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Benjamin Wittes
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Tyler McBrien
It's the Lawfare podcast. I'm Tyler McBrien, managing editor of Lawfare. This afternoon we're continuing to bring you a little something extra on top of our daily Lawfare podcast episodes. Today it's episode seven, the finale of Escalation, our latest narrative series that I co hosted with Lawfare's Ukraine fellow, Anastasia Lapatna. Throughout the show, Nastya and I trace the history of US Ukrainian relationships from the time of Ukrainian independence through the present. You can listen to Escalation in its entirety, as well as our other narrative series on our Lawfare Presents channel. Wherever you get your podcasts. In the season finale of Escalation, my co host Nastya recounts Russia's full scale invasion of Ukraine in February 2022. The Western world is shocked as President Biden and Congress attempt to send weapons to Ukraine to fight back. But fundamentally different perspectives on the fight emerge, leaving Ukraine's fate uncertain and its relationship with the US in jeopardy. This is Escalation. Episode seven, Foiling the Frog.
Benjamin Wittes
Escalation is presented by Deleteme, the industry leader in personal data removal. Deleteme is trusted by 20% of the Fortune 500 and by federal, state and county courts across the United States. Federal for more information on Deleteme and its services for individuals and businesses, go to joindeleteme.com escalation.
Anastasia Lopatyna
Previously on Escalation. If the prosecutor's not fired, you're not getting the money. Oh, son of a. Got fired. This became enmeshed in American politics. Some of the preparations for that phone call did send up some some warning.
Benjamin Wittes
Signals to me that this was not quite right.
Anastasia Lopatyna
My call was perfect. The President yesterday of Ukraine said there was no pressure put on him whatsoever.
Shane Harris
None whatsoever.
Anastasia Lopatyna
My worst fear of how our Ukraine policy could play out was playing out.
Shane Harris
We understand that right now it's elections.
Anastasia Lopatyna
Different camps trying to manipulate around Ukraine. It's late November of 2021, just a few months before the world as I know it will change forever. As the Russians keep surging their troops at Ukraine's borders, one American journalist gets a call.
Eric Cheramella
I get a phone call from a White House official who says we have some intelligence about Russia's possible invasion of Ukraine and we want to give it to you. And the first thing is I think to myself, oh, shit.
Anastasia Lopatyna
That'S Shane Harris, a national security reporter for the Atlantic and before that, the Washington Post. Shane has covered the US Intelligence community's relationship with Ukraine for years. And he knows that this tip could be a huge story. Putin's first invasion in 2014 is nothing compared to what the White House is seeing now. A, a plan for an all out assault on the entire country, a full scale invasion. Shane is worried about this, but not for the reason you might expect.
Eric Cheramella
My stomach kind of drops because this sounds a lot like 2003 and Iraq.
Anastasia Lopatyna
Almost 20 years earlier, George Bush's White House publicly released details about supposed weapons of mass destruction in Iraq. But that ended up being bogus. The resulting war became a stain on the legacy of American foreign policy. And it looms over what Biden's White House is trying decades later with Ukraine.
Eric Cheramella
And I was initially very skeptical and very concerned about this because, you know, White Houses usually do not selectively declassify information like this. But here they're saying, we want to declassify intelligence and give it to you. That was pretty novel.
Anastasia Lopatyna
As Shane talks to the White House, he leans towards caution, but the intelligence seems solid to say the least.
Eric Cheramella
The intelligence that the US collects on this potential invasion is broad and quite precise, down to understanding the number of troops that Putin is committing. They can see the tanks moving, they can see field hospitals being built, they can see blood supplies being massed along the border. All things that you would be doing for an invasion, not a military drill.
Anastasia Lopatyna
Biden's national security team takes this intelligence seriously, in part because they don't think Ukraine will last very long in this fight. Their assessment is that within just a few days, Russian troops could capture or kill Ukrainian President Volodymyr Zelensky. Then they'd install a puppet government of Ukrainian officials who would be friendly to Moscow.
Eric Cheramella
There is a real sense, I think, that this country and this government is just going to kind of collapse. It's going to fold, both because it's not ready to stand up to Russia and because it's not capable of standing up to Russia.
Anastasia Lopatyna
Biden's White House wants to rally as many of its allies as possible to help Ukraine. To do that, they will use some.
Eric Cheramella
Of this intelligence that they're gathering and reveal some of it publicly so that they can undercut the rationale that Putin is going to try to use to invade Ukraine. You know, things like Ukraine's planning to attack Russia. We're just here on a defensive exercise. Or this is just a military drill, nothing to see here. The US Believes that's not true, and they think that they can convince the broader public that it's not true by releasing information.
Anastasia Lopatyna
Shane runs his story. And. And by winter, White House press briefings become full of information about Russia's war plans. As you all have heard us say many times, we are concerned that the Russian government is preparing for an invasion in Ukraine that may result in widespread human rights violations and war crimes should diplomacy fail to meet their objectives. And here, two fundamentally different perspectives begin to emerge. In Washington and in Kyiv. While the White House warns the American public, some NATO allies come on board and get ready to help Ukraine. Others are still worried about antagonizing Putin. But most importantly, many Ukrainians aren't buying the warnings from the Americans. That creates a tension that will only grow in the months leading up to.
Eric Cheramella
The invasion, where Zelensky and other senior Ukrainian officials hear what the US Is saying, but they really just don't believe it. You know, they've seen Russia pull these kinds of feints before. They've seen them mass troops on the border. And importantly, they do not want to ignite a panic in Ukraine.
Anastasia Lopatyna
We are being threatened by a big war. It is not. For the first time, Ukrainian President Volodymyr Zelensky says that panicked statements about an imminent war with Russia is causing economic harm to his country. Zelensky. Zelenskyy's public denial is partially rooted in his desire to keep the country calm and collected. The argument is, well, if everyone gets scared and flees, who'd be left to defend the country? And under that guise of public dismissal, parts of the government are preparing, some in the military and the intelligence apparatus are training, quietly moving their troops around, gearing stockpiles and planning contingencies.
