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CNN NewsNight with Abby Phillip

Trump Mocks Millions Of Americans Who Protested; Politico Reports, Trump Pick Says MLK Holiday Belongs In Hell; Appeals Court Says, Trump Can Send Troops To Portland; U.S. Strikes Venezuelan Boat; Trump Urges Zelenskyy To Accept Russia's Peace Deal. Aired 10-11p ET

Aired October 20, 2025 - 22:00   ET

THIS IS A RUSH TRANSCRIPT. THIS COPY MAY NOT BE IN ITS FINAL FORM AND MAY BE UPDATED.


[22:00:00]

(BEGIN VIDEO CLIP)

SARA SIDNER, CNN HOST (voice over): Tonight, they came, they chanted, they got dumped on.

DONALD TRUMP, U.S. PRESIDENT: I think it's a joke. I looked at the people. They're not representative of this country.

SIDNER: The president mocking millions of Americans with a filthy A.I. video.

Plus, here we go, a court gives the administration a green light to send troops to Portland. How Oregon is trying to stop it.

Also, bad enough to be executed but not detained? As Donald Trump's boat bombs intensify, so do the legal and moral questions.

And --

TRUMP: If we don't make a deal, it'll be -- a lot of people are going to be paying a big price.

SIDNER: -- a tense face to face after Trump tells Volodymyr Zelenskyy to accept Russia's terms.

Live at the table, Keith Boykin, Batya Ungar-Sargon, Pete Seat and Saikat Chakrabarti.

Americans with different perspectives aren't talking to each other, but here, they do.

(END VIDEO CLIP)

SIDNER (on camera): All right. Good evening to you. I'm Sara Sidner in New York.

Let's get straight to what America is talking about. The Trump administration is dumping on Americans expressing their First Amendment rights and an A.I. video he posted shows just how filthy Trump's willing to go against those who oppose him. A warning now, in case you haven't finished your dinner, Trump posted this A.I. video to social media featuring himself, you see him there wearing a crown, flying a fighter jet and then you see that it appears that he is dropping feces on protesters marching in the No Kings rallies over the weekend. An estimated 7 million people showed up to those rallies and there were about 2,000 demonstrations held across the country.

But it wasn't just the president doing the crap-slinging. His vice president posting this fake video showing Democratic leaders bowing to Trump, who has a crown on holding a sword there. The White House mocked Hakeem Jeffries and Chuck Schumer with this little video or pictures put out. So, did the Transportation Department, by the way, putting this out. Trump's communication director took a jab at Kamala Harris' husband with this. And these are the people that Americans are paying to run the government, which, by the way, as you know, is still shut down.

And when confronted with Trump's sewage bomb, here's how the Republican speaker of the House tried to spin it.

(BEGIN VIDEO CLIP)

REP. MIKE JOHNSON (R-LA): The president uses social media to make a point. You can argue he is probably the most effective person who's ever used social media for that. He is using satire to make a point.

(END VIDEO CLIP)

SIDNER: All right. We've got our great panel here. Let's start with you, Pete Seat. You're so lucky you're in the hot seat. The president is supposed to be the president for all Americans. Why is this okay?

PETE SEAT, FORMER WHITE HOUSE SPOKESMAN, GEORGE W. BUSH ADMINISTRATION: Well, they're calling it what it is, and that is a partisan charade. It is being completely overblown. Let me back up for a second. The very same people who mocked Donald Trump for his fixation on crowd sizes, saying it was indicative of absolutely nothing, want us to focus on the fact that 98 percent of Americans had nothing to do with these protests over the weekend. They want to overblow this and exaggerate it and make it sound like it is a massive wave against Donald Trump.

What it is is a Democrat Party stunt, one that was co-sponsored by the Communist Party of America. It is on the flyer, their logo, that should be disavowed. It should have never been allowed on the flyer to begin with.

So, the speaker of the House, I don't agree with all of his language that he's using to describe this, but they're pointing out what it is, and that is just a bunch of partisan politics. If Joe Biden was president, these people wouldn't give a darn.

SIDNER: Do you think that if Joe Biden was president and he posted that video of Republicans who were out there expressing their rights with it, dumping crap on --

SEAT: Well, I don't like a lot of the social media that Donald Trump puts out there. [22:05:01]

He's trolling. You can agree or disagree with the trolling, but it is his style of communicating. He seems to enjoy it and a lot of his supporters do. I don't.

SIDNER: What do you think about this, Keith? As you hear the responses from Republicans have been like, oh, he's trolling, oh, he's joking, oh, this is not a serious protest, even though there were some 7 million people out there?

KEITH BOYKIN, FORMER CLINTON WHITE HOUSE AIDE: You know, where does it end? What are we doing here? I mean, I was at the protest on Saturday in New York City. It was entirely peaceful. There were a hundred thousand people or so who were there down Seventh Avenue in Manhattan. And there were millions of people at other protests across the country. No, it wasn't the entire population. But even when Dr. King led his marches, there were only a small fragment of the black community who was there, but it was a representation of the power of the people standing up against their government. People have busy lives and they took time out of their lives to do that.

And then they have the president of the United States figuratively crap on them for expressing their right to free speech isn't a front to democracy. It's not only juvenile and immature. It's a reflection of where we are as a country today.

