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Trump Fights for Must-Win Florida; Audio Reveals Trump's Love of Fighting, Hatred of Losing; Newly-Released Audio Of Extensive Trump Interview; Will Obamacare Price Hikes Hurt Clinton?; Trump Advisers: Stick To The Issues! Aired 8-9p ET

Aired October 25, 2016 - 20:00   ET


[20:00:09] ANDERSON COOPER, CNN ANCHOR: And good evening. Thanks for joining us.

Tonight, perhaps the best evidence yet is what makes Donald Trump tick. It comes from Donald Trump himself.


DONALD TRUMP (R), PRESIDENTIAL CANDIDATE: If you lose a lot, nobody's going to follow you because you're looked at as a loser. Winning is a very important thing. And the most important aspect of leadership is winning. If you have a record of winning, people are going to follow you.


COOPER: That's just a small sample from more than five hours of tape interviews that a autobiographer Michael D'Antonio did with Donald Trump and his ex-wife Ivana and his three oldest kids. He's made them available to "The New York Times". In just a few moments, you'll hear Donald Trump in his own words reveal more what actually drives him to win and why losing for him may be uniquely hard to bear.

First, though, with two weeks to Election Day, his drive to win a state he simply cannot afford to lose -- Florida.

Jim Acosta reports.


JIM ACOSTA, CNN SENIOR WHITE CORRESPONDENT (voice-over): Donald Trump stepped off his plane in Florida to big cheers, having landed what could be a potent issue for the last two weeks of the campaign.

TRUMP: Americans are going to experience another massive double digit hike. Now, they said 25 percent. Forget 20 -- you'll take 25 percent. It's going to be 60, 70, 80, 90 percent. You're going to have to brush up on your negotiation ability, believe me.

ACOSTA: The GOP nominee is seizing on the latest report on Obamacare that find consumers who buy their insurance through the Affordable Care Act will see their premiums go up on average 22 percent next year.

TRUMP: Obamacare is just blowing up.

ACOSTA: Out to show how that spike will affect working Americans, Trump introduced reporters to some of his hotel employees in Florida.

TRUMP: And I can say all of my employees are having a tremendous problem with Obamacare. You folks, this is another group, is that a correct statement? I mean, you look at what they are going through, what they're going through with their health care is horrible because of Obamacare.

ACOSTA: The problem Trump and even the hotel's general manager later acknowledged those workers don't receive their insurance through Obamacare. They get it from Trump.

DAVID FEDER, TRUMP DORAL GENERAL MANAGER: I would say 99 percent of our employees are insured through the hotel. Through our insurance and maybe there's a few that are insured through Obamacare but very, very few because we supply it.

ACOSTA: Still, Obamacare's latest struggles come at a critical time for endangered Republicans like New Hampshire Senator Kelly Ayotte who turned the news into an attack ad against her opponent.

AD NARRATOR: Maggie Hassan can't stand up to her party. She supports the broken health care law that even Bill Clinton called --

BILL CLINTON, FORMER PRESIDENT: The craziest thing in the world.

ACOSTA: Trailing in the polls, Trump is eager for some kind of campaign game changer, conceding to FOX News, he has to win Florida or else.

TRUMP: I believe Florida is a must-win and I think we're winning it. I think we're winning it big.

ACOSTA: And he once again slammed the allegations from the women accusing him of sexual assault.

TRUMP: I'm innocent and I did nothing. There's zero. These were made up. No. Excuse me. These were made up tales.

ACOSTA: In the election's final days, Trump is offering himself as a fighter for every day Americans who he says are being misled by a dishonest news media.

TRUMP: Just about the biggest part of the crooked establishment are these people right back there with the phony cameras. They are a bunch of phony low lives.

ACOSTA: It's an image of a brawler Trump talked up in an interview two years ago.

TRUMP: I love to fight. I always loved to fight.

INTERVIEWER: Physical fight?

TRUMP: Yes, all kinds of fights, physical --


TRUMP: All types of fights. Any kind of fight, I loved it, including physical.

ACOSTA: Back at his golf course in Florida, Trump asked a few of his employees to sing his praises that their tough-talking boss does indeed look out for working Americans.

TRUMP: I better say good or I say, you're fired. I say who is that guy?


ACOSTA: And Donald Trump will be visiting one of his other properties tomorrow. He's scheduled to attend the ribbon cutting of his new hotel in Washington, D.C. You recall, he was at that hotel earlier this year when he acknowledged President Obama is an American citizen -- Anderson.

COOPER: Jim, thanks very much.

Hillary Clinton is hoping that Donald Trump will soon be returning to his hotel business and she will be making history as the country's first woman elected president. So, today, facing headwinds from Obamacare, but sizable advantages elsewhere, including words she'll be getting Colin Powell's vote, Secretary Clinton spent the day in south Florida, trying to keep one staunchly Democratic county blue.

More on that from Jeff Zeleny.


JEFF ZELENY, CNN SENIOR WASHINGTON CORRESPONDENT (voice-over): Hillary Clinton in Florida tonight, opening a two week fight to the finish.

HILLARY CLINTON (D), PRESIDENTIAL CANDIDATE: I feel good but, boy, I'm not taking anything for granted. I'm going to work as hard as I can between now and the close of the election.

ZELENY: She's firing up Democrats in the biggest of all battlegrounds, 29 electoral votes she believes will block Donald Trump's path.

