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ANDERSON COOPER 360 DEGREES

Donald Trump's Federal Income Tax Documents Revealed; Trump Denies "New York Times" Report, Saying He Paid a Lot in Federal Income Taxes; One on One with Biden Deputy Campaign Manager; Interview with Tony Schwartz on Latest Trump Bombshell; Presidential Debates Over the Years; John Lewis, Good Trouble. Aired 8-9p ET

Aired September 27, 2020 - 20:00   ET

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


[20:00:12]

ANDERSON COOPER, CNN HOST: Donald J. Trump paid nearly 10 Times more money to get his hair styled during his years in "The Apprentice" than he paid in federal income taxes in 2016. Yes, $70,000 on hair. A lot of work.

That's just one item from a massive piece of investigative reporting out tonight in the "New York Times" on how little the president has paid and how financially strapped he actually is. The headline reads, "Long-concealed records show Trump's chronic losses and years of tax avoidance." Here's the lead. "Donald J. Trump paid $750."

I keep wanting to say $750,000 but it's not. He paid $750 in federal income taxes the year he won the presidency. In his first year in the White House he paid another $750.

The "Times'" Susanne Craig, Russ Buettner and Mike McIntyre shared the byline. They write, quote, "The 'New York Times' has obtained tax return data extending over more than two decades for Mr. Trump and the hundreds of companies that make up his business organization including detailed information from his first two years in office. It does not include his personal returns for 2018 or 2019."

Their reporting, which is fascinating, and I urge you to read it, details what the reporters characterize as, quote, "the hollowness but also the wizardry behind the self-made billionaire image."

Joining us now CNN's Kara Scannell who's done extensive reporting of her own on Donald Trump's financing.

Kara, from your own reporting, what did you learn about how the president's businesses are losing money and also how he manages to pay so little in taxes?

KARA SCANNELL, CNN WHITE HOUSE CORRESPONDENT: Well, that's one of the most interesting parts of "The New York Times" reporting is that they describe one of the means and methods that the president had done this. They said that he had made about $400 million from being on "The Apprentice." Not income he had made from any of his actual buildings that he owned or golf courses that he owned. But he made $400 million from "The Apprentice" and then took that

money and funneled it into risky businesses and into new businesses and into some that he already owned. And then he took the losses that those businesses were generating and used that to reduce his tax bill. So it wasn't through, you know, new income that he was making. It was this method and this scheme that he was trying to just use from the "Apprentice" to then get these losses.

And another way that he had reduced his taxes, according to "The New York Times," was by writing off a number of expenses including $100,000 in linen and silver at Mar-a-Lago, $70,000 on haircuts, and about $200,000 in landscaping at Mar-a-Lago. So the president was taking his expenses, reducing his tax bill. And one other method that the "Times" writes about is that he had paid more than $700,000 to his daughter Ivanka in a consulting contract as a way to reduce his tax bill, Anderson.

COOPER: Right. While she was employed by the Trump Organization, so he's paying -- you know, I guess she's getting a salary or whatever she gets from the Trump Organization and in addition as a consultant, she's getting -- and that was revealed because she had to reveal that when she started working at the White House.

I mean, is it clear how much debt the president has and -- I mean, and why that matters is because some of that, according to the "Times," is going to be coming due in the next couple of years, and if he's president, the question is, what's he going to do in order to make that money?

SCANNELL: That's right. That's the big question here. I mean, he's got $300 million in loans that he is on the hook for, for many of his properties. Those are due in about four years. And what "The New York Times" also wrote about is this audit that the president has said he's been under and why he couldn't disclose tax returns. They said that it has to do with a tax refund and that if the IRS were to rule against the president that he would be hit with a $100 million tax bill, so that's potentially $400 million that the president could be on the hook for in the next several years.

And, you know, at the same time that his businesses are not making that much money and only, frankly, made worse by the pandemic and the impact that has had on the actual businesses that he's involved with including his hotels. So, you know, it really raises a lot of questions about how he would go about making this money when he is potentially on the hook for $400 million.

COOPER: Yes. Kara Scannell, appreciate it. Thanks.

Want to go next to CNN's John Harwood at the White House.

John, what's the reaction from the White House?

JOHN HARWOOD, CNN WHITE HOUSE CORRESPONDENT: Anderson, the reaction has been entirely on brand from President Trump. When he was asked at a news conference this afternoon, he ducked on the specifics of "The New York Times" story, he deflected by saying he had paid a lot of state income taxes as opposed to federal income taxes. He denounced "The New York Times" as biased, said that they're going after him because he's a conservative Republican, and he denounced the story itself as fake.