On top of all that, then you have Mike Johnson, the speaker of the House, and other people, the Republican Party, saying this is okay, because it's just Trump being Trump. Well, you know, last week they were saying it was okay for 30 -- 20-year-olds and 30-year-olds to make racist comments about Nazis and stuff like that. But now we have the president of the United States literally attacking a 23-year-old, Harry Sisson, dumping crap on him. And that's okay, because that's fair game. But, you know, when the Republicans are doing and they're calling each other the Nazis, they're just kids. This is just a reflection of the hypocrisy of the Republican Party.

SIDNER: Batya, I think I'm old enough. I think we're probably all old enough to remember when Hillary Clinton used the deplorables comment, said that half of the people that support Donald Trump were a part of this basket of deplorables and Republicans went crazy, condemning her to this day, they still do it. So, why are Republicans covering for Trump when he does something like this, saying these people are a joke, they're not indicative of America, and then he has this video?

BATYA UNGAR-SARGON, AUTHOR, SECOND CLASS, HOW THE ELITES BETRAYED AMERICA'S WORKING MEN AND WOMEN: Well, I want to start by saying I totally support the protests. I think that this is, you know, a very important part of what it means to be an American is to raise up your voice in any form that you wish. We have these First amendment rights and they are precious and dear. I also think that this was not indicative or representative even of the mainstream Democratic Party. These protests were overwhelmingly white. They were overwhelmingly elderly people, older people. Now, again, you know, white boomers have the right to have a mass therapy session about the fact that Donald Trump won. But to call it a No King's protest, to act like he is a king is so utterly preposterous. This is a man who won the popular vote. He won every swing state. He's a person who is enacting the exact agenda he promised he was going to enact while he was campaigning.

And so what they're actually protesting is the absolute perfection of American democracy where a person campaigned on an agenda, won the popular vote and is now enacting that agenda. So, it was actually a protest of democracy, all of which is to say the only way to greet such a preposterous proposition, calling this a No King's rally when it's actually an anti-democracy rally, is to crap on it, I'm sorry, is to basically make fun of it. And I think that has been the Trump administration's approach. They didn't try to stop it, God forbid, because he's not a king. They allowed them to have their say. They allowed them to go out there and then they made fun of them.

SIDNER: How do you make --

SAIKAT CHAKRABARTI (D), U.S. CONGRESSIONAL CANDIDATE, CALIFORNIA: Look, first -- yes. First off, it was the largest protest, I believe, in history, right? We never have protests at an entire -- the entire population of America. So, it was the largest protest. And there's a reason why people were protesting, which is that Trump has not delivered on the stuff he campaigned. Trump campaigned on lowering the cost of living, on bringing manufacturing back to America, on rebuilding people's means of making a living, and he has failed on those front.

The only thing that he has done is he has weaponized the U.S. government to go after his political opponents, and that's what people are upset about. That's why it is bringing mainstream people out. I was out in San Francisco and we marched a few miles. It wasn't old people doing that march. It was people from all walks of life, all races, all ages.

UNGAR-SARGON: Well, I've seen a lot of footage and most of the footage I saw was decidedly older, decidedly -- right. I just want to say on the return, the manufacturing, I mean, that is basically the entire point of the tariff agenda is the re-shoring of manufacturing. Obviously, it doesn't happen overnight, but he has definitely put a lot of energy into trying to make that happen.

CHAKRABARTI: Give me an example of a single country that has built up manufacturing through tariffs alone? Has anything ever done that?

UNGAR-SARGON: What do you mean? Is any country like America comparable to America, have the American workforce, have the American drive?

CHAKRABARTI: Has any -- so you're thinking just tariffs and all of a sudden we're going to get manufacturing back? Manufacturing is --

UNGAR-SARGON: It's already working.

CHAKRABARTI: No, it's not. UNGAR-SARGON: Of course, it is.

CHAKRABARTI: Manufacturing investment was at an all-time high under Biden, has plummeted under Trump because, guess what, when you want to build a factory -- it is accurate.

[22:10:05]

When you want to build a factory, you have to import parts from other parts of the world to build those factories. Manufacturing investment has plummeted under Trump.

SIDNER: I want to bring up something that we heard from the Republican speaker who called people at this rally pro-Hamas, who hate America, so that was one of the lines, and then Republican Tom Emmer called participants the terrorist wing of the Democratic Party. I'm curious how you think anyone can justify that, Pete, saying something like that about Americans who were out just expressing their opinions.

SEAT: Well, and the speaker of the House and Tom Emmer are allowed to express their opinions. I think it's fair to say that the Democratic Party is united in their opposition to Donald Trump but is not united in their opposition to Hamas. We have seen that over the past several years. There are strong elements within the Democratic Party, and it's in large part why Kamala Harris faceplanted. It's because she did not cater to those elements strongly enough.

I do want to make one more point about this whole protest issue, and that is if the participants were intellectually honest in their whole No Kings thing, they would be out there protesting the actual wannabe kings and queens of Washington, D.C., who cannot seem to find another thing to do with their life than serve in Congress. And I'm looking at Ed Markey, who's been there for 48 years, 352 days, and is running for reelection. I'm looking at Ron Wyden and Chuck Schumer, who have been there for 44 years and 290 days. And then when they actually do, and the person you're trying to run against who has been there for almost 40 years herself, Nancy Pelosi.

