"The New York Times" delivers a bombshell on Trump's taxes, opening new questions about possible fraud, tax evasion, and bankruptcy. Former Obama Acting Solicitor General Neal Katyal discusses how to ensure the election isn't stolen and the fight over the Supreme Court. A former Trump Organization executive discusses the uproar over Trump's taxes. Carly Fiorina discusses debating President Trump.
NICOLLE WALLACE, MSNBC HOST: Settle in now, because THE BEAT starts right now with my friend Ayman, in for Ari today.
AYMAN MOHYELDIN, MSNBC HOST: Hey, Nicolle. Thank you very much.
Welcome to THE BEAT, everyone. I'm Ayman Mohyeldin, in for Ari Melber this hour.
We have a big show with that "New York Times" bombshell on Trump's taxes opening new questions about possible fraud, tax evasion, bankruptcy, and a whole lot more, dropping just ahead of the first presidential debate.
Tonight, I have a special interview with someone who actually has tangled with Trump on the debate stage.
Also, former Obama acting Solicitor General Neal Katyal on ensuring the election isn't stolen, the fight over the Supreme Court and a whole lot more, plus a BEAT exclusive with a former Trump Organization executive on the uproar, as his tax secrets are now exposed.
And that is where we begin tonight, fallout from that blockbuster "Times" story on Trump's long-secret and elusive taxes, giving the clearest view, by far, of what Trump is trying to hide. And it is not a pretty picture.
Trump, a self-declared billionaire, only paying $750 in federal income taxes in 2016 and 2017, while paying no federal income taxes in 10 of the last 15 years.
And then there's this precarious and tightening financial vise grip that Trump finds himself in, Trump personally, not the Trump Organization, Trump personally guaranteeing loans totaling $421 million.
Now, most of that bill is coming due soon, at least within the next four years.
Today, Speaker Pelosi had this to say:
(BEGIN VIDEO CLIP)
REP. NANCY PELOSI (D-CA): This president appears to have over $400 million in debt, 420, whatever it is, million dollars in debt.
To whom? Different countries? What is the leverage they have? So, for me, this is a national security question.
(END VIDEO CLIP)
MOHYELDIN: All right, so Trump, often claiming staggering losses from his businesses to offset his tax bill, undermining Trump's claims of his brilliant business track record.
And we're also learning more about Trump's IRS audit, "The Times" reporting it is focused on a $72 million tax refund that Trump got that is now in dispute.
Now, if he loses, he could be forced to pay over $100 million in back taxes. "The Times" also documenting dubious or questionable expenses, including $70,000 for Trump's hairstyling, hundreds of thousands of dollars in consultant fees to his daughter Ivanka.
Here's the big picture in all of this, "The Times" revealing a president that is in a dire financial position with potentially criminal implications, because we know that the Manhattan district attorney is, in fact, investigating Trump for fraud.
The president pushing back, calling it fake news, tweeting up a storm, as you can imagine, but not taking the simple step, the simple step that all previous presidents have done for four decades that could clear all of this up, simply releasing his own tax returns.
Joining me now is Eugene Robinson, Pulitzer Prize-winning columnist with "The Washington Post," Walter Shaub, former director of the Office of Government Ethics, resigning early in the Trump administration, and Christina Greer, associate professor with Fordham University and the politics editor or TheGrio.
Lots to get into here, guys.
Eugene, I want to start with you.
And, more importantly, what struck out to you about these new findings?
EUGENE ROBINSON, MSNBC POLITICAL ANALYST: Well, I think there were two ways to look at this, Ayman.
One is that either the president is a massive tax cheat, right, he just -- he lied, he cheated on his taxes, and the IRS and prosecutors need to go after him, and probably will. That's one way to look at it.
The other way to look at it is, the president really is such a kind of not very good businessman, that he really did have massive, massive losses over a period of years, due to incontinent spending and unwise purchases, especially of all these golf courses.
And he -- so, he had losses, because, after all, when I have income, I have to pay taxes. He didn't pay taxes. Therefore, maybe he didn't have the income.
And he manages to survive with these hundreds of millions of dollars of personally guaranteed loans that he somehow got from compliant bankers. And, therefore, he's in a fairly desperate financial condition.
