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The Bulwark Podcast

Michael Weiss: Trump's Ukraine Cluster**ck

25 Nov 2025

Transcription

Chapter 1: What is the context behind Trump's Ukraine policy?

0.031 - 14.968 Unknown

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28.432 - 45.972 Tim Miller

Hello and welcome to the Bollard Podcast. I'm your host, Tim Miller. Delighted to welcome back one of our faves, a reporter for The Insider, which is a Russia-focused media outlet. He also writes on Substack at Foreign Office, co-author of a book called ISIS. And supposedly he has another book coming out about the GRU, but I don't know. That's been in works for a while. It's Michael Weiss.

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46.032 - 48.094 Tim Miller

You might be too busy podcasting to be book writing.

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48.355 - 56.567 Michael Weiss

It's like a Robert Caro-esque thing, you know. another five years here, another six years there. Eventually we'll make it though. Volume one.

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56.667 - 62.234 Tim Miller

I look forward to that very much. Yep. Are the birds with us today or what do we think? Is it just going to be you and me?

62.614 - 74.85 Michael Weiss

So I haven't slept very much in the last week for reasons I'm sure we'll get into on the show, but I was about to say the birds have been silenced, but that sounds way more menacing than I meant. I just meant that I closed the door to my daughter's room.

74.97 - 92.037 Tim Miller

So Well, we get mixed reviews on the birds, so some people will be sad, others will be joyous. I guess it just depends on how sensitive their audio is. We're going to spend, I think, probably the entire podcast on the crazy developments that are continuing every hour in the Russia-Ukraine negotiations, if you want to call them that.

92.497 - 100.71 Tim Miller

We had our newsletter that came out this morning from Bill Kristol and Andrew Egger, our morning shots, that I just feel compelled to mention. Yeah.

100.69 - 130.663 Tim Miller

to everybody because we're going into the holiday weekend people need a little joy in their life the subhead says this the white house is in free fall how long will it last and i do think in some ways this relates to our topic of the day on russia ukraine which is like trump has really lost the rope on a lot of things domestically and like there are a handful of things that he still feels like he has control over i think the ice operations and the cbp operations being one of them and this

Chapter 2: How are Kushner, Witkoff, and Vance involved in Ukraine negotiations?

358.161 - 369.975 Michael Weiss

He knows everybody. And I think he was briefing – Was it the Russian ambassador to the United States on how to understand and how to read Trump? Perhaps it was Lavrov himself. I forget the details.

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370.075 - 383.748 Tim Miller

You know, it was the ambassador, and then he was telling the ambassador to connect him to Lavrov. That's it. Okay. And then in the Iraq case, I guess Iraq was asking him to speak to the Russians about Assad. They're trying to get rid of Assad.

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383.768 - 401.788 Michael Weiss

Right. So, you know, that's interesting, too, because there's this perception that, oh, the Israelis really hated Bashar al-Assad. I mean, well— They didn't like him, but they preferred him. to the collapse of the regime. And we see that playing out very clearly now. I mean, they have actively tried to sabotage normalizations with the Shara government.

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402.149 - 422.517 Michael Weiss

They don't like the fact that Shara was in the White House, and they certainly don't like the fact that it looks like the U.S. is going to lift sanctions on Syria. Why? Because Assad is sort of the devil we know, and they could play him. He was weak. He was easily manipulated. In fact, when his regime fell, we at New Lines, the other publication I write for, we did a story on documents that were

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422.497 - 438.7 Michael Weiss

retrieve showing that the Israelis were telling him all the time, listen, if you allow Iran to do X, Y, and Z, we're going to come and bomb these places. So he would back off occasionally when given these sort of threatening overtures by the Israelis. So yeah, using Epstein as a kind of

438.68 - 465.236 Tim Miller

connector or fixer for these purposes kind of makes sense it's a little confusing it's a little confusing what to me it makes sense only if he's just like blustering if he's like actually a you know non-state like unofficial back channel actor i guess that raises a few questions about what uh you know who the russians were and why and and who the Israelis were and why.