SIDNER: They've been elected by the people, correct?

SEAT: And so has Donald Trump.

SIDNER: Right.

SEAT: And so has Donald Trump.

BOYKIN: But you're not making any sense. I mean, if you want to talk about old people in Congress, so what? I mean, Mitch McConnell just fell on his face last week and you guys are still supporting him.

I think the real issue here is that Republicans are used to using the same old fear tactics they've been using since the 1950s, since the Red Scare, which is where Donald Trump got all of his lessons basically from his years with Roy Cohn. You know, they used the communism smear, which Pete used it from the beginning. Now they're using the Hamas -- SEAT: It's not a smear when the logo was on -- no one is making that up, Keith.

BOYKIN: Listen, can I --

SEAT: Have you seen the flyer? Have you seen the logo on the flyer? It's right there. But you can't say it's a smear when it's there.

BOYKIN: It's a smear. They're using the communism smear because that's all they got. They want to say that, oh, this is all about a bunch of communists. I was there. Pete wasn't there. You weren't there. We were there in different cities. We saw what really took place. So, you got a bunch of people who have no idea what's going on, just like Trump talking about Portland and Chicago, a place he's never been. We have to have real serious conversations in this country, and, unfortunately, we have an unserious party with Republicans who don't want to have serious conversations.

This is about democracy, a fundamental right of democracy from the Constitution to the Declaration of Independence, to the March on Washington, the Boston Tea parties, all about the right to peacefully pro protest. These were peaceful protests in New York City that a hundred thousand people, not a single person was arrested, contradicting the whole myth that Donald Trump has been perpetuating, these are all a bunch of radical leftists who are out there with Antifa trying to destroy our country and being violent. It's a bunch of lies. And it's time we have a president who brings our country together now tears us apart

SIDNER: While you're hearing these words, you know, terrorists, et cetera, et cetera, from Republicans about the people that were out in those protests, we're also seeing some political reporting. I don't know if you've seen this yet, but there is reporting that there is a group text chain out there from Trump's pick to lead the Office of Special Counsel. And Paul Ingrassia is the person that he has put up. And he texted, according to Politico, that he has a Nazi streak and he told a group of Republicans of operatives and influencers that he believes that MLK Jr. was the 1960s George Floyd and his holiday, as he put it, should be ended and tossed into the seventh circle hell. Where is the Republican outrage to this? I'll start with you, Batya.

UNGAR-SARGON: I'm utterly -- I'm not a Republican, but I'm utterly outraged by this. I think it's disgusting. I think the text messages in that group chat of Young Republicans were disgusting. I think it's appalling that the vice president couldn't unequivocally condemn them. I don't know what he was thinking. The Republican Party needs to have one of those Buckley moments when he kicked the John Birch Society out of the Republican Party, said, you're not part of the conservative movement. The moment is now. And I don't know why they're hesitating.

You cannot build anything with those people. And, by the way, like the people in your coalition on the far right who want you not to condemn anti-Semitism, disgusting, anti-black racism, they're not the people you need to win. I'm the person you need to win, and I'm not voting for that. So, you know, it's very strange to me that they don't seem to understand that. This is not what people voted for. Donald Trump won a record number of black voters, a record number of Jewish voters, and I think it is appalling to throw that in their face and not be able to vociferously and immediately and without hesitation condemn this disgusting writing.

[22:15:11]

BOYKIN: Because Donald Trump has a history of racism himself.

UNGAR-SARGON: No, that not true.

BOYKIN: Are you kidding? Donald Trump started his career with racism. In the 1970s, he was sued for housing discrimination. In 1989, he was a part of the -- he's led a lynch mob against the Central Park Five. In 1990s, he was sued by casino workers for racial discrimination. He led a five-and-a-half year campaign against Barack Obama for allegedly not having an accurate birth certificate. Donald Trump came in office talking about he was going to ban Muslims, and he's called Mexicans were supposedly bringing drugs --

UNGAR-SARGON: He has the most multiracial coalition --

BOYKIN: Donald Trump has a long history -- you didn't deny anything of the things I just said there. Donald Trump just this year said that he's allowing white South Africans to come to the United States, but not black South Africans. What could be more racist than that?

UNGAR-SARGON: So, why does the majority of Latino men vote for him? Why did 25 percent of black men vote for him?

BOYKIN: It was not 25 percent. And still, black people are the most loyal group against Donald Trump, in fact, because we clearly could see through the charade that he was putting up. Donald Trump has a 50- year history of racism.

UNGAR-SARGON: Why did a majority of Hispanic men vote for him if he's --

BOYKIN: I'm not a Hispanic person. I can tell you as a black man that Donald Trump is a racist. That's unquestionable.

UNGAR-SARGON: I don't agree with that at all.

SIDNER: All right. Let me just -- there's a statement from Ingrassia's lawyers here who says, it looks like these texts could be manipulated or being provided with material context omitted. However, even if the texts are authentic, they clearly read as self-depreciating and satirical humor, making fun of the fact that liberals outlandishly and routinely call MAGA supporters Nazis. So that is from Ingrassia's lawyer. We will see what happens. He is going to be up for confirmation. There's going to be a hearing on Thursday. The timing of all this coming out now could be trouble for him, but we will see.

