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S.E. Cupp Unfiltered

New Allegations, New Witnesses After Week One Of Public Hearings; Yovanovitch Says, Trumps' Attacks Very Intimidating; Democratic Primary Shake-Up, Again; Patrick: Race Was Breaking Into "Nostalgia" Vs. "My-Way-Or-No-Way"; Tonight At 8P ET: Results Of Latest CNN Iowa Poll; Trump's War On Expertise & Experience; Author Joel Stein: "Impeachment Is An Elitist Trap"; Trump's Longtime Ally Guilty Of Lying To Congress To Protect Trump. Aired 6-7p ET

Aired November 16, 2019 - 18:00   ET

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


(COMMERCIAL BREAK)

[18:00:00]

S.E. CUPP, CNN HOST: Welcome to UNFILTERED.

Here's tonight's headline, a tale of two realities. You know the saying, you get the government you deserve. It has never felt more true than it did this week in two different ways.

On one hand, we had four credible, courageous witnesses testify this week in the first round of the impeachment hearings. Together, they painted a picture of President Donald Trump trying to shake down the Ukraine's president to publicly announce a probe into Trump's potential 2020 opponent. It was, according to them, a coordinated effort, not just a suggestion in a, quote, perfect call.

Bill Taylor, George Kent, Marie Yovanovitch and David Holmes told us what they knew, nothing more, nothing less. They provided a patriotic service to the American people at times to the detriment of their own careers, their families, even their safety.

When Ambassador Yovanovitch, a 30-year career public servant, whom the president has baselessly smeared, was finished, she got a standing ovation from the hearing room. And, folks, that is definitely a government we deserve.

On the other hand, Republicans have made a decision not to be members of Congress through these hearings, not to do their elected duties as public servants and getting all the facts, facts which are damning. Instead they've decided to be shells (ph) for the president.

Republicans spent the hearings trotting out fictitious timelines, lies of omission, debunked conspiracy theories, anything that would distract us from the facts. They claimed this was a Mueller Report redo, they bitched and whined about hearsay and they trashed the whistleblowers themselves. Instead of asking substantive questions, GOP lawmakers frequently used their time competing to become Trump's favorite toady.

(BEGIN VIDEO CLIP)

REP. ELISE STEFANIK (R-NY): Since we haven't been able to conduct ourselves with normal procedures, I'm just going to use the five minutes for this.

September 29th, in The Wall Street Journal, quote, the whistleblower at the center of impeachment investigation of President Trump will testify in the House very soon. This is a quote b the chairman.

REP. JOHN RATCLIFFE (R-TX): I'd like to renew my request, Mr. Chairman, that Hunter Biden's testimony, that has been requested --

REP. ADAM SCHIFF (D-CA): The gentleman has expired.

RATCLIFFE: requested by the Republicans be considered --

SCHIFF: The gentleman has expired.

RATCLIFFE: -- as legitimate rather than a sham.

REP. DEVIN NUNES (R-CA): Today's show trial has come to an end. We are headed down now to the basement of the Capitol to go until I don't know what time. We will be back there hiding again behind closed doors.

(BEGIN VIDEO CLIP)

CUPP: And then this morning, Congressman Jim Jordan proved he's not interested in oversight or facts. He'd rather be the president's press shop.

REP. JIM JORDAN (R-OH): I think, frankly, things are going well for the president.

(END VIDEO CLIP)

CUPP: That too, America, is the government we deserve. But let's be clear, things are not going well for the president.

First on Wednesday, the top U.S. diplomat in Ukraine, Bill Taylor, dropped this bit of damning new information supporting the narrative.

(BEGIN VIDEO CLIP)

BILL TAYLOR, TOP U.S. DIPLOMAT IN UKRAINE: A member of my staff could hear President Trump on the phone asking Ambassador Sondland about the investigations. Ambassador Sondland told President Trump the Ukrainians were ready to move forward.

Following the call with President Trump, the member of my staff asked Ambassador Sondland what President Trump thought about Ukraine. Ambassador Sondland responded that President Trump cares more about the investigation of Biden.

(END VIDEO CLIP) CUPP: On Friday, former U.S. Ambassador to Ukraine Marie Yovanovitch's testimony supported the allegation that she was fired and smeared because Trump wanted a clear path for Ukrainian officials and Rudy Giuliani's no indicted associates to do these aforementioned investigations. And this career diplomat, who was unanimously confirmed by the Senate and originally appointed by Ronald Reagan, well, stood in the way.

As that was happening, the president actually tweeted out in real- time, more attacks on Yovanovitch, who served this country in actual war zones as a career foreign service official, as she sat in the witness chair because he has no shame.

