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From Comedian to President: The Evolution of Ukraine's President

• Michele McAloon • Season 3 • Episode 135

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The extraordinary journey of Volodymyr Zelensky—from Ukraine's most beloved comedian to its wartime president—represents one of history's most dramatic political transformations. Simon Shuster, who has reported from Ukraine and Russia for over 15 years, joins us to discuss his revealing biography "The Showman: Inside the Invasion that Shook the World and Made a Leader of Volodymyr Zelensky."

Having first met Zelensky during his improbable presidential campaign in 2019, Shuster witnessed firsthand how an entertainer with zero political experience captured Ukraine's highest office by playing a fictional president on television. What started as a seemingly naive political experiment took a profound turn when Russia launched its full-scale invasion in February 2022.

Shuster takes us behind the scenes of Zelensky's remarkable metamorphosis from lighthearted performer to resolute wartime leader. Drawing from exclusive interviews with Zelensky, his wife Olena Zelenska, and top military commanders including General Valery Zaluzhny, the biography presents a nuanced portrait that avoids both hagiography and undue criticism. We explore how Zelensky consciously redesigned his persona when confronted with existential crisis, leveraging his performance skills to project strength and determination when Ukraine needed it most.

Particularly fascinating is how Zelensky revolutionized wartime communication, using social media and direct appeals to bypass traditional diplomatic channels and mobilize global support. His stubborn confidence—sometimes alienating allies with relentless demands—nevertheless secured unprecedented levels of military assistance when Ukraine's survival hung in the balance.

As the war continues with no clear end in sight, we discuss the challenges Zelensky faces in negotiating any potential peace settlement and what the future might hold for this unlikely world leader who found himself thrust into history. Whether you're interested in geopolitics, leadership in crisis, or the power of communication in modern warfare, this conversation offers invaluable insights into how one man's transformation mirrored his nation's fight for survival.

Michele McAloon:

You're listening to Crossword, where cultural clues lead to the truth of the word, and my name is Michele McAloon. Today we have a fantastic interview with an author, Simon Shuster, who has written the Showman Inside the Invasion that Shook the World and Made a Leader of Vladimir Zelensky. Whether you agree with, US should support Ukraine, whether you disagree with it. Whatever the position is in Europe, there's no debate that President Zelensky has made a mark in history. The biography that Mr Shuster writes is a glimpse of Zelensky.

Michele McAloon:

I think that his portrait has not been finished, that he will be on the scene for a long time. He's 43, 44 years old. Whether he's the president of Ukraine or doing something else, he is definitely, without a doubt, a world player, a complex individual, and really shows his evolution through the Russian invasion of his country. So I hope you enjoy listening. If you will be so kind to like and subscribe it helps the numbers and if you want to know anything more about me, go to my webpage at bookcluescom, where you can also contact me. Thank you, Happy listening, Simon Schuster. Welcome to the show.

Simon Shuster:

Thank you, really glad to be with you.

Michele McAloon:

And your cat. His cat is with us in the studio, so we're happy about that. Okay, mr Schuster has written a wonderful book on Zelensky. It's called the Showman Inside the Invasion that Shook the World and Made a Leader of Vladimir Zelensky. It's a William Morrow is the publisher and it's an imprint of HarperCollins.

Michele McAloon:

Mr Shuster has reported in Russia and Ukraine for over 15 years as a staff correspondent on Time magazine. He was born in Moscow. He and his family immigrated from the Soviet Union when he was six years old. He went to Stanford, graduated in 2005, and has spent a lot of time working as a reporter for the Moscow Times, reuters, the Associated Press and other publications. His political coverage of Russia's descent into authoritarianism has included profiles of Putin, interviews with Medvedev and other top officials. He was one of the first reporters in after Crimea was occupied by Russian troops. We are very glad to have him here with us to talk about really the man of the century so far, and this is Zelensky. I have a feeling that this was a man that just was pushed into something that he never, ever expected on the world scale. When did you first meet President Zelensky?

Simon Shuster:

I met him when he was running for president in the spring of 2019. Yeah, so he was just appearing on the political stage.

Michele McAloon:

Okay, I know you had interviewed three other Ukrainian presidents. What brought you to meeting with him? Was it just through your connections and you were able to meet him?

Simon Shuster:

I'm a third Ukrainian president, but I mean, I've been covering Ukraine quite intensively Ukrainian politics society for more than a decade, so it was nothing unusual for me to be reporting on the presidential elections of 2019. They weren't my first go around. I'd already convinced my editors that these elections were interesting and worth a separate feature my editors at Time Magazine when Zelensky appeared as sort of a dark horse candidate for president. So it made sense, given how quickly he was shooting up in the popularity ratings in that race, that we should pay some attention to him as well. So I went to Kiev as I normally would and interviewed him, spent some time with him backstage of his comedy show, but also interviewed the other candidates who were running at the time his main rivals.