Eric Cheramella
There's also, you know, this effort to continue authorizing weapons sales to Ukraine. So in December, President Biden authorized an additional $200 million in weapons to be drawn from U.S. inventories. So that is all a way of both actually arming Ukraine to defend itself and to send a public message to. To Putin. We know what you're up to, and do not even think about trying to start a war with NATO here.
Anastasia Lopatyna
The U.S. sends thousands of Javelins to Ukraine, but they don't expect the Ukrainians to defeat the Russian army with them. The White House thinks the Ukrainians will need the weapons to fight back once they fall under Russian occupation. So once again, the US Wants to support Ukraine, but doesn't want to appear aggressive or provoking Washington decides that it won't punish Russia preemptively, so it can't impose sanctions to try and deter the invasion. And that kind of thinking is a big problem for Kyiv. Here is Zelenskyy explaining it rather bluntly in a recent I only asked for two send us weapons or better yet, strengthen us with preventive measures so there.
Yulia Timoshenko
Would be no war.
Anastasia Lopatyna
Please don't say that. If he comes, if he crosses borders, if he kills, we are imposing sanctions. This is complete bullshit. While Russian forces head for the Ukrainian border, the alliance between Washington and Kyiv is already starting to crack behind the scenes. Then, on February 21, Vladimir Putin delivers a televised address to the Russian public. He repeats the long held myths about Russia and Ukraine's shared fate. I would like to emphasize again that Ukraine is not just a neighboring country for us. It is an inalienable part of our own history, culture and spiritual space. 48 hours later, the White House says the full scale invasion is imminent.
Benjamin Wittes
We want to be crystal clear on this point. Any American in Ukraine should leave as soon as possible. And in any event, in the next 24 to 48 hours.
Eric Cheramella
I think I remember like not sleeping that night and certainly my colleagues in Kyiv did not sleep, but it was this sense that it had all been building towards this moment and now it was happening.
Anastasia Lopatyna
From Lawfare and Goat Rodeo, this is Escalation, a podcast about the United States and Ukraine. I am Anastasia Lopatyna.
Tyler McBrien
And I'm Tyler McBrien.
Anastasia Lopatyna
This is episode seven, Boiling the Frog. We'll be back after the break.
Benjamin Wittes
Support for Escalation comes from Deleteme, the industry leader in personal data removal. We're back with Rob Chevelle, the co founder and CEO of Delete Me, to talk about how his team leads the way when it comes to data privacy. Rob, there's all sorts of services that can scrub my private information from the Internet. Why should I trust Deleteme to do this job for me?
Shane Harris
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Benjamin Wittes
And in short, there's no substitute or.
Shane Harris
Shortcut for that kind of experience. We have by far the most important and best customers.
Anastasia Lopatyna
That includes four of the five top.
Shane Harris
Banks, five of the 10 top technology companies, three of the largest federal government agencies, 12 state legislatures and judicial systems. And we work very hard to make sure that they are happy and trust us on an ongoing basis. But ultimately, the company that Deleteme aspires to be is the one that wants to protect you. And your family and cares the most about making that protection sustainable year after year.
Benjamin Wittes
For more information on Deleteme and its services, go to joindeleteme.com escalation and use the code ESCALATION to get 20% off a personal plan and you can contact them there about a special offer to protect your business too. That's joindeleteme.com escalation code escalation. Now back to the show.
Anastasia Lopatyna
We're back. Thank you. Thank you so much for having me. No problem. It's Friday night in the fall of 2024 and my friend Yulia Timoshenko is having me over for dinner at her apartment in Kyiv. Yulia is a well known Ukrainian influencer. She became famous after posting about the early days of the Russian invasion in English on Instagram. I brought an open bottle of wine. Yulia lived through the invasion as a 22 year old Ukrainian fresh out of college. And she was also one of those Ukrainians who didn't believe that this war was possible. She remembers well the winter of 2021, months before the invasion, when some of her friends were considering visiting her in Ukraine for Christmas and New Year's.
Rob Chevelle
And we had a friend from Macedonia who's like, she was laughing at it. She was like, oh my gosh. Like my mom tells me that I maybe should not go. And what is she thinking? She thinks that like bombs are going to fly over Kiev. Like that's how bizarre it felt. Like, no way. Like you can joke about it without, you know, even.
Anastasia Lopatyna
Now I know this may come off as a bit hypocritical because we've told you that for Ukrainians this war was centuries in the making. And yet at the same time, so many of us were in denial and were ignoring the signs of looming war, including myself. The only way I can explain this is purely psychological. A war like this is just so terrifying that your mind just refuses to believe it's possible. Believing in it or acknowledging the warnings would make it real simple. So you don't you avoid the thought of it at all costs. Julia says her skepticism was rooted in a belief in a better, safer world, the so called rules based international order, where a war like this just wasn't possible.
Rob Chevelle
My disbelief, and maybe a lot of Ukrainians also had, that was based on the trust in the global security system. Like I cannot imagine a European capital right now being besieged by foreign tanks.
Anastasia Lopatyna
In the days leading up to the invasion. I am not even in Ukraine. I'm in college in France studying and working remotely for the Kyivan dependent. The night before, I sat on my bed scrolling Twitter and waiting for another crazy address from Putin. Take me into, like, the night before the invasion. Are you watching the Putin address? I remember I was watching it. What are you doing? Are you watching? Are you sleeping? What are you doing?
Rob Chevelle
I went to pierce my ears with my friends.
Anastasia Lopatyna
Well, if the war starts tomorrow, at least my ears are pierced, right?
Rob Chevelle
Literally, the phrase, me and my friends. I remember us walking and literally joking. Well, you know, if the war starts tomorrow, at least, you know, I have my piercing and I'm looking nice and all of that. And it's crazy as well because, like, knowing what I know about what happened in that specific night. Just, like, few blocks away, there were literally Russian special forces dressed as civilians preparing to assassinate Zelenskyy. That night.
Anastasia Lopatyna
My family was back in Ukraine, as it turns out, in one of the worst locations possible. The Kyiv suburbs, Irpin, Bucha, Rostomel. Places where I grew up, where our family home still stands. My mother didn't even pack an emergency bag or plan to evacuate. We really couldn't even imagine what was about to happen.