And so I don't see much in between those two ways of looking at this data.
MOHYELDIN: Yes. And we're going to get into, like, the national security implications, as House Speaker Nancy Pelosi laid out.
Walter, I'm curious to get your thoughts.
If you were the ethics czar right now -- and, boy, would you have your hands full and a lot on your plate, but let's just talk about this one issue right now. What would you say if this guy bombshell report came out?
WALTER SHAUB, FORMER DIRECTOR, OFFICE OF GOVERNMENT ETHICS: Well, I think the first thing that would jump out at me is the discrepancy that he claimed in his financial disclosure report to have earned $434 million in income from these investments, and now claims in his tax returns that we're hearing about through "The New York Times" that he lost $47 million that year.
That's a serious discrepancy. And "The New York Times" made one small mistake in this otherwise brilliant piece of reporting. They said that the financial disclosure report only covers revenue, and that explains the difference.
But it doesn't. It actually covers what financial payments he has personally received. So, he is claiming in that financial disclosure report that he received $434 million in income from this investment personally, which doesn't match up with a tax return in which he said he lost $47 million.
So, I think that's the starting point.
MOHYELDIN: Christina, the interesting thing is, as you can imagine, a lot of Trump supporters coming out basically dismissing the report, saying this has been -- it's something the president even said yesterday, essentially saying that this was adjudicated, at least politically or publicly, back in 2016.
Here's how some Trump supporters are defending him today. Watch.
(BEGIN VIDEO CLIP)
MOLLIE HEMINGWAY, THE FEDERALIST: Depreciation, itemizing deductions, all of these things he's doing are things that probably all of us do, that most people do when they're filing their taxes. So I'm not quite sure what's supposed to be news.
(END VIDEO CLIP)
MOHYELDIN: What do you say to that argument, Christina?
Because, on one hand, he's trying to say that -- or they're trying to say, Trump's defenders are trying to say that he is very smart for exploiting this system, not paying federal taxes, and even implying that it probably would be something that they all do.
CHRISTINA GREER, FORDHAM UNIVERSITY: Right.
But this goes back to the spaghetti-throwing administration, which is, when you listen to the networks that are supportive of the president, they're trying the strategy of, oh, well it's illegal for "The New York Times" to even look at these things.
OK. That's one strategy. The other strategy is, we have already adjudicated this, there's nothing to see here.
Actually, we haven't because we still haven't seen the taxes. So, they keep coming out with different scenarios for whomever is in their base for them to believe that.
The problem is this, Ayman. The hustle has gone too far. We know that Donald Trump got into the race, A, to harass his Republicans. He wasn't really even a Republican at the time, and -- but to really harass Hillary Clinton.
And we saw Lindsey Graham and Ted Cruz and Marco Rubio think, this guy is a joke, get him out of here. We need the presidency.
So, we know that Donald Trump entered the race for a financial motive to help him make more money. He thought he was going to lose. He thought he had started network or be on a network. It would help him with all of his businesses. He had the Trump Hotel opening in Washington, D.C. He knew that it would help him with his golf courses across the country.
The problem is, now he's president. He still hasn't shown all of the financial dealings. We know that there's probably some real financial and foreign interferences and conflicts of interests that are there.
But the president's always been a little Teflon when it comes to finances. Especially for those of us who've been in New York, we know about his shady dealings and all the bankruptcies that he's had.
But this is actually possibly the Achilles' heel that actually might expose Donald Trump for the fraud that he has been for over three decades. And I think that's what worries him, because it's not just finance Cy Vance, the DA of Manhattan.
It's also Tish James, the attorney general of New York, who's building a series of cases, civil and criminal, against the president right now.
So, Eugene, let me put the politics aside for a moment, and let me pick up on something that you said, which is also what was echoed by House Speaker Nancy Pelosi, this $400 million, this staggering amount of money that Trump owes, we don't know who he actually owes that money to.
Kamala Harris just spoke with my colleague Lawrence O'Donnell about this. Let me play for you this sound bite.
(BEGIN VIDEO CLIP)
SEN. KAMALA HARRIS (D-CA), VICE PRESIDENTIAL CANDIDATE: Lawrence, this is why the American people deserve to have a full accounting of the financial interests, including the indebtedness, of the president of the United States.
