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CNN's The Arena with Kasie Hunt

John Bolton Indicted By Federal Grand Jury. Aired 4-5p ET

Aired October 16, 2025 - 16:00   ET

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


BRIANNA KEILAR, CNN HOST: -- and Smucker's doesn't just want payback.

[16:00:03]

Check this: it wants Trader Joe's to ship all of its remaining product to Smucker's to be destroyed.

BORIS SANCHEZ, CNN HOST: That sounds like a huge waste of some delicious PB&J's.

KEILAR: I love a good PB&J.

SANCHEZ: Yeah, why don't they just --

KEILAR: I make them every day for kids.

SANCHEZ: Donate them to us. Do you take the crust off? Is that what they prefer?

KEILAR: Either way, crust, uncrustables, either way.

SANCHEZ: Either way, THE ARENA WITH KASIE HUNT starts right now.

(MUSIC)

KASIE HUNT, CNN HOST: Hi, everyone. I'm Kasie Hunt. Welcome to THE ARENA. It's wonderful to have you with us on this Thursday.

As we come on the air, federal charges against John Bolton could be handed down imminently. Multiple sources telling CNN that today, the Justice Department is expected to ask a grand jury to indict the former national security advisor and U.N. ambassador.

The lead prosecutor in this case, seen entering a federal courthouse in Maryland this afternoon. Remember, it was just one week ago that a grand jury indicted New York Attorney General Letitia James and that former FBI Director James Ccomey pleaded not guilty to federal charges of his own.

And so, once again, this raises the question, are we seeing justice? Or is this the latest stop on Donald Trump's vengeance tour?

(BEGIN VIDEO CLIP)

DONALD TRUMP, PRESIDENT OF THE UNITED STATES: Did a very bad thing. It's really treasonous. Okay? What he did. I think most importantly, look about -- look at the classified information.

He released massive amounts of classified and confidential, but classified information. That's illegal. And you go to jail for that. And he should have known that. You go to jail for that.

(END VIDEO CLIP)

HUNT: So those comments there were made more than five years ago. That was when President Trump accused Bolton of leaking classified information in his White House memoir, "The Room Where It Happened". Sources say the current investigation centers around Bolton's time in the first Trump administration, and the notes that he made for himself using his AOL email account.

Bolton could be far from the last of the president's perceived enemies, of course, to find themselves investigated by the Justice Department. Here was President Trump yesterday. He was at an event alongside both the attorney general and his FBI director.

(BEGIN VIDEO CLIP)

TRUMP: Deranged Jack Smith, in my opinion, is a criminal. And I noticed his interviewer was I think that was Weissmann. And I hope they're going to look into Weissmann, too. Weissmann is a bad guy, and he had somebody in Lisa who was his puppet, worked in the office, really as the top person.

I hope they're looking at shifty Schiff. I hope they're looking at all these people, and I'm allowed to find out. I'm allowed -- you know, I'm, in theory, the chief law enforcement officer.

(END VIDEO CLIP)

HUNT: Former special counsel Jack Smith, the former Mueller investigation prosecutor Andrew Weissmann, the former Deputy Attorney General Lisa Monaco, and, of course, Senator Adam Sschiff, who was a former Trump impeachment manager. Right now, all four of them might be asking themselves whether they'll be next to be indicted by a Justice Department that does seem to be taking orders openly and directly from President Trump.

After all, less than a month ago, John Bolton was contemplating that same question.

(BEGIN VIDEO CLIP)

KATE BOLDUAN, CNN ANCHOR: Do you believe that you will be charged?

JOHN BOLTON, FORMER TRUMP NATIONAL SECURITY ADVISER: Well, I'd love to discuss the subject, but unfortunately, it's really not appropriate. Now, I'll just say that when the paperback edition of my book came out in January of 2024, I wrote then that I thought a second Trump term would be a retribution presidency, and that's at least one prediction, unfortunately, for the country as a whole, I think I got right.

(END VIDEO CLIP)

HUNT: All right, let's get off the sidelines, head into THE ARENA. My panel is here.

We're also joined by CNN crime and justice correspondent Katelyn Polantz.

And, Katelyn, you have brand new reporting on all of this that we expect potentially to break throughout this hour. What are you learning?

KATELYN POLANTZ, CNN CRIME AND JUSTICE CORRESPONDENT: Kasie, the grand jury is done for the day. We know that now because our own reporter, Kevin Cole, is at the courthouse in Maryland, and they are done for the day. The lead prosecutor on the Bolton case has also exited the courtroom, and we're waiting to see if they had approved an indictment and if there would be an indictment that we learn of today against John Bolton, the former national security advisor.

We're also learning a little bit more about what has been investigated here. There are lots of cases that you just talked about, a lot of different people that Donald Trump really doesn't like, and that he would like to see investigated. This one, it's gone on for quite some time. And Trump was unhappy with that book that John Bolton wrote. And there was a tussle over what should be in that book, what was classified, what was not. Whenever Bolton was preparing the manuscript for it, that may be part of this case, because it was part of the reasoning for the searches of his home and office two months ago.

But actually, it's more about his AOL account and what Bolton was writing in that account at the time, he was the national security advisor in Trump's first term in office. Not only do we know that he was writing notes or even diary like summaries to himself, we also know from our team of reporters working on this. Sources are telling us that he was sharing highly classified information with both his wife and his daughter over email, as well.

Now we do wait to see that if he is indicted, exactly what sort of information or documents might have he -- might he have been sharing? What charges would he be? He be expected to be facing now and then? Of course, what sort of defenses would Bolton want to say here? Were these journals where these the sorts of things that he believes was not classified at that time?

A lot going forward that we still don't know at this time, including whether or not Bolton has been indicted. But we are nearing the end of a day in court, and the grand jury is done -- Kasie.

HUNT: All right. Katelyn Polantz, you're going to hang out with us as we anticipate we may get some new reporting in on this. So, stand by.