Rob Chevelle
I went to sleep, and the last thing that I saw was there was an article or tweet from Blinken that said that, you know, Putin is going to invade Ukraine by morning. And I remember screenshotting that and sending it to my American friend and saying, like, oh, my gosh, can you, like, just tell your secretary of state to chill, because this is really stressing me out for no reason, and I think you should not be stirring things.
Anastasia Lopatyna
As the night sets in. On February 23, Ukrainians go to sleep peacefully for the very last time. Hours later, thousands of Russian troops start quietly crossing into Ukraine from all directions.
Yulia Timoshenko
Vladimir Putin has just addressed the Russian.
Anastasia Lopatyna
People moments ago, announcing what Putin called.
Eric Cheramella
The start of a military special operation.
Anastasia Lopatyna
The Ukrainian president, he will not leave the capital, Kiev, despite being instructed to do so. Russian troops march into Ukraine from the north, east and south. Cities all across the country are getting bombed as emergency air raid sirens wailed. I don't want to fight. I'm not a soldier. I'm not professional military man. But I am not ready to capitulate. The horror and shock of that first day is still indescribable. Every time I try to put it in words, it just never feels quite right. There are missiles raining down on the biggest country in Europe. Columns of tanks rolling towards the capital. Russian airborne units trying to take over airports near Kyiv in broad daylight.
Rob Chevelle
I remember the feeling of, like, it was this sense of like, apocalypses happening around you. And I remember, like, calling my friends, and we're like, oh, my gosh, I love you so much. And they were like, oh, my gosh, please, like, don't say that, because it sounds like you're, like, saying goodbye. And I'm like, I mean, we honestly don't know. Because you don't know. Like, you never lived a day in a war, so you don't know if you die tomorrow, if you die, like, in a few days, like, right now, whatever.
Anastasia Lopatyna
Some people start fleeing. Some line up near shops and banks. While the military and government are scrambling to respond. Russian agents move through downtown Kyiv in search of Zelenskyy. And the president is taken to a special bunker built in Soviet times to withstand nuclear war.
Rob Chevelle
I just remember, like, just laying in my hallway in the apartment and just crying on the floor, and it was just, like, hysterical breakdown because I just realized that I could have been the member of the first generation that had never suffered from Russia. But I'm not anymore. Like, I'm a part of this, like, you know, endless cycle of my people constantly having to go through the worst, from, you know, oppression to execution, to little, like, death from war. And that realization was just so painful to me in the moment.
Anastasia Lopatyna
I wasn't even in Kyiv. But I also remember the sense of paralysis and utter helplessness. You don't really know what to do or what to say because suddenly everyone, everything loses all meaning. Everything but surviving and the lives of your loved ones.
Rob Chevelle
Some of my friends say things like, no, no, no, like, NATO is going to mobilize right now, and they're going to come and stop this. And I was like, girl, I don't want to disappoint you, but nobody's coming. And it's like first hours of the war. They're like, well, you know, it takes, like, what? It takes, like, 13 hours to fly from, like, us, like D.C. or New York to Ukraine. So if they get into the troops, if they get into the planes right now, they're going to arrive by the night. This was not a joke. People truly believed that. And I was like, I don't think they can. Because, no, this global security system doesn't work as we see, because we wouldn't not been here.
Anastasia Lopatyna
The world is watching as Russians try to encircle and occupy Kyiv. The Kremlin planned to get it over with in three days. So their soldiers bring resources to only last that long. And parade uniforms, you know, for a victory march through Kyiv a few days later. The international response is Shock and horror. Russian troops are moving in on the capital, closing in on Kyiv.
Eric Cheramella
The assumptions that we had about security, about balance of forces, about, you know, war and peace, had just kind of been turned upside down.
Anastasia Lopatyna
That's reporter Shane Harris again, who's watching the invasion from Washington, D.C. as the Russian campaign unfolds, he is surprised by what he sees next.
Eric Cheramella
It's kind of not going according to plan.
Anastasia Lopatyna
Ukrainian authorities start handing out weapons to civilians as thousands of volunteers line up to join the army. Regular people start patrolling the streets, taking down road signs to confuse the Russians, making makeshift explosives and sharing coordinates of enemy troops with the military on their own, civilians coordinate everything from evacuations to delivery of food and medicine to donating more than a million dollars to the army in a matter of days. As the Ukrainian people fight off the Russians, President Zelensky gives a defiant speech.
Yulia Timoshenko
We are all here.
Anastasia Lopatyna
Our military is here. Citizens are here.
Yulia Timoshenko
We are all here defending our independence, and we will continue to do so.
Anastasia Lopatyna
Days turn into weeks with no sign of a Ukrainian defeat.
Eric Cheramella
The Russian invasion is just collapsing. It is failing on every level. They are not taking the territory that they claimed they would. They are not decapitating the government. It is not a lightning strike. They are getting bogged down. They're having mechanical failures. Their supply lines suck. They, you know, their communications are getting intercepted left and right, and, you know, Ukraine holds.
Anastasia Lopatyna
The Russians get bogged down in Kyivan suburbs, occupying towns whose names will soon be on every front page and TV screen around the world. The village where my friend Yulia grew up, Zavoroch, gets occupied. My home village gets occupied too. My mom manages to escape just a few hours before Russian tanks show up on its streets. But by the end of March, the Russians are pushed out from all of those places around Kyiv with seemingly all cards stacked against them. Ukrainians win the battle of Kyiv.
Rob Chevelle
If not for the US weapons, if it wasn't for, like, the javelins that we got at the beginning, my own hometown and my parents still would have been under the Russian occupation. I probably would never be able to, like, see them or go, like, you know, because especially with what I do, Russians would just kill me.
Anastasia Lopatyna
We'll be back after the break.
Benjamin Wittes
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Benjamin Wittes
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Benjamin Wittes
For more information on Deleteme and its services, go to joindeleteme.com escalation and use the code ESCALATION to get 20% off a personal plan, and you can contact them there about a special offer to protect your business, too. They that's joindeleteme.com escalation code escalation. Now back to the show.