H. CLINTON: Americans are coming together, at the very moment when Donald Trump is making an unprecedented attack on our democracy --

ZELENY: On a two-day Florida swing, Clinton is hitting Democratic strongholds to bank votes through early voting, one way to minimize any pre-election pitfalls like rising health care costs under the Affordable Care Act.

[20:05:10] Her long embrace of Obamacare --

H. CLINTON: Before there was something called Obamacare, there was something called Hillarycare.

ZELENY: -- suddenly could be an 11th hour liability.

As Republicans pounce today, she was silent about it at her rally. In a Miami radio interview, Clinton said millions of Americans now have health care under the law, but acknowledged major shortcomings.

H. CLINTON: The costs have gone up too much. So we're going to really tackle that.

ZELENY: But former President Bill Clinton under fire earlier this month for pointing out flaws in the system.

BILL CLINTON, FORMER PRESIDENT: It's the craziest thing in the world.

ZELENY: Now telling voters in North Carolina health care should be fixed not repealed.

B. CLINTON: Yes, there's something wrong. But you don't want to choose somebody who is the living embodiment of what's wrong.

ZELENY: With 14 days to go, Clinton is in command of the race but bracing for another wave of controversy. A new batch of campaign chairman John Podesta's hacked emails shows even he was flabbergasted about the decision back in 2009 to set up a private email server for Clinton at the State Department.

When "The New York Times" first revealed the private server in March 2015, Clinton friend Neera Tanden expressing outrage at Cheryl Mills, Clinton's chief of staff as secretary of state , who helped sign off on the e-mail arrangement. Tanden wrote Podesta, "Why didn't they get this stuff out like 18 months ago? So crazy." "Unbelievable," Podesta replied. "They wanted to get away with it," Tanden shot back.

Obama, who is heading back to campaign in Florida on Friday, weighing in last night on "Jimmy Kimmel Live" on ABC, reading a Trump tweet and his own response.

BARACK OBAMA, PRESIDENT OF THE UNITED STATES: "President Obama will go down as perhaps the worst president in the history of the United States, exclamation point. @RealDonald Trump."

Well, @RealDonald Trump, at least I will go down as a president.


COOPER: And Jeff Zeleny joins us now from Coconut Creek, Florida.

Has Clinton said anything at all about these premium hikes other than that radio interview?

ZELENY: Anderson, no. Surprisingly, I mean, this is her signature political issue for the last 20 years, ever since that 1993 Healthcare Reform Act. She was utterly silent about it today at the rally here in Florida. Her aides say she doesn't want to litigate this in the final days of the campaign but the reality here is Republicans are litigating it.

Now, she has talked about this a lot on the campaign trail and at debates. She says that she knows it needs to be overhauled and fixed, but not repealed, because that would take away health care from some 20 million Americans.

But, Anderson, this is a political headache that she was not expecting or looking for here in the final days. It's why they want to bank those early votes now before this becomes even more of a controversy -- Anderson.

COOPER: All right. Jeff Zeleny -- Jeff, thanks very much.

More now on why Florida is such a must-win state for Donald Trump. It's such a prize for both candidates.

For that, let's bring in our CNN political director David Chalian.

David, just how important is Florida in this election?

DAVID CHALIAN, CNN POLITICAL DIRECTOR: Listen, it's the biggest battleground prize there is, 29 electoral votes and the candidates clearly know it, Anderson. Take a look at how many times they have been visiting the state since the conventions this summer. Hillary Clinton has been there six times. Donald Trump is on his ninth visit to the state of Florida since the conventions and I'm sure this is neither of their last visits to the state.

COOPER: Let's take a look at where they chose to visit. What does that tell us?

CHALIAN: Yes. I mean, take a look. Donald Trump was in Seminole County. Look at the 2012 results here. This was a county that went seven points for Mitt Romney. He was on a mission to go to a base county, a Republican county, and drum up the vote there.

Not dissimilar from what we saw from Hillary Clinton. She was in Broward County today. Look at this, this was a county that Barack Obama won 67 to 32 over Mitt Romney. She was doing early get out the vote, also deeply blue county. She was there to turn out her base voters.

COOPER: David Chalian, thanks very much.

Let's bring in the panel now. Clinton supporters Jonathan Tasini and Maria Cardona. Jonathan is a former Sanders supporter and host of Working Life podcast, Maria was a senior adviser to 2008 Clinton campaign. New York 1 anchor and resident Trumpologist, Errol Louis, joins us. So does "Washington Post" political reporter, Philip Bump. Also with us, Trump supporters Kayleigh McEnany and Corey Lewandowski.

Let me start with our nonpartisans and then we'll move over to our partisans. Philip, I mean, for Donald Trump obviously Florida is critical. The problem for him is also he's got to get a bunch of other states as well.

PHILIP BUMP, THE WASHINGTON POST: That's exactly right. I mean, Florida is must-win not in the sense that if he wins Florida, he wins. It's a must win in the sense that he doesn't win Florida, he's dead in the water. He's got to pick up a lot of states. He's got to do better than Mitt Romney did in 2012. That's the baseline to think of.

He's losing to Hillary Clinton in North Carolina right now which Mitt Romney won in 2012. Arizona looks like it might be a toss up. Georgia and Texas look closer. All these states he has to defend but at the same time, he still needs to win in Pennsylvania or in Ohio, and/or in Ohio.