(BEGIN VIDEO CLIP)

DONALD TRUMP, PRESIDENT OF THE UNITED STATES: Yes, basically -- well, first of all, I paid a lot and I paid a lot of state income taxes, too. The New York state charges a lot and I paid a lot of money in state.

[20:05:06]

It will all be revealed. It's going to come out but after the audit -- after the -- I'm being -- they're doing their assessment. We've been negotiating for a long time. Things get settled like in the IRS. But right now when you're under audit, you don't do that. So we're under audit. But the story is a total fake and all of this -- you know, we had the same exact questions usually asked by the same people and that took place four years ago. You remember.

(END VIDEO CLIP)

HARWOOD: Now, of course we all remember that Hillary Clinton brought up the issue of whether Donald Trump paid taxes in their debate four years ago in the 2016 campaign, and when that happened the president bragged about it.

COOPER: Yes, he did. He said --

(BEGIN VIDEO CLIP)

HILLARY CLINTON (D), FORMER PRESIDENTIAL CANDIDATE: The only years that anybody has ever seen were a couple of years when he had to turn them over to state authorities when he was trying to get a casino license and they showed he didn't pay any federal income tax. So --

TRUMP: That makes me smart.

(END VIDEO CLIP)

HARWOOD: Now the question is whether all those blue-collar voters and taxpayers who back the president are going to think that they've paid more income taxes than him because he's smarter than them or because of something else? Joe Biden has framed his presidential campaign as Scranton versus Park Avenue. And you can bet, Anderson, he's going to bring up this issue in their debate on Tuesday night.

COOPER: What's also interesting, John, and I've said this before, is that, you know, yes, as you said, Biden is arguing this is Scranton versus Park Avenue, but even for Park Avenue, according to "The New York Times," this kind of -- I mean, paying $750 that is incredibly rare. I think "The Times" reported something along the average of people in that .0001 percent of the tax bracket of income generally pay about 24 percent in federal income tax. So paying nothing or $750, that's even rare for the rarest of the rare. HARWOOD: Well, Anderson, there are really two different issues here.

One of them is the shenanigans that rich people can get away with to avoid paying taxes. That's one line of attack. But the other is whether the image of success and affluence that Donald Trump has sold himself as possessing as an argument for why he could turn the country around, whether that whole thing is a fake and he's vulnerable on both those counts.

COOPER: Yes. I mean, according to "The Times" he's received hundreds of millions of dollars, I think it was $300 million to $400 million from his father over the years starting at age 3. Trump has always claimed, though, you know, he only got a couple million, I think, which is, you know, more than anybody, most people.

John Harwood, thanks very much. Appreciate it.

Joining us now investigative reporter David Cay Johnston, author of "The Making of Donald Trump."

David, thanks for being with us. Certainly much has been made about what the public would learn if President Trump made his tax returns public. At least part of that question has been answered by reporting from "The New York Times."

What conclusions do you think -- or what conclusions do you draw based on what we've learned?

DAVID CAY JOHNSTON, AUTHOR, "THE MAKING OF DONALD TRUMP": Well, Donald took enormous deductions in 2008 and 2009, $1.4 billion of deductions, and there's nothing I see in "The Times" reporting that would explain deductions of that size. Now why is that important? Well, Donald has been tried twice for income tax fraud. A story I broke five years ago. And he lost both of those cases. He just made up deductions in that case.

And one of the implications of "The Times" story is that he may have just made up deductions. There are questions of, specifically in "The Times" report, about whether improper deductions were taken for certain kinds of legal fees that are personal and whether possibly there was a disguised gift that was turned into a tax deduction involving Ivanka.

There's a lot here, Anderson, that suggests that the Manhattan grand jury is looking at serious (INAUDIBLE).

COOPER: Yes, I don't know much really about tax law at all but if what he's doing -- I mean, that any parent would, you know, ensnare their child in some tax scheme, if that is in fact what this is, is, you know, says something about the parent. But according to this Ivanka thing, she was an employee of the Trump Organization. She's getting hundreds of thousands of dollars as a consultant, so she gets the benefit of that and it's him passing money to her that's, you know, not taxed in the same way that it might be if it was a gift and he takes it as a tax deduction.

JOHNSTON: Right. And you have that exactly right. You can pay reasonable compensation to someone. And that's likely to be an issue. The more important issues are likely to be, however, things like Don Jr.'s legal bills and some other legal bills being charged as tax deductible expenses which would not be appropriate. I think it's also significant $750 over two years, according to "The Times" is just a plug-in number. Line 56 of your tax, that's just a plug-in number.

[20:10:06]

It's not a real figure there. So those are really years he probably paid no income tax. This does make it crystal clear why Donald wants to hide his income tax returns from us and "The Times" doesn't have his returns. They have what's called return information. The state of New York and the IRS share information. There are other people who would have this information for various reasons.