Our panel is also here. Republican strategist and pollster Kristen Soltis Anderson, CNN senior political analyst Ron Brownstein is here. Congressman from Ohio, Greg Landsman, CNN senior political commentator Scott Jennings, and former Trump attorney Bill Brennan. And if that's not enough for you, on the left side of the screen,

we're joined by our ARENA text chain. Additional analysis from some of our top reporters in legal contributors. If you're watching on mute, that one's for you.

Bill Brennan, let me start with you. Just on the legal aspects here. We obviously walked through and the president has been very open about his intentions. There has since been reporting that that Truth Social, where he named names, was supposed to be a private message, but it was public. It's out there -- it's out there, right?

I'm interested to know if you see a difference or distinction between what we've seen with Jim Comey and Letitia James, both of whom who have been out there saying these are politically motivated. There were questions about the attorneys that were in the office where these indictments came from. There was reporting that there were concerns about those. And then what we're seeing here with John Bolton and this classified information, how do you see it?

WILLIAM J. BRENNAN, CRIMINAL DEFENSE ATTORNEY: Well, Kasie, again, thanks for having me. And I absolutely see a huge distinction in this Bolton investigation vis a vis the others that you mentioned. And here are a couple of the differences. This -- if the reporting that's been out there is accurate, this Bolton investigation has been going on for years.

The prosecutor in Maryland, I believe, was a Biden appointee. So, it's not -- it's not -- there can't be any argument made that the president put somebody in there to do his bidding. And the charges are much different from what we've seen with General James and Director Comey.

If, in fact and, of course, at this point in time, Mr. Bolton has not been indicted. And even if he is indicted, he's presumed innocent. Having said that, if in fact, what's being reported is the subject of an indictment and is proven in court, I mean, it would be that the man who came out of national security used AOL -- you know, that old- fashioned you've got mail -- to share with or record notes of highly sensitive, classified information.

I mean, it puts the country at danger. There's rumors that some foreign nation, presumably with adversarial interest to our own, hacked his account. I mean, if he if he did this and there's no indication that he did at this point. But if he did, he should be indicted for stupidity, if nothing else.

HUNT: So, speaking of what John Bolton may or may not have known about how to handle this kind of information, there were several, comments that Bolton made in public that were cited by federal authorities when they wanted to search his house, the warrant application, one of the ones or a couple of those comments that we've put together, we can play them for you. This is what Bolton has said in the past about classified information and how to take care of it.

(BEGIN VIDEO CLIP)

BOLTON: If you're conscious of the need to protect classified information, you remember what the rules are.

If I had done at the State Department what Hillary Clinton did, I'd be wearing an orange jumpsuit now.

You simply don't use commercial means of communication, whether it's supposedly an encrypted app or not, for -- for these kinds of discussions.

(END VIDEO CLIP)

HUNT: So, Scott Jennings, I think he was likely referencing a signal, which is which is an encrypted app. But if he is using AOL, a commercial service, he's doing exactly what he says you shouldn't do.

[16:10:02]

SCOTT JENNINGS, CNN SENIOR POLITICAL COMMENTATOR: Yeah. I mean, he's been around a very long time.

HUNT: And AOL address indicates that he's been around a very long time.

JENNINGS: Yes. And he's an attorney and has held all these positions. And so, he full well knows what the rules are.

And so, I'm like everybody else, I presume him to be innocent. I want to see what the evidence is. Based on the reporting, there were lots of documents in his house that had classified markings on them. Based on the reporting, this email account could be problematic.

And I think something that was said earlier is vital to know this has been going on for years. I think this investigation started during the Biden administration. And so here you have an investigation spanning administrations of both political parties. I think that should tell you how seriously the Department of Justice takes this. And when we're dealing with national security information, they ought to take it seriously. And he's obviously been in contact with a lot of it in his career.

HUNT: I do want to underscore what we at CNN seem to know and not know. There is some ambiguity about the length of this investigation. When it started, there was one that that started under Donald Trump. The Biden administration seems to have dropped that. But then this has clearly been ongoing for some time.

Congressman, how do you see it as a Democrat at the table? I mean, obviously Democrats nationally have been raising a lot of questions, have a lot of criticism for how the presidents been using the justice system. Do you think this Bolton case belongs in the same bucket with some of those other situations?

REP. GREG LANDSMAN (D-OH): Yeah, I don't know. Because there's a lot about the case that we don't know, but it does seem as if the president spends a lot of time on political retribution. He's got this enemies list or people he doesn't like. He's calling them out. He's tweeting them at his attorney general. It's just not what I remember presidents doing. Presidents spend time

on the economy, on public safety, on running a government, national security. He spends a lot of time on this, and I don't think Americans, generally speaking, like political retribution, period.

HUNT: Ron, what do you see?

RON BROWNSTEIN, CNN SENIOR POLITICAL ANALYST: Well, first of all, I mean, I think, focusing on the merits of this case really you have to willfully miss the forest for the trees. I mean, because what we are watching is unprecedented. I mean, the president was standing up in public expressing thoughts to the Justice Department that Richard Nixon only mused about in his darkest hours in the White House.

You can listen to the White House tapes. You can bring in our colleague John Dean. He will tell you that Nixon expressed similar thoughts in private, usually after a few, you know, bourbons or something, but that they were ignored by the Justice Department.

He told the IRS to investigate political enemies, and the IRS commissioner, George Schultz, told the IRS commissioner put, put, put the enemies list in a safe and don't take it out.

And now we are seeing Trump openly make demands that that that is, you know, unquestionably weaponizing the Justice Department, whatever the merits of the individual case, the fact that these people are the ones that are being targeted tells you something. And I -- you know, this fundamentally is not a world that either side should want to live in, unless you believe power is never going to change hands again, which is an ominous thought in itself, because once you establish the idea that the president can feel comfortable going out in public saying, hey, why don't you indict so and so and so and so and so and so, you know, for a Democratic president, there could be a very different list of targets who are now remaining silent, but would be very uncomfortable living in that world.