There all these states he needs to pick up as well. And right now, the math just isn't there.

[20:10:01] Florida is a must win, but so are a lot of other states.

COOPER: Errol, what's more important for Donald Trump, energizing the base or trying to reach out to undecided voters who may still be out there?

ERROL LOUIS, CNN POLITICAL COMMENTATOR: At this point, with just two weeks left, it's probably better and this is what political strategists, Corey may even agree with this, will tell you, is you got to stick to your plan. There's not a lot of time shifting resources around.

The reality is he still has a path to victory, a very -- I mean, he's got to win Florida. That's tough. That's a battleground. If he can, he's got leads in Ohio or he's within four points in Iowa, and in Ohio. That brings him within 11 electoral votes. At that point, if he can get Pennsylvania, always going to be a stretch for Republicans, if he can get Pennsylvania he's in the ballpark. He wins. If he can flip Nevada, he gets closer and closer.

So, you can't start redrawing all of your strategy, you know, shifting all of your resources all across the country with two weeks to go. That's not rational.

COOPER: Phil, though, I mean, with this Obamacare premiums going up, does Hillary Clinton run out the clock as long as she can on this and try to not mention it until she absolutely has to.

BUMP: Yes. I mean, it doesn't do her any good to talk about it, right? One thing she mastered is not talking about things she doesn't want to talk about. But, you know, it's important to remember, there's already almost 10 million people that already voted, including Florida where Democrats and Republicans have run neck and neck.

A lot of votes banked and something that Hillary Clinton can rely on. Plus, she has a much stronger ground game. She's got a lot of folks that are focused on getting people out to the polls for whom it's probably not going to make any difference this Obamacare.

COOPER: All right. We're going to talk to our partisans after a quick break. We're going to take a break. We'll continue the conversation.

Later, Donald Trump in his own words on what drives him and what scares him the most. We'll bring you what he told his biographer in the last interview of this before running for president. It's very revealing and fascinating stuff when we continue.


[20:15:25] COOPER: We're talking about Florida and why both candidates are fighting so hard for it right now.


TV ANCHOR: You have four events today in Florida.

TRUMP: Right.

TV ANCHOR: That's a must-win for you, correct?

TRUMP: Right. I believe Florida is a must-win and I think we're winning it. I think we're winning it big.

TV ANCHOR: Twenty-nine electoral votes. You can't go the White House unless you win in Florida, you would concede that, right?

TRUMP: I think that's probably true.


COOPER: Donald Trump earlier today.

Back now with the panel. Corey, do you think Florida is a must-win for Donald Trump?

COREY LEWANDOWSKI, CNN POLITICAL COMMENTATOR: I do. Absolutely. I mean, look, if you look at the map that Mitt Romney had, he won 206 electoral votes. You need to win Florida. If you give Donald Trump Ohio and Iowa right now, that leaves him 11 electoral votes short. There's a number of paths to get there as we've heard earlier. There's a Colorado path, there's a Pennsylvania path, there's a Nevada, New Hampshire and second district of Maine path.

And I think what you'll see and what Kellyanne Conway, his campaign manager, has talked about is, look, where they are deploying surrogates. Eric Trump was in New Hampshire today. Donald Trump just announced he's going to be back in New Hampshire and Maine on Friday. He'll be making a west coast swing to Nevada.

They clearly look at this differently than what the other polls are saying. Their internal numbers say it's much closer than what many other people think. What's important is if you look at some of the exit polling or some of the polling that's been done recently, look at the numbers that Donald Trump is getting with the African-American community. The Monmouth poll shows he's getting 16 percent in the African-American community in North Carolina. In Pennsylvania, he's getting 29 percent of the African-American community. In Wisconsin, he's getting 15 percent.

These are unheard of numbers for a Republican. That should really scare Hillary Clinton as this race gets much closer.

COOPER: Maria, does that scare you?

MARIA CARDONA, CNN POLITICAL COMMENTATOR: Well, I think Hillary Clinton should be scared and I think she acknowledged it today where she's not going to take anything for granted. I think that's actually how you win.

COOPER: Should she be scared about the Obamacare premiums going up?

CARDONA: Well, I think that she certainly needs to address it when she talks about it.

COOPER: You do think she needs to address it?

CARDONA: I do think she needs to --

COOPER: Because she's not addressed it so far.

CARDONA: Well, she had a radio interview today where she talked about it. But, look, her position is not new. She said before this is a law that needs to be fixed. It certainly should not be repealed. You have 20 million people who have coverage, who wouldn't have it were it not for this law.

But, yes, there are certain problems that need be addressed. That's not anything new. She needs to talk about it.

COOPER: So, Kayleigh, is this an issue you think that can make the difference for Donald Trump in the closing weeks?

KAYLEIGH MCENANY, CNN POLITICAL COMMENTATOR: Absolutely. Because it's so intricately tied to the economy. You have voters who feel like they are hurting economically. And when you look at facing double digit premium increases that directly affects net home income.

COOPER: You think it changes people's minds, people who were thinking about Clinton but you think --

MCENANY: I 100 percent do. And I think it's been an underexplored issue. I know it came up in your town hall. But it didn't come up in either the first or third debate. There's been no meaningful dialogue on Obamacare and this is a place that directly affects the pocketbook. And when people go to the polls, they will remember that $800 premium in some cases they're going to have to pay.