You can believe, and I can tell you as a longtime former reporter for "The New York Times," this story was gone over by editor after editor after editor. I don't -- I did stories that had gone 30 editors weighing in on them and all of it will hold up just as the 2018 story the "Times" did held up my 2017 coverage of Donald's 2005 tax return has held up.

COOPER: What still don't we know? What questions are still out there about his taxes that voters deserve to have answered?

JOHNSTON: Well, I think the single most important question is to what degree did Donald Trump get money from foreign governments or foreign entities? The oligarchs basically are the biggest criminal gang in the world. They report to their boss, Vladimir Putin. And to what extent -- we know that Trump got money from oligarchs. We know that there are cases I and others have written about these deals were not normal business deals. They make no sense when examined as business deals, but they make perfect sense as either money laundering or payoffs.

The second thing we need to be concerned about is that Donald has personally guaranteed over $300 million of loans that would come due during a second Trump term. Well, do you think any bank is seriously going to go after the president of the United States if he doesn't pay his bills? And that's been Donald Trump's pattern throughout his life. He borrows money, he doesn't pay his bills. He doesn't pay his vendors who sometimes go out of business.

He cheats his workers. He cheats governments, and he has this well- established history that's in my writings about him of hiding records, lying and denying about records, and fabricating tax deductions.

COOPER: I remember riding in an Uber, I think it was, in Atlantic City a year or two ago and the driver was a contractor who had done work on, you know, the resort or the Aladdin, I guess it was, and got stiffed.

JOHNSTON: The Taj.

COOPER: Yes. The Taj, and never got paid. Went out of business.

David Cay Johnston, appreciate it. Fascinating reporting from you for a long, long time. Appreciate it.

Coming up next, what does the Biden campaign make of his blockbuster report and how will it factor into Tuesday night's debate? We'll ask one of his top advisers.

And later, the man who helped make Donald Trump the Donald Trump we all know, author Tony Schwarz ahead.

(COMMERCIAL BREAK)

[20:17:03]

COOPER: Tonight's "New York Times" reporting on the seemingly endless ways in which the president has avoided paying taxes completely changed our plans, to spend a nice couple of hours talking about Tuesday's upcoming debate. All is not lost because by now it is pretty safe to bet that the story will come up in Cleveland Tuesday night.

And joining us now is Kate Bedingfield, deputy campaign manager and communications director for the Biden campaign.

First of all, I'm wondering what the campaign's reaction to the reporting from "The Times" is about President Trump's taxes.

KATE BEDINGFIELD, BIDEN DEPUTY CAMPAIGN MANAGER AND COMMUNICATIONS DIRECTOR: Well, thanks for having me, Anderson. I mean, look, it's the latest reminder how clear the choice is here between -- in this race between Park Avenue and Scranton. You have in Donald Trump a president who spends his time thinking about how he can work his way out of paying taxes, of meeting the obligation that every other working person in this country meets every year.

You know, with Joe Biden you have somebody who has a completely different perspective on what it means to be a working family in this country. You know, if you're a teacher, if you are a firefighter working to put food on the table, to save to send your kids to college, and you see in Donald Trump a president who is, you know, hypothetically worth millions and is paying $750 in taxes this year. And not just only paying $750 in taxes but saying things like it makes me smart that I do that.

I think it contributes to this larger sense that we have from Donald Trump that he looks down on working people. He calls them losers. He calls them suckers. He calls our veterans losers. It contributes to a sense that he has a very Park Avenue mentality. Joe Biden grew up in Scranton. His presidency is going to be about helping working families in this country.

COOPER: So how does Vice President Biden actually preparing for this? Because I know the vice president has said publicly that, you know, he's faced bullies all his life. He knows how to deal with bullies. Debating Donald Trump is different than any other potential person he's ever debated.

BEDINGFIELD: Sure. But look, he's going to use the opportunity to talk directly to the American people. I mean, he's -- look, he's not running for fact checker in chief. He's not here to -- he's not going to be there to convince Donald Trump to vote for him.

(CROSSTALK)

COOPER: Because he has said that he would be fact checking on --

BEDINGFIELD: He's not going to be there to convince Chris Wallace to vote for him.

COOPER: Right. He said on the stage, though, that he would fact-check --

BEDINGFIELD: He's going to be there --

COOPER: -- which it seems like a recipe for disaster.

BEDINGFIELD: He's not going to let Donald Trump misconstrue his record, but what he's going to do is use this time to talk to the American people about what he's going to do to build our economy back better, what he's going to do to get the virus under control. Tuesday night is really an opportunity for people to see that Joe Biden is the leader who has a plan, who's going to be able to get the virus under control, make sure that we can get our kids back to school safely, create jobs in this economy.