Anastasia Lopatyna
We're back. It's the end of March 2022, and the Russian military is still bogged down some 20 miles away from the capital. President Zelensky is in Kyiv, sitting at a desk in his office, giving a virtual address for NATO leaders who are meeting in Brussels. The Ukrainian army has been resisting for a month in unequal conditions, and I have been repeating the same thing for a month now.
Eric Cheramella
To save people in our cities, Ukraine.
Anastasia Lopatyna
Needs military assistance without restrictions. On the screen, the president looks like the epitome of the word fatigue. He's dressed in dark green clothes, the style we have since dubbed tactical casual, and his speech is one of the earliest examples of how Zelenskyy and the country will speak to the world for the next three years. Unfortunately, we are not getting as much.
Tyler McBrien
As we need to end this war sooner.
Anastasia Lopatyna
If we got jets and enough heavy.
Tyler McBrien
Armored vehicles, the necessary artillery, we would.
Shane Harris
Be able to do it.
Anastasia Lopatyna
Pretty much all of Zelenskyy's addresses in the next three years will be some form of give us weapons so we can fight back. America's response, however, will be much more complicated. But Putin was wrong. We are ready, we are united, and we stayed united.
Benjamin Wittes
Well, the House and Senate say they.
Anastasia Lopatyna
Expect to approve $10 billion in aid to Ukraine this week in spring of 2022. Congress allocates tens of billions of dollars in funding for all things Ukraine. The US government gets more than 50 countries to join a coalition to coordinate their aid to Kyiv. The US Military starts surging in small weapons and equipment. Javelins, Stingers, howitzers, helicopters, munitions.
Donna Aviv
This was really an unprecedented global operation to pull weapons from various storage sites and stockpiles and units around the world.
Anastasia Lopatyna
That voice is Eric Cheramella. You've heard from him before. He was at the Central Intelligence Agency during Russia's first invasion of Ukraine in 2014. After working in the White House for five years, Eric was back at the CIA to witness the US surge of weapons to UKRA. And he says that by any stretch of the American imagination, those efforts were a huge success.
Donna Aviv
From a purely bureaucratic and logistical standpoint, I think many in the Pentagon would say that they actually outperformed even their wildest expectations about how quickly they could get stuff to Ukraine. For them, this was lightning speed. The problem is obviously for Ukraine, this was painfully slow given the pace of the Russian attack.
Anastasia Lopatyna
As the Russians advance, target civilians and take more and more territory in the east and south, Ukraine asks for more advanced weapons, things like sophisticated air defense, artillery systems, tanks or missiles. And that's when the White House begins its never ending cycle of deliberation. Most of the weapons that the Ukrainians ask for take months or years to be delivered. And the cycle is always the Ukrainians ask. Americans say no. Ukrainians ask again. Americans are still a no. Ukrainians organize protests and online campaigns all around the world to advocate for a weapon, a tank or a missile. And eventually, after thousands of Ukrainians die and the Russians take more land, the American no becomes a yes. And your support is crucial not just to stand in such fight, but to get to the turning point, to win on the battlefield. Every time that we hear that the promised supply of weapons is delayed, Ukrainian soldiers are giving their lives so that we have this time. The White House cites a long list of reasons for these delays. Some systems are very hard to maintain. Some need long and specialized training. Some of them the west only has a handful of. And remember, the Pentagon is planning for all sorts of contingencies all around the world. The weapons the US Would need if, let's say China invaded Taiwan tomorrow. And those are all valid reasons. But there is one more reason for the delays, something that pierces through the entire 30 year long relationship between Cleve and the American fear of escalation. Eric and I debated this countless times and here is one of them. Tell me about the strategy of boiling the frog. This idea that American officials reportedly had that you can't just surge all weapons all at once to Ukraine because that's going to be provoking to Russia. But if you kind of drip it in increments slowly, then that's a better way to do it politically.
Donna Aviv
So the sort of shorthand that I heard Biden administration officials use was this war is existential for Ukraine. And obviously a key US Objective is to support Ukraine. But an equally, if not greater objective is to ensure that the war does not become existential for the United States. Which means at the end of the day, there is a recognition that if there is even a remote chance of the possibility that Russia would go nuclear in this war, then the United States has a responsibility to its own citizens and to the entire globe to prevent that kind of catastrophe. But the boiling the frog strategy was a reflection of the fact that at the end of the day, neither side understands the other side's red lines. And there was an understanding that there is some Russian red line somewhere. We don't know where it is, but we definitely don't want to cross it and trigger a nuclear confrontation with Russia, which would be apocalyptic.
Anastasia Lopatyna
You see, this red lines argument is almost impossible for Ukrainians to swallow because the Ukrainian army has already crossed every single red line there could possibly be. According to Putin, Ukraine has used an enormous amount of NATO weapons in this war. We used them to hit Crimea, we used them to hit Russian territory. We used them to literally invade Russia and occupied Russian land last summer. And in each single instance, the Kremlin warned that if their red lines were crossed, their response would be worse than ever. But in each instance it was not. Nothing has fundamentally changed in the way Russia is conducting its war. Needless to say, a nuclear war didn't happen. So at some point you gotta, are they bluffing? Is this nuclear saber rattling designed to slow the.
Donna Aviv
It's an art, not a science. You can't plug it into an equation. You can't say, well, if we do X, then Y will definitely happen. But as you get more and more data, once the war is underway and you realize, okay, well, the Russians were not as serious about this part as we thought they were. And you recalibrate. That is how you build clarity on, on your side to be able to kind of push the bounds of your policy. But it doesn't happen overnight. And it really does depend on this constant reanalysis of the Russian reaction in this sort of back and forth dynamic. I don't think it should take six months to come up with a new decision. And I do think there was probably excessive hand wringing when it came to certain kinds of weapons systems. But overall the logic to me makes sense insofar as you really don't know how the Russians are going to react and, and the stakes couldn't be higher for the United States, for the rest of Europe and for the planet.
