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More Disciplined Trump Operation Facing Fresh Headaches; Trump Fighting Efforts To Remove Him From Ballot Multiple States; Rep. Boebert Says She's Switching To A More GOP-Friendly District; Trump Vs. Home Alone 2. Aired 12:30-1p ET

Aired December 28, 2023 - 12:30   ET




DANA BASH, CNN ANCHOR: Donald Trump's 2024 campaign includes some of his most disciplined advisers to date. But how is it navigating headaches from outside allies? And maybe the biggest question, the candidate himself.

CNN's Kristen Holmes is digging in on this. And Kristen, you have some new exclusive reporting about this question. And it really is a contradiction because when you think Donald Trump you definitely don't think discipline. But at least it sounds like from your reporting, his campaign is trying to build something around him that is as structured as can possibly be with a candidate with his personality.

KRISTEN HOLMES, CNN NATIONAL CORRESPONDENT: Yes, of course, Dana. So this is what we always want to start with. We're talking about the campaign as in the behind the scenes operations, not the candidate himself. They know who he is, and Donald Trump is going to continue to be who he is.

But when it comes to the actual campaign, what's been striking to me over the last year, as you said, this is the most disciplined campaign team we have seen. He is right now led by Chris LaCivita and Susie Wiles. These are two veteran Republican strategists who have really worked to manage the message and the media around Donald Trump.

And by doing that, that sometimes means picking up the phone and calling people telling them to knock it off if they are leaking to various publications. But what is getting harder as Donald Trump is moving or inching towards the Republican nomination is that as one senior adviser put it to me, people are coming out of the woodwork trying to show that they have an affiliation to Donald Trump, that they have some sort of relationship with him, that they could potentially serve in a second administration.

And those people are going around the campaign, going directly out to the media to try and essentially sell themselves as anonymous sources but sell themselves as potential picks for a second administration. So this is becoming harder and harder for the campaign to lead a discipline cycle.


BASH: And so how does Donald Trump himself play into this dynamic that you're reporting about inside his campaign?

HOLMES: Well, as one strategist told me, Donald Trump's campaign knows that they cannot control him. So they're trying to control everything else around him. I mean, for example, one of the anecdotes that we use in this piece is that at a recent fundraising dinner, Donald Trump looked across the table to a group of donors and said, now who do we think should be vice president and started rattling off a bunch of names.

Well, a few minutes later, a few days later, I got a call that Donald Trump was considering these names for vice president. That's hard to do when your own candidate is putting that out there. And something we know about Donald Trump is he seeks counsel from a huge swath of people.

So if you are trying to control who he talks to, that's going to be very hard. I don't think they think that's possible. But that might be the biggest hurdle in all of this. You can't control the messaging from Donald Trump himself.

BASH: Yes, that is maybe the biggest understatement of the year. Thank you so much. Appreciate it, Kristen. Great reporting.

And one thing his campaign is trying to control but this is going to be up to Donald Trump's lawyers in -- and of course, the people who are involved in these cases is whether he appears on the ballot in multiple states where major 14th Amendment cases are playing out.

The former president is fighting back against those states considering removing or at least have already removed him from the ballot because of his role in the January 6 insurrection. Donald Trump's legal issues, though, extend far beyond that fight. He's currently defending himself in cases involving classified documents, January 6th, fraud, election interference, hush money payments, defamation.

So how will all of these cases play out and when will they play out in this year ahead? CNN's Chief Legal Affairs Correspondent Paula Reid is here to walk us through it. This is very confusing --


BASH: -- and very cumbersome because there are so much. So we're going to try to do it in a linear way, doing it chronologically.

REID: Love that.

REID: January 4.

REID: All right. So this was the deadline for former President Trump to appeal the Colorado Supreme Court's ruling. They removed him from the ballot. They said that if you can appeal to the Supreme Court by then, they'll put their ruling on pause, which means he will be on the primary ballot. And Trump has not appealed even though he is expected to. But late last night, the Republican Party of Colorado appealed this ruling. Now they are actually a party to this case. They have been fighting in court for their right to list Trump on the primary ballot. And it's the understanding of the parties and the legal experts we've talked to that that appeal is enough to put that Colorado decision on hold for now. But we're still waiting for that actual Trump appeal.

BASH: OK, January 9th, five days later, a hearing about immunity.