And I -- and I do share in that concern. Who does he owe the money to? Tell us, who do you owe the money to?
We need to know that. The American people have a right to know that, when the president of the United States acts, he acts with their priorities in mind, not with his priorities in mind.
(END VIDEO CLIP)
MOHYELDIN: Eugene, how serious of a question, fundamentally, is this? Who does this president owe money to?
ROBINSON: I think it's an extremely serious question.
And, look, excessive debt is a routine factor in denial of security clearances, because the theory goes that, if you have excessive debt, you are vulnerable, you are exposed in a way that makes you a less-than-reliable custodian for the nation secrets.
Well, President Trump is the ultimate custodian of the nation's secrets. He theoretically is able to know all of them. And he's in this exposed, vulnerable position. We have a sense that he owes a lot of money to Deutsche Bank. We don't know all the people he owes money to.
And there's other reporting indicating that the 400-and-whatever million dollars of personally guaranteed loans that we know about is the tip of an iceberg in terms of money that he, through the Trump Organization, owes on other deals and owes to other people.
And we don't know who all those people are. So, this is extremely serious. And it raises the question of who Donald Trump is working for and whether Donald Trump can be can be trusted with the nation's security.
Absolutely, it raises...
To that point, Walter, the president obviously has access to all of our country's top, most sensitive secrets. It just doesn't end when he leaves the office. If, in fact, he does lose these elections, he would still be under that leverage of the people who owe that money.
What kind of leverage do Trump's lenders have over him right now and going forward, whether he wins the election or not?
SHAUB: You know, when we look at the extent of the leverage, one thing to keep in mind is that a financial disclosure filer, like the president, is only required to disclose his own personal loans or those he has guaranteed, which means there could be a great deal of business loans that we know nothing about, because he wasn't required to disclose them.
The problem is, with all these personal loans coming due, he needs those businesses to be able to afford to pay back his own loans. So, he becomes vulnerable in a way, as a result of this debt, that goes beyond even the part we can see.
And so we actually do know a lot about who he personally owes the money to. But what we don't know is who his businesses owe money to. We also don't know who most of his businesses' customers are. And we don't know what other arrangements or business deals he has in the pipeline.
We have seen, however, though, that, with the things we do know, they intersect with his work as president. For instance, his administration was investigating Deutsche Bank at a time when he owes Deutsche Bank a great deal of money and may have trouble refinancing it or getting extensions.
And in any other past administration, maybe we could shrug that off and say, well, the attorney general is going to operate independently of the president. But we have seen Bill Barr politicize the Department of Justice in criminal and civil matters in a way that we have not seen at any point in our past, including his recent interference and his appointees' interference in the more -- the Roger Stone case and the Michael Flynn case.
And so we have to worry about the extent to which the government and the president's interests are beginning to merge. And that was always one of the problems with him retaining his financial interests, because they come with a lot of baggage beyond just the investment itself, like a need for a stream of revenue and debts to unknown parties.
MOHYELDIN: Christina, I want to play for you what Trump said about paying taxes back in 2011. Watch.
(BEGIN AUDIO CLIP)
DONALD TRUMP, PRESIDENT OF THE UNITED STATES: No, I pay tax. I pay a lot of tax.
The amazing thing is that half of the country is paying nothing, zero. And even if you don't make a lot, you should have to pay something, just something, to be a part of the game.
But half of the country's paying nothing.
(END AUDIO CLIP)
MOHYELDIN: It's quite remarkable that you have somebody who's constantly undermining the way that the government works, the way it's supposed to collect money from citizens to pay for things.
What do you make of the way he defends gaming the system?
I mean, I thought you were going to play the clip where he essentially insinuates that paying taxes is for suckers.
GREER: We cannot have a nation where we don't buy into it.
I mean, we have probably visited or lived in nations or have relatives from nations where, when they don't have a tax system, we know that that affects what roads look like, what schools look like, what public safety looks like.
So we have to have Americans buying into investing in the system, right? I -- honestly, I'm one of the few Americans, but I do happily pay my taxes, because I actually want good public schools. I actually want to be able to go on roads and bridges that aren't going to collapse.