And it's just astonishing to me that there is not more resistance to this on the Republican side, on the awareness that what goes around comes around.

HUNT: Kristen Soltis Anderson, the congressman mentioned this idea about what Americans want the president to be focused on. I mean, what is your day to say? I mean, do they want him to be focusing on this or other things?

KRISTEN SOLTIS ANDERSON, CNN POLITICAL COMMENTATOR: Well, I think, you know, people knew that Donald Trump could -- was very likely to go down this road when he was elected. But that doesn't answer the question. Did they vote for him because of that, or did they vote for him in spite of that?

I've seen a lot of data and Pew Research Center has a survey where they found four in 10 Republicans do think that Donald Trump has been inappropriately going after his political opponents, legally. They like other things that he's doing a great deal. But maybe this doesn't do it for them. But there are other people in Trump's base who feel very strongly that Donald Trump was wronged in the Mar-a-Lago documents case.

And again, think about the clips that you showed at the beginning. This has gone all the way back to Hillary Clinton's emails. It really does feel like none of our senior government officials are terribly good about protecting important classified --

(CROSSTALK)

HUNT: Well, Joe Biden, Mike Pence, Donald Trump -- I mean, right, there have been boxes, you know, places searched across the board and across.

ANDERSON: Yeah.

BROWNSTEIN: But, of course, we're dealing with cases that go way beyond, you know, document handling. And, you know, I mean, the political vulnerability here may be the inverse, as some have argued to me, that what we're watching is the inverse of the Kamala is for they/them, Donald Trump is for you, because that -- that argument landed so powerfully, not only because of the specific issue of transgender sex change operations in prison, but the idea that Democrats were focused on esoteric issues and not on the core concerns of average Americans, to your point.

[16:15:05]

And I think, you know, Trump is at risk of that because people are not seeing a lot of progress on inflation. His approval rating on the economy is lower than it ever was in his first term. And he gives the impression that his energy and fervor and, you know, passion is on these other problems going after his enemies more than finding a way to reduce like what can he point to today, Scott, that would give a voter who voted for him because they thought Biden had let costs get out of control. What can he point to today where he is kind of like has his sleeves rolled up and he's working to make their life more affordable as opposed to kind of focusing on going through his checklist of people he wants to get even with?

JENNINGS: Well, just this summer, the big, beautiful bill froze and made permanent the tax cuts that he passed in the first term. That's number one.

Inflation rates, it's just not accurate to say hasn't made any progress on that. Inflation rates today are much, much lower than they were under Biden.

But on the world but on the world stage --

BROWNSTEIN: Yeah.

JENNINGS: -- just this week he went out and did something that I don't think anybody else could have done. He made the world a safer place.

And so, I just fundamentally disagree with you. I think people see an active presidency. I think they see him working on a bunch of different issues at once. The border is closed, energy is flowing.

I mean, a lot of things that he ran on, the promises that he made, he's checking them off one by one. And I think most Republicans are more than happy with the results. The people who voted for him, I think are very happy with the results of it.

BROWNSTEIN: I think the big I think its true. He has made a lot of progress on areas of, you know, of his priority, the one where he is not is that people do not feel their cost of living is getting more affordable. That was the core promise that got him elected, and I think that he does face the risk that he seems to have taken his eye off that ball.

JENNINGS: I just think that the merits of the -- you said we shouldn't focus on the merits of these cases, the merits of the cases are all that matter inside of a grand jury. They -- grand jurors look at evidence, the merits of each individual case must be examined. This one especially, I mean, if it goes back, as long as we think.

BROWNSTEIN: There's a lot of difference in grand juries.

HUNT: Bill Brennan, I feel like I see your lips moving on my on my monitor over here. Were you trying to get in? You want a quick last word?

BRENNAN: The congressman, the congressman -- and look, raises a lot of great issues, a lot of deflection. I thought we were here to talk about Bolton.

The issue with ambassador Bolton is whether or not a high government official who comes out of the national security, you know, column, it's not like he was running a EPA who has made public statements that if you do something like this, you should be in an orange jumpsuit. If in fact, he did these things, it's a problem.

And it's a -- you can't blame President Trump for this one because the U.S. attorney supervising it, I believe, is the President Biden appointee. And I think the line prosecutor, I think it's Sullivan, I'm not sure, is a seasoned professional in the national security unit. So, I mean, this is a long-term fight, four or five-year investigation that spans several administrations. And this is one particular investigation you can't pin on Donald Trump's enemies list, so to speak.

HUNT: All right. Stand by for me, Bill. The rest of the panel is going to stand by as well, as we potentially wait for breaking news.

We want to say thank you to our arena text chain. A couple of them will be back later in the hour.

Coming up next, here in THE ARENA, Democratic Senator Elissa Slotkin will be here live charm for funding the government. And tensions are reaching a boiling point on Capitol Hill. The government shutdown will now officially go into next week after another failed vote today in the Senate.

(BEGIN VIDEO CLIP)

REP. MIKE JOHNSON (R-LA), SPEAKER OF THE HOUSE: I don't like being mad Mike. I want -- I want to be happy Mike. I want to be the happy warrior. But I am so upset about this.

God bless America. We're done. Thanks.

(END VIDEO CLIP)

(COMMERCIAL BREAK)

[16:23:15]

HUNT: All right. Welcome back to THE ARENA.

We are following this breaking news that John Bolton allegedly shared highly classified information with his wife and daughter over email while he was serving as President Trump's national security advisor. This, according to CNNs sources. Those revelations coming as we wait to hear whether or not a grand jury in Maryland has indicted Bolton for his alleged mishandling of classified documents.

In THE ARENA now to discuss is Democratic senator from Michigan, Elissa Slotkin. She's a former CIA analyst and sits on the Senate Armed Services Committee, among others.

Senator, thanks very much for being back here in THE ARENA.