COOPER: Jonathan? JONATHAN TASINI, HILLARY CLINTON SUPPORTER: But the problem is, a few problems. One Donald Trump is not capable of talking about any issue. If you look at actually all the debates, he can't put together more than three or four sentences that are coherent in talking about an alternative.

The second thing I'll point out is, the Republican Party in general has no alternative to Obamacare. You may remember other than throw people off care and to not have people be covered for pre-existing conditions which Obamacare solved.

Last thing I'll say is, to Hillary Clinton's credit, she has publicly stated that one of the things she wants to do with Obamacare is improve it by offering what would be called a public option. Many of us have said and I think Hillary -- there will be a debate in the Democratic Party about this, the only way to solve the health care charisma in general is go to single payer Medicare for all systems, which is a public option which she supports is a step for us.

COOPER: But, Corey, it doesn't help Donald Trump when today he's saying -- you know, he's got all his employees and saying, hey, look they are having trouble with Obamacare and it turns out they don't have Obamacare because --

LEWANDOWSKI: Because he's fortunate enough to able to provide them health care through his corporate --

COOPER: Right. But is he the best messenger to try to prosecute a case against Obamacare?

LEWANDOWSKI: If you're a Florida resident, 1.53 million people were on the system and you take the Humana option which is one of the insurers down there. You know what your premium increase is? Not the average 19 percent. That's the average across Florida. It's 36.8 percent increase is what the Florida residents will see next year moving forward.

That is devastating if you are a Clinton supporter or an Obama supporter and you're going to the poll and saying, I'm going to see a 37 percent increase. That's 1.53 million

COOPER: Folks have voted particularly in Florida.

LEWANDOWSKI: If I'm Hillary Clinton I'm putting every person I can in the bank right now, because the more this is talked about, the more constraint she should have, because if my premium goes up 37 percent, I'm very concerned.

COOPER: That does seem to make sense, as more people hear about this, the more they'll vote --

CARDONA: Sure. But I think a couple of things, and we talked about this already, especially in Florida.

[20:20:02] There has been already a million people who have voted. Florida is a state that is tailor-made more Hillary Clinton. You have Latinos who are voting right now at 99 percent more than what they voted in 2012.

COOPER: So, you don't think this Obamacare --

CARDONA: I don't know. I don't think this is going to flip people for a couple of reasons. There's not enough time, number one. And number two, to your point Donald Trump is an awful messenger.

COOPER: I didn't say he was awful. I was asking --

CARDONA: No, no, you asked the question, but the point is he's an offensive line messenger. He sounded absolutely clueless about what it was, not even knowing that Obamacare wasn't something his own employees used. So, when that you have a kind of comparison, people are going to say, at least Hillary Clinton is addressing the problem, not wanting to take it away from me, because let's remember 80 percent of the people are not going to be affected by these hikes.

COOPER: The question is, will people believe they want to throw the whole thing out and start with something Republicans are going to offer or just amend what already exists?

TASINI: Well, people with look at history and know that the Republicans never offered anything but the free market solution which was devastating to people. Tens of millions of people did not have healthcare coverage. I'll give you a good example of what's happening now in California.

One of the reasons the premiums are going up is because of drug prices. Republicans opposed any attempt for Medicare and health plans in the exchange to negotiate over drug prices. There is a proposition in California, Proposition 61, which is attempting to reduce drug prices and the pharmaceutical industry spending $100 million, the pharmaceutical industry which is funding the Republican Party, big donors to the Republican Party is spending a $100 million to defeat this.


COOPER: What Donald Trump says is it is basically free market but free existing conditions are going to be covered and yet, he doesn't explain how preexisting conditions can be covered unless there's a mandate.

BUMP: Right. Well, I mean, it's -- you know, the Republican Party has been trying to put together a plan to be the replace part for repeal and replace for years now. There isn't really a very good option or haven't been many robust options --

TASINI: There's none.

CARDONA: Seven years.

BUMP: I do think it's worth pointing two things about this that I think will lessen the political effects over the course of the next two weeks. First is that most of the people on the Obamacare exchanges are subsidized. You're not going to see this big increase in their own pocketbook, but secondarily, this is also 2017 increase that's going to happen --

COOPER: Kayleigh, you said there is a good option.

MCENANY: Yes, there's this Republicans haven't put forward a plan. Paul Ryan has actually put forward a very detailed, very good plan, involving health care savings accounts --


MCENANY: And for Jonathan to sits there and advocates for the public option, two words: the Veterans Administration. We've had a so called government-run healthcare system and guess what? A lot of veterans died waited for the care, so --

TASINI: Actually, the V.A. --


MCENANY: -- further down this road is a very poor one and that will (INAUDIBLE)

TASINI: Actually, the public option best explained by looking at Medicare, and there is nobody who was on Medicare -- Medicare needs to be improved. But Medicare has kept millions of seniors from going bankrupt and from going into poverty. If he had Medicare for all like all industrialized countries, like Australia, like many of the European countries, we would not have this problem.

COOPER: We got to take a break. I want to thank the panel. Coming up, we have breaking news. New insight in Donald Trump's thought process. We've obtained hours of interviews of Trump two years ago with a journalist who wrote a biography of him. He talks about fame, his love of fighting and his marriages.