Michele McAloon:

Your biography very much shows how, basically, the evolution of Zelensky, how he kind of went from a comedian, a performer, as you say, the showman to a wartime president, and what's really great about your biography. It's not an ode to Zelensky, it's not about how great Zelensky is and it's also not about how bad Zelensky is. You do a very good job of showing the arc of this evolution.

Simon Shuster:

That's the best compliment a journalist could hope for. Thank you.

Michele McAloon:

What's that? A neutral stance on something you're reporting? No, it really does. It shows a man that has faced some serious challenges, more than he expected.

Michele McAloon:

I was actually speaking to a friend of mine and telling him about this biography and he said you know, michelle, imagine kind of what it would be like if Charlie Sheen had run for president and become president and then our country had broken out into war. Now I do not want to insult Zelensky at all. I think Zelensky is probably a lot smarter than Charlie Sheen, but I mean, here was basically a performer. He was a successful performer. He had made a lot of wealth off that. He runs for president, which is actually kind of an improbable step too, and then he becomes a wartime president in a war that actually is being fought on the world stage.

Michele McAloon:

So it's actually a very remarkable trajectory that you are able to cover, and one of your best statements is at the end of your book when you said wars are fought in the minds of men and women long before the shooting starts. And Zelensky turned this. He operated on that plane versus on a smaller plane, and maybe only a showman could do this. Tell us, when people ask you what is Zelensky like. What was he like when you first met him? Because, as your book says, he's a very different person in the end.

Simon Shuster:

Yeah Well, let me respond quickly to the to the Charlie Sheen comparison. I hadn't heard that one before. I wonder why you picked Charlie Sheen, but I, I think in my mind. If I look for parallels in American kind of pop culture, I think Jon Stewart is a good one, partly because Zelensky did so much political comedy similar to Jon Stewart. He really was a commentator and a satirist satirizing politicians.

Simon Shuster:

I also think about Julia Louis-Dreyfus in her role in Veep, playing the vice president of the United States. It's sort of like if Julia Louis-Dreyfus were to throw her hat in the ring for the American presidency halfway through the second season of Veep, because President Zelensky, when he became a presidential candidate, was playing the president of Ukraine on the most popular comedy sitcom on Ukrainian television. So, yeah, there are a lot of ways that you could compare him to foreign movie stars, but that is important to keep in mind that, yeah, his entire career leading into politics was as a showman, as a producer of television, as an actor, a comedian, stand-up, vaudeville, slapstick, musical numbers. I mean, he was really a jack-of-all-trades in terms of entertainment and that is part of the reason I called the book the Showman, because that his, his personality, his character is so rooted in that experience and in that first and very long stage of his career. So that gets to your your question of what he was like. He struck me, as you know, very funny, very charismatic, very fun to be around.

Simon Shuster:

I met him, like I said, backstage of his comedy show which was going on during the presidential campaign. He did not take a pause in his career as a comedian in order to run for president. He did both at the same time and in many ways his comedy shows were his campaign. He appealed to voters through his comedy, through his stage acts, through his sitcoms, through his many TV appearances in the role in which Ukrainians mostly knew him, which was, as an actor and as a comedian, probably the best political satirist of his generation.

Simon Shuster:

So that is the Zelensky I met, but I was coming at it as a political reporter covering a presidential election. So to me, and with my questions in my notebook, they were political and I wanted to know what he would do to address the many grave challenges that Ukraine was facing then. It was then already about five years into a war with Russia over control of the eastern Donbass region. It faced all kinds of diplomatic and economic challenges. So I wanted to see whether this guy had the chops for such a difficult job, and I came away pretty clearly convinced that he was not, that he was naive about what the job would take, that he was a little bit. You know, he was fun and nice to be around and happy-go-lucky and very optimistic and had a great deal of self-confidence, but it didn't seem like he had the experience or the wherewithal to handle the problems Ukraine was facing.

Michele McAloon:

Why did he decide to run?

Simon Shuster:

Yeah, I explore that quite a lot in the book and you know it's an open and live debate, including among his friends and allies. You hear different answers depending on who you ask. When I asked him at the time, of course that was one of my main questions what are you even doing going into politics, and why would you do that, as a celebrity comedian whose life is just like a rock stars? You know, why would you leave all that behind and go into politics? That didn't make sense to me. He gave answers that I didn't find particularly convincing at the time, related to essentially criticizing his rivals, criticizing the political establishment that had ruled Ukraine for decades, the kind of system of oligarchs and political clans that he was fed up with, and he saw them running the country into the ground. He said he wanted to change that, to uproot that system, to drain the swamp. In those ways, in those anti-establishment ways, he was similar to actually Donald Trump in 2016. He ran as a kind of candidate against the system. Those were the reasons he gave. He also said he really wanted to end the war in the Donbass that had been raging since 2014, so about five years at that point. Those were the reasons he gave His friends and close allies talk about other things, such as him wanting a new challenge.

