36. My Last Conversation With Trump

0:00This is a real good story about Bronx and his dad Ryan, real United Airlines customers. We were returning home and one of the flight attendants asked Bronx if he wanted to see the flight deck and meet Captain Andrew. I got to sit in the driver's seat. I grew up in an aviation family and seeing Bronx kind of reminded me of myself when I was that age. That's Andrew, a real United pilot. These small interactions can shape a kid's future. It felt like I was the captain. Allowing my son to see the flight deck will stick with us forever. That's how good leads the way.

0:37Welcome to this special edition of The Rest is Politics US. We are coming to you on a Monday, which is very unusual for us, but it is just a week out from the election. So this is a special episode and keep watching your feed all of this week because we're going to be dropping new episodes every couple of days to keep you up with the very latest news as we enter the final, final stretch of this extraordinary election. and we are sitting in Mr. Scaramucci's very swanky New York office. Can I get a job here? Entrepreneurial, yes. Because I feel like I'm in the wrong business. I've just walked around your office.

1:11You're running this podcast. You might as well run the company as well. It's no problem. I need to be doing. And you would have been great at it, by the way. You would have dominated Wall Street, but here we are. Okay, well, it's never too late. All right, so what were you doing last night? Where were you when the rally took place? I took the train up from D.C. to New York because we're having our live event Monday night in New York City. Came up Sunday night and I came into Penn Station, which is, of course, right next to Madison Square Gardens. As Donald Trump was speaking, he was halfway through his speech, but there were already a ton of people outside.

1:42I don't know if there were people who were leaving because it was starting so late. For people that don't live in New York, what Cady's referring to is Penn Station is located underneath Madison Square Garden. And Penn Station is one of the two central terminals for the island of Manhattan. And so if you're coming up from Washington, which you came up from, you would land at Penn Station. Yes, in the middle of a Trump rally. Which is exactly right. Which is not something that happens very often, of course, because New York City, very blue, very democratic. But what struck me as I came up, and there were a lot of people wearing MAGA hats.

2:15I think I saw more people wearing MAGA hats in the middle of Manhattan last night than I have seen in the whole of the last eight years. and there were people from all different backgrounds, all different races. There were hundreds of people outside. Now, I don't know if these were people that were leaving a little early because Donald Trump started talking so late that they'd already been there since very early in the morning in order to get into Madison Square Gardens. But they were jubilant. They were excited and happy and energized. There was a kind of party-like buzz in the air, I would say.

2:47Let me say a couple of things. So, for viewers and listeners outside the United States, The island of Manhattan, the five boroughs in New York are blue. They're primarily Democratic. But the suburbs, if you go out to Nassau County where I live or further out into Suffolk County, they're quite red. And so people like you, Caddy, were coming in by train to go to that event. And they were coming in by the thousands with their MAGA caps on. And so even though New York will go for Vice President Harris, there is a large pockets of MAGA people in the area and they all found themselves to Madison Square Garden last night.

3:27I want to get into the content of what he spoke about and whether you think it hurts or helps him in this final stretch. And also just to reflect on the extremeness of what was said at that rally, not just by Donald Trump, but by particularly some of the speakers beforehand. But why do you think it was so important to Donald Trump? You have known him for years. You've known him in New York as a real estate developer for so long. And when I came out at Penn Station, there he was, his face huge, up in lights, wrapping around the edge of Madison Square Gardens. Why was he so keen to do a rally in Madison Square Gardens?

4:03Well, I mean, there's a lot of different reasons, but let's start with the first couple of layers. He's never really accepted in New York. He was an outer borough kid, and I don't know what it would equate to in Great Britain or other places around the world, but he was never accepted by the New York police. side of the tracks. Yeah, when Don Jr. said that he had built in New York and he was a big real estate developer here, he was actually a minor developer here. He did a couple of projects and he plastered his name on those projects. He was very, very good at getting media, which the elites found annoying.