And I do want to ask you about this. Obviously, these are allegations that we are reporting. They come in the context of other figures in President Trump's orbit who have been indicted when he has explicitly said that his Justice Department should take them on.

My question to you is, do you think if John Bolton is indicted, it's part of President Trump's vengeance tour, or is it something else?

SEN. ELISSA SLOTKIN (D-MI): Well, I think it depends. I mean, if they find him guilty, if he's actually committed a crime, if a judge using a legal standard, said that he did something wrong, I mean, that's -- I would take that very seriously.

But I think it just really depends on whether these charges are thrown out, whether there's more action. I think it's hard to notice that there's been prosecutions by the Department of Justice of people that the president has been very open, that he does not like. But again, it should be that there's a legal standard for everyone, whether you're a friend or an enemy of the president. And hopefully, we'll learn more when the announcement comes out.

HUNT: What would the risk be? I mean, you are obviously a former CIA analyst.

[16:25:01]

You've got a lot of experience handling classified information yourself. If a national security official were putting classified notes, diary like entries, sending information to his family members on an AOL account as alleged, is that a national security risk?

SLOTKIN: Well, yeah. I mean, we all swear an oath to protect, you know, the data that we have access to when we get read in on classified subjects. I mean, and most of us who are in this business have a top secret clearance.

So you go through a whole training on how you handle that information. And it's an absolute, you know, black and white issue. You do not share it with people who don't have security clearances. So again, I haven't seen anything related to Mr. Bolton. I don't know, in this case, you know, at all any of the details.

But if you put classified information on an unclassified system and then you share it with a bunch of people who don't have access, who are not cleared, you've got two problems. So, again, we'll wait to see what the facts are.

This was similar to the Signalgate issue when the, you know you know, secretary of defense and a bunch of others were putting sensitive operational information on an unclassified system and then looped in a journalist who doesn't have a security clearance. That's a problem that should be handled appropriately. Wasn't really accountability on that score. But, you know, I think we're going to have to wait and see what the facts actually lead to in this case.

HUNT: Fair enough. Let me ask you about the government shutdown, which, of course, is continuing into next week. Now with, the 10th vote failing lawmakers heading out of town.

I want to play what Senator Thune said this morning about the offer he says he's extended to Democrats, as well as the Democratic Leader Chuck Schumer's response to that. Let's take a look.

(BEGIN VIDEO CLIP)

SEN. JOHN THUNE (R-SD), MAJORITY LEADER: I told him, I said, and I've said we are willing to have the conversation. I've said, if you need a vote, we can -- we can guarantee you get a vote by a date certain at some point, Democrats have to take yes for an answer.

SEN. CHUCK SCHUMER (D-NY), MINORITY LEADER: We're not negotiating in public, plain and simple. And Leader Thune has not come to me with any proposal at this point.

(END VIDEO CLIP)

HUNT: Are you aware of -- you know, it seems like there are two versions of the truth going on here. But if Senator Thune did make that offer and say, we'll guarantee you a vote, should Democrats take it?

SLOTKIN: Well, I'm certainly willing to sit down and talk about it. I mean, I -- you know, I'm going to start with the issue of health care, period. But I'm certainly willing to entertain an option like that. But adults just get in the room and talk about it, right? And I think, you know, in this case, Senator Thune, we were literally 20 feet away from each other on the Senate floor about an hour and a half ago. If there was a deal to offer, if there was a negotiation to be had. I mean, it's not hard to find us, and especially those of us who are ready to have a conversation, who know that a government shutdown is bad and we want to end this.

But you can't negotiate it through the press. You can't talk in the hallways and say you've made an offer when all you've done is look at a camera and said, you know, this is what I'm thinking about.

Come to us like adults, like we teach our kids to do. You get in a room, you throw out the media, no offense. And you have a real conversation.

And it's not hard. And I get that. Democrats are not going to win everything, right? I'm a realist. The Democrats don't have the House, the Senate, the White House. So I'm a big girl. I'm not going to, you know, expect to win every battle.

But I'm going to start with health care because we're in a health care crisis, because everyone I know is getting letters saying that their prices are going precipitously up by January 1st because of their bill that they passed on July 4th. And so that's where I'm going to start.

And, and we've had the 10th vote today, same vote, same numbers. Nothing's changed. So, you know, doing the same thing over and over again and expecting a different result is, you know, sort of the definition of crazy, as they say, let's just have a conversation. We can solve this in 72 hours.

HUNT: If this shutdown extends past November first, which is the deadline Democrats have set up as saying, okay, this is when open enrollment starts. If we don't do this by November 1st, it's a problem for people. If we pass the November 1st mark and it seems like were potentially on track to do that, should you just reopen the government at that point?

SLOTKIN: I mean, look, the president is already spending on things he wants, not spending on other things that, you know, where he's trying to punish blue states or whatever. He's already acting in a way that doesn't -- it certainly doesn't build trust.

So, in my mind, again, if you already have people willing to talk about health care, let's have the conversation. This isn't rocket science, but I do think what you're seeing on the Democratic side is a pretty stiff spine that in the face of a health care crisis where were getting letters and calls and emails into our office, I'm not going to just roll over and play dead. No.

HUNT: Would you from a policy perspective here?

[16:30:01]

And again, I do go back to Democrats in the past have said, don't shut down the government over policy points. But since we are talking about health care, this this question seems to be a one-year extension of the subsidies in Obamacare. That is something that some moderate Republicans have proposed doing.

Do you think Democratic leaders should seriously consider that? Because some progressive Democrats have said that's a nonstarter?

SLOTKIN: You know, I think, again, I think that's a good starting place. But I don't know that that's where we end up. I think for me, I want to -- I would like to see a much longer extension, not just one year.

So we're back in the middle of an election cycle next year, having the same exact conversation that we're having today. I would rather see it go much further out. But again, these are the things that we can get in a room and negotiate.

So, you know, I don't -- I don't think it's healthy for anyone to be sort of putting out in the press, well, I'm going to do this or I'm going to do that. I won't do this. I won't do that.