All right, coming up next, breaking tonight, an appeals court just gave Trump and the administration the green light to send the National Guard to Portland. Another special guest is going to join the table with us. Plus, Trump called them drug trafficking terrorist who the Pentagon tried to kill, but a couple of people survived the attack and now they're letting them go. Why?

(COMMERCIAL BREAK)

[22:20:00]

SIDNER: All right. Breaking tonight, a federal appeals court just gave President Trump the green light to send National Guard troops to Portland, and it comes after a district judge ruled the administration, specifically Trump himself, had inaccurately characterized protest at an ICE facility as violent, and that didn't justify the National Guard presence.

Two of three judges on the panel today wrote in their decision, even if the president may exaggerate the extent of the problem on social media, this does not change that order that -- the other facts that would justify his move to send those troops in.

Mercedes Colwin is joining us now in our fifth seat as our legal eagle. What surprised you or not about this particular ruling from the Ninth Circuit?

MERCEDES COLWIN, TRIAL ATTORNEY: It really was surprising because the threshold really wasn't talked about. There is a threshold for the president to step in and send militia. It has to have the violence that we talked about. There has to be an inability by the state because they have the sovereignty to control their militia and to protect their citizens. If they're not capable of doing it, where's the violence?

And that's why Judge Graber came in, this was the dissenting judge, and I thought she really called to task the majority judges, and by saying, which I love this quote, which is why I want to read it, she said, given Portland's protesters well-known pension for wearing chicken suits, inflatable frog costumes are nothing at all when expressing their disagreement with the methods employed by ICE, observers may be tempted to view the majority's ruling, which accepts the government's characterization of Portland as a war zone as merely absurd.

She really calls to question those two judges by saying there wasn't activism by the underlying judge. The underlying judge who ruled on the TROs was calling it the way she saw it. It's not a war zone. There isn't this extreme violence. States have the sovereignty to have this type of control and this protection over the -- at their sovereignty, end of story. For the president to step in, that is unconstitutional.

Obviously, Judge Graber -- and not only Judge Graber, she was calling for en banc review, but also the city and state attorneys have asked for en banc review, which is a review by the entire panel of the Ninth Circuit, which are the 11 judges, which it's certainly headed that way.

SIDNER: The chief circuit judge and ten other judges wants them all to come in and look at this case, not just have the three judges.

I do wonder, Saikat, what you think this means not just for Portland, but for other cities, like Chicago, where the Trump administration is saying, hey, we've got this win here. Now we can do what?

CHAKRABARTI: Well, and he's talking about San Francisco, which is where I'm running to represent. And, honestly, when I hear Trump talk about this, what I'm hearing is taxpayer dollars being set on fire. Because he's saying he's going to send National Guard into San Francisco to clean up crime. Crime in San Francisco is at a historic low right now, right? What's the National Guard going to do? They're not going around picking up drug dealers off the street or criminals off the street. In D.C., they're going around picking trash off the street. It's the world's most expensive beautification program, right?

And so this has nothing to do with crime. Somehow we have all this money for the National Guard, for ICE, but no money for healthcare, right? This has nothing to do with crime. What this has to do is he wants to create chaos and lawlessness, and he's hoping that some protesters are going to throw a rock and create conflict, so then he has this excuse to declare martial law. But we just saw 7 million people protest on the streets through No Kings, and there was zero violence and zero arrests.

[22:25:00]

So, I don't think he's going to get what he wants.

SEAT: But throwing rocks is exactly what happened in Portland, and you focused on the dissenting opinion.

COLWIN: Sure.

SEAT: But the majority actually saw it very differently and they admonished the district court judge for completely ignoring what happened in June, July, August and early September.

And just a couple of things that happened that are in this ruling mentioned, for more than three weeks, the ICE facility was closed because of the protests. Protesters erected a traffic barrier. They placed a pole at the lobby door to try and stop people from coming and going. They fired M-80 fireworks at officers through a mortar at the front entrance, injuring an officer. As recently as last month, agents, ICE agents reported being stalked and followed home by some of these protesters. That's just some of what is in this ruling.

You can't tell me that's peaceful protesting. You can't tell me there was no violence. The protesters were also taking homeless residents or people that were homeless in the vicinity and coercing them to cause disruptions to continue this protest and make it violent and try to impede law enforcement from doing their job.

COLWIN: But, Pete, that's why you need to actually go through the threshold. Of course, there might have been this incidence that you're talking about, but you have to look at the threshold. It can't be unfettered power to the president, which is why there's state sovereignty. What proof is there that the state couldn't control these issues? What proof do you have that the state, local officials couldn't step in and try to control the situation.

SEAT: I think this list is a pretty good example of it.

COLWIN: But that's why you need a full hearing. Right now, we're talking about a preliminary ruling. And what the judges were talking about and the two, the majority judges, were admonishing the lower judge by saying, by the way, that was activism by your part, and you really didn't look at the full breadth of it, and you didn't really focus on the president's constitutional power. So, there was an admonishment back and forth from all these judges.

But, ultimately, Judge Graber said, hold on, I think we have to really look deeply into this threshold. When can the president step in? And we don't have that answer.