INTERVIEWER: When you think about balancing your ambitions and your relationships with people you love, what's changed over the years?

TRUMP: Well, it's very hard for somebody to be married to me.



[20:27:29] COOPER: Some new audio that had just come out contains some pretty fascinating moments and insight into Donald Trump's thought processes and also his first wife Ivana. The audio is from extensive interviews that journalist Michael D'Antonio did with Trump two years ago. The tape showed Trump loves fighting, hates losing and will not readily admit to failure. I mean, this was even before he announced he was running for president.

Our Kyung Lah has more.

(BEGIN VIDEOTAPE) TRUMP: You vote for her, you're crazy, OK? I'll tell you. She is the worse.

KYUNG LAH, CNN NATIONAL CORRESPONDENT (voice-over): It's a Donald Trump we don't often see. Not campaigning but instead contemplated, like when he talks about how he won't accept losing.

TRUMP: You can be tough, and ruthless and all that stuff, and if you lose a lot, nobody is going to follow you, because you're looked at as a loser. Winning is a very important thing and the most important aspect of leadership is winning. If you have a record of winning, people are going to follow you.

LAH: As we've seen this selection, this is a leader who enjoys a flight.

TRUMP: I like to punch him in the face I'll tell you.

LAH: And the tapes reveal that willingness began as a child.

INTERVIEWER: In eighth grade?

TRUMP: And I loved to fight. I always loved to fight.

INTERVIEWER: Physical fights?

TRUMP: Yes, all kinds of fights, physical --


TRUMP: All types of fights. Any kind of fight, I loved it, including physical.

LAH: Ex-wife Ivana Trump also sat down for a rare interview. Ivana explained how six months into their relationship, she saw how Trump reacted when she outskied him.

IVANA TRUMP, EX-WIFE OF DONALD TRUMP: And then the ski instructor I told him, "Don't tell Donald that I can ski, OK? Because his ego, it's so big. He's not able to going to ski.

I went up. I went two flips up in the air, two flips (INAUDIBLE) in front of him. I disappeared.

Donald was so angry. He took off his skis, his ski boots and walked up the restaurant.

INTERVIEWER: So he left you?



IVANA TRUMP: He could not take it. He could not take it. He went foot bare up to the restaurant and said, "I'm not going to do this (EXPLETIVE DELETED) for anybody, including Ivana." INTERVIEWER: Oh, jeez.

IVANA TRUMP: He could not take it, that I could do something better than he did.

LAH: For Trump, everything is a competition, especially business.

TRUMP: I never had a failure, because I always turned a failure into a success.

LAH: The theme weaves through his interviews, refusal to acknowledge any business failures.

[20:30:05] TRUMP:: I bought something -- I throw out into a bankruptcy. I made an unbelievable deal. Wiped out a lot of the debt. Came back. The next day I read the story. "Trump files bankruptcy". I get all these people that don't understand business saying oh did you go bankrupt. Do you understand that?

UNIDENTIFIED MALE: You talks about this a lot.

TRUMP: I do. I always do.


TRUMP: Because I tell you why I do. What always bothers me is false stuff. Untruths. That bother me.

UNIDENTIFIED FEMALE: But what doesn't bother him? Fame. Trump admits he needs it.

TRUMP: It's happened from -- from the time I was fairly young. It just happened.

UNIDENTIFIED MALE: Did it unnerve you at first?


UNIDENTIFIED MALE: Or make you feel unsafe ever.

TRUMP: No. I think what would unnerve me if it didn't happen.

LAH: Trump said he doesn't see much need more reflection but takes a moment to talk about marriage.

UNIDENTIFIED MALE: When you think about balancing your ambition and your relationships with people you love, what's changed over the years?

TRUMP: Well it's very hard for somebody to be married to me.

LAH: Ex-wife Ivana and her interviews says what ended after theirs after three children with him, Trump's affair with Marla Maples.

IVANA TRUMP, FORMER WIFE OF DONALD TRUMP: She's a stupid girl. She doesn't have a brains. I have no idea what Donald was doing with her. But she broke us over marriage because immediately when I find out his affair, I file for divorce.


IVANA TRUMP: I was the one, yeah. Because if you cannot trust your spouse, you know, well it is over.

LAH: Trump up ended the presidential election with much more than fiery rhetoric. The interview show he did it with a singular unyielding belief in himself.

TRUMP: The most important thing is being able to have the proper vision and then never quitting. You know, a lot of people say oh you can never give up. Well, you can give up if you have a stupid vision. So I always say vision is the most important thing. You need the proper vision and then you have to have the ability to get it done.

LAH: Kyung Lah, CNN, Los Angeles.


COOPER: And this recording is from 2014 when Pulitzer Prize-winning reporter Michael D'Antonio interviewed Trump and his family. Michael is the author of "The Truth About Trump" and he gave us the recordings.

I spoke with him a short time ago.


COOPER: It seems like so much of Donald Trump has been influence influenced b y his father and his father was all about, you know, fighting back, being aggressive. What else do you think he took away from his dad?

MICHAEL D'ANTONIO, TRUMP BIOGRAPHER: Well I think this whole idea of being super tough, you know ...

COOPER: That comes from his father?

