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Anderson Cooper 360 Degrees

Biden Team Looking To Paint Trump As A "Lose Who Is Too Dangerous And Reckless" To Be President; NY Primary Race Represents Larger Battle Happening Inside Democratic Party Between Various Factions; Judge In Hush Money Case Partially Lifts Trump Gag Order; Trump Legal Team Says Mar-A-Lago Search Warrant May Have Violated His Rights In Bid To Get Evidence Tossed; Julian Assange Pleads Guilty To Conspiracy Charge In Deal To Avoid U.S. Prison Time; $230M Gaza Pier Built By U.S. Military Back In Place; Used For Less Than 20 Days. Aired 8-9p ET

Aired June 25, 2024 - 20:00   ET

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

[20:00:00]

SUNLEN SERFATY, CNN WASHINGTON CORRESPONDENT: Debates against Hillary Clinton in 2016, he showed up and he was mostly disciplined, more subdued, a total surprise when compared to the past. And that's certainly one reason, Erin, that Biden team here, they're preparing for this eventuality that Trump could show up on Thursday night. He could break that trend, show up more disciplined and on a message. Erin?

ERIN BURNETT, CNN HOST: All right. Sunlen, thank you very much. And thanks to all of you. We'll see you tomorrow night with our special coverage ahead of the CNN presidential debate. AC360 starts now.

ANDERSON COOPER, CNN HOST: Tonight on 360 with the CNN presidential debate just two nights from now, we have breaking news on the Biden camp's aim to paint Donald Trump as, quote, "too dangerous and reckless," unquote, to be president. That and what the former president acknowledges he did too much of the last time they debated.

Also tonight, polls closing shortly in New York, Congressman Jamaal Bowman's attempt to keep his seat in a contest hitting the Democratic Party's left and center over Israel and Gaza.

And from Gaza tonight, CNN's Jeremy Diamond with an up-close look at the pier, which American forces built to bring in humanitarian supplies, but has been plagued with troubles.

Good evening. Thanks for joining us.

It is crunch time times two ahead of Thursday's CNN presidential debate. We begin tonight with new reporting for the second night running of a tougher attack the Biden campaign appears to be preparing their candidate to follow when the two men meet. Also, new word on how differently they're practicing or not for the big night. And a hint from the former president that he wants to dial back one aspect, at least, of his demeanor from 2020. Reporting on that and more tonight from CNN's MJ Lee at the White House, Kristen Holmes at the Trump campaign and CNN Political Director David Chalian at the debate site in Atlanta.

MJ Lee starts us off. So what have you learned about this contrast the Biden team is hoping to make against the former president?

MJ LEE, CNN SENIOR WHITE HOUSE CORRESPONDENT: Well, Anderson, even though domestic policies are really top of mind for the Biden team, I am told by a source that foreign policy has come up in these debate prep sessions at Camp David, led by the President's National Security Advisor Jake Sullivan.

And the President, of course, is preparing for the possibility of foreign policy coming up on Thursday night. And as one campaign official put it to me, they said that when it comes to foreign policy, the contrast that the President is going to try to draw on Thursday night really could not be more stark.

They said, "President Biden stands up to dictators and defends freedom - Trump is a loser who is too dangerous and reckless to ever be anywhere close to the Oval Office again."

One famous line from Donald Trump that a source had said is likely to come up Thursday night is his recent claim that he would be a dictator on day one. But I do think it's worth noting a challenge for the Biden team potentially as they're preparing for these foreign policy issues is that some of Donald Trump's positions on foreign policy issues are really murky and ambiguous.

You know, on Gaza, he actually hasn't said much publicly on Ukraine. He has said that he would have resolved the conflict in one day, but he's never elaborated on how exactly he would have done that. And certainly the other side of that coin is the President is going to try to make an affirmative case for his leadership on the world stage as well.

COOPER: And I know you've learned more about the level of detail the Biden team is incorporating into the preparations for the debate.

LEE: Yes. I mean, this is really the stage where they are trying to fine tune every single detail and make sure that the President can be as prepared as he can be. And I'm told by a senior advisor that that includes knowing exactly what he is going to see once he is behind that podium, that he watched the President of video that a staffer had taken during a walkthrough of the CNN studio in Atlanta so that he could get a sense of exactly what he'll see once he is standing behind the podium.

Now, you'll recall that the Biden team did win that coin flip. And what they chose was the right podium position. That means that he is going to be on the right side of the state - of the TV screen for the audience that is watching. President Trump is going to be on the left side.

And you might say, you know, these are really superficial details, but perhaps not, because I think for any team and particularly clearly for the Biden team, no detail is too small and I do think we're getting a sense of how seriously they are taking all of the debate preparations.

COOPER: And they've been doing - I mean, is it true they've been doing mock debates? And if so, how are they structuring the practice debates?

LEE: Yes, we reported that the mock debates started in earnest yesterday. We know that the President has been using a podium as a prop and that there are different advisers that are standing in for Donald Trump, for our colleagues, Jake Tapper and Dana Bash, though, no word yet on exactly who is playing those roles.