UNGAR-SARGON: But the majority also -- and tell me if this is if they're wrong on this, they also were very clear that the bar that has to be met is a subjective one. It is the president's interpretation of whether the city is under control or requires him to step in. And because it is his subjective decision, therefore it was activism on the part of the lower judge.

SIDNER: One of the issues about whether the city is under control, I think we need to be clear, this is two blocks in Portland. Our reporters have been on the ground there. They have seen just how far this goes, and it is literally just a couple of blocks that are impacted. Again,, though, there are people outside of the ICE facilities who have been protesting for a while.

BOYKIN: This is nonsense. Anybody who was seeing what was going on in Portland knows, anybody who lives in Portland would tell you that this is total baloney. Donald Trump has contrived this whole fantasy in his mind without even visiting Portland. And the two -- Judge Graber said in her dissenting opinion that in the two weeks prior to Donald Trump's September 27th announcement, there were no incidents at all, and police said that it was a very low energy protest with maybe 10 to 15 people a night. That's not a huge protest.

But what happens is, as you mentioned earlier, Donald Trump creates chaos. He wants the chaos so that he could send people in. The same thing he did in Los Angeles where I was there, I was there the day before he called the National Guard in. It was a crowd of people, but it was no violence. He calls the National Guard. Suddenly, it erupts into a huge conflict.

And this is the problem, going back to what I was saying earlier about Lincoln, since the Civil War, every president except this one, has understood that the primary responsibility of the president is to keep the union together. This guy doesn't seem to care. He wants a civil war. He's encouraging people to fight each other, Americans to fight each other, and that is wrong. That's what's anti-American.

SEAT: Not a single one of the things that I mentioned happening before the -- BOYKIN: You didn't anything about January 6th. You're going to talk about throwing rocks, you didn't say anything about January 6th when Donald Trump was the commander-and-chief.

SEAT: Didn't you just write on your note cards, January 6th, January 6th, January 6th?

BOYKIN: And didn't even bother to call in the National Guard when he had a responsibility to protect the United States Capitol. So, don't tell me anything -- don't tell me anything about --

SEAT: It's because he knows I'm the January 6th rant.

BOYKIN: Because January 6th was a threat -- to an existential threat to the United States.

SEAT: I am not disagreeing.

BOYKIN: And you're talking about people throwing rocks in June as a comparison to January 6th?

SEAT: This is a threat to us enforcing the laws of this country.

BOYKIN: It's not comparable.

SEAT: Our immigration laws. The president you supported, Joe Biden, supported lawlessness at our border.

BOYKIN: You would feel a lot safer in Portland outside the detention facility that you would in January? You might not, but I wouldn't because you would probably be a part of the group.

SEAT: I stand by what Jon Stewart said.

BOYKIN: On January 6th --

SEAT: I stand by what John Stewart said years ago. Oregon is Washington's Mexico and California's Canada.

[22:30:00]

SIDNER: Hey, I don't think Oregon would appreciate that.

SEAT: That's fine. They can tweet me.

BOYKIN: Go to Portland instead of sitting here on CNN in New York City. Go to Portland and have a conversation with the people there instead of yapping off here about what's going on in there. Listen to the people who are on the ground. Don't listen to Donald Trump in the White House.

(CROSSTALK)

CHAKRABARTI: And the thing is, the way you know that Trump is instigating is what's happening in San Francisco? Why is he going to send the National Guard to San Francisco? None of those things happen in San Francisco. Why? What's the point?

SEAT: I don't know. I'll be honest. I haven't heard him say that so I can't --

(CROSSTALK)

BOYKIN: He just -- he said that every -- he's going to find somebody who threw a rock somewhere and accuse them who's going to use that to justify sending the National Guard.

(CROSSTALK)

CHAKRABARTI: This game where Trump will say exactly why he's doing something. And then we all pretend that it's all these other legal reasons. He's telling us why he's --

(CROSSTALK)

COLWIN: This decision has a ripple effect, though. We've got to watch what happens in the other states, except obviously California, San Francisco being one of them. But this is probably the bellwether is to see what might happen especially when you're talking about the way the decision was written and the way that you've interpreted, that it seems to be this subjective deference to the president as opposed to what --

(CROSSTALK)

UNGAR-SARGON: Can't you say he's not a very good king because all of these decisions keep coming out in his favor and he has not yet violated a single court order. Even the stupid ones

(CROSSTALK)

BOYKIN: He did. He violated Kilmar Abrego Garcia --

(CROSSTALK)

SIDNER: All right.

(CROSSTALK)

BOYKIN: -- the U.S. Supreme Court --

(CROSSTALK)

UNGAR-SARGON: -- even the stupid ones that get turned over.

(CROSSTALK)

SIDNER: We got to go. We're going to come back. Mercedes Colwin, thank you so much for joining the panel.

COLWIN: My pleasure.

SIDNER: Next, if they were dangerous enough to kill, why did the administration release them? New questions about Trump's boat strikes in the Caribbean. We'll be right back.

(COMMERCIAL BREAK)

[22:36:04]

SIDNER: Why is the Trump administration releasing people they claim are "Narco" terrorists back to their home countries? President Trump posted this video of a strike on a supposed drug boat last week. This weekend, though, they announced that two of the people on board after that strike survived. But instead of detaining, arresting, and charging them, they are being returned to their respective countries.