D'ANTONIO: Never giving up. When Donald said to me you hit me, I hit you back 10 times harder. That's Fred Trump. And also the thing that never left me was Donald telling me this story about him being sent away to the military academy. And it was a matter of this kid is acting up at school. We're going banish him.

COOPER: Really?

D'ANTONIO: Yeah, and all of a sudden the two sisters and two brothers are cozy at home in this mansion attended by servants and ...

COOPER: Trump was the only one sent to away.

D'ANTONIO: He was. And I think it's -- it may have suited him. You know, he might have been the kind of rambunctious kid that the parents felt they needed the discipline. But Fred's toughness and his coolness. I think he was a pretty cold guy too. I don't think there was a lot of warmth and love flowing.

COOPER: It is interesting because Trump often talks about, you know, how his dad was based out in Queens and how he wanted to come to Manhattan. I mean it's clearly I don't know if it's a -- maybe it's too far to say it is a criticism of his father, but he does seem to point out that he sort of came to an area his father never ventured into.

D'ANTONIO: Absolutely. I think he wanted to one up them.

COOPER: One up him.

D'ANTONIO: You know, so there's a kind of exceeding the dad saying that went on, even though Fred was one of the richest men in America. His fortune was $200 million.


D'ANTONIO: So this is not a guy of no consequence.

COOPER: And also, I just wanted the things that Hillary Clinton kept sort of poking of Donald Trump during the debate, by saying your father gave you $14 million to start out and Donald Trump says that is just not true.

D'ANTONIO: It's much bigger than that.

COOPER: It was bigger than that?

D'ANTONIO: Yes. The father arranged for all the political connections which were priceless and the financing for his first project which was more than $40 million. So Donald was born on third base and likes to take credit for getting there but his father put him there.

COOPER: He also doesn't seem to look back at the past very much.

D'ANTONIO: No. You know, he said to me I don't like to analyze myself or think about the past because I'm afraid of what I'll see. So, you know, unlike most of us who look to learn from our mistakes and may reflect on what well what went into making me this kind of person? Donald is straight ahead and his very future oriented.

You know, he ended our time together prematurely. We were supposed to meet six times and instead we only met four for formal interviews and it was just at the moment when I felt he was opening up. When he was starting to tell the truth. And I -- at the end of our last interview I said, you know, I kind of like you today. And he went back a little bit and then smiled. And I almost felt like this is the thing that people see in Donald that they like but he doesn't let it show very often.

[20:35:24] COOPER: He does have a charm -- I mean in a, you know, one-on-one saying and I think when got a glimpse of that even at the end of the second debate, you know, which have been a very contentious debate. When this person in the audience asked, you know, can you say something nice to your opponent. He sort of a sense him which seemed very genuine about Hillary Clinton being a fighter and doesn't give up and the he respects that at about her.

D'ANTONIO: I think it was genuine and this is the frustrating thing for those of who us who have spent time with Donald. His both of his ex-wives said the same thing to me that they thought they could kind of spark that thing in him and keep it alive and help it to grow and it never happened.

COOPER: There is also a real -- I don't know if it is a fear of humiliation but humiliation seems to be a recurring theme.

D'ANTONIO: Yeah, this is why he talks about how they're making fools outs of us. Our foreign competitors or they are laughing at us.

COOPER: Which is something he's been saying and putting in, you know, in newspaper ads drawing back.

D'ANTONIO: Personal life.


D'ANTONIO: You know, so why does this guy always think about humiliation? Why does he worry that people are laughing at him?

I suspect that somebody laughed at him a lot when he was young and he's been trying to make up for it ever since.


COOPER: We have more with my interview of Michael D'Antonio in the next hour of "360". Similarly fascinating insights to Donald Trump.

Just ahead, the fallout from price hikes in ObamaCare premiums, we'll talk about that a little bit, Donald Trump and other Republicans are blasting Hillary Clinton, President Obama. Questions will they be able to leverage sticker shock into actual votes?


[20:40:46] COOPER: As we've said, millions of Americans who get health insurance through ObamaCare just an October surprise not a good kind. Their premiums are said to climb an average of 22 percent next year. President Obama of course considers the affordable care act to be one of his signature accomplishments. And Republicans have been down and dismantled since it was passed in 2010. And now just two weeks from election date, they have new ammunition.

Here is Michelle Kosinski.


UNIDENTIFIED FEMALE: Does this produce the payment you are feeling?

MICHELLE KOSINSKI, CNN CORRESPONDENT: ObamaCare sticker shock 22 percent more on average in premiums this coming year. Compared to only a 7 percent increase in 2016 and throw more fuel onto the Republican fire to repeal it.

D. TRUMP: ObamaCare is a disaster. You know it. We all know it.

GOV. MIKE PENCE, (R-IN) VICE PRESIDENTIAL CANDIDATE: President Obama last week compared ObamaCare to the Samsung Galaxy 7 phones that have spontaneously burst into flames.

Well, what a coincide Mr. President, because that's exactly what we're going to do with ObamaCare. We're going to pull it off the market.

KOSINSKI: The numbers in some cases are staggering. Arizona's average increase will be 116 percent. So Indiana's premiums will actually go down by 3 percent. The Democratic governor of Minnesota where premiums will prize 50 to 67percent declared.

GOV. MARK DAYTON, (D) MINNESOTA: The reality is the affordable care act is no longer affordable.

KOSINSKI: Today, the administration pushing back saying the vast majority of people on ObamaCare won't feel those increases.