But this is really, Anderson, about replicating the experience that the President will have on Thursday night, as much as that is even possible. And that includes, of course, just going over all of the substantive issues that could come up, going over the different ways in which Donald Trump might behave. And it also includes just a test for his stamina. He's going to be standing there for 90 plus minutes, and they want him to be as focused and as sharp as possible.

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And folks that we have talked to who have been involved in the past have said the person that is playing Donald Trump in these mock debates, they have a balancing act. They want to give him that experience, but they want to make sure that there isn't too much theatrics involved, because that could end up being really distracting.

COOPER: All right. MJ Lee, thanks very much.

I want to go to CNN's Kristen Holmes, not far from Mar-a-Lago.

How is the former president preparing for this debate and what topics are his allies advising him to focus on, do we know?

KRISTEN HOLMES, CNN NATIONAL CORRESPONDENT: Well, Anderson, it's been far less consistent and traditional than what we have seen from President Joe Biden. A lot of that because his team is trying to fit what Donald Trump does, who doesn't really like to sit down and focus. Instead, it has been shorter conversations, policy sessions and, as Donald Trump often does, calls with allies, advisors seeking their advice.

Now, when it comes to what exactly they want him to focus on, they want him to focus on three things in particular, the economy, especially inflation. They want him to focus on immigration as well as crime. These are things that they have seen the data on. They believe that voters think that Donald Trump is better on these issues than President Joe Biden. They also are trying to talk to him about how to pivot away from questions on democracy or abortion.

Yes, they are coming up with answers, but how to get back to those three topics that they believe are key that will help president - former President Trump, quote, unquote, "win that debate on Thursday." Now, Donald Trump himself actually got rather candid in an interview with The Washington Examiner talking about his debate prep.

Two things of note here, one is what he said about how it's difficult. He said it's very hard to prepare for the debate. You've got to know this stuff from years of doing it. And I know all the leaders, and I know what I know. I think debating is an attitude more than anything else."

But not just attitude, Donald Trump clearly also reflecting on his previous attitude, particularly in those 2020 debates with Joe Biden. He specifically mentioned how he interrupted Joe Biden too many times during that debate, clearly going back through those debates and trying to hone his strategy heading into Thursday.

Again, his team believes he can do well if he stays on message, particularly focused on those three issues, Anderson.

COOPER: And how did the former president and those around him talk about the debate format? Do they think it will help or hurt him?

HOLMES: Well, it's been really interesting to see kind of an evolution among his closest allies and advisors who, one, they are publicly bashing the format, which they, of course, agreed to. But they have said that it doesn't benefit Donald Trump, that having an audience doesn't work for him, having muted mics. But it has really been a shift behind closed doors and in private conversations I've had with these allies and advisors.

One, they originally said that they thought the lack of audience would hurt Donald Trump, that they thought he couldn't be energized without it, that he really builds and feeds off of that audience. Now there has been a shift in this mentality that that might actually be good, that we've seen Donald Trump go on these kind of rants when he's in a big rally with a lot of his supporters where he's off topic and completely unfocused. Perhaps, and this is the hope again of his allies and advisors, that without an audience he can actually stay on message.

The other part of this is those muted mics. You heard Donald Trump himself saying that he interrupted Joe Biden too many times in that first debate in 2020. This really takes that element out of it. He's not going to have the capability to continue to go after Biden while Biden is speaking. And some of his closest advisors actually believe that that could help him. But obviously, Anderson, we are in kind of uncharted territory here, particularly because it is former President Donald Trump and who knows how these elements are going to play out until Thursday when they're on that stage.

COOPER: Yes. Kristen Holmes, thanks so much.

I want to go to Atlanta with CNN Political Director David Chalian has more on the format.

As Kristen Holmes just mentioned, the set of rules the two sides agreed to and how different this debate night will look because of it. So talk to us about the rules. DAVID CHALIAN, CNN POLITICAL DIRECTOR: Well, Anderson, one of the biggest changes I think the viewer at home will see is no audience will be a part of this debate. It will be the two candidates and the two moderators in the room there.

Kristen you heard mentioned that the microphones will be turned on for the designated speaker at the time they are designated to speak in the debate. His opponent's microphone will be turned off at that time. Timing lights are visible to the candidates throughout the debate, so they'll know when their time is running out. And the two candidate podiums are eight feet apart from each other. Obviously, that's a lot closer than these two candidates were to each other on the debate stage compared to four years ago when we were in the height of COVID.

COOPER: And what are the rules regarding how each candidate is supposed to respond to questions?

CHALIAN: So the way that the debate is set up and these are, you know, CNN's format that both campaigns agreed to in order to participate in the debate was that there would be a big macro topic and Candidate A will get a question on that topic. They will have two minutes to answer that question. Then there will be one minute response from Candidate B, if you will, and another one minute response from Candidate A.

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And then it flips the other way, staying within the broad topic area, but a different slice of a question related to that topic. Candidate B will get two minutes at that starter question. Candidate A gets a minute to respond. Candidate B gets a minute to respond. Of course, Jake and Dana, at moderator discretion, can ask a one-minute follow- up, Anderson.

I would note also, though, these candidates, once they hit the debate stage, there is no staff, no aides. They can't communicate with their team until after the debate has concluded. So, the viewer will be seeing on - at home the sitting president and the former president, unprecedented debate, and they will not, during the course of the debate, be consulting with any aides.