REID: Big day. This is an oral argument for this appeal. This has prompted a judge to put the entire federal January 6 trial on pause while the special counsel and Trump's lawyers argue in court about whether he has immunity or whether he's at risk of double jeopardy, Dana.

Sources close to the Trump legal team, they're pretty sure he's not going to prevail on the merits. This is all about timing. Because whatever happens at the appellate court, likely to be appealed to the Supreme Court. They have already declined to step in here and just decide this so the trial can move. But that trial cannot start until the subpoena is resolved. So yes, this is a fascinating constitutional question, but really that day is all about timing.

BASH: OK, then let's go up to New York two days later, January 11th.

REID: This is closing arguments in that civil fraud trial. This has to do with the Trump Organization. It's not a criminal case, but it's deeply personal to the former president. We saw him in court multiple times. They'll be closing arguments. Then we expect the judge, this is not a jury thing, but the judge will make his decision, and we expect whatever that is will be appealed.

BASH: OK, and then five days later, still in New York.

REID: Yes.

BASH: E. Jean Carroll.

REID: E. Jean Carroll back in court this time, focusing on damages for her second lawsuit against former President Trump. I mean, just look at that calendar. The first two, three weeks alone, just jam packed with really serious legal jeopardy. We've never seen anything like this.

BASH: OK. So as you said, that is just the first 16 days of 2024. Audience, viewers just get ready to maybe be a little bit overwhelmed with what we're about to show you. But that's kind of the point. That is the calendar in the first eight months of the of the year of 2024, of the election year and what he and his legal advisers, what his lawyers are going to have to be dealing with along, of course, with his campaign advisers.

REID: Absolutely. So we also have the hush money trial. Remember, this is the first criminal indictment that he faced. This will be in the late March. This is the Stormy Daniels hush money case that was brought by the Manhattan D.A.


People kind of forgot about it because they thought the January 6th case would go then and that case would be kicked. Well, it's unclear now. And the biggest question now is also the Mar-a-Lago documents case, perhaps the most serious case in terms of national security and legal risk for the former president.

That is currently penciled in in late May, but a lot of the timing was dependent on the January 6th case. It was widely expected that that might get pushed. But if the January 6th case is delayed, the judge may have less really authority to push that back. Though it's a very technical case and there are reasons that she might try to push that back.

So, I have no vacation scheduled this year at all, but Dana, it's not clear what if any federal trials he will face this year.

BASH: Yes. Usually our legal correspondents get to take a breath when all of the political reporters in an election year are working hard. Sorry.

REID: Since 2016.

BASH: Sorry. Sorry, Paula. Thank you. It was really helpful. Thank you for doing that with us.

REID: Of course.

BASH: And coming up, some members of Congress are retiring rather than facing a tough reelection race. Colorado Republican Lauren Boebert has a different strategy -- switch to a safer district. That's next.




REP. LAUREN BOEBERT (R-CO): Today, I am announcing my candidacy for the 2024 Republican nomination to represent Colorado's Fourth Congressional District in the United States House of Representatives. It's the right move for me personally, and it's the right decision for those who support our conservative movement.


BASH: That was Lauren Boebert announcing that she will run in a different congressional district in 2024 from the one she represents now. She doesn't actually live there, but it is friendlier to her brand of politics, one that she has been very vocal about at a national level for the past three years.

My panel is back with us. Let's just kind of set the table with some facts. First of all, she only won in 2022 by 546 votes, and yet it's not like the third district that she represents now is a purple district. It is a red district. Donald Trump won there by more than 8 percentage points. It's not as red as the one that Ken Buck is going to leave empty because he is retiring.

Donald, you see, he won there by, you know, more than almost 25 percent. Donald Trump did by 18 percent. So look, Democrats, Republicans, they district shop. It's not a new phenomenon. It's been happening for a very long time, but it is fascinating that she is doing this right now, especially given how close it was in 2022.

KASIE HUNT, CNN CHIEF NATIONAL AFFAIRS ANALYST: It was so close. And it was so close because they ran against Lauren Boebert. I mean, those numbers tell you everything you need to know. A Republican generic is likely to win the third congressional district. But people -- she just wasn't -- there was a lot to run against her, right? And she clearly saw the writing on the wall.

And she said in that announcement video, this means that we'll get a -- you know, I can win in the fourth district and we'll get a Republican in the third district and it'll be all better for all of us. You know, I don't know that there are a ton, you know, of her Republican colleagues. I mean, I don't -- some of them will probably say it publicly, but I don't think there's going to be any love lost for her if she doesn't return to Washington, even among her fellow Republicans here.