465.276 - 491.248 Michael Weiss

It may surprise sort of ordinary listeners, but I think this is kind of how the world works. You know, these horrific people, billionaires or multimillionaires, but, you know, they worm their way into the corridors of power. They leverage their contacts and their friendships with people in positions of power to acquire more wealth or to acquire more contacts of other people, including, you know,

492.308 - 505.136 Michael Weiss

potentates and dictators abroad, and they sort of connect people. Epstein was almost like his own private intel shop, in addition to being, you know, a Bond villain and a pedophile with an island.

505.216 - 512.072 Tim Miller

So QAnon was kind of on the right track. It's just their era was a little bit off, as far as my license concerns.

Chapter 3: What are the implications of Trump's political standing on foreign policy?

663.802 - 687.33 Tim Miller

This exclusive Black Friday Cyber Monday deal is their best of the year, so order now before it ends. Support the show by mentioning us at checkout. Terms and conditions apply. Let's start with a quick TikTok for people of what was happening. Because I have to tell you, for me, it was hard to follow who was pitching what and who was on what side and who had leaked what.

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687.47 - 705.37 Tim Miller

And as I was starting to read up on it, there's much happening. I had a very busy week. And I was like, you know what? I'm just going to have Michael Weiss on the podcast next week and he can explain it to me so I don't have to read all the articles. I'm at a remedial level here on what has happened. As best as I can tell, the Russians... sent a friend of Kushner to meet with Witkoff.

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705.871 - 713.403 Tim Miller

And that began a series of events that included multiple competing drafts of a peace plan. But you explained it to me.

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714.044 - 726.604 Michael Weiss

So let's back up a little bit and sort of provide some context. So Trump had this ignominious summit with Putin in Alaska, which did not go well. There were some sort of

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726.584 - 753.874 Michael Weiss

rhetorical framework for future discussions meetings about meetings to take place in the future but it was very clear just looking at the optics of that thing nothing was substantively agreed to why because putin left early like there was no lunch no salmon or moldy tuna fish served whatever it was halibut in alaska i think would have been halibut in alaska and you know some of the reporting i've done since suggests that even in route to anchorage on air force one

753.854 - 776.328 Michael Weiss

Trump was shown by the director of the CIA, Ratcliffe, that look here. I mean, this is the intelligence we have on the war. The Russians are kind of desperate. They're not doing well. They're losing X number of soldiers, you know, let's say a thousand soldiers per square mile of territory that they take. And this kind of impressed Trump. Why? Not because he's pro-Ukraine.

776.408 - 798.454 Michael Weiss

He hates Ukraine and he has a visceral dislike for Volodymyr Zelenskyy. tied to his first term when Zelensky found himself tangled up in his impeachment saga, through no fault of his own, by the way. And he certainly wants to have a good relationship with Putin. He likes Putin. He can't understand why Putin doesn't like him back in the way that he just thinks is natural.

799.015 - 814.415 Michael Weiss

But one thing I think that kind of gets lost in sort of this sort of black and white portrayal of the situation is Donald Trump also likes power. And he likes to see traditional or historical adversaries of the United States beaten and battered, right?

814.996 - 831.988 Michael Weiss

Like he can be friends with the worst people in the world, dictators, war criminals, but that doesn't come at the expense of we're number one, right? So when he sees Russia sort of getting hammered, when he sees a country that was meant to have been written off, Kiev in three days will fall, in two weeks Russia,

Chapter 4: What details are revealed about the Russia-drafted peace plan?

1300.57 - 1317.634 Michael Weiss

The International Criminal Court indicted one Vladimir Putin for what crime? Kidnapping Ukraine's children, right? Bringing them to Russia, essentially then brainwashing them. You're not Ukrainian. You don't have parents in Ukraine. You're Russian. And then basically auctioning them off to Russian parentage.

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1317.614 - 1335.076 Michael Weiss

This is the underlying offense for a war crimes indictment against Putin put in a document saying, oh, now we cop to it and we promise to return the kids, right? So, Kirill Dmitriev is not so incredibly savvy as you like to think because he's actually admitting to Russian war crimes in this thing.