Anastasia Lopatyna
This strategy of boiling the frog to me and to a lot of other people in Ukraine seems sort of directly incompatible with the reality of the battlefield and the military doctrine. Right? Because when you're fighting a war and you're trying to win a war, timing matters, right? Like your ability to do things quickly matters. And so when you have a situation in which your ally, the US is kind of telegraphing for a year that they're going to give you a particular system, not only does it pull you back because you can't act on it because you don't have that system, but also your enemy now knows what's coming. Like, do you see the point I'm trying to make? That you can't really win that way, can you? This got me to the main question I needed answered. When American officials were crafting this policy and they were executing this policy, what were they hoping for?
Donna Aviv
I think that's exactly the right question because there were slightly divergent strategic objectives from the get go. The Ukrainian objective, I think after the surviving the initial wave was total victory and pushing the Russians out to the 91 borders.
Anastasia Lopatyna
Eric is right. That was the goal. The problem is the Americans never believed in it.
Donna Aviv
I think from the US side they were always agnostic about what the final sort of outcome would look like. The objective was to preserve Ukrainian sovereignty, democracy and ability to defend itself with sort of less of a clear objective when it came to territory. Ukraine's leadership and society were committed to this kind of form of total victory that I don't know that anyone on the US side really ever bought into, not because they didn't want it, but because they didn't think it was realistic.
Anastasia Lopatyna
Now put yourself in the shoes of the Ukrainians. Your country was just invaded by your arch enemy, an enormous nuclear power that for Centuries has been trying to wipe you off the map one way or the other. Your enemy is eviscerating your cities, killing tens of thousands of civilians, raping women and children, beheading your soldiers. Everyone thinks you're doomed, yet somehow you manage to fight back. Your people are united. Your army is far more capable than anyone realized, and the entire world seems to be backing you. So you have a choice to finally liberate your country, to pay back for all of that suffering that your ancestors went through. What else could be your objective, if not a total victory? How could you accept living millions of your people under Russian occupation and terror after the world saw Bucha, after Mariupol, after Bakhmut, how could you settle for anything else? This tension over what victory really means came up constantly. The official line from Washington, our commitment to Ukraine will not weaken. We will stand for liberty and freedom.
Shane Harris
Today, tomorrow, and for as long as it takes.
Anastasia Lopatyna
But the longer the war went on, the more frustrating this line became because it begged a natural question. As long as it takes to do what? We'll be back after the break.
Benjamin Wittes
Hey, escalation listeners. Benjamin Wittes here. Escalation would not be possible without the support of Deleteme, the industry leader in personal data removal for over a decade. I'm back with Don Aviv, the CEO of Interfor International, to hear more about his experience as a Deleteme customer. Don, can you tell me a story or an example of Deleteme solving a problem for you or making a difference for your business?
Shane Harris
Absolutely. So we support a vast number of celebrities and their families, and in this specific instance, one of our celebrities who's a celebrity that you will have heard of, she and her family were being inundated with threats and concerns by both stalkers and overzealous fans. And they were finding personal information out there and utilizing that to contact, communicate, and attempt to reach out to her and her family. And we leveraged Delete Me and the unique blend of interest or four services to mitigate those threats. So Delete Me has done a lot for our clients. It's helped us knock down a tremendous amount of personally identifiable information that's out there that is harming and hurting our clients around the world. So it's been a force multiplier for our extended suite of products that we provide our clientele.
Benjamin Wittes
For more information on Deleteme and its services, go to delta joindeleteme.com escalation and use the code ESCALATION to get 20% off a personal plan and you can contact them there. About a special offer to protect your business, too. That's joindeleteme.com escalation code. Escalation. Now back to the show.
Anastasia Lopatyna
We're back. American historian Timothy Snyder says that when the Ukrainians won the battle of Kyiv, that should have been a sign, a sign to Americans that Ukraine is capable of a total victory.
Yulia Timoshenko
When the Ukrainians won the Battle of Kyiv, at that moment, a switch needed to flip, which never really flipped. This is a conventional war now. Like, it's somebody's going to win and somebody's going to lose, and the Ukrainians could win, and we need to talk about it in those terms. And that was seen as being not just wrong, but somehow beyond the pale.
Anastasia Lopatyna
Part of the problem, Snyder says, was that Biden was looking at Russia's war through the lens of the Cold War, and that thinking affected every decision he made.
Yulia Timoshenko
The President believed that this was a sort of Cold War crisis. You've already built in that the risk is nuclear war, like with Cuba. Right. You've built that in. And then the Russians, of course, play you on it, which they were going to do anyway.
Anastasia Lopatyna
Snyder thinks that's the wrong framing. The correct one was this is a.
Yulia Timoshenko
Conventional war and somebody's going to win and somebody's going to lose. And conventional wars involving nuclear powers are quite common. The whole idea that because a country has nuclear weapons, therefore they have to win or they get to threaten everybody. Like, if that were true, then that would mean that America could never lose a war, and it would mean we'd never lost a war. It would mean that Russia or the Soviet Union have never lost wars, but they have. They lose them all the time.
Anastasia Lopatyna
But the US Never looked at it this way, Snyder says, in part because of Russian imperialism. And there's one of Snyder's speeches that explains this problem particularly well.
Yulia Timoshenko
Part of being an empire is controlling the discourse. And to a large degree, the Russians have been able to control the strategic discourse, setting up for us new rules in war which have never existed before.
Anastasia Lopatyna
That's Snyder talking to the US Congress, describing how Americans weapons restrictions hurt the Ukrainians. For three years, Ukraine couldn't use Western weapons to attack military targets inside Russia. So things like weapons caches, military bases, airfields, places that Russia used every single day to kill civilians were out of bounds on Washington's orders.
Yulia Timoshenko
When you invade another country, the entire war should take place on the territory, the country you've invaded. No one has ever said that before because it's completely absurd. And yet somehow it's been accepted in the United states as normal that this war should be fought on Ukrainian territory.
Anastasia Lopatyna
Snyder says. The American understanding of this war is full of contradictions like these.
Yulia Timoshenko
Another idea that the Russians have that we've accepted is that it's normal, for example, when you and I were in Kyiv, for ballistic missiles to rain down on the city where we were trying to do normal business, but it's somehow not normal for ballistic missiles from Ukraine to go into Russia. Why is that? Why is it normal for one country and not for another?