Everyone watching has had to go to work and sit in a room and negotiate with people they don't agree with, and come up with a compromise. So let's do that and we can figure out the details.

HUNT: All right. Senator Elissa Slotkin of Michigan, thanks very much for being here. Always great to have you.

SLOTKIN: You bet. Thank you.

HUNT: All right. Coming up next here in THE ARENA, what we know about a take two for Donald Trump and Vladimir Putin. But first, a pair of critical debates now just hours away, Zohran Mamdani and Andrew Cuomo will face off in New York and candidates for a job in another state head to the stage for the first time since text messages from one of those candidates upended that race.

(BEGIN VIDEO CLIP)

REP. HAKEEM JEFFRIES (D-NY), MINORITY LEADER: The attorney general candidate has appropriately apologized for his remarks, and I know his remarks have been condemned across the board.

(END VIDEO CLIP)

(COMMERCIAL BREAK)

HUNT: All right. We have breaking news right here on CNN from our Katelyn Polantz who has been reporting on the possible indictment of John Bolton, the former national security advisor for President Trump and his first term.

Katelyn, what do we know?

POLANTZ: Kasie, John Bolton, the former national security advisor, to Donald Trump, a long-time federal government official, has been indicted by a grand jury. We are learning that through two different sources from our producer, Hannah Rabinowitz, at the Justice Department.

And we have confirmed that the grand jury was in today with the lead prosecutor on that case. The same prosecutor who had been on some of the documents of the search of Bolton's house just two months ago, or not even two months ago. A prosecutor who also has some experience in investigating these sorts of things. He was a prosecutor that was also working on the Biden classified documents handling investigation that led to no charges.

But in this situation, the bulk of this case, it's been going on for several years. And our understanding is that it's about John Bolton's use of an email account with AOL, an email account where he was writing diary like notes and summaries of his time as national security advisor to himself, at times even sending them to his wife and daughter.

And that is the sort of thing that the Justice Department does say frequently, not just in the climate of a Trump administration, that that's something that you should not do. We have seen many charges like this before of other high-ranking officials, and that also with John Bolton in those search warrants and what were very likely to see in court going forward is that the Justice Department saying he should have known better -- Kasie.

HUNT: Katelyn, can you take us through here, the timeline of investigations into John Bolton and just what we know and don't know about the administrations under which they were started?

[16:35:11]

Because there was a probe into his book that started under the first Trump administration that the Biden administration later dropped. Can you just walk us through what we know, what we don't know about whether these two things are related?

POLANTZ: Yeah, Kasie, I think as far as thinking about this, in which administration did it start? It's not about that. Its more about when there was information coming into investigators that led them to want to investigate the possible criminality here that would lead to an indictment today.

I'm still waiting to see exactly what the indictment says about what type of documents they would be that would be mishandled. What is in there about timing of an investigation or even timing of when these original acts would have taken place and the federal government learned about them. But, Kasie, the arc of this investigation, there were two things that happened. Both of those things became part of the search warrant.

One, John Bolton was writing his book, and when he was working on the manuscript, was in touch with federal officials to clear everything, to take things out of that book that might be classified. He worked with them for some time and then got into a tiff, essentially with the Justice Department and the Trump administration.

They didn't want him to publish it. He wanted to publish it. It did go to publish. And that was something Donald Trump wanted him investigated about. That's one aspect.

But this AOL account, that's another thing that has had a long history of being investigated, both by people in the Biden administration, career prosecutors, as well as career prosecutors.

Still, in the district of Maryland in this administration. And the arc of that investigation, it came to the Justice Department because John Bolton, his email was hacked by a foreign government. And during the intelligence collection around that, as far as we know from our sources, it became clear to the American federal government that there might be stuff in his email account that probably shouldn't have been kept in an unsecured way.

HUNT: Well, and the hack by a foreign government of his commercial email account would sort of underscore the point that you're making there.

Okay, so our Kristen Holmes, senior White House correspondent, just asked President Trump or was in an event with President Trump where he was asked about this indictment. Let's watch that.

(BEGIN VIDEO CLIP)

TRUMP: -- know that. You tell me for the first time, but I think he's a bad person. I think he's a bad guy. Yeah, he's a bad guy. It's too bad. But it's the way it goes.

(CROSSTALK)

REPORTER: -- the case against him?

TRUMP: That's the way it goes, right? That's the way it goes. Well, I, what?

REPORTER: Have you reviewed the case against him?

TRUMP: No, I haven't, I haven't, but I just think he's a bad person.

(END VIDEO CLIP)

HUNT: That is the voice of our Kristen Holmes there.

Katelyn, he sort of handled that a little bit differently than he sometimes talks about some of these other cases. But, of course, underscores his personal feelings about his former national security advisor.

POLANTZ: Yeah, Trump has for some time said that he wanted to see Bolton face consequences, especially for that book. It was very damaging for Trump at the time, and he even went to court to try and stop Bolton from publishing, and was not able to do so.

But in recent months, Trump has been pretty reticent about speaking about Bolton. He said publicly he wanted others to be charged. Adam Schiff, who has not been charged with any crime, James Comey who has. Letitia James, who also has. Bolton has not really been at the forefront of the people on Trump's list lately. One thing I do want to add, though, we are now hearing from both Hannah covering the Justice Department, Hannah Rabinowitz and our own Evan Perez, that Bolton is expected to self-surrender as soon as tomorrow in federal court in Greenbelt, Maryland.

So, it's not going to be a long time until we start seeing more of the meat of what this case may be. And the court proceedings get off to a start very quickly -- Kasie.

HUNT: Very interesting.

All right, Katelyn, stand by for us. I know you're going to have more information coming in, both from you and, of course, our great Justice Department team.

Our panel's here. We also still have Elliot Williams, legal analyst, and Bill Brennan with us as well.