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1335.096 - 1345.849 Michael Weiss

And then there's like weird stuff like Poland will park European jets that belong to Ukraine's air force on their territory. So, now we're telling the Poles what they're going to do. The whole thing was just kind of –

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1345.829 - 1362.059 Tim Miller

Well, you have to assume that part of this is all part of the corruption. I mean, Witkoff has two sons. One of them runs Trump's crypto business. And then the other one runs the Witkoff family real estate business that has deals with Cutter. and other such countries. So like, who the hell knows?

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1362.299 - 1370.209 Michael Weiss

Kushner did like the largest leverage buyout with the Saudis on the back of the Gaza deal, right? They were making money hand over fist in the Gulf.

1370.549 - 1387.75 Tim Miller

So who knows? And they're also trying to do deals in Serbia. My point is like, you know, you assume anything that's weird in there, you just assume it's because it's some kind of back channel deal. One other thing when I was Googling and found out that Dimitrov, I do have to ask you, since you're educating me, I want to quiz you on one thing. Do you know how old is Kirill Dimitrov?

1387.73 - 1399.871 Tim Miller

I mean, not his exact age. I think he's in his 60s. He's 50. He's 50. He looks like he could be your father. Well, yeah. This is the Russians. The Russians age differently. It's the vodka and the cold weather. It's important to get down to humidity.

1399.911 - 1403.697 Michael Weiss

Yeah, and the trembling fear of doing the wrong thing.

1405.651 - 1419.007 Tim Miller

So anyway, yeah, this guy is, when you look at him, it's like, it's hard to imagine that he looks kind of a feat as well. It's kind of hard to imagine that this guy has, he seems like the kind of person that might get pushed out of a window, I guess is all I'm going to say.

Chapter 5: What challenges does Ukraine face in the current conflict?

2367.172 - 2386.395 Michael Weiss

Patriot missile systems, right? The Gimlers for HIMARS, all of that fun stuff. What is happening now? And this is another point of kind of intrigue for Donald Trump. He makes a big deal of saying we're not giving anything to the Ukrainians for free. The Europeans are buying it, right? NATO is buying our kit to donate to Ukraine.

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2386.375 - 2401.836 Michael Weiss

So the Europeans need to come to town, tell Trump, this deal is a pup, or at least it was until we rewrote it. And even if the Ukrainians wanted to do this, they couldn't for the following reasons. We can't do the things that the Russians are demanding of us, and we won't, frankly.

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2402.117 - 2420.132 Michael Weiss

And oh, by the way, if this is about a drug deal or you need to be bribed with something, let us announce a $50 billion investment into the Pearl system that you have built with NATO. So we'll pay. We will enrich the military-industrial complex. And then you want to take bribes from Lockheed Martin or Raytheon, that's your prerogative, man.

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2420.152 - 2426.811 Michael Weiss

But we will give you the money that the Russians are offering and then some. And we'll do it kind of in an above-board fashion, right?

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2427.112 - 2437.885 Tim Miller

You're saying that's what should happen. I'm just sitting here reading my CBS, which says that Umarov on the Ukrainian side is saying that the plan is for Zelensky to come to D.C. soon.

2438.526 - 2447.837 Michael Weiss

Don't say I didn't tell you so. I mean, you know, how many times do you know Zelensky in the room with Trump? Never. At best, it's not like the last time was OK.

2447.817 - 2450.059 Tim Miller

Last time we talked him off the ledge.

2450.1 - 2468.921 Michael Weiss

No, the last time is when Trump was like dangling tomahawks only to say, no, they're not getting him. That was kind of a letdown. They came here to be told yes. So that was a humiliation. The time before that was okay. But again, why even risk? Is it going to be just okay? Or is it going to be taken to the tool shed? You don't need to go down that route.

2469.041 - 2477.05 Michael Weiss

The things that need to be hammered out don't need a sort of Rose Garden or Oval Office meeting to be hammered out. It's an email, not a meeting. You know what I mean?

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