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Will a Trump Meeting Help Putin Take More of Ukraine?
CNN One Thing
Aug 13, 2025
President Donald Trump is set to meet Russian president Vladimir Putin on Friday in Alaska for a high-stakes meeting about the war in Ukraine. But will the country Russia invaded have any say into how it ends? A Russia expert explains how Putin’s time in the KGB has prepared him for this moment and why he will likely consider the meeting a success before it even begins.
Guest: Jill Dougherty, former CNN Moscow Bureau Chief
Have a question about the news? Have a story you think we should cover? Call us at 202-240-2895.
Host: David Rind
Producer: Paola Ortiz
Showrunner: Felicia Patinkin
Support: Emily Williams
Episode Transcript
Ukrainian President Volodymyr Zelensky
00:00:03
Very beginning of the war....
President Donald Trump
00:00:04
You're not in a good position. You don't have the cards right now. With us, you start having cards.
Ukrainian President Volodymyr Zelensky
00:00:10
Right now, we're not playing cards... .
David Rind
00:00:11
When Ukrainian President Volodymyr Zelensky visited the White House back in February, President Donald Trump and Vice President J.D. Vance gave him a verbal beatdown for the ages.
Vice President JD Vance
00:00:22
Have you said thank you once this entire meeting?
Ukrainian President Volodymyr Zelensky
00:00:25
A lot of times...
Ukrainian President Volodymyr Zelensky
00:00:25
No, in this entire meeting have you said, thank you?
David Rind
00:00:28
Historians could not recall any foreign leader being treated like that in the Oval Office, ever, let alone on live television. Tensions have cooled since then, but Trump has not been afraid to criticize Zelensky as he works to end a war he once promised to solve in just 24 hours. He's also criticized Russian President Vladimir Putin, not so much for invading a European ally completely unprovoked, but more about him not agreeing to a deal sooner.
President Donald Trump
00:00:53
And I'd been disappointed, because I'd have, like, a great call with him, and then missiles would be lobbed into Kiev or some other place, and you'd have 60 people laying on a road, dying. I said, that's cold. That's cold, but...
David Rind
00:01:06
'Well now, Trump is preparing to meet face-to-face with Putin in Alaska later this week to see just how serious he is about bringing three years of bloodshed to an end. But after thousands of deaths and ruined lives, what could peace cost Ukraine? And will they even be part of the discussions? My guest today is Jill Doherty. She's a former CNN Moscow bureau chief and an adjunct professor at Georgetown University and author of the book, My Russia, What I Saw Inside the Kremlin. We're gonna talk about what lessons both leaders might take away from their infamous 2018 meeting and why Putin may have more on his mind than Ukraine this time around. From CNN, this is One Thing. I'm David Rind, we're back in a bit. So, Jill, as you and I sit here on Monday evening, Trump and Putin are still scheduled to meet on Friday in Alaska. Obviously, things could shift between now and then, but for the moment, this meeting is on. Can you just briefly explain how we got to this point?
Jill Dougherty
00:02:13
Well, I think big picture is that President Trump wants this war over. And so you could argue that this is kind of like an artificial deadline. I mean, nobody was saying, we have to meet on Friday, et cetera, or even end this war right now. But that's the mission that President Trump has set out.
President Donald Trump
00:02:36
A lot of people are dying, and I think we're getting very close, and we're going to be announcing later on. We're going have a meeting.
Jill Dougherty
00:02:43
How we got here was he pretty unexpectedly said, you know, I'm going to meet with Putin.
President Donald Trump
00:02:49
And we'll announce a location. I think the location will be a very popular one for a lot of reasons.
Jill Dougherty
00:02:56
And then we find out, and it's going to be in Alaska. Now, each side is really pretty frantically trying to yank this all together with some type of purpose by Friday.
David Rind
00:03:10
I have a very basic question here, Jill. Why is Putin allowed to make a trip to the U.S.? Isn't there an international warrant out for his arrest?
Jill Dougherty
00:03:18
Well, yes, but OK, so the International Criminal Court did issue a warrant for the arrest of Vladimir Putin for war crimes, alleged war crimes in Ukraine. But the problem is, the United States does not recognize the court and its decisions, and neither does Russia. So even though you might say, oh, it's very strange that he's coming to the United He will not be arrested when he's here because the U.S. Doesn't recognize that court.
David Rind
00:03:51
'So, you lived in Moscow for years, you have covered Vladimir Putin for a long time, you even studied at the same Russian university as him. So what do you think makes a one-on-one, face-to-face conversation with him so tricky and so fraught?