Simon Shuster:

I mean he had reached the pinnacle of his career as a comedian. There wasn't much he could do, the prospects of him. I mean he did dream and I think he still does dream of making it in Hollywood and winning an Oscar, but that is not likely for a Ukrainian comedian who doesn't speak English. So he'd reached basically the top of his chosen profession and he was ready for a new challenge and he saw politics providing that. He wanted to give it a go and see if he could pull it off. I mean, it was in many ways this kind of weird experiment in the magic of mass communication and TV campaigning, campaigning through comedy, and he saw that as a very fun challenge. I think that was also a factor.

Michele McAloon:

Let me ask you a question about nationality here, because you always have to talk about that with Ukraine. I mean, he saw himself as fully Ukrainian, even though his main language was Russian, and that was that's not abnormal. But he grew up in the town of Kriby Ry, but he saw himself as fully inculcated is fully part of Ukrainian society, correct?

Simon Shuster:

Yeah, sure.

Michele McAloon:

Yeah, ukrainian nationality is. It's always very complex. It just is because it's had so many influences through the years. So he takes president. It's 2019 when he becomes president. Ukraine is still is at war with Russia. It's been at war with Russia for five years. By this point, he's navigating the politics of Ukrainian society. He's actually doing fairly well in the beginning, but he has a drop towards the, towards the war. I think one of my biggest questions that I've always had is why didn't Zelensky believe the intelligence that the invasion was imminent in 2022?

Simon Shuster:

Yeah, I mean, there's no particular mystery there. I do look at this pretty closely in the book, the lead up to the war, the intelligence that he was looking at and his failure to foresee what was coming, despite the ample warnings he was getting from the United States, didn't particularly care for the book at least the excerpts that he read because it was so critical and explored so deeply that failure to foresee what was coming in 2022. And that's something that's politically very sensitive for him and that he's criticized for in Ukraine quite a lot. But you know it's easy to criticize him with the benefit of hindsight. Looking back, it's indisputable that the Americans were right, the American intelligence was dead on. But that's easy with hindsight. At the time you know what I did and what I remember very clearly, having lived through those moments of doubt leading into the invasion, when there was such a lively debate internationally and in Ukraine about what was coming.

Simon Shuster:

So Zelensky, as the president of the country, was getting a variety of intelligence and warnings from different sources many European countries. He was talking to Macron in France. He was talking to Schultz, the German chancellor. Boris Johnson was then the prime minister of the UK. So he was talking to the Americans. He was getting direct briefings from Bill Burns, the head of the CIA, and it was quite a smorgasbord of intelligence that was presented to him. And at the same time he was getting intelligence from his own services. The Ukrainian, who are quite strong and, you know, have an interesting pool of sources in Russia. That differs quite a bit from the kinds of intelligence collection that the US does. We can talk about that if you want. But the point I'm trying to make is that he was presented with quite a variety of predictions, quite a wide spectrum.

Simon Shuster:

Generally, I would say there was consensus that some kind of sharp escalation in the war in eastern Ukraine was going to happen. There wasn't a lot of disagreement about that. But there was a lot of disagreement about what it would look like and the scale it would take. So the Americans were predicting the most extreme scenario of a full scale invasion with Kiev as the main target, aiming to kill or capture Zelensky himself, unseat his government and take over most, if not all, of the country. And then he was hearing many other things from, for example, the French and the Germans who were talking to Putin. Scholz met with Putin I don't remember exactly how many days, but within a few weeks of the invasion starting, putin told him don't worry, herr Kanzler, I will not invade. Macron was hearing the same things from Putin and was repeating publicly Putin's assurances that Russia would not invade.

Simon Shuster:

So you can imagine, you know, you have to put yourself in Zelensky's position in that moment, not with the benefit of hindsight, but in that moment, what do you choose to believe? And I think for me, I also didn't believe the American intelligence. So I was very much in solidarity with President Zelensky at the time, didn't expect what Russia ended up doing. Main reason for me, actually and this is also a big factor for Zelensky Main reason for me actually and this is also a big factor for Zelensky is that it just seemed so stupid for Putin to do this. It seemed so obvious to me and to Zelensky that it would be an absolutely brutal war, that the Ukrainians would fight back, that it wouldn't be such a gamble and risk so much and spend so much in money and blood treasure for this adventure. So it seemed crazy. All of that seemed perfectly reasonable, those arguments at the time and he chose to believe the less extreme scenarios and predictions and he chose to believe that Putin is not a psychopath. He was wrong.

Michele McAloon:

And he chose to believe that Putin is, or even Obama even earlier, was using. Was he one of the first ones to really use, like the television and social media that was available at the time for his early presidency or for his election? But also he was doing that in his presidency and he's definitely used that during the war.

Simon Shuster:

Yeah, I don't think he was the first. Every politician uses every medium available to him or her to win votes and maintain support. I think Zelensky was innovative in a lot of ways Well in his presidential campaign, in the way that he used comedy. This phenomenon of playing the president on TV is just a fascinating experiment in politics because the show where he played the president sort of invited millions of viewers in Ukraine to mistake him for the president in the world of the sitcom that he as a writer on the show controls. So he wrote himself as a supremely likable, humble, effective, uncorrupted leader. So of course many viewers, consciously or subconsciously, were sort of tempted to see in him the potential for that kind of president in real life, even though of course in real life he cannot script events and he does not control reality. So in that way it was just a really unique situation. I'm really not aware of anything close in terms of the way he won the presidency through, in many ways through this sitcom where he played the president.