SYLVIA BURWELL, HEALTH AND HUMAN SERVICES SECRETARY: 85 percent of those folks actually have the tax credits or the subsidies that help them and those subsidies are designed to move as premiums move. So for those folks they will be insulated from those changes.

KOSINSKI: Insurers are having trouble affording all those who signed up but who have more health problems than expected. Some major insurers have pulled out in some states all together, not enough young, healthy people are joining to offset those cost. That means now fewer choices and higher rates.

The White House agrees there are issues but focuses on the positives. More Americans covered. No lifetime limits. No more denial of coverage for pre existing conditions. And according to the latest government analysis, most people are able to find an affordable plan. The president continues to sell it.

BARACK OBAMA, PRESIDENT OF THE UNITED STATES: Now is the time to move forward. The problems that may have arisen from the affordable care act is not because governments too involved in the process. The problem is that we have not reached everybody and pulled them in.

KOSINSKI: Michelle Kosinski, CNN, The White House.


COOPER: Well, a lot to talk about. Joining me now, CNN senior political analyst and former presidential advisor David Gergen. Also chief political analyst Gloria Borger.

So David, I mean Trump is obviously trying to use the rise in ObamaCare care rates to chip away at Clinton's lead. Do you see that working, because Michelle reported there was some big increases in premiums? DAVID GERGEN, CNN SENIOR POLITICAL ANALYST: Well an in an ordinary campaign Anderson, this would be big, big news and it would hurt the in competent effect Hillary Clinton and her campaign. Because after all that the Republicans Trump have been -- can say for long time we're going to see this kind of spikes and when the Obama people come back and say that well, you know, a lot of people are going to get subsidies, who are going to pays for their subsidies. Taxpayers do.

COOPER: Right.

GERGEN: So if the money comes out of somebody's pocket to pay for all this. But having said that, first of all Trump has run such an incendiary campaign, I think it's really difficult to out of pry people away. And secondly, he himself fumbled when we went out today to talk about this. He didn't say -- he first talk about all the agony his employees were going through because of ObamaCare. He didn't seem to realize that he in fact, his company was actually covering a number of people. The side was the story the subsequent damage control story. So the whole thing is that, I think is going to have less impact than what ordinarily occur.

COOPER: Yeah, I mean Gloria, he certainly step on, you know, his ability which yet again raises question is he the best messenger to, you know, effectively prosecute the case against ObamaCare and against Hillary Clinton on this?

GLORIA BORGER, CNN CHIEF POLITICAL ANALYST: ObamaCare has always been an issue of his but not his signature issue like building the wall for example. And he clearly doesn't have a lot of facility in terms of talking about healthcare is, you know, as David was pointing out. I think a problem he's got also is 7 million people have already voted. And I think that the people who hate Obama and ObamaCare are already Trump voters.

[20:45:18] So the question is how many undecided voters or Independent voters could this potentially move and at this point I

think the cake is kind of baked on that issue. People have decided on ObamaCare. And also he's not really the one to prosecute the issue because he can't stay on a single message. He had a revealing interview with Rush Limbaugh today in which he said people want me to stay on ObamaCare. But I have to defend myself on the women issues.

COOPER: Right.

BORGER: Limbaugh asked him about it. And he just admitted it. Other people say stay on jobs. Stay on ObamaCare and repealing and replacing it. So I guess it is two theories. And he said I would rather fight it. People say you shouldn't do that and just go along and by fight it he means, fighting it on the women front. So he hasn't given up on that.

COOPER: And David, when Trump says as he often does, that he would repeal and replace ObamaCare, the other question is what he going to replace it with? And he really offer a lot of specifics and he also says that he's going to -- that pre existing conditions are going to get covered which is just hard to square that? GERGEN: I think that's right Anderson. And what we do now know is that some sort of national healthcare that applies to everybody is going to be our future. We're not going to go back to the system we had before. And the Republicans, you know, have the opportunity here to devise and show us a market base kind of plan, one with a lot of incentives and say hey here is a better way to do it. But, you know, Trump hasn't come up with that plan.


GERGEN: And he doesn't have a Republican alternative that he's advancing. So it's -- I think Gloria is absolutely right. He doesn't have a lot of facility in talking about something ...


GERGEN: ... which is actually very fundamental to his campaign.

COOPER: Yeah, we got to leave it there. David Gergen, thank you. Gloria Borger as well.

Just ahead, Trump supporters in the pivotal state of Florida talk about issues that are most important to them and which have Donald Trump's policies they like most.


[20:51:08] COOPER: As we said in Florida today, Donald Trump slammed Hillary Clinton and President Obama were big price hikes in ObamaCare premiums. But he was quick to attacking so-called phony polls, rigged elections and the women who have accused him of sexual assault.

For months many of his advisors and surrogates as Gloria pointed in Rush Limbaugh's as well, then urging him to ditch the side bar attacks and sticks to the issues.


D. TRUMP: I think that, frankly, I'd like to discuss the issues. I'm not looking to kick anybody out or be nasty to anybody.

BEN CARSON, (R) FORMER PRESIDENTIAL NOMINEE: Like I've said many times, we need to talk about the issues.

UNIDENTIFIED FEMALE: People do want to talk about these issues.

KAYLEIGH MCENANY, TRUMP SUPPORTER: I think voters are voting on issues.