Anastasia Lopatyna
The fundamentally different perspectives that we've been talking about throughout this entire podcast have now culminated into two distinct worlds. In Washington, it's a bureaucratic world of procedure and escalation management. And in Kyiv, it's a world of suffering and destruction and begging the world to do more to stop it. Despite being extremely close allies, the US and Ukraine never aligned their visions. They moved towards essentially two different goals and of course, perceived their results completely differently, too. This divide was laid bare in the last few months of Biden's tenure as president. The White House officials publicly defended their record.
Shane Harris
Now, nearly three years later, Putin has failed to achieve any of his strategic objectives.
Anastasia Lopatyna
And in Ukraine, the reaction was a mixture of laughter and disappointment. There are those in the west who don't mind a long war because it would mean exhausting Russia, even if it's at the cost of Ukraine and its people. This was fall of 2024. Things were bad, but they were about to get much, much worse. We'll be back.
Benjamin Wittes
Hey, escalation listeners. Benjamin Wittes here. I wanted to pause here to thank Delete Me. Delete Me is a digital privacy service, and across this series we've been talking to the leaders at Delete Me about their work. But today I'm here with a Delete Me customer. We're back with Donna Veev, the CEO of Inter4International, a global investigative and security consulting firm for celebrities, executives and other clients in the public eye. Don, why did you seek out Delete Me? To help protect your customers.
Shane Harris
So we did an assessment of all the vendors out there, both large and small, that handle the removal and identification of personally identifiable information. And we came towards Deleteme as a best in class provider.
Benjamin Wittes
What would you say to other businesses that are considering using Deleteme?
Shane Harris
Well, they should. If you're not focused on personally identifiable information in this day and age, then you're remiss in protecting yourself and your network. So it's done a tremendous amount from our clients, both far and wide. But I would say at minimum, it's helped protect them from the risks and threats out there by bad actors.
Benjamin Wittes
For more information on Deleteme and its services, go to joindeleteme.com escalation and use the code ESCALATION to get 20% off a personal plan and you can contact them there about a special offer to protect your business, too. That's joindeleteme.com escalation code escalation. Now back to the show.
Anastasia Lopatyna
We're back. Good morning. It's now 5:35 here in the east.
Yulia Timoshenko
Now with the breaking news we are.
Anastasia Lopatyna
Projecting at this hour. The 47th President of the United States, Donald Trump, will be elected to return.
Eric Cheramella
To the White House.
Anastasia Lopatyna
Not consecutive. It's a very strange feeling, to be honest. Very, very, very scary. The day after the 2024 US presidential election, I caught up with my co host, Tyler McBrien. We were both still processing everything and just trying to predict what was next for Ukraine with Trump back in power.
Tyler McBrien
A lot of what Trump will do, especially in foreign policy, is unpredictable. But I think it's probably safe to say he'll pursue a quid pro quo type relationship. I could see him being very amenable to the idea that Ukraine is a province of Russia. Always was. Is not. I mean, I could see him subscribing to a Putinesque warping of history. I don't know. I think history could repeat itself. But in many ways, we're also in uncharted waters just because of his chaos.
Anastasia Lopatyna
Many Ukrainians would talk about how Trump is unpredictable. We don't know what Trump is going to do. Maybe he's going to be really tough on Russia. Maybe he's going to be very tough on Putin. Maybe he's actually going to increase funding for Ukraine. Even though there is countless evidence to show that the possibilities of him actually helping Ukraine are extremely, extremely small. People would still hold on to this tiny belief of possibility that he will be good for us. But, I mean, I think we have to be honest with ourselves. Ukraine is awaiting some really dark, really dark times. The news over the next few months confirms a lot of Tyler and my worst fears. Trump takes office and immediately starts repeating baseless lies about Ukraine. Then, just after we launch this podcast, Zelensky meets Trump at the Oval Office. And, well, you know what happened next. Have you said thank you once this entire meeting?
Donna Aviv
No, in this entire meeting.
Anastasia Lopatyna
Have you said thank you?
Shane Harris
You went to Pennsylvania and campaigned for the president.
Anastasia Lopatyna
Trump ordered a pause to all U.S. military aid. This, of course, comes after Friday's blow up between President Trump and Ukrainian President.
Shane Harris
Volodymyr Zelensky in the Oval Office.
Anastasia Lopatyna
I was actually in the United States with my family when this all unfolded and the atmosphere couldn't have been any weirder. I remember wearing this shirt that said God Bless Ukraine and thinking, is this shirt that three weeks ago reflected American policy now going to be considered provocative? Will I get stares? As Trump was berating Zelensky, I stood literally a mile away from the White House in the middle of the street, watching it all happen on the screen of my phone. The anger was so visceral that I teared up because the whole thing was truly unbearable. It felt as though Trump was talking to me, my family and every other Ukrainian attacking us for truly the most natural instinct of all, wanting to feel safe in our own homes. I also couldn't help but think, wow, how things have come full freaking circle on everything that Tyler and Max and I have been working on this whole last year. We tried making a show about the US And Ukraine and importantly with as little of Russia in it as possible. But that was really hard because the Kremlin kept creeping into almost every decision the White House ever made about Ukraine. President Trump announced Russian President Vladimir Putin agreed to begin negotiations to end the war in Ukraine.
Benjamin Wittes
In absent from the talks was any representative for Ukraine President Volodymyr Zelensky.
Anastasia Lopatyna
There is this recurrent theme that comes up over and over again. The US Never really wants to go as far in confronting Russia as Ukraine does because the US has wider interests. It has more to lose. But for Ukrainians, the Russians have already taken everything. So at key moments, the United States backs off. Remember the Chikinkuyev speech when Bush Sr. Promised to the Kremlin that he won't support Ukraine's independence?
Shane Harris
Americans will not support those who seek.
Anastasia Lopatyna
Independence in order to replace a far off tyranny with a local despotism. Or the Bucharest summit when NATO left Ukraine in a dangerous gray zone. NATO will say that Ukraine and Georgia will become members but won't actually do anything to implement it. The worst of all possible worlds. Remember the Russia reset under Obama. And we failed at that.
Shane Harris
Let's be clear.