The White House has long claimed the now seven strikes on boats in international waters are justified as part of its war against drug cartels. But while they are heavy on the videos, they have revealed little to no evidence of the cartels or drugs aboard. If that is the case, then why release the two people the administration alleges are terrorist drug traffickers who are killing Americans?

In our fifth seat tonight, Max Boot, senior fellow at the Council on Foreign Relations. And I will begin with you. Why would you release people who you are saying are a detriment to the United States because they are bringing -- allegedly bringing drugs into the country?

MAX BOOT, SENIOR FELLOW, COUNCIL ON FOREIGN RELATIONS: Right, it doesn't make any sense if you take it face value the administration explanation, but they've released very little evidence about what they're doing. And I think there's a general feeling among legal scholars on both the left and the right that what they're doing is not legal.

I was as struck yesterday. Here was a post on X from Ed Whelan, who is a former Scalia clerk and a prominent conservative legal activist saying the attack was very likely illegal, even if the victim was a drug trafficker. There are lawful ways of dealing with drug traffickers. Deliberately killing them without trial isn't one of them. And that's what the administration is doing.

You know, if the administration wants to go out and boil up boats that it claims are engaged in drug smuggling, it needs to go to Congress and ask for an authorization for the use of military force, which is not something that they have done. And beyond the fact that there is no compelling legal rationale for what they're doing, the policy rationale is also very shaky.

I mean, obviously nobody likes drug cartels but they presented no evidence that these drugs are actually headed for the United States. In fact, a lot of the drugs in the Caribbean are headed for Europe or West Africa. And President Trump always cites all of the overdose deaths of the United States. Well, most of those are from fentanyl, but the fentanyl is not coming from Venezuela. It's not coming from the Caribbean. It's coming from Mexico, and a lot of it is coming through the Pacific.

So, it doesn't make a lot of sense. And I think we need to get a lot more answers before the administration continues conducting these lethal strikes with dubious legal authority.

SIDNER: I'm curious Pete. We're hearing from Rand Paul who has been pretty vocal about this saying at one point, all of these people have been blown up. We don't even know their names. We don't know anything about them. We've heard nothing of the evidence. What is your take?

I mean, are you okay with -- and are Republicans okay with America saying, you know what, we're going to do this without any of our normal -- our normal checks and balances. Thank you. Thank you very much. Our normal checks and balances -- we're just going to go after and we are just going to kill people because we think they are drug cartels.

SEAT: We don't know -- to Max's point, we don't know the underlying intelligence that may point to what is being trafficked on these boats. I would wish that the administration would disclose that information. We have to recognize though when it comes to foreign policy that the president does have great latitude to take action and Donald Trump would not be the first president to take advantage of that latitude.

But I would also pose the rhetorical question of, know, if we believe that the United States has a moral, humanitarian, and national security obligation to help impoverished people around the world, why don't we think that we have a moral, humanitarian, and national security obligation to stop drug trafficking no matter where the drugs are going? Because I do hear this point about, well, it's not coming to the United States. That's fine. It could go to Europe. It could go to Africa.

[22:40:00]

Who's to say that it won't then come to the United States at some point in time? "Plan Colombia" which was hatched during your former boss's administration -- the Clinton administration with the Colombian government, part of the purpose of Plan Colombia was to stop cocaine coming to the United States. This is a problem. Cocaine comes from Colombia, from Bolivia, from Peru, and Donald Trump is taking the tact that he wants to stop it literally in its tracks.

BOYKIN: Because it's not about stopping drugs. It's about regime change. Donald Trump is -- I call Donald Trump the great stunt queen and this is one of his stunts. Donald Trump is basically using this as a diversion for everything else. If he really wanted to do something about drugs, as Max said, we would go after fentanyl in Mexico, but we're not -- we're not bombing Tijuana. We're not bombing Cancun. We're bombing ships in off the coast of Venezuela and Trinidad.

These are not even Venezuelan people all the time. We've got two people who were just -- who were just killed, who were Trinidadian. We have one person from Colombia, another from Ecuador, who just returned to their own countries, suggesting that they weren't such grave threats that they had to be killed. How do you try to kill somebody one minute and then free them and release them to their own country at the next minute? You know, it's reflective of just how bad the situation is when you

have somebody like El Chapo, the most notorious drug lord in our modern history, who even he got brought back to United States, was put on trial and convicted in the court of law. But we're taking low level -- we're taking low level people on boats in the Caribbean who we have no knowledge about, who are blowing them up. And we call that American leadership? That's immoral. It's illegal and it's wrong.

SEAT: So, on this topic, you're pro court of law. On the last topic, you were trashing the court and their decision.

BOYKIN: I think -- no, no. First of all, that's a cheap shot. The last topic I was saying, I agreed with the distinct judge, not the two Trump appointees who you were agreeing with. That's all I said.

CHAKRABARTI: Look, Trump is not even pretending that this isn't about regime change. He's already talked about going after the land next, right? He's going -- he's already sent a CIA operation into Venezuela. He's getting us into another endless war and it's a distraction. It's a distraction from the fact that he's completely failing as a president right now.