(BEGIN VIDEO CLIP)

SCHIFF: As we sit here testifying, the president is attacking you on Twitter. And I'd like to give you a chance to respond. I'll read part of one of his tweets.

Everywhere Marie Yovanovitch went turned bad. She started out in Somalia, how did that go?

[18:05:02]

And now the president, in real-time, is attacking you, what effect do you think that has on other witnesses' willingness to come forward and expose wrongdoing?

MARIE YOVANOVITCH, FORMER U.S. AMBASSADOR TO UKRAINE: Well, it's very intimidating.

(END VIDEO CLIP)

CUPP: But believe it or not, the most significant development in all of this came late yesterday behind closed doors. During a deposition of Taylor's aide, David Holmes, in his opening statement obtained by CNN, he discusses being at a restaurant in Kiev with Ambassador Sondland and overhearing his phone call with President Trump, which the first witness of the week referenced.

Holmes says, after the call, I asked Ambassador Sondland if it was true that the president did not give a blank about Ukraine. Ambassador Sondland stated that the president only cares about, quote, big stuff. Sondland replied that he meant big stuff that benefits the president, like the Biden investigation.

It's all digging a deeper hole for Trump to wiggle his way out of. It may have gotten deeper today. Budget official Mark Sandy testified for five hours behind doors about the Ukraine aid pause and two more transcripts have been released, those of former NSC official Tim Morrison and special adviser to Vice President Pence, Jennifer Williams, both will testify publicly next week.

Here's the deal. Three public witnesses, one behind closed doors, each telling the same story, each with nothing to gain and everything to lose. And yet, two different realities, one side saying this is bad, there are clear abuses of you power, indeed impeachable offenses, the other is saying, none of this matters. These people, these career public servants are -- I want to get the wording just right from the pundits -- yes, a narcissistic diplomat snowflake, neurotics and self- important nerds.

You can decide what the president did wasn't impeachable. That's fine. That's your right. But three rich pundit dudes who have given not a single day to public service, trashing for devoted public servants along the way, well, that's just disgraceful.

Joining me now is former White House Communications Director Anthony Scaramucci.

I mean, look, it was a quick -- quick 11 days, but you actually served. You were a public servant. What do you make of this task?

ANTHONY SCARAMUCCI, FORMER WHITE HOUSE COMMUNICATIONS DIRECTOR: S.E., you've never felt more alive than when the president of the United States is calling you an unstable nut job.

CUPP: I guess.

SCARAMUCCI: So, I mean, that's why the ambassador says it is intimidating. Because happens is it unnerves you. He's the president of the United States. And so he knows he's doing that. He's got 150 million social media followers. And so when he's hitting you like that, it's a super bowl audience plus the half.

And so it's disgusting, by the way, and it is a form of fascism. Because when the president of the United States is using the powers of the presidency to go after individual citizens, that's exactly -- that's right on the Umberto Eco checklist of fascist.

But his acolytes are going to project. They know he's a narcissist, they know he's a malignant narcissist, they know he's a very desperate guy with very, very low self-esteem, so they project all that stuff on the people that are just telling the truth and many people know what's really going on.

CUPP: You know Trump. Do you think him going after her in real-time, as you've seen there, is that a signal of his concern that she's a bad witness for him?

SCARAMUCCI: Yes, it's a combination of things. It's impulse control, it's an inability to control the situation. He knows he's over his skis. He knows that that's the tip of the iceberg. The Ukraine calls are the tip of the iceberg of traitorous activity and ranked criminality.

And so he knows as this thing starts to cascade on him and people feel comfortable if they don't get intimidated by them. If they are tweeted out by him and the actually don't care and they live their lives without fear or they think about their patriotism, he knows that there's many more things that are going come out about, not just the Ukrainian stuff. There're 193 nations in the U.N., there is no way President Trump had one or two calls like this. There's got to be 25 or 30 calls like this.

CUPP: Well, all got to know --

SCARAMUCCI: And so stay strong is the message. And don't be intimidated by this guy. This is America. He's just another person in America. And he's supposed to be -- my fellow Republicans, he's supposed to be below the law, okay? There is nobody above the law in our system and he's a ranked criminal. Let's call it for what it is and let's stick together as Americans so that we can move on past this guy.

Don't be intimidated by him though. That's the big message.

CUPP: We all got to know Marie Yovanovitch. She obviously was not intimidated. I mean, I'm sure she was a little frightened. But she did the hard work.