And, Elliot Williams, let me start with you here. We've been -- you were in our text chain earlier talking about John Bolton's AOL account. This, of course, seems to be the central piece of the indictment here. And as Katelyn just walked through this, apparently came to light amid a hack of a from a foreign adversary, an intelligence investigation into that.

What would you underscore here as, of course, we consider this in the context that we're all living in here of the second Trump administration?

ELLIOT WILLIAMS, CNN LEGAL ANALYST: Yeah. Certainly. And, you know, Scott made the point a little bit earlier. Everybody is innocent until proven guilty. That's how it works. Someone is charged with a crime.

I will say. And Berit Berger, again, I went to law school with and we were chatting about this earlier in the text thread. We were talking about this very point. I cannot say, Kasie, how many warnings you get as a young Justice Department attorney about the handling of classified information.

[16:40:04]

And that includes don't email things to yourself. Don't take your notes out of the room. Do not write on classified or sensitive documents, because every time you alter or manipulate a document, you could be exposing yourself to trouble.

Do not show things to other people. Do not share things with other people. You can only look at certain things in certain rooms.

And more than anybody else -- again, John Bolton innocent until proven guilty. But if there's any human being who ought to know better about sharing information, it's him.

Now again, it remains to be seen how much information the administration has about him, and more to the point, and we said this in the text exchange to, you know, even if he is guilty, you know, the extent to which Trump, the president has been speaking about John Bolton's guilt could jeopardize the integrity of the investigation. The more you talk about the president talks about wanting people to be locked up and wanting his opponents to be locked up. The more he sort of casts a little bit of a cloud over the seriousness of the prospect -- of the prosecution.

But again, we get so many warnings about the use of classified information that every time someone screws it up, you just sort of have to scratch your head about the stupidity that goes into mishandling information like this.

HUNT: Right. Well, and -- I mean, Bill Brennan to that point, this is someone and we know from the search warrant that came down for his home that his comments that he had made in public about others who were accused of mishandling classified information or using a commercial app to communicate in the case of the Signalgate issue, that John Bolton was well aware of, what Elliot Williams underscored here, how you should handle this information.

BRENNAN: Elliot makes an excellent point, Kasie. The training is just so -- people are inundated with these warnings. Don't share. Don't email.

And if he came out of maybe HHS or EPA, he could possibly raise some defense that I didn't know, but he was the national security department. I mean, ignorance of the law, which doesn't work anyway half the time, is going to be no excuse in this case.

And I'm going to steal a word from Elliot. Its either his stupidity, and he is not a stupid man, so it's probably his arrogance that led to this. If, in fact, he did it.

I can't say enough, the fact that he's indicted does not mean anything. He's presumed innocent, but it doesn't look good. This is a five-year investigation, and warrants were authorized by federal judges for his residence and his office. And the prosecutors handling this are Bi -- the U.S. attorneys that President Biden appointee with a long history in the Department of Justice and the line prosecutor is from the National Security division, who worked on other cases of a similar nature.

And, you know, the type of allegation here, Kasie, is troubling because there's that iconic photograph of allegedly classified documents behind President Biden's 1967 Corvette in a garage for someone to get to them, you'd have to break into President Biden's garage, move his old Corvette, if it starts, and maybe get these documents.

In this case, it's on AOL, which anybody can hack. And apparently a foreign government did. And it puts this nation at risk if, in fact, he did this. And how is he going to look at a jury and say, I didn't know. This is the guy who's telling people not to do this, who made remarks about Secretary Clinton. If I did what they say she did, I'd be in an orange jumpsuit. He may get his wish. HUNT: I will say, let's not impinge -- you know, Corvettes are

awesome cars, okay? And old ones run very well. But I take your point about physical versus digital data.

I want to bring the conversation back to the panel.

BRENNAN: Yes.

HUNT: Congressman Landsman, when you think about this and I mean, you've probably encountered classified information in the job that you have. I mean, how do you think about it?

LANDSMAN: I mean, you don't mess around with classified information. So obviously, if and, you know, folks are right, this is training that he's gotten more so than even me as a member of Congress. Like, you know, if in fact, this is true, it's a huge problem.

I will say we don't know. And I think everyone has agreed. We don't know. And everyone is presumed --

HUNT: Innocent until proven guilty.

LANDSMAN: So my issue here is that as I listen to this and I've been watching, you know, this over the course of several months where you have these stories of people getting indicted or, you know, lists and folks you know that are being talked about or being referred for prosecution. It's like -- it's all like political insiders, and it just feels like a bunch of politicians going after each other.

[16:45:05]

I just think about the people back home in southwest Ohio. I think that's how they see it, which is like, yeah, sure. Classified information. I'm not making a, you know, a comment about that.

I'm just -- the larger issue of these political insiders going after each other. It seems like it's never ending. And it takes away the focus on them.

HUNT: Yeah.

Scott?

JENNINGS: I can't add much more than what's been said by the lawyers, but I do have a question to them, and it' s what --

HUNT: Yeah, go for it.

JENNINGS: -- I'm thinking about. And that is this. If I know you don't know everything, but if you were in the shoes of the defense lawyer for Bolton, would you be thinking right now how to plead guilty to lesser charges? Or would you be thinking right now that, hey, maybe my clients public jostling with Trump is enough to go for an acquittal? Where would your mind be on that right now in advising a client?

HUNT: Yeah. And, Elliot Williams, you're in the box. Let's start with you.

BRENNAN: That's a great question.

WILLIAMS: Well, it wouldn't be -- the Trump stuff wouldn't be an acquittal. It would be to get the indictment thrown out for being improperly, being improperly bought. It was as if by, you know, he was prosecuted selectively.

So, you know, let's think about that. No, I don't think you would have a defendant plead here, and I'd be curious to hear what John says.

I think the way you would do it is just make it question the intent and just say that, well, inadvertently, I live in a big house. I got a lot of documents.

I was in government for 30 years. Some of these are documents from the Bush administration, your honor. My goodness. I just don't know what's in my house. And that might be enough to get out of it.