He's failing on the cost of living. He's failing on his actual campaign promises. He's failing on health care. And so, he's setting us up for this huge expensive war in Venezuela that is going to be an endless war. It's going to make Iraq look like baby's player, right? Venezuela is going to be horrible. And that's what Trump is going after. Why? I don't know. He --

(CROSSTALK)

SEAT: Do you believe in the power of American leadership?

CHAKRABARTI: Yes, I believe in the power of American leadership.

(CROSSTALK)

SEAT: It doesn't sound like it.

CHAKRABARTI: I don't believe in -- I don't believe America should just go in and overthrow governments whenever it wants.

BOYKIN: Thank you.

CHAKRABARTI: I think we have power and with power comes responsibility.

SEAT: Yeah, do you believe in that the obligation of the country to stop the flow of drugs?

CHAKRABARTI: Do you believe in the rule of law?

BOYKIN: Thank you.

CHAKRABARTI: Do you -- do you believe in the rule of law? Because there is no -- because we cannot -- (CROSSTALK)

SEAT: But you don't have the facts. I don't have the facts which I acknowledge.

CHAKRABARTI: I do have a fact. I do have a fact. There is nothing in a lot of says terrorism covers drug smugglers. There's a different process used for drugs smugglers. You can't just execute drug smugglers even if they are drugs smugglers. You can't just execute them with -- that's going beyond rule of law. And what really concerns me right now --

(CROSSTALK)

SEAT: And this is why the Democratic Party has a toxic brand.

(CROSSTALK)

SEAT: Because you're supporting drug trafficking.

(CROSSTALK)

CHAKRABARTI: Hold on.

(CROSSTALK)

SIDNER: Let's bring up the fact that when it comes to people who have been accused of terror --

(CROSSTALK)

SEAT: But that's what Americans hear.

(CROSSTALK)

SIDNER: Hold on. When it comes to people who have been accused of terrorism, they also have gotten to go to trial here in this country.

UNKNOWN: Exactly.

(CROSSTALK)

SEAT: But that's what lot of Americans hear. Rather than say, yes, we need to stop drug trafficking. We need to figure out how to stop it.

BOOT: There are lawful ways to fight drug trafficking. A Coast Guard is conducting interdiction operations all the time. They've been doing it for years where they seize the boats, arrest the crews, take the cargo. That's the lawful way of doing things. And they can figure out who's who. But when you're blowing things up, you don't know who's actually getting killed.

CHAKRABARTI: And here's what concerns me is, we're saying -- Trump is saying, I can define who's a terrorist, and that means I can kill him. At the same time, we're seeing executive orders defining whole parts of Democratic Party as domestic terrorists. BOYKIN: Thank you.

CHAKRABARTI: Right? Here we're seeing SPM 7, which has any anti- American or anti-capitalist or anti-Christian speech, is extremist speech. We have a task force of 4000 agents who are being taken off of drug trafficking and human trafficking, and the actual crime, and being put on prosecuting those people who are saying anti-capitalist things. Do you think that's okay? Can you put two and two together about what's going on here?

SIDNER: We will answer that question, coming up. We're going to leave it there for that conversation. next. Things apparently got very tense again between Donald Trump and Volodymyr Zelenskyy. Is the president asking him to do something he simply can't? We will talk about that ahead.

(COMMERCIAL BREAK)

[22:49:17]

SIDNER: Tonight, cede land or face destruction? That was Donald Trump's warning to Ukrainian President Volodymyr Zelenskyy on Friday during a very tense meeting at the White House. On Sunday, Trump told reporters the fighting must stop at the current battle lines.

(BEGIN VIDEO CLIP)

DONALD TRUMP, PRESIDENT OF THE UNITED STATES OF AMERICA: They should stop right now at the battle lines, go home, stop killing people and be done.

UNKNOWN: What do you think should happen with the Donbas region?

TRUMP: Let it be cut the way it is. It's cut up right now. I think 78 percent of the land is already taken by Russia. You leave it the way it is right now.

(END VIDEO CLIP)

SIDNER: Now, he was asked today if any progress had been made and he said this.

(BEGIN VIDEO CLIP)

UNKNOWN: Just a few weeks ago at UNGA, you said that Ukraine could possibly win the war and keep its territory, but now --

[22:50:00]

(CROSSTALK)

TRUMP: Well, they could. They could still win it. I don't think they will, but they could still win it. I never said they would win it. I said they could win it. If we make a deal, that's great. If we don't make a deal, it'll be a lot of people are going to be paying a big price. (END VIDEO CLIP)

SIDNER: Trump's about-face on land swapping follows a Thursday call with Vladimir Putin ahead of a proposed summit with the Russian leader in Budapest. Max Boot, author of "Reagan, His Life and Legend" is still here with us. I'm going to start with you. You've written a lot about this. I have been to the region. I've been on the ground. And when you talk to Ukrainians about giving up land, it is sacrilege. Like, there is a visceral response when you say these things.

Can Zelenskyy get anything done here? Because every time there seems to be a leaning towards the United States, for example, giving long range missiles, he gets a call from Putin and things seem to change. What's happening?