People might not know much about David Holmes because he testified behind closed doors. He has served in the U.S. Foreign Service since 2002 in places like Kosovo, Bogota, Kabul, Moscow. He actually won an award for constructive dissent, which honors foreign service officers who challenge the system from within.

[18:10:03]

He won that award in the Obama administration.

Are Republicans picking the wrong fights with these guys?

SCARAMUCCI: I think so. I mean, they're remarkably hypocritical. If you just put a Democrat in that seat, like Barack Obama or William Jefferson Clinton or Hillary Clinton, had this level of lawless behavior, they'd be going up like bottle rockets. And their pundits would be calling for an impeachment and removal of office.

And so problem is we're in this partisan ranker (ph) now. But what we really need is statesmanship. We really need one or two people to step back, S.E., look at this thing for exactly what it is and say, hey, you know what? I don't want to be a partisan. I don't care about my personal interest or my personal power. I care more about my country.

CUPP: Or my party, yes.

SCARAMUCCI: And, frankly, they're going to destroy the party. I mean, if they continue to go with this guys, he will likely lose the election. Let's pray and hope that he does. But he wins the election, it's sort of game over for the Republican Party. This will be a man off the hook for four or five years with his --

CUPP: Yes, and reinforce.

SCARAMUCCI: -- Twitter feed, I mean, it would be a disaster. CUPP: So it would take 20 Republicans, as you know, in the Senate to remove the president. Knowing these guys, I don't think they're going to do that. But voters will also get a say in 2020.

Despite all this, I think he's still going to win. Do you?

SCARAMUCCI: Well, you have to tell me who he's running against. If he's running against one of the socialists, like Elizabeth Warren or Bernie Sanders, he will likely win because America is not ready for that. They don't want that.

CUPP: Who can beat him?

SCARAMUCCI: Well, Barack Obama is sending messaging, okay? Deval Patrick is entering the race for a reason. The message coming from President Obama is, hey, don't blow up the entire system, okay?

CUPP: Yes, right.

SCARAMUCCI: Get somewhere into the middle. Get somebody that's a moderate that can gain the enthusiasm of the independence and the patriotic Republicans. And if they do that, they'll crush President Trump. But if they don't do that and he survives this and they put up a ranked socialist, yes, he may win.

But he really shouldn't win because you let this guy in the White House four years with a bunch of yes people, sycophants around him, controlling that Twitter feed. And we know, we think, he's turned the -- listen to what John Bolton said. He's turned the foreign policy of the United States into a personal transaction business.

John Bolton, more or less, admitted that at a Morgan Stanley event. So, guys, is that what you really want for the country? For what reason exactly? It doesn't make any sense to me, S.E.

So I am proud to speak out about it, I'm proud to speak out against him and I'm also proud to let people know. Don't be intimidated. Okay, let's go. We're Americans, okay? We're not living in Russia or China. We should be able to speak our minds and we should be able to build a coalition against this sort of reckless and lawless behavior.

CUPP: Former White House Communication Director Anthony Scaramucci, thanks for your time tonight.

SCARAMUCCI: Happy Saturday. Thank you.

CUPP: All right. Ending the week with a self-inflicted wound, it wasn't great for the president and may appear in an article of impeachment. I'll ask about a member of the tasked with those articles about that, next.

And the 2020 Democratic primary started with a dizzying array of dozens. So as the field finally starts to narrow, is there still room for one more?

(COMMERCIAL BREAK) [18:15:00]

CUPP: Just hours after the first week of public impeachment hearings drew a close came the biggest news in a week of big news. An aid to the U.S.'s top diplomat to Ukraine described overhearing President Trump's phone call with Ambassador Sondland at a restaurant in Ukraine on July 26th, the day after the call to Ukraine's new president.

In his opening statement, David Holmes testified that he and others could clearly hear the call because Sondland had to move the phone away from his ear, the president was speaking so loudly. Sondland told Trump that Ukraine's president, quote, loves your ass and would do anything asked of him, including investigating a political rival.

After the call, Sondland told Holmes when it came Ukraine, President Trump only cares about the big stuff that benefits him, namely the Biden investigation.

This afternoon, White House budget official Mark Sandy wrapped up his closed-door deposition. A source tells CNN he testified that he didn't know why the military aid to Ukraine was withheld, but that the unusual step taken by a political appointee led him to raise the issue with the OMB General Counsel.

And two more transcripts also released this afternoon, aide to Vice President Pence, Jennifer Williams, and aide to former NSC head, John Bolton, Tim Morrison, Morrison testifying that Ambassador to the E.U. Sondland was seen as a problem. All three will be among the eight, yes, eight witnesses scheduled for televised hearings next week. Ambassador Sondland will certainly be asked about that Trump phone call.