You know, Donald Trump has had four years and he's presided over the loss of 200,000 American lives, tens of millions of jobs lost. I think it's one in five small businesses in this country are closed right now because Donald Trump has been unable to get the virus under control. So there's going to be a very clear contrast between the two of them in terms of leadership on the stage on Tuesday night.

[20:20:05]

COOPER: Have you been -- I mean, you probably won't say, but have you been doing mock debates? I mean, have you been -- because again, as you know, Donald Trump, if you watched the -- you know, one of the debates he did with Hillary Clinton, you know, he says things under his breath. He has quick retorts. He, you know, will go to any -- you know, there's a shamelessness to him that allows him to say anything that comes into his mind to another human being.

BEDINGFIELD: Sure. And Joe Biden is going to be prepared for that. But I think the thing here to remember is that there's now four years of Donald Trump's presidency. There is a Trump record that is going to be up for debate on Tuesday night. And so, you know, I think if the only thing Donald Trump has to offer the American people on Tuesday night are, you know, personal insults and interruptions and rude asides, you know, that says a lot about him.

And if you're an American voter deciding whether you want four more years of that or you want four years of Joe Biden who's going to put forward real plans to help people get back to work.

COOPER: Yes.

BEDINGFIELD: To get their kids back in school, to -- I think there's going to be no question there.

COOPER: Vice President Biden yesterday defended himself against the Trump campaign's attempt to paint him as a socialist saying President Trump is, quote, "sort of like Goebbels," comparing him to the Nazi propaganda minister. Does Biden stand by that comment and should we expect to see that kind of name calling from him Tuesday? Because obviously, you know, invoking Nazis is quite a stretch.

BEDINGFIELD: Look, his point was that you cannot trust what comes out of Donald Trump's mouth. That's a tragedy. Donald Trump is the American president. You can't trust what comes out of his mouth. What you're going to see from Biden on Tuesday night is I think an incredibly a different path, a different choice. If you're somebody who's looking at four years of Donald Trump and you're asking yourself, do I feel safer, do I feel more secure than I did four years ago, and the answer is no, you're going to see an alternative in Joe Biden.

He's going to be laying out his positive policy agenda and I think the comparison between the two, between a president who cannot tell the truth and somebody in Biden who has told the truth his entire career, who has been a champion for working people, again, I think that that comparison is going to be really, really self-evident on the stage on Tuesday night.

COOPER: Kate Bedingfield, I really appreciate it. Thanks very much.

BEDINGFIELD: Thank you.

COOPER: We should quickly note we invited someone from the Trump campaign to join us as well tonight but the timing didn't work out.

Up next, the potential fallout, if any, from tonight's reporting in "The New York Times," will this be a big deal with the voters? We don't know. I'll talk it over with our political gurus and get their take in a moment.

(COMMERCIAL BREAK)

[20:26:57]

COOPER: Breaking news, "The New York Times" has details on President Trump's federal income taxes. There are reports saying they showed, quote, "chronic losses and years of income tax avoidance," according to them. According to the "Times," the tax data provides the, quote, "most detailed look yet inside the president's business empire," and they say it reveals the hollowness but also the wizardry behind the self-made billionaire image of the president. When the president was asked about the reporting tonight, he called it fake news.

Joining us now is Scott Jennings, a former special assistant to President George W. Bush and a CNN political commentator. CNN political analyst and "USA Today" columnist, Kirsten Powers and CNN political commentator and a former Democratic South Carolina state representative, Bakari Sellers.

Kirsten, first of all, what's your reaction to the "Times" reporting?

KIRSTEN POWERS, CNN POLITICAL ANALYST: Well, I mean, substantively it's obviously a huge story and it's something that I think should matter in an election. It should be offensive to people that if someone pays -- I don't know anybody who's paid that little in taxes honestly, who, you know, is above -- is out of college or, you know, maybe that was the last time I was paying that little amount of taxes.

So I think that that is highly problematic and it speaks to some -- first some structural problems, I think, things that he can take advantage of and I think it also speaks to some of his own kind of shady behavior. That said, I don't think it's going to move any of his voters. They're locked in with him and I don't think there's anything that could happen that's going to -- you know, this certainly would not be the thing.

I can't imagine what the thing would be that would move them away. It's possible if there's some people on the fence this could maybe sway them, though at this point there are so few people on the fence. I don't know how big of a factor it's going to be. And he's going to tell his voters that it's fake news and it's not true, and so they're not even going to feel any need to even consider it.