Simon Shuster:

I think your question also gets at the way he used it during the war.

Simon Shuster:

That's another field of innovation where he was very effective in the way that he used social media and traditional media like television, to make appeals for international assistance and support in a war where Ukraine could not survive without a massive influx of foreign weapons and money and various kinds of assistance.

Simon Shuster:

So he really needed to keep the world on his side and what I argue in the book and I try to demonstrate as clearly as I can, is that he found these very innovative ways to engage in diplomacy and public diplomacy to keep the world on his side, even when politicians were tempted to turn away or stay on the sidelines. He found ways to appeal to the hearts and minds of the people in the foreign democracies whose support he needed, to create grassroots pressure on the political leaders in those foreign democracies to make it difficult for them to leave Ukraine in the lurch, to turn their backs on Ukraine. He appealed directly through various, you know, very kind of captivating moves, speeches, modes of communication, these videos, kind of in the style of TikTok, to really grab people's attention, to keep them watching, to keep them engaged with him as a character, with Ukraine as a cause, and that made it much more difficult for foreign leaders in foreign democracies to deny his requests for assistance.

Michele McAloon:

What changes did you see between him between 2019 and the war? Did you see a maturation process for him? Or because by that he had been through the Minsk II agreements, the Minsk I, the Minsk II agreements that it all really sort of failed? I believe he had had an interview with Putin by this time. What changes did you see in him?

Simon Shuster:

Yeah, dramatic changes. I mean the way the experience of the first few months of the full-scale invasion changed him was really in some moments scary to watch because his personality transformed so dramatically. Even in the months leading up to the invasion, when it was clear that something very grim and deadly was about to happen on some scale, we weren't sure how bad it would be out to happen on some scale. We weren't sure how bad it would be. But even then his administration was open, easygoing, known for a kind of expansive approach to the kinds of advisors who would come through the door and cycle in and out, and it was very kind of open to brainstorms, briefings. Many of the people who worked in the administration over the years compared it to a kind of Silicon Valley startup in its sort of easygoing, life-loving, life-affirming attitude environment. You can imagine how drastically that has to change when that administration finds itself holed up in a bunker waiting for Russian commandos to burst through the doors at any minute and kill everyone. You have to change, you have to adapt. So the way they adapted to get more directly to your question Zelensky became, he took on a role of a wartime leader, as he imagined a wartime leader to be.

Simon Shuster:

In one of our interviews for the book he talked about giving himself a kind of pep talk where he said, basically, the world is watching you. Now you have to act the way a head of state must act. This is how he phrased it. What does he mean by that? To unpack that a little bit there is no set rule book for being a wartime leader facing down a nuclear superpower that wants to kill you. There's nothing that can really prepare you for that. So you have to draw on maybe historical examples like, say, churchill or other wartime leaders. You have to look to maybe films you've seen again, books you've read and sort of form in your mind a personality or a character that you must then embody to serve as the wartime leader that your country needs. That was his thought process.

Simon Shuster:

In some ways, and again as I argue in the book, I think his experience as an actor, his ability to take on roles as an actor on screen and on stage, helped him to have the flexibility of mind to very quickly shift into a new mode of behavior, a new mode of thinking, really a new persona.

Simon Shuster:

And we saw that persona. Many people who didn't know Zelensky before the full-scale invasion saw him on their screens, fully formed in this kind of pseudo-military uniform that he wore the green t-shirt, the beard quickly taking shape in the first couple of weeks. Shirt the beard quickly taking shape in the first couple of weeks and this kind of aura of the wartime commander very confident, stern, tough, emotional, you know. And all these qualities were part of the role that he designed for himself, and he and his team talked to me in our interviews about this being very deliberate. They designed this character, the leader, the wartime leader that Ukraine needed, and Zelensky stepped into that role and came to embody it fully, so fully that his previous self, as far as I can tell, spending time with him now, is lost. That old Zelensky is gone and I can't imagine him ever returning.

Michele McAloon:

Wow, folksy kind of hero type of guy, I tell you, his decision not to leave Ukraine, not to leave Kyiv when the invasion started, is just a moment of just sheer leadership, of sheer morality, because if he had left, I think many are convinced that Ukraine would not exist today. Russia would have rolled over it. What do you think about that?

Simon Shuster:

It's fair, I mean I don't want to give them too much credit because the resistance, the military resistance and also the fighting that the regular civilians engaged in and volunteering to fight, taking up arms with everything from hunting rifles to kind of homemade drones, whatever, I mean that was very instrumental and critical to Ukraine's defense.