Joining me to discuss next steps is Democratic Congresswoman Karen Bass. She's on the Judiciary and Foreign Affairs Committees. Welcome, Congresswoman.

Ambassador Sondland has already testified. Now, given subsequent testimony that followed, do you believe he perjured himself in that initial testimony?

REP. KAREN BASS (D-CA): Well, I actually think that he did. I think that's why he rushed to clean it up. I was there in the SCIF for that testimony. And I will tell you, he came across a little cavalier. But I think after several other people testified to what he participated in, he rushed to clean it up. But it's possible that he didn't clean it up enough. And so it will be very interesting to see what he has to say this week.

CUPP: And I hope he's getting some good legal advice to tell the truth --

BASS: I hope so.

CUPP: -- this week. What are you hoping hear him clarify this week that he didn't already talk to the last time? BASSH: Well, first of all, the last time, he didn't say that the situation actually happened, the quid pro quo. He didn't say that. He cleaned it up to add that. But he didn't tell us about that phone call. And so now this time, what I would expect him to say, and I'm sure his counsel will tell him this, that he needs to say that that phone call took place, the phone call that was overheard in the restaurant, and that we know that the Russians must have listened into.

Can you imagine someone picking up cell phone in a public setting and talking to the president of the United States?

[18:20:00]

It's just outrageous.

CUPP: It's almost like these people don't know what they are doing.

I want to ask you about the Republicans' --

BASS: And don't care.

CUPP: And don't care, right.

I want to ask you about the Republicans' defense that this is all hearsay. It's an odd defense given that hearsay has led to the convictions of countless bad guys. But it is also not hearsay. The president told us what he did. He's defended tying up the aid in exchange for investigations. And David Holmes heard him say it as well. So your thoughts on that strategy.

BASS: Well, I think that they have been prepped in the president's method of responding, which is to deny. So, first, they said it was hearsay. Then they said we were meeting behind secret doors and no one was allowed in. They wanted to see the transcript. So we've done all of that and then it still isn't enough. They are doing that because they cannot deal with the substance of what they are learning.

And so when they say it's hearsay and when you have the ambassador come forward and say, well, actually, I was on the call, so what will they say then?

What I anticipate their next move will be will be to say, well, yes, all that happened but it really wasn't that serious. They can't deal with the substance and so they go around.

And if you think about it, it's the exact same method that the president uses. They are performing for an audience of one. And it's very sad to see my colleagues lower the standard so far they are willing to go along with what they know is criminal behavior.

CUPP: Yes. This week, we heard a number of Democrats shift from calling what the president did, quid pro quo, to a crime, bribery.

BASS: Bribery, right.

CUPP: Is that because you are worried the American people are confused?

BASS: Well, no. I think it's because quid pro quo, one, might be complicated for some people to understand, but it really minimizes it. Bribery is clear. It is a crime. It is in the Constitution. And I believe that that's exactly what happened.

I mean, he essentially told this new president, somebody that had never been in office before whose country is under attack, I am going to withhold aid from you unless you do what I need you to do, which is to interfere in an upcoming election. That's what I think is so serious about it.

Because if you think about the Mueller report, Mueller report was telling us about what the president had done in the past. As far as I am concerned, this is the president in the middle of a new election attempting to interfere in an election and involved in criminal behavior.

What he did while the ambassador was testifying to threaten her, which, to me -- I mean, it was witness intimidation. But I think that even bigger than that, he was sending a message to anyone else that was thinking about coming forward. This is what I will do to you if you speak up.

CUPP: Congresswoman, Karen Bass, thanks so much for your time tonight.

BASS: Sure. You're welcome.

CUPP: Another week, another late entry into the clown car that is the Democratic primary. Nearly 75 percent of Democratic voters are happy with the primary field as it is right now. So what gives?

And Iowa has held first vote status for almost 50 years. Why then are Democrats and their candidates becoming increasingly vocal about changing that? That and a lot more, still to come.

(COMMERCIAL BREAK)

[18:25:00]

CUPP: Over the past few months, Democratic candidates for president have been traveling the country, making their pitches to voters. They've debated. They've done interviews. They've given speeches. They've held rallies. They have fundraised. They've built up staffs. They've gone to state fairs and fish fries.

And the process of the Democratic primary has worked. The field is narrowing. Voters are consolidating behind a handful of candidates who have captivated Democratic voters. The first votes go down in Iowa in less than three months. In election terms, that's right around the corner.