4:35So, you know, he couldn't get into certain golf clubs. He didn't get treated with the respect that he felt that he deserved. So the Madison Square Garden thing to him is iconic for several reasons. Muhammad Ali fought Joe Frazier there in 1970. Frank Sinatra made a comeback there in 1974, packed the house as a singer. The Rangers have won the Stanley Cup there. The Knicks in the 70s won a world championship there. It is a celebrated, very famous, perhaps the most famous arena in the world, or certainly here in New York. and he wanted to say that he did that arena. That's part of his ego. He was trying to fit that in his box.

5:19You were very nice to invite me on Morning Joe, which is a famous morning television show here in New York that's broadcast nationally. There's something about it and I just want to get your reaction to it. There's such a big overbite to it that I think he's very worried. I just, me personally - You mean the confidence, the having the rally in Madison Square Garden? Yes, because there's an overbite. Or as Shakespeare would say, doubt does protest too much. If I'm telling you I'm going to win, I'm going to win, I'm going to win. I'm going to do a rally in New York instead of being in a swing state.

5:50I'm losing New York, but I'm going to do a rally here. Okay. Now the 4D chess players in Trump land will say, well, he did that to capture the media's imagination. And he got 8 million viewers on Twitter or whatever the numbers were and blah, blah. But again, those are people that are voting with him anyway. You could say the strategy was to help those down-ballot House members, Republicans, who they need to win again. But he didn't actually have them up on the stage with him. They were keeping as far away from this rally as they could, by the way. Okay, caddy. Come on. I was just saying that maybe there was a strategy.

6:26But I got to call you on it, okay? He doesn't really care, okay, about the down-ballot. You know that and I know that. Okay, so what is he doing? He's feeding his ego and he's playing the overbite. What does that mean, playing the overbite? I think I'm going to lose. So I'm going to give you an overbite of bravado that I'm going to win. If I'm insecure about something, I'm going to overcompensate by making you think that I'm not insecure about that thing. He had a tell last night. He said that Speaker Johnson, that's Mike Johnson, the Republican Speaker of the House, who will be in the House after the election, right?

7:06So even if the Democrats take the House, it doesn't turn over until January. So Mike Johnson will be there to decide or help decide the procedures after the election. He said, hey, you know, I got a secret. Mike and I have a secret. Those are tells to me. You pointed out before we went live here, he's going to New Mexico? He's going to Virginia. And he may even go to New Hampshire again, because I was wondering about those states too. He's not going to win Virginia. He's not going to win New Mexico. And he's not going to win New Hampshire. So why at this stage in a campaign, you've got a week left to go.

7:41The candidates time is incredibly precious. They don't have massive resources in that campaign. They're having to ask other people to pay for their rallies for them. So why send him out to those places? isn't i guess in line with your theory would be they are showing enormous confidence in this final stretch and i was texting with a senior advisor on the campaign just yesterday who was saying we're going to win every single battleground state except wisconsin we're going to turn out huge numbers of young male voters and we could even win the popular vote i mean this is like that's stratospheric levels of confidence okay but that's actually not going to happen and he knows that because male voters don't vote.

8:24Okay. They just don't. He's relying on people that don't vote. She's relying on people that vote. Okay. So, he may win the election because it's a very close election, but I don't think he's going to win it like that. Also, here's the other thing. Let me throw it back to you. He loses the election, but he's got everybody drinking the Kool-Aid on his side thinking that he's overwhelmingly winning. Doesn't that set him up for the conflict that he's looking for? Yeah. And then you have Elon Musk saying that on Saturday, Elon Musk said that January the 6th was in nowhere violent insurrection. And this is the interesting bit.

8:55He also said mail-in ballots are a recipe for fraud. That is one of the theories about this overconfident is either they are overconfident because they really are overconfident or they're overconfident because they think that this is a way to say after the election, but every poll said we were going to win and look how confident we were. And we had numbers showing we were going to win every battleground state therefore if we haven't won it must be but do they have what i'm saying is this is this will they're setting themselves up to say it was stolen okay it was rigged just two quick things though okay you got a comedian up there saying that there's a pile of garbage in the middle of the ocean it's puerto rico okay so i did not go over well that was a lead balloon you've got people saying that they want to slaughter the other side i think it went over well in the room anthony i don't think it didn't go over well in the room but it wouldn't didn't go over well on the outside because the Trump campaign had to say that they denounce the rhetoric and they don't agree with the comedian, okay?