COOPER: All right. David Chalian, thanks so much.

CHALIAN: Sure.

COOPER: Joining us now is Biden biographer Evan Osnos, Republican strategist Scott Jennings and former Trump White House communications director, Alyssa Farah Griffin.

Evan, you've reported and spent a lot of time with President Biden over the years. How does he prepare mentally, emotionally for big moments like this?

EVAN OSNOS, CNN CONTRIBUTOR: You know, he does a lot of preparation. He can, right down to the last minute, he'll be marking up a speech. In this case, of course, there's no speech. Really, this is not about stuffing your head full of facts and figures. This part of the process is about poise, getting enough command and comfort with what's about to happen that when you get up on stage, you are comfortable lacing those facts into your comments and, let's face it, also preparing for whatever it is Donald Trump's going to try to do to get under your skin.

And we know for a fact, as, you know, MJ mentioned earlier, that they have got - helping him try to visualize the space. That's very important. Even all the way back in 1960, Richard Nixon didn't really have a good sense of the room in a debate. He spent too much time looking at the clock. People thought he didn't look enough into the camera and it hurt him, so that's the kind of thing they're thinking about.

COOPER: Alyssa, based on MJ Lee's reporting, what do you think of the way President Biden seems to be preparing for this versus the former president?

ALYSSA FARAH GRIFFIN, CNN POLITICAL COMMENTATOR: Well, he's certainly leaning into hunkering down. I'm actually surprised by the level of specificity and detail we're getting from White House sources about ...

COOPER: Seems like a lot.

GRIFFIN: ... how he's preparing and the kind of topics he's focusing on. I assume that's meant to telegraph that he sees this as highly important. But I also think it raises the stakes and expectations of how he's going to perform. What he's going to run into is this, Biden loves to defend his record. He feels like he's not gotten enough credit for it.

But what happens is you're looking backward. He also needs to be able to defend his record, but look forward and present a forward looking vision. And all the while being up there against somebody who is known to try to throw him off of his balance, who's going to try to throw in jobs when it's his time to speak and I think it's always a little bit harder for the incumbent in these debates.

COOPER: Yes, I mean, Scott, legendarily ...

SCOTT JENNINGS, CNN SENIOR POLITICAL COMMENTATOR: Yes.

COOPER: ... incumbent presidents have a really hard time on first debates. They haven't been confronted, you know, the way they do on a campaign. They, you know, they are used to people sort of kowtowing to them.

JENNINGS: And if you're Joe Biden, you can't believe you've got a 38 percent approval rating. You can't believe these polls that say that people remember the Trump presidency more fondly (INAUDIBLE) ...

COOPER: And you just need to explain it to them, why?

JENNINGS: Yes. You just listen to me talk about how smart I am, you will also know when I think about these two, I think about them being like musicians and Biden is going to be like a technical. He's reading off the sheet of music. And Trump is sort of like the guy with the cowbell, you know, exploring the studio, one technical, one vibe- driven.

And, you know, in this thing, are people really listening for specific policy ...

COOPER: Right.

JENNINGS: ... or are they looking to see are you plausible? Do you seem like you could be plausible for four years? This is hurting Biden because people think he's too old to serve another four years.

COOPER: I think this is - I mean, Evan, this is why I think it's just going to be so fascinating, you know, I co-moderated the second debate in 2016, the Hillary Clinton debate right out the Access Hollywood tape. And that was where Trump was sort of wandering around on the stage.

And I mean, the tension was so extraordinary. This is that tension times, I don't know what, to Scott's point of sort of, you know, Biden is about policy and Trump is about kind of riffing in this weird political jazz.

OSNOS: But it's also in the end, the thing that Americans are really looking for is somebody who is in command, in command of the moment, in command of themselves, somebody who's able to convey a sense that they understand the gravity of the job. You know, a lot of this in the end comes down to who can convey the sense that they will be a more normal president.

Bruce Reed, one of the senior policy advisors who's spending a lot of time with Biden in debate prep said to me earlier this year, look, America is a normal country and Americans are normal people. What he means by that is fundamentally there is a level of exhaustion out there. We all see it when we talk to voters, when we talk to our friends and family. People want to have politics take up less space in their minds and part of the goal is the person who can get up on that stage and say to you, look, I've got this.

And it's not clear in a lot of people's minds that Donald Trump has the capacity for self-control or let's face it, that Joe Biden can convey the kind of vigor that he needs to on that stage.

COOPER: I mean, listen, the advantage Biden had the last time was, you know, he was not the incumbent and Trump was.

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And there was a lot of animosity and a lot of, you know, angst. And he was more of a blank - Biden was more of a blank slate. He's now in the position where he's not a blank slate and Trump is, you know, our memories, we're short ...

GRIFFIN: Well, I painfully ...

COOPER: ... our memories are very short.

GRIFFIN: ... I painfully re-watched the first debate and you very much see that Donald Trump is more on his heels. He's defending the COVID response. Joe Biden's able to work in jabs at him. Yes, the onus is more on the incumbent, but let's think for a second how much has happened since Trump left office. Roe v. Wade comes down, January 6 happened, you have 88 felony indictments, you've got the criminal felony charges, you have both candidates investigated for mishandling classified documents. There's actually a wealth of things for Donald Trump to have to defend as well.