Anastasia Lopatyna
Like we failed to deter who. For Washington, all of these things were just the reality of managing great power competition with the nuclear Russia. But for us, it's existential. The US can't declare victory if Russia suffers huge losses, but keeps some Ukrainian territory. But we can't. That's millions of Ukrainians living under occupation. That's historic Ukrainian territory and that's tens of thousands of stolen Ukrainian children. So at every stage, the United States is satisfied with something a lot more cautious than satisfies Ukraine. Except this time it's worse, because this time it doesn't feel like a repetition of that cycle. The country that we used to look up to that once was our biggest ally now seems to be on our enemy's side. And I'll be honest, this leaves Ukraine, which by the way, used to be one of the most pro American countries in the world, deeply embittered with the United States. At that disastrous Oval Office meeting, Zelensky made a declaration that prompted a sharp response from Trump. First of all, during the war, everybody has problems, even you. But you have nice ocean and don't feel now, but you will feel it in the future. God bless. You don't know that. God bless. God bless. Don't tell us what we're going to feel. We're trying to solve a problem. Don't tell us what we're going to feel. That right there sums up the difference between the two countries. Ukrainians are convinced that they are the dam holding back the Russian waters from the West, While Trump represents an extreme example of a common American perception that this war is very far away, one of them is wrong.
Tyler McBrien
Escalation is a production of Lawfare and Goat Rodeo. You can follow the show on Apple, Spotify, or wherever you get your podcasts to stay up to date on new episodes. And please leave us a rating and a review while you're there. Escalation's lead producer is Max Johnston. The show was reported and written by Anastasia Lapatana, Tyler McBrien, Max Johnston and Benjamin Wittes. Executive producers at Lawfair are Benjamin Wittes, Natalie Orpet and Scott Anderson. Executive producers at Goat Rodeo are Max Johnston, Ian Enright and Megan Adolsky. Additional production assistants at Goat Radio from Isabel, Kirby McGowan, Rebecca Seidel, Kara Schillen, Jay Venables and Hazel Hoffman. Additional production assistance at Lawfare from Anna Hickey, Patrick Cole and Quinta Jurecik. Sound design, scoring, mixing and engineering from Max Johnson and Ian Enright. Our theme is Enigma by Charlie Edwards. Additional music from Blue Dot Sessions and Alibi Music. Our cover art was designed by Marie Kinovich.
Benjamin Wittes
Escalation is presented by Deleteme, the industry leader in personal data removal. Deleteme is trusted by 20% of the Fortune 500 and by federal, state and county courts across the United States. For more information on Deleteme and its services for individuals and businesses, go to joindeleteme.com escalation.
The Lawfare Podcast: Escalation, Episode Seven – Boiling the Frog
Release Date: June 12, 2025
Overview
In the season finale of Escalation, titled Boiling the Frog, The Lawfare Institute delves deep into the complexities of the United States' relationship with Ukraine amidst Russia's full-scale invasion in February 2022. Co-hosted by Tyler McBrien and Anastasia Lopatyna, this episode meticulously traces the historical ties between the two nations, the strategic decisions made by U.S. policymakers, and the profound impact on Ukrainian society. Through expert interviews, firsthand accounts, and in-depth analysis, the episode elucidates the divergent perspectives that have shaped the conflict's trajectory and the fragile alliance between Washington and Kyiv.
1. Prelude to Invasion: Rising Tensions and Intelligence Warnings
The episode opens with a recounting of the months leading up to Russia's invasion. In November 2021, as Russian troops amassed along Ukraine's borders, U.S. intelligence began signaling an imminent threat.
Harris highlights the similarities between the intelligence warnings preceding the Ukraine invasion and the misleading justifications used by the U.S. in the 2003 Iraq War. This historical parallel underscores the gravity of relying on intelligence without transparent verification.
2. Divergent Perspectives: Washington vs. Kyiv
A central theme of the episode is the starkly different viewpoints held by U.S. policymakers and Ukrainian leaders regarding the conflict's nature and the appropriate response.
U.S. Strategy: The Biden administration, aware of the potential for rapid Ukrainian collapse, opted for a cautious approach. They aimed to "use some of this intelligence... to undercut the rationale that Putin is going to use to invade Ukraine." (06:02)
Ukrainian Reality: Contrarily, Ukrainian President Volodymyr Zelenskyy maintained a public stance of denial about an imminent invasion to prevent public panic. However, behind the scenes, Ukrainian military and intelligence were actively preparing defenses.
Notable Quote: Zelenskyy confronts the dissonance: "I only asked for two send us weapons or better yet, strengthen us with preventive measures so there." (09:38)
This discrepancy between public statements and private preparations highlights the tension and mistrust that would later strain the U.S.-Ukraine alliance.
3. The Invasion Unfolds: Personal Accounts and Immediate Reactions
As February 2022 dawns, the invasion commences with devastating effect. The episode features poignant personal narratives that capture the chaos and emotional toll of the first days of war.
Anastasia Lopatyna's Recollection: "I wasn't even in Kyiv. But I also remember the sense of paralysis and utter helplessness... Everything but surviving and the lives of your loved ones." (20:34)
Rob Chevelle's Emotional Response: "It was this sense of like, apocalypses happening around you... Some of my friends say things like, no, no, no, like, NATO is going to mobilize right now... This was not a joke." (19:10)
These testimonies emphasize the immediate human cost of the invasion and the preliminary underestimation of Russia's military capabilities by both Ukrainians and international observers.
4. The Resilience of Ukraine: Defense and Global Support
Despite initial setbacks, Ukraine's unexpected resilience reshapes the conflict's dynamics. Civilian mobilization and effective use of Western-supplied weaponry play crucial roles.
Military Adaptation: Ukrainian forces, bolstered by thousands of civilian volunteers and strategic use of supplied weapons like Javelins, began to turn the tide against Russian advances.
Defiant Leadership: President Zelenskyy's unwavering resolve is encapsulated in his speech: "We are all here. Our military is here. Citizens are here defending our independence, and we will continue to do so." (23:17)
Strategic Impact: By March 2022, Russian forces were pushed back from key areas around Kyiv, marking a significant early victory for Ukraine and frustrating Russian strategic objectives.