9:52So that's a definition that didn't go over well to the outside. It's red meat for MAGA, but it's not red meat for the independents you're trying to get. Right. Right? But here's the thing. The fish always stinks from the head down. If Trump is calling the United States a garbage can, you don't think he's going to have a supporting cast member call something else garbage? Of course. I agree. That's what happens. everything descends from trump he's creating space for this nonsense there's a wall street executive that's supporting him he's on head of the transition team know the guy for a very long time not going to mention his name on the podcast it's not that important but he was screaming into the microphone like he was at like some kind of evangelical this guy's not that that's not his personality phenotype to scream like that but he's tied into MAGA now and everything's reverberating down from Donald Trump and this is the danger if he wins the election and he could win that it's not just him but it's the minions he's bringing caddy that are not even Steve Miller said America is America only for Americans okay in 1933 Adolf Hitler said Germany is German only for Germans Yeah, well, we better do this podcast together soon because that means I'm out the country.

11:10Seriously. I'm going to be with you. I mean, come on. You know, I mean, I'm - This is for Americans only. I haven't got that passport yet. By the way, I just let people know, I ain't leaving, okay? He's going to have to put me in the gulag, okay? I'm not leaving. That's my country. I'm not leaving either. This guy's nuts. I'm not leaving either, even if it is only for Americans. We'll have to do something about that. The Italians would say tutti pazzi. You know, he's got like a chicken running inside his head. I mean, the guy's nuts. I agree that there's a permission structure. of the campaign would have known exactly which speakers they would have chosen the speakers.

11:37And if you choose to put somebody up like that comedian on stage, you know, the kind of things he has a history of saying, and you are inviting that to be said. You want that to be said at a Trump rally. It was in the prompter. They read the prompter speeches before they went up there. And then to distance themselves from it afterwards. And a whole bunch of Republicans, by the way, congressmen, senators have distanced themselves much quicker than the Trump campaign did because they look at the numbers. Senator Fetterman put out a tweet saying there are 200 ,000 Puerto Ricans who vote in guess where?

12:08The critical state of Pennsylvania. So this has been reverberating is my understanding around the Pennsylvania community as well. Okay, time is precious for a candidate and yet you go and spend three hours talking to Joe Rogan. I'm full disclosure here. I listened to an hour of that podcast and I'd had enough. I couldn't quite bring myself to spend three hours of my very precious Saturday in gorgeous sunshine listening to Joe Rogan talking to Donald Trump? I have family members that eat red meat. They don't take the vaccine. Every conspiracy theory is true. They listen to Joe Rogan. Every podcast, they download it.

12:47They listen to the whole thing. I mean, you know, I grew up in a blue collar area. These are my family members. Every one of them to a person said to me, could not get through the podcast it was a rambling wreck of nonsense and joe himself was trying to tell him you got to get the weave you're getting a little bit too wide with the weave i mean you got to get back into the focus here okay so so i don't know did that help him now let me say this we both know that podcasts work because they're free form and you're unfettered from corporate suits that will potentially rein you in so joe's got 10 million downloads 11 million for the trumpster he picked up 22 million i think the joe rogan the joe rogan podcast helped him and i wish she had done it and i wish she'd done it before him so you don't even have to listen to the rogan podcast you know he was on the rogan podcast it helped him yeah it makes him sound and look approachable even if he's a nutty grandfather.

13:49Okay, now why, can I put this to you please and maybe you know the answer because I don't, why wouldn't she do that? Joe's approachable, he's a conversationalist, he didn't hit Trump on anything, he would never go after her. Why was she uncomfortable doing that podcast? I mean, I was and am still in the camp that she should have done Joe Rogan, just reach those 10 million and predominantly male listeners and that is clearly still where she has a problem. What has her concern? I think she is somebody who is conscious and she has said this in a variety of interviews that she chooses her words very carefully.

14:27And she is conscious that she is in a coalition that is has got Dick Cheney at one end and Bernie Sanders at the other end. And she is desperately trying to hold that coalition together. And the campaign has made the decision that the way you hold that coalition together is kind of by being as vanilla as possible, by not offending any different bits of this very unlikely. Because you could turn them off, they may not vote for Trump, but they just don't show up and vote for you. They could just stay home. And so I think her strategy is to play it effectively, to play it safe. Now, I actually think that in the closing days of this campaign, she's doing something for a candidate who is so cautious.