So what I'm curious to see is how much are his advisors able to break through to him to say, don't get caught up, you know, re-litigating January 6 or talking about the stolen election and go back to the economy, to the border. Issues that he's actually strong on.

COOPER: I mean, he's got the chances of him re-litigating the - his thoughts on the election. I mean, it seems almost inevitable.

JENNINGS: The smart answer is, look, everybody here has different opinion than me. You know what my opinion is. I know what yours is. What we need to talk about is inflation and immigration. If he did that every time it was brought up, that would be a huge win.

I mean, there's a lot of things for him to do here. I hope he actually speaks to the moment we're having on anti-Semitism in this country. Remember, Joe Biden launched his campaign. He said, because of Charlottesville, we've got this issue in Los Angeles this week. We have these anti-Semitic events all over the country. I know it's not one of the top issues everybody's talking about, but to me, it is fundamental to how Biden got into this race and why he said he was running. And I think Trump could cause some havoc on that stage if he used it at the debate.

COOPER: He did, I mean, sit down to dinner with a neo-Nazi, didn't he? I mean, so he has weaknesses on that front as well, does he not?

GRIFFIN: Oh, he certainly does. And that is a conversation that, by the way, should be had. And I suspect our moderators will be prepared to fact check if anyone whitewashes either of their records. But I think Scott's right that he can call into question what you were supposed to kind of bring about here. You're supposed to get us past this moment.

But that's where Biden, the onus is so much on him to remind people of the worst things Donald Trump has done and said.

COOPER: The other thing, Evan, is does the former president just attack Biden on - you know, the former president has been saying awful things on the campaign trail about, oh, he's on drugs. He's, you know, not all there. Does he just do that directly to him for the bulk of this debate throughout this debate?

I mean, I - when I heard that David Chalian was saying that there's eight feet between them, I mean, one of my thoughts was, does he honor that eight foot distance? I mean, does he? OSNOS: I think that this podium arrangement will kind of confine him to his side of the ring, frankly. It'll be pretty weird if he begins wandering over there. But I have no doubt he's going to bring up this notion, this kind of idea that they're pumping up Biden with something to make him perform.

Look, the fact is, I don't expect Biden to shy away from this if he's going to be attacked on a personal basis. One of the words you begin to hear from the campaign, and I've heard it from Joe Biden himself, talking about Donald Trump is the word loser. I would not be surprised to hear Joe Biden use that word on stage to see what the reaction is from his opponent.

COOPER: Yes. Evan Osnos, Scott Jennings, Alyssa Farah Griffin, we will be watching. It's going to be an extraordinary night.

Primary night tonight, polls closing shortly in New York, where this Democratic squad member is fighting to keep his seat in a race that's dividing the Democratic Party.

Also tonight, the classified documents case, Special Counsel Jack Smith's answer to the former president's claim that key evidence should be excluded because of how it was obtained.

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[20:22:30]

COOPER: It's primary night in four states tonight: Utah, Colorado, South Carolina and New York. Non-presidential races only, but several are getting national attention. In Colorado, Republican congresswoman Lauren Boebert is running in a different district than the one she currently represents.

And in New York City's northern suburb, Democratic congressman Jamaal Bowman is facing a challenge from a more centrist Democrat in what has become both the most expensive congressional primary ever and a fight over the party's position on the Israel-Hamas conflict. Polls closed at the top of the hour. CNN's Miguel Marquez is outside Bowman headquarters for us tonight. So what are - what's the mood there like tonight?

MIGUEL MARQUEZ, CNN SENIOR NATIONAL CORRESPONDENT: Very quiet so far, but typically on election night it is. We still have about 45 minutes to go before the polls close here. But look, I think Bowman does face an uphill battle. All the voters that we have spoken to, the real anger is not so much on his views about Israel, because even a lot of American Jews are upset by what's happening in Gaza. But it was his take. It was the way that he called it 75 years of occupation, a genocide and that he sort of apologized, but sort of didn't and I think that has taken a toll.

Four years ago, he came to power in this same district, riding the - on that wave of anger over the racial justice movement and George Floyd and everything that was happening in the - in our country at that time. Now that tide seems to have turned against him. Look, there's a lot of money in this race, $25 million, about $15 million of it AIPAC is spending through its Super PAC.

The airwaves here have been saturated with commercials that are anti- Bowman. The mailers have gone out. People are just talking about 10 or 12 of them arriving in their mailbox every day. So it has been a lot of money shoved into a very small race, Anderson?

COOPER: And what have you been hearing from voters and what's turned out been like?

MARQUEZ: Yes. And I should say that the Bowman's campaign and others are very, very upset the way this outside money has come into here. But the voters, you know, we've seen campaigns where a lot of money is spent and still it doesn't break through. Voters here are very, very upset. The ones that are most upset are the moderates, Jewish voters. About 7 percent of the district is Jewish, but a lot of voters are upset with the way that he's gone after Israel.