So, naturally, now is a terrific time for someone most people have never heard of to enter the race. So who is Duval Patrick? Let's meet him, shall we? He's a former two-term Massachusetts governor. Up until this weekend, he held a post as a managing director at Bain Capital, yes, that Bain Capital of evil Mitt Romney fame (ph). He's a close personal friend of Barack Obama and, until recently, sat on the board of the Obama Foundation.

He announced this week he's officially getting in and made his first campaign speech earlier today.

(BEGIN VIDEO CLIP)

FMR. GOV. DEVAL PATRICK (D-MA), PRESIDENTIAL CANDIDATE: I am not running, my friends, to be president of the Democrats. I am running to be president of the United States. There's a difference. I'm not talking about a moderate agenda. This is no time for a moderate agenda. I'm talking about being woke while leaving room for the still waking.

(END VIDEO CLIP)

CUPP: Folks, I said it last week. I'll say it again. Have you guys lost your minds? Nearly 75 percent of the Democratic voting public is satisfied with the current field. All this does is telegraph to voters that Democrats are worried that they cannot beat Trump. And they should be worried if more people by their late entries into a primary that's been well underway for year.

With me now is Assistant Editor of The Washington Post, CNN Political Commentator David Swerdlick, along with Republican strategist, Shermichael Singleton.

Shermichael, you can sense my exasperation.

SHERMICHAEL SINGLETON, CNN POLITICAL COMMENTATOR: I can. I can.

CUPP: What is Deval Patrick's plan here?

SINGLETON: I mean, look, I'm not sure, S.E. But what it does showcase is that there are concerns among the Democratic elites and establishment and donors that perhaps they don't think Joe Biden can bring it across the finish line. They're concerned with candidates like Elizabeth Warren, who they think if it's not Biden, it's likely Warren, who could not win in a general. I think most folks would agree with that.

And so I think Deval Patrick jumping into this is an indication that there is serious concern within the Democratic Party.

CUPP: This is your field. He should have run when everyone else started to run.

SINGLETON: For almost four years ago, yes.

CUPP: I mean, David, I'm from Massachusetts. I know who Deval Patrick is. But people don't know this. Our office is like next to a giant mall. I don't think you could find five people in that giant mall who have heard of Deval Patrick. Isn't that a huge problem for him? DAVID SWERDLICK, CNN POLITICAL COMMENTATOR: You probably could not find five people. I don't think that's his problem. He has three problems. One --

CUPP: Okay. Wait, that's not that one of them?

SWERDLICK: No. There's already a little bit of this reporting out here about him in 2014 interceding on behalf of his former brother-in- law with some state officials.

[18:30:03]

That is not a good look. I can't believe he didn't do his own sort of due diligence and his APA research on himself on this.

S.E. CUPP, CNN HOST: OK. So we got a skeleton, what else?

SWERDLICK: We've got a skeleton. If true, we'll not be a good look in a partner.

CUPP: OK.

SWERDLICK: Two, I don't know how he's going to get the individual donors and the polling up to get in the November and December debates. By then the game could be over.

CUPP: Debates, OK.

SWERDLICK: And then, financially, that was a great line about being woke but leaving room for the still awakening, but I just think that you have a situation where people are looking for someone who's a little bit of a pugilist and his brand is mild mannered going into this. It's going to be tough when you're going in cold.

CUPP: Shermichael, isn't Trump loving this?

SINGLETON: Of course, he is.

CUPP: This hands ringing and who's going to save us, the late entrance, talk from Bloomberg and even Hillary Clinton of joining it. I mean, doesn't this work to his advantage?

SINGLETON: Of course, I mean, the RNC is planning on what Trump and other Republic leaning organizations are spending at least a billion dollars next year.

CUPP: Yes.

SINGLETON: And what is showcases is that Democrats are all over the place. There's been so much talk on Republican infighting. But, S.E., it's very clear that there is a paradigm shift within the Democratic Party between progressives and moderates and they're both fighting for control of the party right now.

CUPP: It's a good point. SINGLETON: And I think what that indicates for republican strategists

in some of those key battleground on swing states is that they're going to have a difficult time trying to coalesce around one single message.

CUPP: Well, they're dividing money. They're dividing voters. They're dividing donors, of course.

SWERDLICK: Democrats are all over the place now. In fairness, conservatives moved from conservatism to Trumpism, so Democrats are having a fight ...

SINGLETON: But Trump won. I don't like Trump, but he won.

SWERDLICK: ... no, I understand.

CUPP: That should be a warning to Democrats.

SWERDLICK: OK. No, no, perhaps. Democrats are having this internal intramural fight between the moderates and the progressives. And it's not settled yet and I think that's what gave room for Deval Patrick, Governor Patrick, and also Mayor Bloomberg to get in the race. I will just say.