Simon Shuster:

And Zelensky was the figurehead, he was the face of that resistance, certainly on the world stage, but in terms of commanding troops into battle and really fighting the Russians back in the first weeks and months of the invasion, I'd say the military commanders have, you know, deserve more credit for those achievements on the battlefield.

Simon Shuster:

But definitely, you know, if he had run, I think, the state hierarchy again, apart from the military, but the hierarchy of the state, the bureaucracy, governors, mayors, everyone who kind of keeps the state functioning, I think the chances are much higher that it would have crumbled.

Simon Shuster:

And I know from talking to some of these officials that to them it meant a lot that the boss, the president, stayed in his post and gave explicit orders for everyone to stay where they are. He did in those first days sort of decide that okay, we do, just in case, need to form a kind of backup government and he sent roughly 40 or 50% of the ministers in his government to Lviv, to Western Ukraine, to kind of be there, just in case Kiev fell. But for the most part he told everyone to stick around and he showed them that he was doing the same. And his physical presence in Kiev, his physical presence in the seat of power, of presidential power, in his presidential compound, really served as an inspiration. And it's hard to predict what would have happened if he'd fled, but I think the hierarchy of the state would much more likely have crumbled without him, that's true.

Michele McAloon:

Let me ask you a question and you touch upon it in the book, especially when you're talking about General Zeluzhny but what was his relationship with his military commanders in the field?

Simon Shuster:

Yeah, it was a big evolution, I mean, I'd say in the book. There are two relationships that I explore throughout the book and I sort of find them extremely revealing about Zelensky's character. He, of course, is the central character, it's his biography. But the two relationships I'm talking about are between him and his wife on one hand, and then the other one is between him and his top military commander, general Valery Zaluzhny, who for about the first two years of the full-scale invasion, commanded the armed forces of Ukraine. So that relationship is complex and fascinating and very revealing about both men. I'd say. You know, they knew each other starting in 2019, actually, by chance, zaluzhny was not then in 2019, was not the commander of the armed forces, he was about two levels down from that. He was already a general, but he was not I don't think he was even a member of the general staff, of the kind of Joint Chiefs equivalent in Ukraine. Anyway, he was given the job of briefing Zelensky when Zelensky took power in 2019, of basically introducing him to like, okay, this is our military, this is what we do, this is who we are, this is what we're fighting. Yeah, he gave the briefing, you know. So they met then and Zeluzny made a good impression.

Simon Shuster:

One thing that I was surprised to learn in talking to Zeluzny and getting to know him for the book is that he is super funny. I've never laughed so hard in an interview as I did with General Zaluzhny. He's extremely charismatic and just a lovely guy to be around and he had ambitions growing up to do stand-up comedy like Zelensky. They were also able to connect in their early meetings, their first meetings, when they were getting to know each other on that level. I mean, they're both to gag, they're both very funny.

Simon Shuster:

Zaluzhne is the furthest thing from a kind of stiff ramrod posture type of general and then, you know, skipping ahead quite a bit here. But when the full-scale invasion was approaching they had disagreements. Zaluzhne was pushing for a much more robust set of preparations to prepare the border, to call up reserves, to dig trenches, I mean all kinds of stuff, and Zelensky was telling him not to do those things because they could cause panic in society. That was a tense moment for sure in their relationship. They disagreed about how Ukraine should prepare. In their relationship they disagreed about how Ukraine should prepare Once the invasion was underway.

Simon Shuster:

What I observed between the two men was an enormous amount of respect, especially Zelensky respecting Zeluzhny. He did see in those early days and weeks of the invasion he saw Zeluzhny as a hero, a real savior, had the privilege of being with Zelensky when he had a call with Zelushny at one point and I was really struck by just how reverent his tone was in speaking to the general and then skipping ahead quite a bit again. I mean, this is all like- Right sure.

Simon Shuster:

I've been great detail in the book, but what you saw in the months that followed is Zelensky, the president, began to feel a great deal of confidence in his own decision-making abilities as a military commander, not only as a diplomat, not only as someone who's fighting for hearts and minds, but in deciding specifically how military resources should be allocated, what battles to engage in, what not to engage in. And he started making these decisions, as is his right under the constitution. But they were often not aligned with the decisions that Zaluzhny would make. So they began to clash on questions of strategy and that's when they really their falling out became basically irreconcilable. It was very ugly behind the scenes. They were clashing all the time, even though in public they were saying you know everything's fine, you know there's no split. But by the end of the first year of the full-scale invasion their relationship was terrible, and then it took another year for it to lead, finally in the beginning of 2024.

Simon Shuster:

Zaluzhny's dismissal. It's a complicated story and there's a reason why I spent so much time in the book exploring it, because it shows you also the evolution of Zelensky and the way that he, you know, for better or worse, began to see himself also as a military commander, even though he had no such relevant experience saw that during the counteroffensive the failed counteroffensive in 2023.

Michele McAloon:

So talk to us a little about Alina Zelenska. Their relationship, as you describe it in the book, seems very fraught. It doesn't seem like I don't know if that's what you wanted to portray, but to me as the reader, it's not a smooth relationship. It's a difficult relationship.