We were at Mount Vernon today at the city hall. That should be a very big Bowman district and a precinct. We were - from 6 AM to 6 PM, when we left to come over here, how many voters do you think voted in that precinct?

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Nineteen. That should - number should be a lot bigger and that should be very worrying for Jamaal Bowman tonight.

COOPER: Yes.

MARQUEZ: Anderson?

COOPER: Miguel Marquez, thank you so much.

A perspective now from CNN's Political Commentator Van Jones.

So if Bowman loses, what does that say?

VAN JONES, CNN POLITICAL COMMENTATOR: Well, I mean, it would suggest that, at least in that district, the tone of how you deal with the Israel-Palestine conflict is important. Look, a lot of people are concerned about what's happening in Gaza. A lot of people don't like those images, but it's how you deal with it.

And I think AIPAC has decided they want to make an example of him, so, you know, money matters. But I think also you've got to represent your own district. And you have a very big Jewish district that felt, apparently, that this was not the way they want the issue handled.

COOPER: What does this say about the, you know, sort of the dispute between the establishment's of the wing - the left wing of the party?

JONES: Well, listen ...

COOPER: Not just in this race, but sort of writ large.

JONES: Well, I mean, but part of it is this issue does split the Democratic Party because there are two values that people who Democrats hold and they're in conflict with each other. One is, you do want to defend Israel, especially from Islamic terror and that kind of stuff. You know, Hamas being a terrorist organization. You don't want terrorists killing people, especially killing children at festivals. So that's the value.

But the other value is human rights for Palestinians. You don't want unarmed civilians being killed in large numbers. And so you have a party - this is not just an easy thing. You have a party that's being split down the middle in terms of the seams of what our values are.

And so what you need in a situation like that is sober leadership. I think Biden has been trying to show that leadership, even though people on both sides are very, very upset about the side that they're on within our party.

COOPER: The money that's been spent on this race is extraordinary.

JONES: It's unbelievable. Well, listen, and that's the challenge because AIPAC has to be careful here, because on the one hand, they want to make an example out of somebody. But at the same time, you can win the battle and lose the war long-term. If you start mass manufacturing martyrs, you know, I was trying to stand up for a cause I believed in and I got gunned down by AIPAC. Then, you might win that battle. But long term, the brand of AIPAC may be this is a bullying organization. This is a vicious organization.

And then that becomes something bad for the long-term. And also, just going - picking off individual congress people doesn't necessarily move public opinion in the right direction on Israel. So the long-term public opinion war could be harmed if there are too many of these kind of heavy handed attacks.

COOPER: Interesting. Van Jones, thanks very much. We'll see what happens.

Coming up, a third day of hearings in the Mar-a-Lago documents case wrapped up a short time ago. What the judge had to say about arguments by the Trump team attempting to suppress boxes of evidence seized by the FBI. That's next.

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[20:31:53]

COOPER: A busy day of legal news for the former president. Just moments ago, he reacted to Judge Juan Merchan's lifting portions of the gag order, restricting what he can say about former trial witnesses. He'll remain barred from talking about prosecutors and the court staff here in New York, at least until his sentencing on July 11th.

Speaking on Newsmax, he said, quote, "I think partial is very unfair and now they lift just a piece of the gag order, not all of it. The gag order has to be lifted in its entirety." Also today, Judge Aileen Cannon concluded three days of oral arguments in the classified documents case, and she didn't make any rulings from the bench.

She appeared skeptical, though, of arguments by the Trump defense team that the 2022 Mar-a-Lago search warrant was overly broad. The former president's attorneys sought to suppress boxes of evidence seized by the FBI because they said that investigators should have been more specific about where in the 50 plus room property they intended to search.

Judge Cannon stood by the original warrant saying, quote, "I have a hard time seeing what more needed to be included."

Joining me now, former Trump attorney and CNN Legal Commentator Tim Parlatore, former Federal Judge Nancy Gertner, and former Federal Prosecutor and Bestselling Author, Jeffrey Toobin.

Tim, you once represented the former president in the Mar-a-Lago case. You looked through the boxes with those classified documents. Do you think the search warrant violated the former president's rights? And I'm wondering what you make of the special counsel's accusation that the former president kept boxes in a -- what he called a haphazard manner?

TIM PARLATORE, CNN LEGAL COMMENTATOR: Well, I think that, you know, to take your last point there, the fact that the boxes were, you know, stacked the way that they are, that's the way every single administration has done it going back, you know, many, many administrations.

The difference here is that when he left office because of kind of the chaotic nature of the transition, Nara, for whatever reason, chose not to get a facility to move the boxes to as they had done for every other administration. So he uses the first one where it went to his house.

So the fact that the boxes are kept like that, honestly, that's more of an indictment of the White House document handling procedures than the Trump administration itself, because every single administration has had classified documents mixed in with unclassified documents with personal effects, things like that.

So, you know, that one's not really, you know, something that's going to move the ball. However, on the flip side of it, this warrant is not something that I ever thought was overbroad in the where to search because, you know, warrants are supposed to say, you know, what to look for, where to look for it.

You're supposed to have some probable cause as to that, but somewhere in the building for pieces of paper, that makes sense to me. The part of the warrant that I always thought was a little bit overbroad was allowing them to seize other documents, things that were, you know, presidential records that were not, you know, criminal in and of themselves.