COOPER: Scott, I mean, Donnie Jr. during the campaign in 2016, you know, called his dad sort of the people's billionaire. Obviously a lot of this I think, as Kirsten said, it is baked in but it does sort of -- I mean, do you think it will rub some people the wrong way who are supporters of his to think that, you know, not only was he not paying taxes but even for people in that incredibly wealthy tax bracket, according to the "Times," he's an outlier in terms of how little he pays?

SCOTT JENNINGS, CNN POLITICAL COMMENTATOR: I mean, it could. You know, I mean, if you're thinking about this race could come down to a few thousand votes in a few states, yes, I mean, something like this could. I think -- look, we already sort of knew this. This came up in 2016 as I think was alluded to earlier in the show. I mean, he thinks this makes him look smart because he's got good accountants and he manages his tax situation in a way that gets him out of a tax burden.

So I assume that's what he'll say on Tuesday night. It's another thing that gets in the way of what I assume he'd rather be talking about which is the court or how he's going to manage the economy moving forward or so on and so forth. It does speak to a strategic question, if he ends up losing this race, I think we'll ask should he have released these earlier? It doesn't look like there's anything criminal here.

[20:30:02]

And he takes legal tax breaks that as I understand it are common to real estate investors. But if you believe that, then it's like, well, he could put it out and said, hey, this is why this is OK and this is why this looks this way.

I think at the debate Tuesday, Anderson, what he has to watch out for is a stunt. You know, if I were Joe Biden's people, I might be thinking something like, I don't know, have Biden walk out on the stage with a $750 check, and say, hey, I heard you were having money problems, you know. Like you'll have to manage a stunt on the fly if the Biden campaign is nimble enough to pull one off. So I don't know if it's going to affect the election or not. But I sort of feel like maybe this ground has already been gone over to some degree.

COOPER: Bakari, how do you see it?

BAKARI SELLERS, CNN POLITICAL COMMENTATOR: Well, one, I slightly disagree with Scott in that this probably is criminal. There is a great deal of wizardry as I think "The New York Times" actually said it was in hiding of the ball that exists in his tax records. But with all that being said, I mean, will this affect an election? I actually will say it probably will. The reason being is because Barack Obama in 2012 actually painted Mitt Romney throughout the entire cycle as mighty rich who didn't really pay taxes.

That resentment is real. And because that resentment is real I do think it will have a lingering effect today. But to Kirsten's point, there aren't that many undecided voters. So we'll see how it plays out. We know that Donald Trump does not play by anybody's rules. We know that Donald Trump likely dabbles in a gray area which will lend people -- a lot of people including myself who is a lawyer, to believe that there's some criminality there.

But with all being said, will this affect the electorate? Let's wait and see. Will this affect what happens on Tuesday night? I doubt he'll bring a check out on stage, although that's a really, really brilliant idea, Scott. I just believe that this is going to be more ho hum than people can imagine.

COOPER: Kirsten, what do you think in terms of looking forward to the debate, you know, Kate Bedingfield was just saying the vice president is not going to be a fact checker which is something that Vice President Biden had said he wanted to fact check President Trump, which is obviously you can spend an entire evening just focusing on that and not actually say anything about your own policies. What do you expect for Tuesday night?

POWERS: Well, I do think for Biden he needs to not get pulled down into the mud. That's going to be one thing that I think, you know, a lot of the Republicans got pulled into that the last time around in the primary debates where they sort of tried to -- that was somehow they were going to beat Trump by, you know, going lower than he did. That's not really Biden's style.

But, you know, when people push you sometimes you say things that you might not otherwise say. And the fact of the matter is, nobody is going to be able to be Trump more than Trump is. So Biden just needs to be himself and I think that he needs to stay focused on the things that people really care about. They really care about the court, they really care about health care, they really care about the pandemic. They really care about the economy.

These are the things that people are going to be voting on and so, you know, as much as he can focus on that and be energetic and be able to kind of shake off the blows that are coming at him then I think he'll have a good night.

COOPER: Scott?

JENNINGS: Yes, I think Biden can play this one of two ways. He could go out and try to fully engage. The smarter way might be to just say, look, I'm going to ignore this guy. Nothing I say to him or about him is going to matter to him or to you or to you, Mr. Wallace. I'm just going to ignore him, I'm going to talk to you about my priorities. And I'm just going to, you know, pretend like he's not there. That would probably drive Trump insane. Right?

And if you're Trump, I think the way you play it is just to go relentlessly at Biden because every time he's been challenged during this long campaign he sort of lost his temper. He challenged a farmer to a push-up contest. He screamed in Elizabeth Warren's face during a primary debate. He doesn't react well to in-your-face, you know, challenges that debates are public forum. So I think if I were running the Biden debate prep I would be thinking of an -- you know, an ignoring strategy and if I were running the Trump debate prep, I'd be thinking, how do I get Joe Biden to lose his temper as early in the night as possible?