Simon Shuster:

Yeah, it's definitely a tough one.

Simon Shuster:

Yeah, and I'm just eternally grateful to her for how open she was with me. Man, I don't think I could have written the book without her help. We had several interviews, really long and in-depth, and she's a very honest, open person. She can't stand BS. She would often in our interviews, correct things that the president had told me and she would be like, no, no, no, that's not how it happened. Here's the real story. So I'm just very grateful to her for her openness.

Simon Shuster:

Yeah, the relationship was tough. I mean, there are many reasons for it. I think the fundamental reason is his workaholism. He is just going back to his career as a comedian. He focused on the work, just obsessed with doing his job, giving everything to his work, whether it's in the film industry or running for president or politics, and he leaves less time and space in his life for his family than his wife would like, and there were many occasions not many occasions, but several occasions when she publicly called him out for his failings as a father and as a husband.

Simon Shuster:

She certainly, you know that came through in our interviews as well. But yeah, the reason is, you know, he devotes himself so fully to the job, whatever job he's doing in the context of the full-scale invasion, the way that manifests itself was they were living apart. Yes, for security reasons. Zelensky and his security detail certainly had good reason to believe that it would be more dangerous for his family to live with him than somewhere apart in a secure location. But it was also, you know, I'm quite convinced it also had to do with his desire to just not be distracted, to be able to give himself up as fully as he possibly could to the leadership role that had been thrust at him.

Michele McAloon:

Simon, you've seen him have some difficulties with foreign leaders, especially American foreign leaders, and, believe me, it's not all his fault and we'll talk about the Trump debacle. But how much of his personality has played into this? On the phone, and he wanted more weapons and Joe Biden got really angry about it. He also, you know, the thing with Trump that just keeps the gift, that keeps giving, is the Hunter Biden scandal and the Burisma scandal of trying to negotiate that. How much of his personality has played into and I guess maybe I'm asking you to dish negatively on, I don't know, but of into his relationships with foreign leaders, always you to dish negatively on, I don't know, but of into his relationships with foreign leaders.

Simon Shuster:

Always happy to dish. It's a huge factor. It's been so interesting to observe what's often called the role of the individual in history.

Simon Shuster:

You know you have all these institutions, some that have existed for centuries that you think are so stable, and these institutions of state either clashing or cooperating in different ways. But what we see in Zelensky and we've seen in various personalities through history, is that one individual can shake up an entire system, an entire global order, in very unpredictable ways. In many ways I think this book is another example of that, a very telling and revealing one in many ways in the ways that his personality traits that came again largely from his career in show business really shaped the war, the way the war went and the level of support that Ukraine got from foreign allies. So, to be more specific, two of the they're not the only two, but two of the most stable qualities in his personality are stubbornness and confidence. He has an almost I don't know where he gets it, but he has a really kind of preternatural belief in himself that is consistent again, going back to his teenage years, starting out in show business as a young comedian. He believed he could conquer the world and sometimes it was delusional, sometimes it was kind of a show Right Showman's right.

Simon Shuster:

It's not clear how deep it went, but he had this ability to sort of rally people around himself. Right Shungan, right it, even if the odds look incredibly unlikely. Just believe in me and we'll get it done. And he used that quality. It's again. It's been consistent throughout his life. He used that quality to rally and inspire foreign leaders in ways that were really fascinating to observe, to the point where I'm not sure I should like call anybody out specifically. But yeah, why not? Like it looked like it looked to me. Observing him in in his relationships and meetings with foreign leaders, they were like almost had a crush on him or they saw in him some kind of role model.

Michele McAloon:

They're fanboys, right yeah.

Simon Shuster:

Yes, fanboys. I am thinking of Emmanuel Macron. I don't mean for that to be insulting to him, but it was very interesting to observe. Their relationship has evolved quite a lot. Right now they're very close. They talk on the phone daily, usually a few times a day, but I've seen when they're together. Macron is just really enamored of Zelensky and very impressed by him, and part of that is this kind of confidence, this aura of confidence that he exudes.

Simon Shuster:

Yeah, and then the stubbornness is another quality maybe less admirable, I don't know, but also very useful where he just doesn't give up.

Simon Shuster:

If he sets his mind on something, he will set aside all politeness protocols, all the rules of behavior and all the niceties protocols, all the rules of behavior and all the niceties, and he will demand it from you until you give it to him. This kind of stubbornness is often what got him into trouble with foreign allies, like President Joe Biden, who found it annoying and frustrating. And another one is Ben Wallace. The former now former British defense minister publicly dressed Zelensky down for seeming ungrateful and constantly making these demands, even when he was receiving a great deal of help, still coming with more and more demands without even taking a breath to kind of show gratitude or a pause in his stream of requests. That is also typical or classic Zelensky, this kind of unending, stubborn willfulness. That is also fundamentally him, I guess. On balance. Maybe it's a little too early to say, but on balance I think it served him and his country well during the war, even though it has led to tensions with specific leaders in specific moments.