Jill Dougherty
00:04:06
You know, I was thinking about that on Friday. So you're going to have both men, both leaders sit down, we think, and how does Putin prepare? You know what does Putin want to do with that meeting? So I think the interesting part about that, and of course, I'm not trying to psych out Putin because we never know exactly what he's going to do, but I would say based on what I've seen over the years and I've watched him, literally since even before he became president, so a quarter century. He's really, he's a really good study. So he knows the issues. Now he has his own sometimes warped interpretation of those issues, but he does know the issues and he's used to dealing with people. He's used dealing with world leaders. He knows his brief, as they say, and I've seen it in person. I can tell you, David. Many years ago, like when he first came into office, I was with other U.S. Correspondents at the Kremlin Library.
Vladimir Putin (translated)
00:05:11
We believe it is correct and appropriate to deal with defensive weapons and offensive weapons at the same time.
Jill Dougherty
00:05:19
And no matter what question was thrown at him, and this is very early in his administration, he had an answer.
Vladimir Putin (translated)
00:05:26
To make a choice between different...
Jill Dougherty
00:05:28
And he would go on and on with facts and figures, and I'm not quite sure whether they were all correct, but probably most were. So he knows, let's say, the issues. But then there's the other side, which I think is almost more interesting, which is psychological. So, Vladimir Putin, when he was a KGB officer way back in the Cold War, his job was to recruit people for the KGB. So, what he does, it has a lot to do with psychology. In other words, what he did as a KGV agent was to recruit people by letting them think that he was a good person, a nice person, somebody they should deal with, somebody they want to be with. And so he manipulates people, and he plays to people.
President Donald Trump
00:06:22
I have President Putin, he just said it's not Russia. I will say this, I don't see any reason why it would be.
David Rind
00:06:30
Is that, do you think, what we saw back in 2018 when Trump, you know, bucked his own intelligence community when it came to Russia interfering in the 2016 election?
Jill Dougherty
00:06:40
Totally, oh yeah, yeah, that's a classic example of that.
President Donald Trump
00:06:44
So I have great confidence in my intelligence people, but I will tell you that President Putin was extremely strong and powerful in his denial today.
Jill Dougherty
00:07:01
What could Putin do this time? I think, you know, number one, he's probably going to try to convince Trump that he's serious about wanting peace. Now, as Trump himself has said, he said that a million times, and then he ends up bombing and killing people. But I think that's number one. Yes, yes, I want peace. Number two will be to convince Trump that Zelensky does not want peace, that Zelensky is the problem, he's the obstacle.
David Rind
00:07:33
Oh, so this is the reason the war isn't ended. It's not me, it's the other guy.
Jill Dougherty
00:07:38
Exactly. Yes. You know, there's another thing which would be try to separate the United States and Europe. That's a constant attempt by Putin to do that.
David Rind
00:07:49
Well, if we think he might try to cast Zelensky as the impediment to peace, isn't it an issue if Zelenski won't even be there? Like as of this moment, it seems like he won't be there and he'll get informed after the meeting.
Jill Dougherty
00:08:02
'Correct. But it also works very well for the thinking of Vladimir Putin, because why doesn't Vladimir Putin want to meet with Zelensky right now? He would say, well, number one, Ukraine isn't a country. I mean, Putin actually says that. Ukraine is not a country, Ukrainian culture doesn't exist, etc., etc. But he also says that Zelensky was elected. Six years ago. So they have five-year terms in Ukraine. And Putin would say, so he should have been out of office a year ago. But he didn't get out of office. He stayed on. And he did actually stay on, because they have martial law. They're at war. And so they haven't had an election. And I think what Putin's trying to do is maneuver so that eventually they would have elections in Ukraine. And that Zelensky would be kicked out of office. That would be ideal for Vladimir Putin.
David Rind
00:09:06
And this is something that we heard from Trump a few months ago. He said he was a dictator without elections, and that would seem to be a Russian talking point.
Jill Dougherty
00:09:15
Oh, totally. And I'm sure he got that originally from Vladimir Putin or somebody who has been listening to Vladimir Putin.
David Rind
00:09:30
It seems to me that Trump is really kind of playing the mediator role here rather than having a vested impact into actually what happens to Ukraine's borders. Like he just wants the war to be over. He said on Monday, it's not up to me to make a deal. He wants to see what's on Putin's mind. Does that change the calculus for either side that the US has just kind of this go between?
Jill Dougherty
00:09:51
Well, you know, he's so President Trump says, I'll know in two minutes whether Putin wants a deal or not. And if I think it's a fair deal, then I'll pass it on to Zelensky and eventually to the Europeans. Now, yeah, he is kind of the go boot between he's not deciding, but he is deciding to a certain extent. I mean, he was going to decide whether it's a legitimate, fair deal. And then he'll pass it on to Zelensky. He has a role in this. He's actually defining what the deal will be. Otherwise, he won't send it on to Zelensky.
David Rind
00:10:30
Yeah, and he also said there's a world where he leaves the meeting and he realizes that it won't be settled and that nothing really changes despite all the pomp and circumstance of having this big meeting on US soil. What happens then?