Insight from Rob Chevelle: "If not for the US weapons... my own hometown and my parents still would have been under the Russian occupation." (24:38)
This segment underscores the critical importance of timely and effective military aid in shaping conflict outcomes.
5. The Boiling the Frog Strategy: Gradual Support and Its Implications
A pivotal discussion in the episode revolves around the U.S.'s "boiling the frog" approach—a strategy of incremental support to Ukraine to avoid provoking Russia overtly.
Strategic Debate: The hosts and guest Donna Aviv dissect the implications of slow, phased weapon deliveries. Aviv explains, "The boiling the frog strategy was a reflection of the fact that at the end of the day, neither side understands the other side's red lines... too high a risk of triggering a nuclear confrontation." (33:15)
Operational Challenges: While effective from a bureaucratic standpoint, this strategy often left Ukraine waiting months for critical weaponry, hindering their immediate defensive capabilities.
Impact on Ukraine: Anastasia Lopatyna critiques the strategy: "You can't just win that way, can you?" (36:39) The delays and predictability allowed Russia to anticipate U.S. support, diminishing its strategic surprise and effectiveness.
This analysis highlights the complex balancing act the U.S. faces between supporting Ukrainian sovereignty and managing global nuclear tensions.
6. Diverging Objectives: Ukraine's Total Victory vs. U.S. Prudence
The episode delves into the fundamental misalignment between Ukrainian aspirations for total victory and the U.S.'s cautious support aimed at avoiding direct confrontation with Russia.
Ukrainian Standpoint: Ukraine seeks not just to repel Russian forces but to reclaim all occupied territories, driven by historical and existential imperatives.
U.S. Perspective: The U.S. maintains a policy focused on preserving Ukrainian sovereignty without committing to the full territorial restoration, due to concerns over escalating the conflict.
Timothy Snyder's Analysis: Historian Snyder argues that the U.S.'s Cold War mindset hinders a clear understanding of Ukraine's needs, stating, "The correct [framing] was this is a conventional war and someone’s going to win and someone’s going to lose." (43:07)
This section elucidates the strategic disconnect that complicates alliance cohesion and conflict resolution.
7. The Turning Point: Ukrainian Victory and Shifting U.S. Policies
By mid-2022, Ukrainian forces successfully defend Kyiv, demonstrating formidable resistance and strategic acumen.
Strategic Success: Despite overwhelming odds, Ukraine's defense strategy, coupled with effective international support, prevents Russian occupation of the capital.
Continued U.S. Support: Following initial victories, the U.S. and its allies bolster their commitments, though underlying strategic differences persist.
Dan Aviv's Perspective: "The American understanding of this war is full of contradictions like these." (44:30) He critiques the U.S. response as overly cautious, limiting Ukraine's ability to achieve comprehensive victories.
The episode underscores the critical juncture at which Ukrainian resilience challenges and potentially reshapes international support paradigms.
8. Political Shifts and Future Uncertainties: The 2024 U.S. Election
As the conflict continues, the 2024 U.S. presidential election introduces new uncertainties regarding the future of U.S.-Ukraine relations.
Trump's Return: The election of Donald Trump polarizes expectations, with Ukrainians uncertain about his administration's stance on the war.
Unforeseen Consequences: A pivotal moment occurs when Trump pauses all U.S. military aid to Ukraine following a contentious meeting with Zelenskyy, severely undermining Ukrainian defenses.
Personal Narratives: Anastasia Lopatyna describes witnessing the fallout from Ukraine: "That leaves Ukraine, which by the way, used to be one of the most pro-American countries in the world, deeply embittered with the United States." (54:50)
Historical Context: References to past U.S. policies, such as the 2001 Chikinskyv speech and the Bucharest Summit, illustrate a recurring pattern of support followed by strategic restraint.
This segment highlights the fragile nature of international alliances and the profound impact of domestic politics on global conflicts.
9. Conclusion: The Fragility of Alliances and the Path Forward
The episode concludes by reflecting on the enduring challenges facing Ukraine and the imperative for a cohesive international response. Despite setbacks and divergent strategic objectives, the resilience of the Ukrainian people and the critical role of international support remain paramount.
Final Reflections: Anastasia Lopatyna underscores the existential stakes for Ukraine: "The US can't declare victory if Russia suffers huge losses, but keeps some Ukrainian territory. But we can't. That's millions of Ukrainians living under occupation." (54:50)
Call to Action: The narrative urges for renewed commitment and strategic clarity to support Ukraine's sovereignty and prevent further humanitarian crises.
Notable Quotes with Timestamps
Tyler McBrien: "Different camps trying to manipulate around Ukraine. It's late November of 2021..." (02:37)
Shane Harris: "I think to myself, oh, shit." (02:58)
Anastasia Lopatyna: "The horror and shock of that first day is still indescribable." (18:17)
Yulia Timoshenko: "We are all here defending our independence, and we will continue to do so." (23:17)
Donna Aviv: "If we do X, then Y will definitely happen." (33:15)
Timothy Snyder (Referenced): "The correct framing was this is a conventional war and someone’s going to win and someone’s going to lose." (43:07)
Key Takeaways
Strategic Misalignments: The U.S.'s cautious support strategy often conflicted with Ukraine's urgent need for comprehensive military aid, leading to strategic frustrations.
Resilience and Adaptation: Ukraine's ability to mobilize civilian support and effectively utilize supplied weaponry played a crucial role in defending against Russian advances.
Political Influence: Domestic U.S. politics, exemplified by the election of Donald Trump, significantly impacted the continuity and effectiveness of international support for Ukraine.
Imperative for Cohesion: The episode underscores the necessity for aligned strategic objectives and unwavering international commitment to effectively support Ukraine's sovereignty and resilience against aggression.
Final Thoughts
Boiling the Frog serves as a compelling exploration of the intricate interplay between geopolitical strategy, international alliances, and on-the-ground realities of war. By weaving together expert analysis, personal testimonies, and historical context, The Lawfare Podcast provides listeners with a nuanced understanding of the challenges and imperatives facing Ukraine and its allies in a rapidly evolving conflict landscape.