KELLYANNE CONWAY, TRUMP'S CAMPAIGN MANAGER: I think Donald Trump is at his very best, at his very best when he talks about the issues.

MELANIA TRUMP, DONALD TRUMP'S WIFE: And he talks about the issues. And that's what American people want to hear. It's about issues. About jobs.


COOPER: That advice the often ignored, though, by Donald Trump. But we wanted to know just what exactly are the issues his supporters want to hear him talking about?

Randi Kaye went to find out.


RANDI KAYE, CNN CORRESPONDENT: What exactly are the issues that bring supporters to Donald Trump? For some of them at his rally in Florida, it's the Second Amendment.

How do you feel about his stance on guns? What does that mean? Thumbs up?

IAN SMITH, TRUMP SUPPORTER: I am thumbs up Second Amendment. I love my guns.

KAYE: This Trump supporter also believes he will protect her right to own a gun.

SUSANA WRIGHT, TRUMP SUPPORTER: I like that he wants to support the average citizens' right to own guns and protect ourselves not only from criminals, but from our government, if they would go dictatorship or go too much control.

KAYE: Voter Ian Smith likes Trump's talk of sealing our borders and imposing term limits for Congress, too. But when pressed about why he likes Trump's plan to repeal ObamaCare, Ian was short on details.

Have you -- do you know what his plan is or no?

SMITH: I do.

KAYE: Do you want to share?

SMITH: It's top secret.

KAYE: Now you sound like Donald Trump.

SMITH: I'll tell you when I get in there.

KAYE: This woman told me she also likes Trump's idea to end ObamaCare, but when our conversation turned to trade, our interview went south.

UNIDENTIFIED MALE: Evening the playing field will help. Let them pay to bring their goods in here, like we pay to take our goods to them for export. Let them pay to import.

KAYE: So you're all for him renegotiating NAFTA and getting rid of TPP?


KAYE: Yes.

UNIDENTIFIED MALE: OK, there you go.

UNIDENTIFIED FEMALE: I know you're trying to make us look stupid, right?

KAYE: No, I'm actually -- really? No. I'm actually doing a story about what policies.


KAYE: People are attracted to.

UNIDENTIFIED FEMALE: Well, you looked at our shirts and said ...

KAYE: I thought we were having a nice discussion, actually.


KAYE: This man may have prompted that, but recording our every move, accusing us of asking gotcha questions and angry we weren't wearing CNN identification.

Have you identified who you're with? Have you identified who you're with?

UNIDENTIFIED MALE: I'm an independent media.

KAYE: OK, well, how am I supposed to know that?

He made sure to alert everyone we interviewed before we could that were CNN until it backfired with this woman.

UNIDENTIFIED MALE: CNN interviewing you.


KAYE: Great, thank you. What brings you out to see Donald Trump? What policy attracts you?

NEWBOLD: I like the fact that he is pro-life. I like the fact that he is pro-constitution, and I'm all about creating jobs in America, for Americans.

KAYE: She isn't sold, yet, though on Trump's immigration policy.

NEWBOLRD: There's still some gray areas. I don't understand. And I want him to flesh that out a little bit more.

KAYE: Immigration is a huge draw for this voter.

AMANDA MURPHY, TRUMP SUPPORTER: When we look at his immigration policy, what he is saying is extreme vetting. Now, that does not mean religious vetting. That means extreme vetting. I want a policies in place so that we're doing what we need to know to make sure that Americans are safe. KAYE: In the end, we found many here who, despite their unwavering support for the Republican nominee, could not name a single policy Donald Trump stands for.

[20:55:02] But what policies do you like of his?


KAYE: What do you like the best? Is there a specific policy that you like that he's put forward? Do you not want to talk about that?


COOPER: And Randi joins us now from Orlando, Florida. It is interesting that just two weeks before the election, some of the supporters, you know, don't name a particular policy. Maybe it's more the character they like, the personality of Donald Trump, the strength that they believe he exudes.

KAYE: Absolutely, Anderson, and many of them actually, when I asked them about policy, sounded just like Donald Trump. They would say to me, all of his policies are great. They're all going to make America great again. Everything is going to be wonderful, but yet they still couldn't name a specific policy that they support.

Now, there were those who could name policy, as you saw. And those people were really passionate about the fact that Donald Trump says he's pro-life. They certainly like the fact that he's still talking about building a wall. They like the fact that he's going to -- he's saying that he's going to appoint like-minded justices to the Supreme Court. They like all of that.

But still there are people who just two weeks out now from Election Day, want to hear more. I asked one woman about Donald Trump's plans for ISIS, saying that he was going to bomb them and going to bomb the oil fields, and she admitted, you're right, he doesn't have a plan for ISIS, but she's convinced that he's going to surround himself with smart people, smart generals, and he will, eventually, have a good plan for ISIS if he is, indeed, in the White House.

Another woman I talked to about Social Security. And she said, Donald Trump keeps saying that he's going to stage Social Security, he's going to make it great again, but she still wants to know how, Anderson.

COOPER: All Randi Kaye, Randi thanks very much.

Just ahead on this two-hour edition of "360," Donald Trump pounding the trail in the must-win state of Florida, slamming President Obama with a surge in ObamaCare premiums. Can he turn the sticker shock into votes?

We'll look at that ahead.