CUPP: Yes.

SWERDLICK: If Klobuchar, Bennet, Ryan, Delaney had not faltered and if people didn't see Biden as teetering, then I don't think you'd a Patrick or a Bloomberg thinking about this race. But that's the way it's perceived.

SINGLETON: But Democrats have to figure out if they want to have these big grandiose ideas that they cannot pass legislatively.

CUPP: Fact, yes.

SINGLETON: That people when you look into swing states ...

SWERDLICK: Yes, that's true.

SINGLETON: ... when they're saying we're going to take your healthcare away, that's a hundred million Americans, they're talking about free college, free university. And people in the middle of the country said how are we going to pay for many of these things, S.E.? And that's not a guarantee that they'll vote for Trump, but they certainly may stay home and that's just as good as voting for Donald Trump, anyway.

CUPP: It's messy. You all are messy. Can you guys fix - I mean, get your ish together. OK. You guys are staying right there, because we're going to talk about something totally different next. But I think this is interesting for the Democrats.

The Biden camp has been lowering expectations in Iowa, but he's actually not the only Democrat concerned about the first state up. We'll tackle that next. (COMMERCIAL BREAK)

[18:36:38]

CUPP: In THE RED FILE tonight, Iowa or bust as we await the results from the latest CNN Des Moines register poll out of the state coming tonight at eight o'clock. Joe Biden has been falling in the polls there over the past few weeks. Warren and Pete Buttigieg have surged.

But Iowa's demographics have some Democrats wondering why the state gets such outsized importance. It's 90 percent white and so neither a reflection of the country nor the Democratic electorate. Julian Castro has been the most vocal candidate to complain about it. Ironically, Castro signed a pledge supporting Iowa as the first in the caucus status earlier this year, but his press secretary said he won't be held hostage to tactics that indefinitely prevent reform.

OK. Also rubbing Democratic contenders the wrong way, the caucuses are held on a Monday night in February which some believe is hard on working families. So should Iowa lose its status as first in the nation? Back with me, Assistant Editor at The Washington Post and CNN Political Commentator, David Swerdlick along with Republican Strategist, Shermichael Singleton.

David, Iowa has been first since the '70s, which means Democrats have had like 50 years to reconsider it. They have had years to prepare for Iowa. It's not a secret. It's coming first. These complaints seem to me a little whiny. You know what's happening, plan accordingly.

SWERDLICK: OK. It's whiny in this sense, you're running for president, you knew the rules going in.

CUPP: Yes.

SWERDLICK: Run according to the rules.

CUPP: Exactly.

SWERDLICK: Having said that ...

CUPP: OK.

SWERDLICK: ... it is preposterous that Iowa and New Hampshire get to go first.

CUPP: I think you just hate Iowa and New Hampshire.

SWERDLICK: No. No. Yes, because of the demographic analysis that Secretary Castro laid out. These are not representative states, but you don't even have to get to the demographic analysis.

CUPP: OK.

SWERDLICK: Any first grader can tell you that people should take turns, why do these states get to go first? CUPP: Oh, a creative thinking.

SWERDLICK: They will say, "Well, the people of Iowa and the people of New Hampshire take it seriously. We turn out to these events. We go to the diners. We shake the hands." Guess what, if Oregon and Tennessee were first, they would also go to the state fair and to the diners and talk.

SINGLETON: I agree.

CUPP: That's actually not even true. I mean, only a sliver of Iowa's population participates in the caucuses in 2016.

SINGLETON: Yes. Yes.

CUPP: Fifteen percent turned out for the Democratic Caucus. So I mean, yes, they're involved, they're invested, but the turnout is not actually high.

SINGLETON: Right. It's good PR.

SWERDLICK: Of course not.

SINGLETON: They have good PR.

SWERDLICK: It is.

CUPP: But Shermichael there are parts of the map and the calendar that hurt Republicans as well.

SINGLETON: Yeah, I mean ...

CUPP: California moving up so early. That's not great for Republicans.

SINGLETON: No, it's not.

CUPP: I mean, they can't game the calendar in the map so that either party gets either advantage. Like, this is the map, this is the calendar.

SINGLETON: And I think both sides have to be mindful of this. The electoral map is beginning to change. That's just the reality, right?

CUPP: Right.

SINGLETON: And you're looking at states like Georgia, you're looking at states like Texas that very well in five or 10 years could be blue states. And you're looking at states like Pennsylvania, Wisconsin, and other states that may become solidly red.