TIA MITCHELL, WASHINGTON CORRESPONDENT, ATLANTA JOURNAL-CONSTITUTION: Right. So what she's doing is almost guaranteeing that Republicans won't lose a seat in Congress, right? Because now that there's a generic Republican on the ballot in the third district, it's more likely, I guess, that Republicans can hold onto that seat.

But she's not necessarily guaranteeing that she will return to Congress because there's already a crowded field in the fourth district with the incumbent announcing he's not going to seek another term. Now, does she come in with a lot of name recognition? Sure, but not always for the right reasons.

So what -- I mean, it's early, it's day one, but it's going to be interesting to see if she clears the field in the fourth district or whether people say, no, we don't want someone like you representing us in Congress. We've got other, you know, tried and true Republicans who we think are just as conservative with you without the baggage.

Now, I will say that in Marjorie Taylor Greene's district, that didn't work. People wanted the bombastic and controversial lawmaker. We'll see if that's the same in a state like Colorado.

BASH: She's got the bombast. She's got the controversy. And from her perspective, she's got the conservative credentials, not to mention being extremely pro-Trump. She also has some baggage from -- since the time that she won reelection in 2022. We'll just put up some of the headlines.

Kind of can't forget, if you pay attention to politics, she had to apologize because she was kicked out of a show, a live show that she was watching. She falsely denied that she was vaping. She had to address an incident where she was allegedly being -- well, we saw the video -- being groped.


BASH: It wasn't allegedly being groped by the man she was with.

MIN KIM: Right. I mean, and that's just since 2022. And so if you thought -- if you saw how close that race was in 2022 and saw kind of all the headlines that she was making for all the reasons, you see why Democrats are actually feeling pretty good about that district until obviously this morning when you -- when we saw the announcement from Congresswoman Boebert.

And this is also a district and a congresswoman that the White House is having -- been having a lot of fun with. President Biden actually traveled there. You don't see him going to a Trump plus 8 district all too often, but he went there and the White House felt it was effective for him to go there, first of all, to tout the Bipartisan Infrastructure Law, one of the biggest achievements of his presidency.

There's a wind energy manufacturer in Pueblo, Colorado, where he spoke, and he was happily calling out Lauren Boebert for voting against that law.

BASH: There are lots of serious issues before this country and before the world. That isn't entirely what the former president is focused on this week. We're going to show you what Donald Trump's latest grievances, and it is not getting enough credit for the success of "Home Alone 2". This is serious.

Stay with us.



BASH: "Home Alone 2", it is a holiday classic. Who can forget Kevin McCallister aka Macaulay Culkin, getting separated from his family and lost in New York. He ended up at the iconic Plaza Hotel where the hotel's then owner stopped to give him directions.


UNIDENTIFIED MALE: Excuse me. Where's the lobby?




BASH: Three years ago, Director Chris Columbus explained how Trump ended up in that movie. He said Trump bullied his way in, demanding a cameo in exchange for letting them shoot inside the plaza. That interview with the director resurfaced this week. Trump saw it apparently and he posted this on social media last night.

He said, "I was very busy and didn't want to do it. They were very nice, but above all persistent. That cameo helped make the movie a success. But if they felt bullied or didn't want me, why did they put me in and keep me there for over 30 hours? Because I was and still am great for the movie, that's why."


OK. You know, these are the things that give us a window into what matters to the former president right now. I mean, I don't know if he was --

HUNT: I mean --

BASH: He saw that or if he was watching, trying to boost the royalty --

HUNT: The idea -- I mean it makes too much sense that of course, if he was going to allow cameras into the Plaza Hotel, which he owned, he must be in front of one of them at some point. I mean, I don't know if you -- I -- you -- Donald Trump -- I mean, this is the thing about him, right? He -- I remember shooting a stand up at his first Iowa State Fair and it was packed and my cameraman was standing on a ladder.

The whole thing was teetering and Trump walks to the crowd, looks at me, finds my camera, says to me the words -- you know, I asked him a question, he points at it. So anyway, I believe Chris Columbus.

BASH: Right.

MITCHELL: And I think it also shows how he's been able to manufacture his celebrity. Put himself in positions to be perceived as a big star, and that's how we have the Trump we have today.

BASH: OK, well said. You can do the "Home Alone" face if you want.


BASH: Thank you so much for joining Inside Politics. CNN New Central starts after the break.