But since none of those documents are charged, it's not really something you could suppress anyway, so it's kind of irrelevant to the hearing. COOPER: Jeff, what do you think of the Trump team's strategy here?

JEFFREY TOOBIN, FORMER FEDERAL PROSECUTOR: I think it's working great. I mean, this case is on a slow boat to nowhere. I mean, this judge keeps kicking these cans down the road. These are issues that could have been resolved much simpler. There is absolutely no reason to have hold -- held this three-day hearing at all.

[20:35:01]

But Trump's lawyers, understandably, doing their job, are encouraging the judge to just delay and delay and delay and that's what she's doing. I think it's a very poor advertisement for the federal judiciary and the fact that, you know, she has not set a trial date and not resolved these motions. But Trump's lawyers have got to be very happy about how it's going.

COOPER: Judge Gertner, I mean, do you agree with Jeff? I -- and -- I mean, by the end of today's hearing, Judge Cannon seemed frustrated with both the prosecution and defense. Certainly, I'm sure the prosecution is very frustrated with her. How would you have handled these things?

NANCY GERTNER, FORMER FEDERAL JUDGE: About a year ago, I would have handled these things. But, you know, the issue that everyone keeps on raising is, is this a product of her, a, inexperience, b, competence, or, c, bias. And I heard on this program, another judge, a good friend of mine who said, but it was her inexperience.

But if you are inexperienced, the first thing you do is you actually default to precedent. So yesterday's hearing about the, you know, the motion to dismiss on the grounds that, you know, that the special counsel was wrongly appointed, the precedent was overwhelming. And what a typically inexperienced judge would do and say would follow that.

But one of the first things that you learn in baby judge school, and yes, that's what it's called, is case management, and that is set a trial date, and she has not set a trial date. And what is hanging fire out there, what has not been resolved, for example, there's a motion to dismiss on the grounds of presidential immunity. Well, these acts took place after he was president.

So, there are issues out there which he has not resolved which should have been easily resolved. And yesterday's hearing felt like an audition for Judge Cannon to seek higher office, inviting essentially the right legal scholars to challenge the special counsel when those challenges have failed over and over again for years and years and years.

So I agree with Jeff, although I have a much more complicated explanation than he did.

COOPER: Jeff?

TOOBIN: Well, I just think, you know, the point Nancy making is making about case management is exactly the problem here. And that's got to be especially frustrating to Jack Smith's team because case management is not usually something that you can appeal. It's not a -- an incorrect legal ruling, it's simply not knowing how to be a judge or intentionally not deciding cases when they should.

So the problem for Jack Smith is that he's kind of trapped with her. He can't appeal incorrect rulings, he's stuck as she delays and delays and delays and that's something that, you know, he just really can't do anything about.

COOPER: Tim, Evan Corcoran --

GERTNER: I actually --

COOPER: Sorry, Tim, Evan Corcoran, another former attorney, is a key witness for prosecutors. I'm wondering what you make of Trump's argument that prosecutors shouldn't be allowed to use evidence against from him because he has -- I mean, according prosecutors, some damaging evidence about the things the former president said to him.

PARLATORE: You know, there are parts of what he has to say that I think do fall under the crime fraud exceptions, specifically the parts where he's saying when and where he's going to search, because to the extent the prosecutors can use that to show that this informs when and where Walt went to go move boxes.

But I think that the scope of Judge Howell's order in D.C. was way too expansive as to what she ruled was within the crime fraud exception. You got to remember. So, I was there at that hearing. It was behind closed doors. And the way it worked, you know, the government filed the motion. We weren't allowed to read it, but we had to respond to it.

We went into the courthouse. Jim Trusty gave an argument when it turned over to the special counsel and make their argument. They said two things, one of which is a lie. And then they said, before we continue, we'd like the defense to leave the room. So we had to go sit in the hallway for 45 minutes to an hour, come back and then the judge looked at Jim Trusty and said, Mr. Trusty, would you like to respond?

So, I think that it is something that's certainly ripe to go through again. And I think a lot of what Evan Corcoran has that's actually quoted in the indictment, it is classic attorney-client privileged information. When you have a client that's never had a criminal grand jurisdiction and they ask you, what do I have to do? Do I have to respond to it? What happens if we don't respond to it?

And in this case, who's very specific of saying, I saw what David Kendall did for Hillary Clinton where they deleted 20,000 emails. Nothing happened to them. Are we allowed to do the same thing? Those are the kind of questions that you want clients to ask you.

And if you say, no, we can't do that --

COOPER: Yes.

PARLATORE: -- and the client says, OK, there's nothing wrong with it.

COOPER: Judge Gertner, in New York, Judge Merchan lifted portions of the gag order in the criminal case, restricting what the president can say about witnesses in the trial, just two days before the CNN debate. Just on that, do you agree with the judge's decision?

[20:40:01]

GERTNER: I think that's right. I think that when the gag order has to be -- has to dovetail with the underlying case. And before the trial, he was concerned about witnesses who were about to testify and certainly about the jury. Now that there's been a verdict and in between verdict and sentencing, he is concerned about attacks on prosecutors, no longer attacks on witnesses.