15:04She's actually doing something that is quite risky. And that is that she is going hard on democracy and Donald Trump. But I'm hearing a little bit of disgruntlement from Democrats and reporters who are reporting the situation in Pennsylvania and in Michigan. And there is a big pro-Kamala super PAC that has put out an email saying this going so hard on democracy and attacking Trump is not helping in this final stretch. She needs to make this more about her and what she's going to give to the American people. And I wonder if that's a bit of a risk for her. Yeah, I do agree with that. Remember what I said?

15:40They got to define her, defend her and attack him. Let's go with more definition right now. OK, we're going to take a quick break and then we will come back to talk about controversy surrounding The Washington Post and newspaper endorsements. And actually, do they even matter?

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17:08Welcome back. We are going to discuss in this half of our extra bonus episode, a week out from the election, this story that blew up over the weekend of the Washington Post storied newspaper deciding not to endorse a candidate. and I wanted to get your thoughts because I actually don't think this is a journalism story as much as it is a business story that this is a newspaper that has a history of endorsing candidates and that had written an endorsement of Kamala Harris that was meant to be published that day before the publisher announced that they were not actually going to endorse anymore 12 days out from the election and I think this is more about our businesses who are now coming to the thinking that it's quite possible 50-50 chance that Donald Trump gets elected, are they kowtowing to what Donald Trump wants in anticipation?

18:04Will Lewis, the publisher of the Washington Post, a Brit who came from the Wall Street Journal and from London newspapers and Fleet Street, has adamantly pushed back saying this is absolutely not what happened. It's much better for democracy if newspapers don't endorse because that allows newspapers to be free and independent and not to look like they are politically biased but i wonder if this isn't more of a business story and a billionaires like jeff bezos who owns the washington post thinking i just have to be a little careful here so a couple things i think it's important to apply some historical context the washington post is arguably the boldest historical paper in the united states uh when phil graham died katherine graham's husband and he committed suicide unfortunately he had victimized the bipolar depression she took over she was a housewife it was her dad's paper actually okay and so she took it over uh she really had a hard time adjusting but she had courage caddy she published the pentagon papers she allowed a woodward and bernstein to investigate the sitting president of the united states where it appeared like his campaign had broken into the opposing side's campaign office in the Watergate Hotel, and it became the famous Watergate story, which led to Richard Nixon's resignation.

19:25So it's been a time in America where the institutions were holding, and we took the free speech seriously, and so did the American president. Richard Nixon really didn't push back. I only a little, but he left. And so now you fast forward 50 years, you've got this big bully intimidating people, and you've got a group of billionaires that you know what, Caddy? They want to stay billionaires. And so just me, when I've observed these people in my life, they are ruthless and rational. You don't get to be a billionaire for no reason, okay? You're ruthless and you're rational. Are you principled? No, principled is number 50 on the list.

19:59Let's go with ruthless and rational. So they're looking around saying, this guy's intimidating. Kamala Harris is not putting me in jail, but this guy could come after my business. He could hurt me. And he's a transactionalist. Let me do a transaction with him. I guess the difference with Kay Graham is, and the Nixon era, is that Catherine Graham wasn't overseeing a massive business empire that had other interests that she was worried about the government coming down and hurting if she went after the president. And what seems to be happening here, the accusation from members of the Washington Post editorial board have called this a terrible decision.

20:39And what they are arguing is that Jeff Bezos is worried about all his other business interests. If Trump is elected, that Trump could hurt those other business interests. Kay Graham didn't have that to worry about, right? So she was operating from a more independent position and she followed through on the journalists. But this is the problem. How's history going to judge that? Okay, we're 50 years from now. People are going to look back and say, this spineless dude caved to a proto-fascist. But industrialists have always done this. The industrialists in Germany, they caved to Hitler. The industrialists in Italy caved to Mussolini.