Michele McAloon:

Question which Zelensky showed up at the White House this winter with Trump.

Simon Shuster:

Yeah, the stubborn, confident one. Those qualities were very much on display and when I watched the footage from that meeting in the Oval Office, you know, one of my thoughts was this is classic Zelensky and it was classic Trump, unfortunately.

Simon Shuster:

Yeah, I'm less of an expert on Trump. You know I've written about the Trump administration in various contexts. I'm not a Trump biographer, so I hesitate to kind of say with such confidence that this was classic Trump maybe. But with Zelensky he really came into it with a lot of advice from people to please follow the rules, and the rules are bow and scrape, kiss the ring, be nice, be quiet, be humble and just get through the meeting.

Simon Shuster:

This is tough with Zelensky. He doesn't do well with diplomatic courtesies. He never has. He finds them demeaning and stupid and often counterproductive, counter to the kind of diplomacy that he feels he's very good at I think with fairly good reason which is the direct man-to-man. I'm going to convince you that we need to be partners, a kind of negotiation from position of strength and confidence. That's what he does well. He doesn't do bowing and scraping very well. He's had to do it over the years but it doesn't come off as very convincing and he hates it. So what I saw, the Zelensky I saw in that meeting was pretty typical. He refused to do what so many leaders have done in coming to visit Trump there, either at Mar-a-Lago or in the Oval Office, to kind of show fealty and humility, and maybe that's bad, but that's what he did.

Michele McAloon:

You know, it just perplexed me because he had shown up to I think he had shown up to Mar-a-Lago prior to Trump being elected and I think the meeting went well. From what I read in the press, no no, he refused.

Simon Shuster:

No, there was an idea for them to meet at Mar-a-Lago in September of 2024, a couple of months before the elections. But the Ukrainians actually said no, we're not going to Mar-a-Lago. That's too demeaning. They said this privately. We met in Trump Tower. Oh, okay, that was the compromise. Okay, trump Tower, but we're not going to Mar-a-Lago.

Michele McAloon:

Okay, yeah, I knew there had been a meeting and from what I read, it had gone well. So another question why does he insist on not using interpreters? His English is not great Sitting in these meetings and that was the one thing that I watched when that meeting just went. Awful is, if he had had an interpreter it would have slowed the meeting down. And then he goes on Fox News and he does an interview and he needs an interpreter for like three or four basic words. So why not use an interpreter? That slows the conversations down. The diplomatic conversations down let people take a breather, but he insists on speaking English down. The diplomatic conversation down. Let people take a breather, but he insists on speaking English. And again, is that this confidence that he exudes?

Simon Shuster:

Yeah, it's partly the confidence. I'd say. More specifically, it's his need and desire to make a direct connection with his audience, whether it's a one-on-one conversation or it's a conversation with a group of university students or millions of people watching on TV, he wants to make a direct connection to them and that's much harder when you're doing it through an interpreter. So, yes, he has relied on interpreters over the years quite a lot, because his English is definitely a work in progress, it's improving and it has improved dramatically just in the last few years. I mean, he sees it in some ways and again I think justifiably as his kind of superpower this ability to reach into people's hearts and minds and make a direct connection. To win their sympathy, to win their support, he needs to be able to connect with them directly, eye to eye, and he needs them to hear his voice. He feels that that is a dimension of his confidence, but it's his confidence in his abilities as a negotiator, as a communicator, as a showman in many ways, and interpretation hinders that. You're right that it's much safer. It slows the conversation down.

Simon Shuster:

That was a criticism that he got after the Oval Office blow up from many corners. Certainly the US Embassy in Kiev was annoyed that he didn't use an interpreter. His own diplomats also pointed this out and I remember following him around in that period. He did change. He changed his habits a bit. So he began using interpreters more and began avoiding English. So he got a bit more bashful after that experience, which was painful in the Oval Office. But still it speaks to his desire to make a direct connection with him, or you, or in contact.

Michele McAloon:

I'm sure you're in contact with people around him, but I mean, it's not going well for Ukraine. That's no secret. What do you see the future for Zelensky?

Simon Shuster:

What does that look like? Definitely keep in touch with the team. I last interviewed him about a month ago, on March 21st in Kiev. It was the first extensive interview that he agreed to give after the Oval Office debacle. It was about three weeks after that Oval Office meeting that he was finally comfortable meeting and talking on the record. Your listeners can read about that Time Magazine. We published a story on that recently. So, yeah, I keep in close touch, definitely with his team and as often as possible with him.