CUPP: Yes.

SINGLETON: So that ultimately will change that the electoral strategy and the map count for Republicans and Democrats in future elections.

CUPP: Yes.

SINGLETON: So I'm not particularly concerned with whether Iowa or New Hampshire is first, because in the long run the maps are going to change and the strategy that you've designed to get the number of electoral votes necessary to win in a primary and ultimately in general they will be different then versus what we see today, so I'm not too concern about that.

SWERDLICK: Top it up, Iowa. Top it up.

CUPP: And to play devil's advocate, I guess ...

SWERDLICK: Sure.

[18:40:07]

CUPP: ... do Democrats worried that appearing to discount white voters in Iowa sends the wrong message?

SWERDLICK: I think because Castro knows that he doesn't have a chance here, that he's in a situation where he can say what the more competitive candidates can't.

CUPP: Right.

SWERDLICK: But, yes, let me go back to just you got in the race, you knew the rules about fundraising, about calendar ...

CUPP: Complaining about the process. You're not winning if you're complaining about the process, yes.

SWERDLICK: ... about super delegates. You're not winning if you're complaining about the process. All Democrats should listen to President Obama on this. In 2008, people were skeptical that a black candidate could win in Iowa.

CUPP: That's right.

SWERDLICK: He won Iowa. The Obama campaign, if you think back 10 years ago, they did everything according to an AB question of will this help us win, oh, you don't like that I don't wear a flag pin, flag pin on.

CUPP: It's gone.

SWERDLICK: OK.

CUPP: Right.

SWERDLICK: You don't like me in my shirtsleeves, jacket on. That was - they wanted to win.

SINGLETON: Oh, no, they do want to win but again as I was just saying, the maps are changing.

SWERDLICK: Right. SINGLETON: So David, it really doesn't matter if those states remain

the number one and number two 10 or 15 years.

SWERDLICK: I agree with you that it doesn't matter in terms of like who's going to have a demographic advantage.

SINGLETON: Actual electoral strategy. Of course, not.

SWERDLICK: But to me it has always been silly that two small states have a monopoly on setting the (inaudible) ...

SINGLETON: I think this is Julian Castro looking for attention, S.E., because he's (inaudible) ...

CUPP: I think, ding, ding, ding, ding, but let me also just - we'll end with some facts. The Democrats who wins the Iowa caucus is usually the nominee. It's only gotten it wrong twice in '92 with Tom Harkin, and '88 with Richard Gephardt one.

Not the case for Republicans.

SINGLETON: That's right.

SWERDLICK: Yes.

CUPP: Usually, it does not predict the Republican nominee. Otherwise, we'd have President Santorum or President Huckabee. OK, David, Shermichael, always good to speak to you guys. Thank you so much.

SINGLETON: Thanks, S.E.

SWERDLICK: Thanks, S.E.

CUPP: The President shot at an esteemed career foreign service official, it shouldn't have come as a surprise. He doesn't respect experts. Next up, in defense of people who actually know stuff.

(COMMERCIAL BREAK)

[18:46:24]

CUPP: OK. Never mind that Donald Trump is a self-proclaimed billionaire, Ivy League graduate, certified member of the corporate establishment, by definition part of the elite. He spent his first term attacking anyone who disagrees with him as the establishment.

Whether that was the career foreign service professionals in this week's impeachment hearings or folks in the Intelligence Community. Any number of long gone advisors who dared break ranks with him, people he appointed or hired who got in his bad side went from one of his guys, the best people, to establishment hacks, swamp creatures and deep state traitor.

Establishment under Trump really just means critic. It's also come to me in a war on expertise, knowing stuff and having experienced that something is a blemish, a mark of one's out of touchness with real people. A sure sign of one's disaffection for Trump's America.

That war on so called elitism is corroding our politics. People who care about things like decency, honor, the truth, well, they're wimps and nerds virtue signaling for their own self righteous sense of self. Real men were told Trump's kind of men don't have time for decency, honor and the truth.

No, real men are crass, they're macho, they insult their enemies and lying is just part of the job. That was partly Trump's appeal in 2016. It will likely be part of his appeal in 2020. Joining me now is an elite himself, Joel Stein, who is the author of the new book In Defense of Elitism; Why I'm Better Than You and You're Better Than Someone Who Didn't Buy This Book.

First, I want to get your thoughts on impeach, Joel, because it's related. You wrote in The Washington Post that impeachment is an elitist trap. What do you mean by that?

JOEL STEIN, AUTHOR, "IN DEFENSE OF ELITISM": Well, first of all, clearly, I'm not a real man and I'm OK with that.