Again, a critical element in any crime is going to be the defendant's level of intent. What he knew at the time, what crime or what acts he knew he was committing, and merely having a document or a lot of documents accidentally in your house can get you not charged with a crime or acquitted by way of example, this was why, in many regards why Donald Trump was charged with a crime, but Mike Pence was not. Or Joe Biden was not.

You know, folks consider the prosecutors, consider what is the level of culpability we can assign and what do we can we prove that the defendant knew at the time? And if he can say, I just didn't know everything that was there, I'm so sorry. Maybe he gets out of it.

HUNT: Bill Brennan, what say you?

BRENNAN: Well, to answer Scott's question, which is excellent, I can tell you from 39 years of representing criminal defendants in federal court, we kind of do a Mr. Miyagi. We prepare for war, and we pray for peace.

We look at the sentencing guidelines on one hand, and we run the numbers, and then we start looking at the discovery. We prepare for a trial. We hope it won't go to trial.

But I'll steal. I'll tell you what my argument would probably be, because you can't say to a jury with a straight face, Bolton didn't know any better. I'll steal the congressman from Ohio's argument. I would deflect, I'd talk about, you know, lawfare and targets, and id do anything but talk about the facts of the case, because it doesn't sound like they helped me.

On the on the peace angle, I would run, I'd get with the prosecutor. I think it's Mr. Sullivan, as soon as humanly possible. And I'd say, where do you see this headed? Where do you see it land on the guidelines.

The guidelines are a grid. They go from 1 to 43. You know, one is a zero to six month recommendation, 43 is life. And you try to get those numbers from the first inning of the game. You try to get those numbers in a pen somewhere. So at least you're looking at a tight version of what you might be facing.

But they're not mutually exclusive. You can be negotiating a plea deal while you're picking a jury. So, you do a little bit of both. You do the congressman's deflection defense, and you do the let's work this out. Negotiation with the prosecutor.

HUNT: Mr. Miyagi, as you say, Ron Brownstein.

BROWNSTEIN: The case against Bolton will stand or fall on its -- on its own merits. And if he had a serious violation, he should face serious consequences. But I think for most Americans, the significance here is that we are watching people who the president has deemed as his enemies systematically being indicted by the Justice Department, what the merits of each case may vary, may be stronger or weaker, but that pattern is a reality.

To Elliot's point about, you know, why does Trump keep saying this stuff about, that he's glad to see this person indicted, or he want that person indicted when it might weaken the prosecution. That may be less important to him than sending the signal that if you cross him enough, there is a real risk that the Justice Department could come after you. That may be more important to him than not polluting the case with these improper comments, because he is sending that signal to all potential critics in society. You go far enough. Look what might happen.

HUNT: I want to bring into the conversation Rahm Emanuel. He needs very little introduction now. You've been here quite a bit in THE ARENA. You have many titles, including ambassador. Youve been chief of staff in the White House.

You've handled plenty of classified information yourself in a variety of settings. What's your reaction to what we're learning here about this indictment that was just handed up against John Bolton.

RAHM EMANUEL, CNN SENIOR POLITICAL & GLOBAL AFFAIRS COMMENTATOR: Look, I think -- I'm not a lawyer, but you have two tension, two moments of tension. One is obviously a judge approved going into John Bolton's home. So there must be some foundation that warrants a judge to sign off on that.

On the other hand, it has been noted here in the panel, you have also the president of the United States saying, I want you to go after my opponents.

So, you have this legal case wrapped in a wrapping paper of a political case, and the defense is going to be this is a political prosecution. The prosecution case is going to be here's the basis of why we're prosecuting him for violation of a very explicit piece of national security, which is the sharing of -- the kind of use of documents on public domain that should be secret or top secret, whatever the valuation was.

And so, you have a legal case within a wrapping paper, in a box of a political case. And that and those two are in tension.

HUNT: Yeah.

EMANUEL: That's what I see about on this. I'm always shocked, though --

HUNT: Yeah.

EMANUEL: Because the FBI when you get, you get situated and ready for situation room or any documents you have, they put the fear of God in you.

HUNT: That's what exactly what I was going to ask you. Like, I mean, how -- like what is it? Why are all these like, I don't like I do not understand how there are so many people who screw around with this stuff?

EMANUEL: Well, well, one is it's good to be technologically, you know, incompetent because then you can't transfer anything in that way.

But I really do -- I want you to say, I mean, I think one of the reforms that has to happen is every six months, you're going to get a reeducation that puts the fear of God on this document. You don't even leave --

(CROSSTALK)

HUNT: They make me do cybersecurity training here for my company more frequently, apparently.

EMANUEL: Well, you -- you don't even leave them on your desk, okay? You're not allowed to do that.

So, the idea if you're going to run off and go to another meeting or something like that, the idea that you had this stuff and you were transferring it onto another thing, to me, it's like your guard went down. You're too familiar with it. You're too kind of conversant. You're trying to make both the office and home.

As I used to joke in the White House, thank God it's Friday. Two more work days until Monday, and the barrier goes down and you start sharing. I don't know why they do this. I don't know why it happens.

Innocence is not going to be, or kind of I forgot or whatever because you're actually telling everybody else to follow the rules. And here you are not following the rules, assuming again he's innocent, assuming that's what happened here.

HUNT: All right. We want to get to -- Rahm, if you could stand by for me. Katelyn Polantz has a copy of the indictment with new reporting in it.

Katelyn, what do you got?

POLANTZ: Kasie, the charges, there are 18 of them, and they are for transmitting and having classified information in his possession. I'm just going to read a little bit of this because it lays it out pretty cleanly in the indictment on or about April 9th, 2018, through on or about September 15th, 2019. So that's the time that John Bolton was national security advisor in the Trump administration.

On a regular basis, Bolton sent diary like entries to individuals one and two that contained information classified up to the top secret SCI level. Bolton wrote many of these diary-like entries by transcribing his handwritten notes from his days activities into word processing documents, which he then electronically sent to people through a commercial non-government messaging application.