COOPER: Bakari, how about you?

SELLERS: Yes, you know, I think that Joe Biden is a better debater than most people give him credit for. We saw throughout the Democratic primary, we saw him take punches from everyone, from Julian Castro to Kamala Harris, to Cory Booker. And he still stood on stage. I mean, he even had one-on-one debates with Bernie Sanders. It's been a long time since. And we do know that incumbents actually perform poorly.

I mean, all you have to do is go back and look at Barack Obama's debate -- his first debate against Mitt Romney and it was an awful performance by the president of the United States. Even I will tell you that Mitt Romney destroyed Barack Obama during that debate. So I actually believe that Joe Biden does have an upper hand going into this debate, but it's very difficult, Anderson, and you deal with it all the time on TV.

I don't know how you just talk to somebody who lies repeatedly all the time as if it's second nature. And so this is going to be something that Joe Biden is not accustomed to.

[20:35:04]

In political debates it's not really a thing that you just go out there and somebody has a complete allergy to the truth. So this is going to be an awesome experiment for the Biden campaign because they'll have two more after this. But Donald Trump is a pathological liar who has something that just, you know, eats at him about telling the truth. So we'll see what happens on Tuesday night.

COOPER: Yes. I take long showers afterwards. That's how.

Thanks, everybody. Appreciate it. Up next --

SELLERS: Are they warm? Are they warm, though?

(LAUGHTER)

COOPER: It depends.

The author who made then citizen Trump a household name decades ago when he wrote the "Art of the Deal," hear what Tony Schwartz has to say about the breaking news on Trump's income taxes ahead. We'll be right back.

(COMMERCIAL BREAK)

COOPER: Tonight's breaking news "The New York Times" on the president's taxes, his looming debts and talent for exaggerating his wealth except to the IRS will come as no surprise to our next guest, Tony Schwartz. He's author of the president's first book, "The Art of the Deal," which he wrote and the president's name is on the cover, as is Tony's I think but the president -- but Tony wrote it. He's also out just with the audible original, "Dealing with the Devil: My Mother, Trump and Me."

Tony, out of all this reporting, I'm wondering is there something specifically you find most of a revelation about Trump?

TONY SCHWARTZ, CO-AUTHOR OF DONALD TRUMP'S "THE ART OF THE DEAL": The sheer brazenness of it, Anderson. Even goes beyond what I would have expected. The kind of mind that would think I can get away with paying no taxes on hundreds of millions of dollars of income. It bothers me to hear other people saying, well, it won't necessarily make a difference and who really cares?

Let's understand this. We have a felon in the White House. This is one of the great tax frauds in IRS history. He is running a criminal enterprise. This, no matter what the effect is on any given voter, is big, big news.

[20:40:05]

COOPER: I want to quote one of the most striking lines in the piece and one that's probably guaranteed to rile up President Trump, quote, "Ultimately Mr. Trump has been more successful playing a business mogul than being one in real life."

I was fascinated to read in "The Times" that he started inheriting money from his father when he was 3 years old as part of some sort of tax scheme of his dad's, I guess, to transfer assets from father to son, and yet, according to "The Times," you know, ultimately was transferred over I think it was like $300 million to $400 million.

SCHWARTZ: Yes, so we know that he inherited $400 million. Some of that he stole from Mary Trump and Mary Trump's father, and much of it from other places. But the thing is that what you have here is the middle of Trump's vulnerability because he equates his personal worth, whatever amount of worth he thinks he has deep down, with his net worth and what's so clear here is that he is a horrible businessman. Just as he's been a terrible president.

So I think from the point of view, for example, of Biden in this debate to poke at Trump's obvious financial ineptitude, what he is good at being, and let's not miss this, he's good at cheating. He is really, really good at cheating. But you know what, there's karma. The chicken comes home to roost. Even the people who run big John Gotti and the others who run big criminal enterprises usually get tracked down eventually. This is what's happening here.

COOPER: The reporting goes into a litany of ways that the president has benefited financially from the presidency itself. They say, quote, "His properties have become bazaars for collecting money directly from lobbyists, foreign officials and others seeking face time, access or favor," and it certainly raises questions about if there's another four years of the administration what is going to take place because the president has huge debts that are coming due in the coming years.

SCHWARTZ: Well, let me say this. Relative to the horrors that Trump can inflict on us if he is re-elected and feels he has no more boundaries and no more barriers, whether or not he has big debts is not going to be the issue that America faces. They're going to face the potential of martial law, the potential of, you know, trying to enlist the military or law enforcement in rounding up his enemies. I mean, there are all kinds of things that are going to happen.