Jill Dougherty
00:10:43
'You know, I would be very surprised if that happens. I think that Trump definitely wants a deal. He wants this war over. And Putin doesn't necessarily want this war over because he thinks he is winning it. And he has been able to maneuver to be in a position that he thinks is pretty strong. Now, in reality, his economy is getting weaker and has more problems with inflation, etc. But Putin wants something else. Putin doesn't only want to get what he wants in Ukraine. He also wants to revive the US-Russian relationship. And that's where you get this interesting, I think, new wrinkle, which is the Russians are now saying, hey, you know what? There are deals that we could do up in the Arctic. We'll be in Alaska. We're close to the Arctic, Arctic has a lot of riches and minerals and all sorts of things. And with the ice melting up there due to global warming, there will be new trade routes. So that means that the United States and Russia can get back on track and have a great relationship. And here is the incentive. We can do deals together.
David Rind
00:11:56
So the location itself is kind of a win for Putin just setting foot in this specific part of the U.S.
Jill Dougherty
00:12:04
'Exactly. And not only because of that. I mean, that's one reason. And you're right, David. But there's the other one, which is the kind of more ironic one, which is that Alaska used to, as we all know, belong to Russia. You know, we bought it in 1867 for $7.2 million, which of course is nothing these days. So the Russians Kind of in a sense, there's a little bit of trolling going on, you know, maybe we can take it back But I can tell you there's some nationalists, you, know a hard-line Nationalists who say we never should have sold it. It wasn't really a good deal. And besides it wasn't a deal It was just lending it to the United States for a hundred years and we want it back now I don't think Putin's gonna say hey Donald could I have I think I ought to get Alaska back I do not think he's going to do that, but there are some in Russia who would say, yeah, let's get it back.
David Rind
00:13:06
But when it comes to the actual heart of the matter for Ukraine...
President Donald Trump
00:13:09
Because there'll be some land swapping going on. I know that.
David Rind
00:13:12
Trump seems to suggest that Ukraine will have to give up some land and a swap for this war to end, something Zelensky has rejected time and time again.
President Donald Trump
00:13:20
To the good for the good of Ukraine. Good stuff, not bad stuff. Also, some bad stuff for both. So it's good and it's bad.
David Rind
00:13:29
What are the ramifications for Europe and the world if that does end up happening?
Jill Dougherty
00:13:34
Yeah, it's really, really difficult, because, you know, let's look at the big picture. If Ukraine is forced to give up territory, regardless of whether, you know, it is realistic, quote, or not, it means that Vladimir Putin is being rewarded. He's being given land that he conquered, that he invaded with force. So what the world community would be would be saying you can actually invade another country and take land, and you may be given it. And that is a really, in my book, a terrible precedent. Now, that doesn't mean that the war won't end with some type of land given up, but I can tell you for Zelensky, it's very, very difficult because a lot of Ukrainians, yes, they're getting, some of them are getting war weary, you know, three and a half years and all the people who've died. But they also do not want to give up land. It's not just land. It's a not a monopoly game.
Nick Paton Walsh
00:14:44
When President Trump talks about what parts of Ukraine to quote swap with Russia, this is ground zero. Real towns where bomb shelters loom over beaches.
Mykhailo
00:14:55
I feel like I just float away from this reality.
Jill Dougherty
00:15:00
This is people think about the people who live in those areas that have been really attacked by Russia taken over by Russia and occupation by Russia can be really brutal. I mean you know not to mention people being arrested people being raped and tortured. That has definitely happened and then under the mildest conditions they will have to become Russians. They will have two vote the way they're told to vote. It's a really... Very serious situation for people left behind.
Nick Paton Walsh
00:15:34
What do you think about the idea? Trump and Putin meeting so far away in Alaska and deciding the fate of a place like this.
Mykhailo
00:15:45
We all, people I know, will have to leave. But frankly speaking, I don't think it's gonna happen. What Trump did wrong, he just took him out and said, Vladimir, I want to talk to you. I like you. He didn't care that every day Ukrainians die.
David Rind
00:16:09
Well, Jill, thanks so much for the perspective. I really appreciate it.
Jill Dougherty
00:16:12
Oh, I'm really glad we had a chance to talk, David.
David Rind
00:16:18
On Wednesday, President Trump is scheduled to sit down virtually with Zelensky and other European leaders ahead of his summit with Putin. In a joint statement, leaders from all but one of the 27 EU countries stressed that Kiev must have a say in its own future, writing, quote, the path to peace in Ukraine cannot be decided without Ukraine. In response, Zelenski said he was grateful for the support and warned that Russia must not be allowed to deceive the world once again. That's all for us today, thank you for listening. As always, please leave us a rating and a review wherever you listen, takes about 15 seconds max and it really does help other people find us. We'll be back on Sunday, I'll talk to you then.