CUPP: You're not. I can tell you, you're not.

STEIN: Yes. No, you know that.

CUPP: Yes.

STEIN: Yes. I fear that the way that a lot of Trump supporters and a lot of people in this country are looking at impeachment is the way they look at the elite. And when I talk about elite, I'm talking about, as you put it so well, the intellectual elite, not the money elite.

CUPP: Right.

STEIN: The people who don't want a yacht. They just want to give a TED talk. These are our people.

CUPP: Yes. Yes.

STEIN: And I think that the other people think of impeachment as kind of trickery as lawyerly as people just looking out for themselves in D.C. and playing games and not looking out for the interests of the people. And I feel like this easily could backfire.

CUPP: Yes.

STEIN: Because if you're not going to get Trump out of office, what is the end result? And I fear that it's just going to make a lot of people like Trump more.

CUPP: Yes. I mean it does seem like we, the elitists, are deeply bothered by these amorphous things like lying and cheating.

STEIN: Yes.

CUPP: And Trump defenders not so much, where does that come from?

STEIN: Well, I think that there's a belief among Trump and his supporters that there is a corrupt world. It's a soprano's view of the world and that the elite are really good at corruption and what you need is a leader on your side who's probably equally corrupt, but on your team and fighting the lying with their own line.

And that's a dangerous view of the world, because America is not as corrupt as everyone keeps saying. And things are not nearly as bad as they are. And if you keep saying it is, it becomes that way and then we're in real trouble.

CUPP: Yes. In your book you write about visiting the county in Texas where the highest percentage of Trump voters live.

STEIN: Yes.

CUPP: What would you tell someone like Elizabeth Warren about those people?

STEIN: I would say that those people are scared of you and that you should listen to their pain and not just sum it up economically. I think people who are going through these changes that people like you and I who live in cities don't think are such a big deal, like gay marriage or transsexual rights.

[18:50:09]

These are huge changes that are happening in rural America and they're not comfortable with them. And to just boil it down to economics is wrong. Like people feel like the country is changing ...

CUPP: Or bigotry.

STEIN: All kinds of different changes are happening. If you're a white Christian, you're in rural America, you feel acceleration more than you feel speed. And even though you're still the most powerful group, you have less power than you used to and things have changed. And to not realize that that's happening, I think, is a problem among our people.

CUPP: Well, just as I don't like to paint all Trump voters with a broad brush, I'm wondering if we should be careful not to paint elitist with all of the same brush too. I'm well-educated. I went to Ivy League schools. I live in a city. I'm comfortable, financially. But also I vote Republican most of the time.

STEIN: Oh, yes.

CUPP: I hunt and fish. I know church going folk. I mean, all of us elites are not all the same, right?

STEIN: Well, there's Republican elites and there's Democrat elites, but we all can get along and hang out together. And we all basically live the same way, eat the same foods, believe in the basic things. But I do think this country and Europe too ... CUPP: Yes.

STEIN: ... this is not just America at all and India, all kinds of places are tearing apart from the old conservative liberal sides to an elite versus populist side.

CUPP: Yes.

STEIN: And people like you and I who probably wouldn't have agreed on that much six years ago are agreeing on a lot more now.

CUPP: Totally, right.

STEIN: And if we don't come together against populism, we are going to suffer. If we keep fighting the old fight of who dipped - how much communism, how much capitalism.

CUPP: Joel Stein's new book is In Defense of Elitism, I really enjoyed it. Thanks, Joel.

STEIN: Oh, thanks for reading it.

CUPP: All right. We'll be right back.

(COMMERCIAL BREAK)

[18:55:50]

CUPP: All right. RIP Roger Stone, he isn't dead but his era of dirty trick sure is. Stone was found guilty of lying to Congress and witness tampering this week. Charges included five counts of false statements, one count of witness tampering and one count of obstruction of a congressional proceeding, guilty on all.

The charges stemmed from his efforts to make contact with WikiLeaks during the 2016 campaign. He faces as many as 20 years in prison, if the President doesn't pardon him first. Now, stone has cultivated his own larger than life status as a professional villain; pranking, lying, smearing and self-destructing his way through political circles for decades.

While some found him charming and eccentric, others certainly found him odious and even dangerous. In his own words, I have always said the only thing worse than being talked about is not being talked about. I for one cannot wait to not talk about Roger Stone for a very long time.

OK. A quick programming note, don't miss the HBO Documentary, Nixon by Nixon: In His Own Words which airs right here on CNN. That's at 9 p.m. Eastern. That's it for me. Ana Cabrera and CNN NEWSROOM is next.