Simon Shuster:

During this last interview actually, I asked him a lot about how he sees his own future and whether he's tempted, for example, to reach the best peace deal. He can sign it and just walk away and resign and leave the aftermath to someone else, to some successor, but I didn't get the impression at all that he is considering such a move. He does see himself in a leadership capacity, definitely through the negotiations, through to not only a ceasefire but some kind of lasting peace agreement. That is what he is single-mindedly focused on now reaching a peace deal that is stable, that will not collapse and allow Russia to attack again in the foreseeable future and beyond that. Whenever I pushed him on the question of what happens then? What do you want? What do you see for yourself? Beyond that, he was vague. I had the impression that he hadn't thought about it all that much, and that is also pretty typical of Zelensky. He's not a long-term planner. His planning horizon is like two weeks at best. He doesn't think much about the future. He doesn't like to talk about it. He's not very interesting to talk to him about like distant future because his mind just doesn't naturally go there. He doesn't spend a lot of time thinking about it. He's very much like what are we doing today, what are we doing next week? So in some ways the interview was a bit frustrating in that regard.

Simon Shuster:

I was hoping to get some clearer picture of how he sees his own future beyond the peace deal with Russia. These days depends on the terms. But the available terms we're seeing on the table today make it look like political suicide for any politician that puts their signature on that document. Which is why I was asking him so intently and in various ways like how are you going to navigate that? Because it's so painful. So much has been lost, so many lives, so much territory, so many lives uprooted and interrupted and destroyed.

Simon Shuster:

Any kind of deal with the devil, even if it brings about peace, is going to be unpopular with a large and very vocal portion of the Ukrainian citizenry and that's going to be hard to negotiate and navigate politically. So I don't know how he's going to do it. I don't think he has a clear idea, but he often doesn't. He's a master of improvisation and a master of communication. So his idea of himself is we'll figure it out. Of communication. So his idea of himself is we'll figure it out, let me talk to them, we'll get the deal, and then I will convince the people of Ukraine that it's a good deal and it's the best deal we can get. That's how he operates. He sort of does the best he can as a communicator. In the moment he doesn't plan so far ahead.

Michele McAloon:

Yeah, you kind of show that in your chapter. Trojan Horse with Minsk too, and how he kind of did that, that's really interesting. Was he the best president for this time in history, do you think? Or you think history's too? It's too short to tell.

Simon Shuster:

Saying that he's the best president for the moment would veer way too far into hagiography and praise, which is not my job and I don't like to do it. We have no idea, right? Sure, you could totally argue that again with the benefit of hindsight. If there had been a president who did believe the Americans and did prepare more fulsomely for the invasion, that things would have gone differently and maybe Ukraine would not have lost as much territory as it has. Cities like Mariupol or others in the South may not have been lost, so you can make that argument. We don't know. These are hypotheticals, right? I hear these arguments all the time in Ukraine and in the expert community in the West. What if this, if that? We don't know.

Simon Shuster:

But, I think what I definitely am comfortable saying. I think what I definitely am comfortable saying and I argue in the book, I hope, convincingly is that his skill set proved incredibly useful for his country in a war of our era, a war in the context of instant information, social media, and a war in which the Ukrainians needed international support for their very survival. It was a set of circumstances that aligned with his character traits in a fascinating way and in a way that I think was very lucky for the Ukrainians that they had a leader who had the ability to grab and hold the attention of the world in a way that only a true showman can. So I think in that way, yes, he really was the right man for the job in many ways, but was he the best? I don't know.

Michele McAloon:

Yeah, that's true and that's probably an unfair question, but that was a great answer. Well, do you've got any future books on Ukraine in the future?

Simon Shuster:

Do you've got any future books on Ukraine in the future? Yeah, thank you. Thank you for asking. Always happy to plug future projects.

Simon Shuster:

I'm working on another book now. It's about drone warfare and military technology in the context of Ukraine and the lessons that will carry over into the future of warfare, for years and generations to come. The way that Ukraine has fought this war, through drones particularly, and other forms of technology, have revolutionized warfare in a way that is so dramatic that really no war between industrialized powers countries will be the same. They will all resemble the war in Ukraine much more than they resemble wars of the past, and I'm writing about that with various characters. President Zelensky is also a character in the next book. General Zaluzhny is also a big character, but it goes much lower down in the kind of hierarchy of the state and the military and society to look at the way the ecosystem of military tech formed. What went wrong, what went right, what lessons could be learned from it, what were the obstacles, what were the accelerators. Hope to finish it. Yeah, this year would be maybe a bit ambitious, but that's my goal. So, yeah, the next chapter to follow.

Michele McAloon:

Well, I can't wait to read that book that you're I think you are nailing it on the head that a warfare has changed. Now warfare is still warfare, warfare is still about violence, but the way the instruments that we're using to fight war have changed drastically from, and this has been, I think, so pivotal. I think a lot of people don't understand that. I wish the West was producing more drones than they are. The Ukrainians have been brilliant in producing drones and using drones, so I really look forward to that book and hopefully you'll give me an interview for that book. So thank you very, very much for your time, and I encourage people to go look at your website, which is simonschustercom, and to find you in Time Magazine and to pick up this book. It's a fascinating read. It's not a hard read, but it really does kind of also tell the history of what has happened over the last three and a half years, and so it's a brilliant book actually.

Simon Shuster:

Thank you. Thank you so much, I'm really honored.

Michele McAloon:

Thank you All right.

Simon Shuster:

Okay, till next time, thank you, thank you.