And so it made sense to narrow it. And after sentencing, it's the justification for a gag order. It disappears entirely. So I think it makes sense and shows that he's titrating this to the underlying case. And that's what he should do.

COOPER: Judge Gertner, Jeff Toobin, Tim Parlatore, thanks so much. Appreciate it.

Coming up next, how WikiLeaks founder Julian Assange found himself a free man after years of pursuit by the U.S. government.

(COMMERCIAL BREAK)

COOPER: Julian Assange is a free man tonight after pleading guilty to a conspiracy charge as part of a deal with the U.S. Justice Department.

[20:45:02]

A short time ago, on his way back to Australia, where he's from, the WikiLeaks founder touched down on U.S. territory in the Pacific Ocean for a court appearance. Assange entered a guilty plea on one count of conspiring unlawfully to obtain and disseminate U.S. classified defense-related information.

CNN's Nic Robertson has details.

(BEGIN VIDEOTAPE)

NIC ROBERTSON, CNN INTERNATIONAL DIPLOMATIC EDITOR (voice-over): On his way to apparent freedom, WikiLeaks founder Julian Assange bailed from British jail and now hours from completing a plea deal with the U.S. Department of Justice, accused of playing a role in one of the biggest security breaches in U.S. history.

Assange was essentially on the run from the day his WikiLeaks first published U.S. secrets in 2010. Initially, about the war in Iraq, including this video of a U.S. apache gunship killing Iraqi civilians and two journalists. His next release, thousands of secret documents about the Afghan war, then a massive data dump of sensitive global U.S. diplomatic communications, tens of thousands of secrets in the wind. Lives of spies potentially compromised.

DONALD TRUMP (R), PRESIDENTIAL CANDIDATE: WikiLeaks, I love WikiLeaks.

ROBERTSON (voice-over): Perhaps most consequentially while on the Lamb in London in 2016, publishing leaked emails from the Democratic National Committee and Hillary Clinton's campaign manager during her presidential election campaign against Donald Trump.

For 14 years, Assange was a fugitive, first fleeing Sweden, following a 2010 arrest warrant linked to rape allegations, which he denied, landing in the U.K., soon facing extradition back to Sweden. Eventually, jumping U.K. bail in 2012, taking asylum in the Ecuadorian embassy in London.

UNIDENTIFIED MALE: And a courageous Latin-American nation took a stand for justice.

ROBERTSON (voice-over): Ultimately wearing out his welcome, expelled seven years later, promptly arrested, taken to the U.K.'s maximum security Belmarsh prison, facing and fighting extradition to the United States.

STELLA ASSANGE, WIFE OF JULIAN ASSANGE: It's Wednesday, the 19th of June.

ROBERTSON (voice-over): His wife, who is also his lawyer and mother of his two children, who was outside his U.K. jail just a few days ago, now waiting for him in Australia.

ASSANGE: It will be the first time that I get to see him as a fully free man. All this is -- it's so alien to the way we've -- it's been until now for the past 14 years.

ROBERTSON (voice-over): His freedom, it seems, in part due to diplomacy.

ANTHONY ALBANESE, PRIME MINISTER OF AUSTRALIA: Regardless of the views that people have, Mr. Assange's activities, the case has dragged on for too long. There's nothing to be gained by his continued incarceration and we want him brought home to Australia.

ROBERTSON (voice-over): In recent weeks, Australia's Prime Minister increasingly advocating for Assange's return. The White House denying it had any involvement in the plea agreement. Ironically, Assange's get out of jail deal, a better kept secret than his historic leaks. He was on the plane heading towards home hours before the news broke.

(END VIDEOTAPE)

ROBERTSON (on-camera): But we're just beginning to get a few more details of what Assange was thinking during that whole process of the release of all that information. The judge asked them what crime he thought he'd committed and he'd already said that he was guilty of a crime and the judge was drilling down.

And Assange said that it was his job as a journalist essentially to encourage sources to provide information and push that information to the public. He said he felt that the First Amendment was contradicting the espionage act, although he accepted that would be difficult to prove in court. But that seems to be where he's landing his argument for what he did and why he did it, Anderson.

COOPER: All right, Nic Robertson, thank you.

We have more details now on this deal Assange's reach (ph). I'm joined by CNN Senior Justice Correspondent Evan Perez. So what more have you learned?

EVAN PEREZ, CNN SENIOR JUSTICE CORRESPONDENT: Well, Anderson, this is a deal that has been in the making, obviously, for more than a decade. You know, there have been discussions between Assange's lawyers and the Justice Department over the years, and always they never seem to go anywhere.

But, in the last three years, you see the Australian government, as Nic just pointed out getting more involved. And last October, for instance, Anthony Albanese, the Prime Minister of Australia brought it up directly with President Biden. You've seen certainly in the last couple of years, every time Australian officials met with U.S. officials, they brought it up.

[20:50:04]

You know, I'm told that back in April, Anderson, there was a letter that was written from Australian officials to Attorney General Merrick Garland, suggesting an outline of a possible deal. Something that looks a lot like what they ended up arriving at.