21:14They're ruthless. They're rational. Don't expect, like, you know, when the scorpion bites the alligator or whatever the story is, I'm a scorpion. These people, that's what they do. They're not, you don't expect them to be the Churchillians of your society. They're not the Churchillians. Washington Post reporters have pointed to the fact that Blue Origin, which is one of Jeff Bezos' companies, executives from Blue Origin had a meeting on the day the editorial was going to be published with people from the Trump campaign. And they're saying, hold on a second, is this a coincidence? Is this exactly what we're talking about, that Jeff Bezos is trying to protect his Blue Origin business interests?

21:52And therefore, they pulled that editorial. material again will lewis the publisher of the washington post pushing back against that saying there is absolutely no connection this is the paper that lost khashoggi in the catastrophe in the turkish embassy of the saudi arabian government and at the time by the way when khashoggi was killed the washington post and its journalists did extraordinary reporting on the views of the intelligence community and on the liability of those people in saudi arabia around the death of one of their own members i have a lot of friends that work at the washington post who are columnists at the Washington Post and they are furious about this decision because they say it sends exactly the wrong signal of the press.

22:28Even if it was not the case, it sends a signal of the press. Let me ask you the ramifications. The guy's not even in office. These dudes are already caving to the guy. And so what does this mean for other media companies? Should Donald Trump get into office? Are they going to just roll for the guy? So Donald Trump has already said the media organizations Donald Trump has mentioned by name, CBS, ABC News, MSNBC, which is the channel that I appear on, CNN, he's already said that he would like to go after all of those organizations for various reasons. MSNBC, for example, is owned by Comcast. Now, MSNBC is very widely watched TV channel here in America.

23:15It's not a massive revenue maker for Comcast. Will Comcast stand up for the independence of MSNBC journalists to criticize Donald Trump in the way that they have done for years? If Donald Trump wins, I think that's a question that's worth asking. Or will they feel the pressure of the Trump administration to tone down the outlet? So you're a Brit, right? I think so. Okay. So what would your man Churchill say? He learned about Churchill. What would your man Churchill say about all this? He'd be happy about all this? No, I think Churchill recognized the need for a free press. And why? Why is the free press so important?

23:54Well, because a free press is how you have an informed citizenry. And it's, I mean, this is Jefferson, right? His great revelation was you must have an informed citizenry to make the healthiest of societies. And therefore, you must have a free press that allows for an informed citizenry. Can I tell you the last time I spoke to Donald Trump? Did I ever tell you a story? No. It was Easter Sunday. So I think it was like in April of 2019. We get the exact date. But he called me. I thought he was calling me to wish me a happy Easter. I'm still supporting him at the time. Yeah, he wasn't though. Lovely.

24:24He wasn't calling me to wish me a happy Easter. So I had written an op-ed in The Hill. And it was an op-ed. It was polite. It was an open letter to the president. Mr. President, the press is not the enemy of the people. in addition to what jefferson and churchill would have said about the press i added it's a check on power the fourth estate just to make sure that people are not being corrupt with their power but it also does something to economic innovation caddy because if we teach ourselves and our children that they can speak and think freely they go on and create facebook and apple computer and google in countries where they are silenced or you have to go to a re-education camp If you're in China, you talk about the leadership, they put you in a re-education camp.

25:06So what do they have to do? They have to steal our intellectual property. They've limited the scope of the free-range thinking of their citizenry by not having a free press. So the press is also important for entrepreneurship and innovation. President Trump did not like that, by the way. So when he called me, he laid into me. He didn't say Happy Easter. He said, I thought you were on my team. You're like a deep stater. The press is the enemy of the people. The press is the enemy of the people. You better start saying that, that the press is the enemy of the people. Okay? And he hung up the phone.

25:39And I said, okay, this is not going well for me because I'm never going to say that. I believe that the press is not the enemy of the people. And then he started talking about nativism where he wanted those congresswomen to go back to the countries they originally came from. And then that's when the fight really started. That's when we really had our Twitter fight. That's when you got into it. Oh, yeah. It was fun. Because I'm not Ted Cruz. You think I'm going to take bullshit from Trump? I mean, give me a break. So just to bring it back to Madison Square Gardens before we wrap, there was a line there that he does in all of his rallies where he turns around and he looks, he gets the audience.