BOOT: Yeah, I don't think -- I don't think President Zelenskyy is the problem. I think there is growing recognition in Ukraine that any kind of peace settlement is probably going to involve freezing the front lines where they are. But that's not what Putin is asking for. Putin is saying to Ukraine, you have to turn over land. Russian army is not actually occupied. Give me more land. That's a non-starter. But that seemed to be what Putin was saying to President Trump on Thursday.

Trump's policy, I find kind of baffling and incoherent and deeply troubling because Trump keeps saying, as he said on Friday, Putin wants peace. And there's no evidence that Putin wants peace because if Putin wanted peace, he would just stop the war. At the same time, President Trump shows signs of understanding Putin's real game, because he'd go back to even April, he was saying, I think that Trump -- that Putin -- Trump says I think Putin may be tapping me along.

He kept complaining that Putin talks nice on the phone, but then goes out and bombs cities. And so the upshot of that is that if you want to convince Putin to make peace, you got to turn up the pressure on him. And President Trump has been close to doing that on a couple of occasions. In August, he was talking about a deadline for sanctions on Russia if they didn't agree to a ceasefire, but then Putin gets this summit in Alaska.

Nothing happens, but the threat of sanctions goes away. And now, we've basically seen the same movie play out again in Washington where Trump talks about sending Tomahawk cruise missiles to Ukraine. Then Putin calls them up, and all of a sudden there's no more Tomahawks being sent to Ukraine. And instead, there was a lot of tough talk from President Trump with President Zelenskyy at the White House on Friday.

So, this is basically just allowing Putin to sweet talk Trump to kind of run out the string and to prevent any kind of effective diplomacy on the part of the U.S. If Trump wants to win that Nobel Peace Prize, if he wants to stop the war, he needs to get tough with Putin. And I think there's a general recognition that he needs to do that. But for some reason, he's not.

SIDNER: Pete, do think Trump is being played by Putin?

SEAT: I think we're being played by both sides. I don't think either side in this war is being honest. Ukraine wants Russia to lay down their arms and return all conquered territory. Russia wants territory concessions and likely is never going to agree to a lasting peace. So at best, we're at a stalemate, at worst, we're faced with unabated death and destruction.

And I don't think, really, any leader is being honest about that. You know, Europe constantly says, oh, we stand with Ukraine, we're with Ukraine. Other than holding some summits here and there, what are they really doing?

BOOT: Europe is actually providing more defense aids to Ukraine than we are right now.

SEAT: But the reality is, I mean, you're the analyst on this, Max. How long, if Europe gives the maximum amount of armaments, the United States does the same, when does this end? At what point does Putin, like what's the pressure point that gets him to back down?

UNGAR-SARGON: And you have to understand that -- you know, the problem with Zelenskyy right now is he does not have any cards. His one card is the question of how long the American people are willing to keep funding this war. And the answer to that is they are done with this.

(CROSSTALK)

BOOT: That's, yeah, but we're not -- we're not providing --

(CROSSTALK)

UNGAR-SARGON: And so, Donald Trump has to try to figure out how to get both of them to the table. Now, the failed liberal model of diplomacy suggests that when you have a weaker party and a stronger party, what you do is, you bolster the weaker party. You bring down the stronger party. You create this artificial parity, and then they'll negotiate. It never works because you take away everyone's incentive to negotiate. The weaker party doesn't want to negotiate because they've been elevated, and the stronger party doesn't want to negotiate because they've been brought down.

BOOT: That's just --

UNGAR-SARGON: Trump's view is the exact opposite. He is a real estate guy. He says the only way you get to a deal is you exacerbate the power differential because then everybody has an incentive to come to the table.

(CROSSTALK)

UNKNOWN: And that's why --

UNGAR-SARGON: And I want to make one more point. When this war began, Crimea was part of Russia. Ukraine was not part of NATO, and the Donbas region -- Ukraine, Donetsk and Luhansk were independent republics. There was a civil war there. They were not part of Ukraine. And the idea that this ends and that territory that when this began --

[22:55:01]

(CROSSTALK)

BOOT: That is not accurate.

(CROSSTALK)

BOOT: There was a Russian-backed insurgency to take control of them.

(CROSSTALK)

UNGAR-SARGON: -- does -- goes back to Ukraine -- that's just a not -- that's never going to happen and everybody knows that. So, this will never end when everyone's living in a fictional world that is not going to bring an end to the killing and the death.

(CROSSTALK)

BOOT: Don't -- do not place the war criminals and their victims on the same moral plane. The Ukrainians are willing to make sacrifices for peace. The Russians continue their unabated war of aggression. That is what is going on here.

SIDNER: All right, we're going to end it there. Everyone, thank you so much for being here.

UNKNOWN: Thank you, Sara.

SIDNER: Something Fit for Hollywood. We're going end with this. Details on that dramatic jewelry heist at the Louvre in the middle of the day when there are folks inside one of the most popular museums in the world.

(COMMERCIAL BREAK)

[23:00:20]

SIDNER: We leave you with this. A brazen heist at the Louvre in Paris, and it took just seven minutes. Video shows thieves breaking into displays and escaping with priceless French crown jewels dating from the Napoleonic era. Eight of the nine artifacts still missing, and the thieves are, as well. And thank you for watching "NewsNight". "Laura Coates Live" starts right now.