But, yes, he's already subject to and beholden to the people from whom he is accepting money. You know, Michael Cohen says in his book, which actually is probably the most interesting book that's been written about him. What he says is, Trump saw this run for president for himself as a way to get richer. He was jealous of Putin who he believes is the richest man in the world by virtue of what Putin has stolen. And he saw this as that opportunity. And until he is prevented from it he will continue to go at it step by step by step.

COOPER: Tony Schwartz, appreciate you being with us. Thanks very much.

We have more breaking news tonight. A legal victory for TikTok. A federal judge blocking the government ban on downloading the app, which is due to take effect at midnight Eastern Time. TikTok is challenging Commerce Department restrictions as unconstitutional and a violation of due process. Other restrictions dealing with company's carriage of TikTok's internet traffic were not touched by the order.

Coming up, the rich history of presidential debates, the highs and lows when we continue.

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COOPER: The modern era of presidential debates began in a Chicago television studio back in 1960 when Richard Nixon met John F. Kennedy. That launched a tradition that's acquired more and more importance over the years.

And Tom Foreman tonight has a look at the highs and lows of presidential debates.

(BEGIN VIDEOTAPE)

REP. DAN QUAYLE (R), VICE PRESIDENTIAL CANDIDATE: I have as much experience in the Congress as Jack Kennedy did.

TOM FOREMAN, CNN CORRESPONDENT (voice-over): The most memorable line in modern debate history may have come in the 1988 vice presidential contest. Republican Dan Quayle made a pitch and Democrat Lloyd Benson slammed it home.

SEN. LLOYD BENSON (D), VICE PRESIDENTIAL CANDIDATE: Jack Kennedy was a friend of mine. Senator, you're no Jack Kennedy.

UNIDENTIFIED MALE: The ground rules for this as agreed by you gentlemen are these --

FOREMAN: In the heavily scripted and choreographed world of modern presidential campaigning debates offer a rare chance to see party nominees head-to-head, no advisers, no do-overs.

RONALD REAGAN (R), PRESIDENTIAL CANDIDATE: Are you better off than you were four years ago?

FOREMAN: And few have ever produced as many memorable moments as the master of campaign one liners.

REAGAN: There you go again.

FOREMAN: Ronald Reagan.

REAGAN: I will not make age an issue of this campaign. I am not going to exploit for political purposes my opponent's youth and inexperience.

GEORGE H. W. BUSH (R), PRESIDENTIAL CANDIDATE: A lot of what this campaign is about, it seems to me, Bernie, is the question of value.

FOREMAN: The ability to seamlessly weave common language and policy points is rare. George H.W. Bush could do it. So could Barack Obama.

BARACK OBAMA (D), PRESIDENTIAL CANDIDATE: I'm glad that you recognize that al Qaeda is a threat because a few months ago when you were asked what's the biggest geopolitical threat facing America, you said Russia, not al Qaeda. You said Russia. In the 1980s they're now calling to ask for their foreign policy back.

FOREMAN: Bill Clinton could turn that trick, too.

BILL CLINTON (D), PRESIDENTIAL CANDIDATE: Most people are working harder for less money than they were making 10 years ago. I think we can do better if we have the courage to change.

ADM. JAMES STOCKDALE (I), VICE PRESIDENTIAL CANDIDATE: Whom I? Why am I here? FOREMAN: Still, some of the most remembered moments have been

surprises from then President Bush looking at his watch as if he had somewhere else to be, to Gerald Ford inconceivably arguing Soviet satellite nations were not under Moscow's thumb.

GERALD FORD (R), VICE PRESIDENTIAL CANDIDATE: Each of those countries is independent, autonomous.

SARAH PALIN (R), VICE PRESIDENTIAL CANDIDATE: Say it ain't so, Joe. There you go again pointing backwards --

FOREMAN: To Sarah Palin serving up red meat for comedians in almost everything she says.

TINA FEY, COMEDIAN: Hey, can I call you Joe?

UNIDENTIFIED MALE: Of course.

FEY: OK. Because I practiced a couple zingers where I call you Joe.

(END VIDEOTAPE)

[20:50:01]

FOREMAN: All of that plus the sheer importance of it all gets a massive audience. Last time around the first debate drew more than 80 million viewers, people looking for some of those memorable moments or maybe something to help make up their minds -- Anderson.

COOPER: Tom, thanks very much. A lot to watch for.

Still to come, a new CNN Film on the late congressman and civil rights leader John Lewis. I'll speak with NBA star and CNN contributor Draymond Green who will be live tweeting throughout the film. We'll be right back with him.