Another thing in this indictment, I still am reading through it, but there's two other things that I'm seeing right now. One is that some of this information were printed -- it was printed out and kept in his home in Maryland and then seized during that search, less than two months ago. That is something that the indictment notes.

Another thing the indictment notes is in 2018, when he was writing, or communicating with one of the people he sent some of these diary-like memos or journal entries to. They asked, why are we using this? And Bolton responded, according to the indictment for diary, in the future, exclamation point, exclamation point, exclamation point -- Kasie.

HUNT: For diary in the future. All right, Katelyn, you keep reading through that. And we will come back. If you find anything that you think we should share immediately with the viewers.

Elliot Williams, can I just get you to react to what we just learned from Katelyn?

WILLIAMS: Yeah. So, a couple of things I can't remind the public enough. And indictment is written by prosecutors, a grand jury only has prosecutors in it, and it's a one-sided document. But whoo boy --

HUNT: He's got a right to a defense,yes.

WILLIAMS: He had what is really bad, what is described there. And it's the kind of thing that every person who's been on this panel thus far, who's had classified information, is warned about.

[16:55:04]

They warn you when you come in, they warn you when you leave and you get periodic trainings and reminders about how to handle the documents. So, the idea about transcribing things and putting them down and so on is just foolish.

You know, Kasie, one thing to respond to your own question about these things in people's homes, I will note that at a certain level of government, at the national security advisor level or the secretaries or so on, they'll often have a secure facility in their house and will have it, you know, I remember the attorneys general that I worked with often did, and they'll trick out a room in their house where they can view and regard classified information. That might be a way some of these folks end up with these things in their homes.

Now, again, there's still a process and a procedure for handling it. And they're warned as aggressively as anybody else about how to do it. But just -- it's not outside the realm of possibility that someone at that level of government might have access to such materials in their house.

HUNT: Right.

WILLIAMS: But again, what we're reading here is really, really bad.

HUNT: Yeah. I mean, typically we would refer to that as a SCIF, right, where you can handle a secure compartmentalized information.

Elliot, can I just ask you, considering you clearly have some knowledge of this if you leave government, do you have to give up your SCIF and send the documents back? I would assume that's part of what is expected?

WILLIAMS: Yeah, yeah. And actually, you certify -- I mean, certainly I did again, I've never been a cabinet secretary. You certify, to the best of my knowledge, I have handed over everything in my possession and the understanding is when some -- when you become aware that you have something in your possession, you turn it back, like I have boxes from my time in government to -- if I were to discover that there was a classified or sensitive document there, of course, you know, I have an obligation legally to turn it over.

And I would assume that the secretaries and the national security advisors and whatever else are signing the same documents and committing to turn things back when they discover that they're in their possession.

HUNT: Yeah.

Rahm Emanuel, can I just get your reaction to what we heard there from Katelyn Polantz? And I do think it is worth underscoring here. There are 18 counts in this indictment. Again, innocent until proven guilty. But you'll remember that indictment of Jim Comey was just a couple pages long. This is considerably more detailed.

EMANUEL: I mean, again, you had -- you had a five-year investigation, not just something off the cuff. And then second of all, you have a judge approving a warrant. So, my guess this is a little more thorough, a little more comprehensive. I actually have just a personal interest if I understand this correctly. It was a foreign intelligence entity that alerted the United States. I think I got that right?

HUNT: That's -- Katelyn has been reporting that, yes.

EMANUEL: Yeah. Well, I'm very interested which foreign entity knowing the relationship between the president and what he feels about John Bolton tipped off the United States intelligence agencies to what John Bolton was done.

And that's just -- that has nothing to do with the legal case. It has to do with politics. But you have a foreign government knowing how the president of the United States feels about John Bolton tipping off the United States to John Bolton's legal vulnerability.

That is not in the legal 18 page, 18 sections of what he's being indicted for. But there's a layer of politics that is below the legal case that for those of us who love politics, is a little fascinating.

HUNT: Okay, I'm going to continue to ask some questions about that.

Congressman, you seem itching to jump in.

LANDSMAN: Yeah, just a couple of things. One is I -- you know, obviously a judge and jury will decide whether or not he's guilty of these things. So, everything I say from this point forward has nothing to do with the case, just my own experience.

When I get a classified briefing, they will sometimes hand you documents. I make a, you know, I typically put the document sort of in front of me, and then the minute I'm done reading it, I push the document away because I don't want it anywhere near.

JENNINGS: I remember doing the exact same thing, like slowly pushing it away, like I've read proximity to it.

LANDSMAN: I've read it now.

Number two, again, I'm not making a judgment. I just -- my wife and I are very close. My daughter and I are very close. I share with them the very highlights of my day. Just, you know, it was a good day. I did this, I did that.

The idea that I would be sending them anything. I'm not saying it was classified, just the diary alone seems a little weird.

JENNINGS: To Elliot, based on the charges that we've seen, how much prison time could you get if you were convicted on all this?

HUNT: And, Elliot, we are up against the clock. But go ahead.

WILLIAMS: Oh, I'd have to look at it. I mean, most things are usually five-year maxes and they would stack them together. It's not a ton of prison time.

HUNT: Very quickly.

BROWNSTEIN: Serious bad behavior. If it's -- if it's proven. I do have to wonder if John Bolton had introduced was -- still introducing Donald Trump at rallies last year and was still on board the team, whether any of this would be happening today?

HUNT: Well, you do think about Eric Adams, for example, who also was facing a very long investigation that --

BROWNSTEIN: Serious charges that vanished in the air.

HUNT: -- that did cease. BROWNSTEIN: Okay. We, of course, have been covering throughout our

hour the indictment of John Bolton on 18 counts related to the handling of classified information.

Our breaking news coverage is going to continue right here on CNN. "THE LEAD WITH JAKE TAPPER" starts right now.