered with different ways to make their monarchy representative, couldn’t figure out. But the Americans did it.
When we think of the Constitutional Convention, we forget that it was held because America was falling apart. It looked like it was going to devolve into civil war. It was an act of, in many ways, desperation. To see if they could somehow make this experiment work. They didn’t do it legally. They did it extra-legally.
There was nothing that enabled or allowed them to get together and then create a whole new constitution out of whole cloth. They were as audacious as they were brilliant. They acted like marble gods because they felt that some day they would be viewed as marble gods — and indeed they have been.
I think they made that inflection point. My book, The Great Upheaval, is about the 1790s. I think that’s really where they laid the groundwork to be this great power. How amazing is it that the French, during their great revolution, looked to the Americans and they sought to emulate them?
Here was this tiny insignificant power, at the periphery of the world — and the Marquis de Lafayette, after the success of the American Revolution, went back to France and he tried to import American ideas.
He saw the French devolve into bloodshed, into the guillotine, into violence. Something the Americans never did. That, in some ways, is the greatest gift the Americans have given to the world. That inflection point didn’t come in 1945 after they became a world power, winning World War II. It didn’t come after World War I. It didn’t come after succeeding in the Civil War in which we abolished slavery and kept the Union whole. It came at the very beginning.
What the Americans gave as the greatest gift to the world was a framework for resolving political differences. Not through bloodshed, not through warfare, but peaceably through politics. Too often, we have this misguided notion that the Founding Fathers got along well with each other. It’s often said today that American government is broken; people say, wistfully, “If only we could be more like the Founding Fathers.”
Nothing could be further than the truth. They hated each other, despised each other passionately. Washington hated Jefferson. Jefferson hated Washington. Jefferson hated Hamilton. Hamilton hated Jefferson. Of course, Aaron Burr and Hamilton had a duel which ended up killing Hamilton. Madison, the father of our constitution, couldn’t stand Washington.
They hated each other because the stakes were so great. But nonetheless for all their passions and their hatreds and their dislikes and distaste for each other, they still adhered to that basic compact resolving peacefully. That is an extraordinary gift to the world.
OR: Do you think, given America’s current political polarization, we have drifted away from that republicanism?
Winik: This is one of the questions of our time. What’s concerning is that so many American people worry that democracy is under threat and that we could devolve into autocracy. I see this as a citizen, to be sure, but I also see it as an historian. That gives me some critical detachment. I would say the following. I would say that American democracy has come under assault repeatedly throughout its history and we have come through. We have had good leaders. We have had bad leaders. We have had strong leaders. We have had weak leaders. We have had wise leaders and we have had flawed leaders. Somehow, in spite of all that, when we most need it, we have always found the right leader at the right time. We’ve somehow navigated the difficult shoals of uncertain times.
By many accounts, Abraham Lincoln is our greatest president. He’s certainly one of our two greatest presidents along with George Washington. He was the most improbable of presidents to get elected. He was a one-term Congressman. A failed Senate candidate. He had no military experience except for 80 days drilling with a wooden rifle in the Black Hawk War. He was a bit of a hick. He spoke funny.
How was this the man to lead us in the greatest Civil War that the world has possibly ever seen? How was this the man to have the oratory that would give us strength and sustenance? How was the man to stitch up the nation and keep it whole at the end of that war, as I wrote about it in my book April 1865?
Yet somehow he rose to the occasion and he did it in spite of having a number of Southern states where he wasn’t even on the ballot. Whatever one may say today about Donald Trump or the uncertain circumstances we live in, it’s nothing compared to the Civil War. Nobody could have predicted, looking at the time, that Abraham Lincoln would be a good president. Let alone a great president. But he rose to become one when the nation most needed it.
Now, does that mean that this is the way it will always be? Well, democracy is a compact. Democracy works because the American people believe it works. Because our leaders believe it works and because they respect the basic institutions. What is so important about America is the institutions are bigger than any one figure. Bigger than any one president. These institutions are there to ensure the greatest amount of debate and also to ensure that minority rights are protected as well as the majority rights.
It’s a remarkable system. It would be hard for me to imagine anything undoing that because we have all these different pockets of resistance and all these different pockets of differing points of view. I don’t see that changing under President Trump.
OR: Do you feel that the understanding of history in general is at a low point?
Winik: I travel all around the country speaking about history. I find that there’s a great hunger for that history. There’s got to be a reason why history books as written by the leading public historians sell so phenomenally as well as they do. Nonetheless, in the age of Twitter and other instant forms of mass communication, I worry that things are becoming a little too ahistorical.
I think it’s important for Trump to appreciate what other presidents have gone through — if only just to see that he’s a temporary steward of this great experiment called America. The idea that we can somehow reinvent the wheel is hubris in the extreme. All our leaders, whether they’re Presidents, members of Congress or Senators, or Supreme Court justices need to learn from history as do the American people. History is our story. It’s who we are and it’s where we came from.