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COOPER: As we close this two-hour Sunday edition of 360, I want to remind you of the new CNN Film debuting in just a few minutes at the top of the hour, "JOHN LEWIS: GOOD TROUBLE." He attended thousands of protests, faced 45 arrests, served 33 years in Congress, what a life. Here's a preview.

(BEGIN VIDEO CLIP)

REP. JOHN LEWIS (D-GA): My philosophy is very simple. When you see something that is not right, not fair, not just, say something, do something, get in trouble, good trouble, necessary trouble.

[20:55:12]

LEWIS: We have to save our country, save our democracy.

(END VIDEO CLIP) COOPER: It's a powerful film. I want to welcome Draymond Green, an NBA forward for the Golden State Warriors, CNN contributor and a TNT Sports analyst. He'll be live tweeting throughout tonight's film.

Thanks so much for being with us. You've been outspoken on social issues. You're an admirer obviously of the Congressman Lewis. What will viewers learn from watching the film tonight?

DRAYMOND GREEN, CNN CONTRIBUTOR: First off, thanks for having me. And secondly, I just hope viewers learn that in looking at what Representative Lewis has been doing his entire -- or was doing his entire life and seeing where we are today, understanding that change won't just happen today or tomorrow, and that it's a long fight that we're fighting. He was fighting this fight way back in the '60s and yet we're still facing some of those same problems today.

So I hope that our viewers learn that this fight isn't near over. It's still -- it's just the beginning. And to continue fighting and know that change doesn't happen overnight. But if we can continue to band together and push forward, that we will create change.

COOPER: You know, as we mentioned, one of Congressman Lewis's philosophy was when you see something that that's not right, not fair, not just, say something about it. And that message, I mean, certainly still just as important today, in today's climate. Do you think enough people embrace that idea?

GREEN: I think at times people do embrace that idea. You know, when you're looking at athletes today, I think athletes are embracing that and, you know, continuously being told to shut up, but yet we continue to come together and use our platforms to push what we believe is right. And so I do believe in that and, you know, you look at guys like Trader Truth, you know, when he says getting in good trouble.

I think Trader Truth is getting in a lot of good trouble and he's trying to do great things for the black community who's constantly facing systemic racism day in and day out. That's good trouble. And so I think at times we are doing that, but we need to make sure that it's happening all the time.

COOPER: It's also interesting to me how, you know, athletes today like yourselves, you know, get criticized for speaking out on issues. People look back at Muhammad Ali with great reverence now. But at the time when Muhammad Ali was young and was speaking out in very controversial ways, he was vilified. I mean, he was -- society set out to try to completely destroy him, take him out of a boxing, you know, send him to prison.

And it's only in retrospect that people now look back and say, oh my god, what he did was amazing and he was this remarkable person. I wonder how history will see people speaking out now, you know, 20 years from now. I think it will look very different to those people who are maybe criticizing you and others right now.

GREEN: Well, I think that's always the case. And I think that is the case with anything in life. When you start talking about change and going against the grain or at least what people think you should be doing, they never accept that until change does happen. They see that that change is for the better, then they can look back and say, oh, I now understand what he was doing. I mean, the reality is, some people can't see as far as past tomorrow.

And so to think that they're going to understand the message that we're trying to get across, the change that we're trying to make happen, to think that they'll understand that is blasphemous. So, you know, I don't really worry about people saying shut up and dribble, or, you know, stick to sports, you're an athlete, you have nothing to do with politics. This isn't politics we're talking about.

We're just talking about being treated fairly just like everyone else. So I think those people just like the same ones that said Muhammad Ali was off his rocker 30, 40, 50 years ago, those people will look back in 20, 30 years, and they'll understand.

COOPER: Yes. As we mentioned, you're going to be watching the movie at the top of the hour sharing your reaction in real time on social media. How can people connect with you?

GREEN: They can connect with me on Instagram or Twitter, same @Money23Green. I'll be live tweeting. Extremely excited to watch. You know, the congressman gave so much of his life to our country and to continue to try to create change. So I'm extremely excited to watch and continue to learn more.

COOPER: Cool. Well, Draymond Green, I really appreciate you being with us. It's such an important film. I mean, did you ever get to meet Congressman Lewis? I mean, he was such an extraordinary just human being.

GREEN: I never got the opportunity. But I've heard a ton of great things.

COOPER: Yes.

GREEN: Yes, but like I said, I'm just looking forward to watching this movie.

COOPER: Cool. Thanks so much and thanks so much for live tweeting during it and talking with folks.

That's it for this special Sunday edition of 360. The CNN Film, "JOHN LEWIS: GOOD TROUBLE," starts now.

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