And then, of course, there was in May, where the Justice Department had one last effort to try to get the High Court in London to get him extradited to the United States. That failed, and that I believe at least from talking to sources, Anderson, was really the impetus to try to make this deal happen in the last couple of weeks.

COOPER: Was the felony charge a sticking point for U.S. officials?

PEREZ: Absolutely. And one of the things that we've heard repeatedly from Assange's side was that he didn't want to plead guilty to a felony. He wanted to -- he would agree to plead guilty to a misdemeanor. And certainly inside the Justice Department and at the FBI, they were opposed to anything that did not look like a felony.

There was also some officials who believe that he should come back to the states and actually served at least some prison time in the United States. Keep in mind, there's also the fact that he served essentially five years in British prison trying to fight that extradition, and that's about the time that you would get for this crime if you were to be found guilty.

So in the end, that's the reason why you see this deal worked out the way it did. And, of course, one of the last things that Assange insisted on, Anderson, was that he wanted to make sure that he did not come to court in the continental United States. That's why they chose that court in Saipan.

COOPER: Evan Perez, thanks so much.

Coming up next, an up close look at that $230 million pier built by the U.S. military along the Gaza coast. It's finally operational, but has been plagued by problems.

(COMMERCIAL BREAK)

[20:55:56]

COOPER: Tonight, a dire warning on the humanitarian crisis in Gaza. According to a new report from a U.N.-backed group, nearly half a million people in Gaza face starvation and there's a risk of famine. While food shipments have increased in the north, not enough is getting to those in need.

The U.S. military launched a temporary pier along the coast in mid- May. It's now back in place after being taken out of commission because of rough seas. For the first time, CNN's Jeremy Diamond got an up close look at the pier.

(BEGIN VIDEOTAPE)

UNIDENTIFIED MALE: We do that. You'll see with a lot of different bridging systems here.

JEREMY DIAMOND, CNN CORRESPONDENT (voice-over): From ship to pier, aid trucks are rolling into Gaza, interlocking steel platforms roar with each passing wave. But after weeks of mishaps, the U.S. military's $230 million pier off the coast of Gaza is finally operational. But this aid isn't actually feeding anyone in Gaza, at least not yet.

DIAMOND: We're currently aboard the U.S. military floating pier off the Gaza coastline. Yesterday, the military says they were able to get about 800 pallets of aid off of this pier and into Gaza. But the problem now is the World Food Program, which is supposed to be picking up that aid, they say the security conditions just aren't there for them to be able to pick up that aid and distribute it to the people of Gaza.

DIAMOND (voice-over): These are some of the now more than 6,000 pallets of humanitarian aid the U.S. military says are sitting in an open air warehouse across from the pier. The World Food Program paused its operations at the pier more than two weeks ago, citing safety concerns.

Across Gaza, humanitarian aid groups say Israeli military operations and a rise in lawlessness and looting are bringing their aid operations to a crawl. And it couldn't come at a worse time. As experts say, people in Gaza are once again at high risk of famine.

The U.S. military invited CNN to the pier for the first time to show how it is ramping up the flow of aid to Gaza, and how it is getting this beleaguered project back on track after rough weather damaged and took the pier out of service for weeks. CAPTAIN JOEL STEWART, U.S. NAVY: The sea is a difficult task mistress, unpredictable. Each wave is different than the last. So dealing with that is a challenge, but we've adapted to that. And I think we're in a better position now than we were initially.

DIAMOND (voice-over): About 40 truckloads are now arriving at the pier each day. Still well short of the military's initial estimates of 90 to 150. A complex effort aid officials say would have been best spent pressuring Israel to get more aid in by land.

STEWART: This was never meant to be a long-term solution to the problem. This was meant to be one more way until we could find ways to open those gates up, to get that pressure to open the gates.

DIAMOND (voice-over): Access to the U.S. pier also provided a rare vantage of the destruction to Gaza's coast.

DIAMOND: It really is remarkable to see the Gaza coastline up close like this after nearly nine months of war. All we can see along this shoreline are buildings that are either completely flattened, completely destroyed or those that are simply shells of themselves.

DIAMOND (voice-over): It is also the daily backdrop for U.S. soldiers like Sergeant Ibrahim Barry, a practicing Muslim who started working on the pier operation in March, during the holy Muslim month of Ramadan.

SGT. IBRAHIM BARRY, U.S. ARMY: Knowing that they're going through these harsh conditions and still fasting, still holding on to their faith and getting the little bit that they can, that's what -- it was another motivation right there.

(END VIDEOTAPE)

DIAMOND (on-camera): And look, Anderson, people like Sergeant Barry have done their part. They've gotten the aid off of these ships onto the pier and then onto the Gaza coast. Now, the question is, what are leaders in the United States, in Israel, in Gaza going to do to improve the conditions on the ground for the distribution of this aid so that groups like the World Food Program can go to this pier and pick up the aid and start distributing it to those in need?

And tonight, the United Nations is saying that it is raising concerns with the Israelis about a security coordination at those land routes as well, with the top U.N. spokesman warning that the risks, frankly, he says, are becoming increasingly intolerable on the ground. Anderson?

COOPER: Jeremy Diamond, thank you very much.

That's it for us. The news continues. The Source with Kaitlan Collins starts now. See you tomorrow.