And so Donald Trump is setting up a really dangerous precedent, because, if too many Americans say, well, if he's not paying taxes, I'm not going to be a fool and pay taxes, right -- we know that they will probably have different punishments from the IRS.
But we can't have a multitude of Americans saying, you know what, forget it. Like, if he's not going to do it, I shouldn't have to either.
That's how our system breaks down. And we have always seen, in these past-three plus years, Donald Trump consistently eroding the norms and some of the laws of our democracy, and really taking what is a work in progress and pulling it back decade after decade, just in almost every single thing that he does as far as policy, whether it's the Muslim ban or the trans ban in the military, or how he speaks about African and Caribbean nations, or how he wants law and order and supports vigilantes.
I mean, the list goes on and on.
MOHYELDIN: Yes, it certainly does.
Christina Greer, Walter Shaub, Eugene Robinson, thank you to all three of you for starting us off this hour.
And a quick programming note. You just heard there Kamala Harris talking to Lawrence O'Donnell. You will be able to catch that full interview tonight at 10:00 p.m. Eastern right here on MSNBC.
All right, coming up after this short 30-second break, we're going to get an insider's reaction to these tax revelations from a former top executive inside the Trump Organization.
And we're going to talk to someone who challenged Trump on his business failures in a national debate.
But, first, a former prosecutor weighs on whether Trump could face charges on all of this after he leaves office. That is still a very big question.
That's when we're back in just 30 seconds.
MOHYELDIN: All right, we're back with two experts on a question at the heart of the Trump tax story: Did Trump simply exploit loopholes that were illegal, or did he actually break the law? And does it go beyond whether Trump's simply evaded taxes or not?
"The Times" reporting on unidentified consultants fees that helped reduced Trump's tax bill. Some of those fees can be matched to payments received by his daughter Ivanka Trump. There are also questions about whether Trump falsely inflated business losses to evade taxes. That is something we know the Manhattan district attorney is already looking into.
And then there is this. Trump classified one of his properties, an estate called Seven Springs, as an investment property. And he has written off $2.2 million in property taxes as a business expense.
Here it is, an ornate century-old mansion built over 200 acres just outside of New York City, indoor pool made out of marble. "The Times" reporting there are questions about if it was actually used for business. If so, what kind of business?
Here's Eric Trump talking about it back in 2014.
(BEGIN VIDEO CLIP)
ERIC TRUMP, EXECUTIVE VICE PRESIDENT, TRUMP ORGANIZATION: This is a place that is really special to myself. It's really special to my brother, my father, really the whole family.
It's just really our compound. And I have spent so much of my life here. It's a special place for me and one that I will always remember and one that I will always be very close to.
(END VIDEO CLIP)
MOHYELDIN: All right, so the Trump Organization Web site still describes Seven Springs as a -- quote -- "retreat for the Trump family."
Joining me now is former federal prosecutor Renato Mariotti and Heather Vogell, an investigative reporter for ProPublica who has been reporting on Trump's taxes for years.
Renato, let me begin with you.
When you look at the laws that are on the books, what laws jump out to you as potentially most relevant in all the documents and information we have learned so far?
RENATO MARIOTTI, FORMER FEDERAL PROSECUTOR: Certainly, making a false statement on tax return or tax fraud, that's one that jumps out.
Tax evasion also looks like a potential violation. And then, of course, you also have potentially a false statement for a financial institution, because it appears that some of these representations (AUDIO GAP) financial institutions (AUDIO GAP) lenders.
MOHYELDIN: Heather, I can't think of anyone who has been digging into Trump's numbers and records over the past couple years as much as you have.
What's your biggest takeaway from "The New York Times"' reporting?
HEATHER VOGELL, PROPUBLICA: Well, this was really a stunning feat of reporting on behalf of "The New York Times."
(AUDIO GAP) in this area is that, all of a sudden, we have in the public domain all of this information about the specifics of profits and losses for so many different properties around the country and indeed around the world.
It could be interesting, potentially, to local officials, local prosecutors in several different areas who may not have had access to this federal (AUDIO GAP) or had a reason to request it and who may be interested in comparing it with what they have in their books.
So, I think that the reach of the story is very long. And there are a lot more questions to be asked.
MOHYELDIN: Renato, one of the things that a lot of people have been talking about over the years, not just recently, but over the years, is this kind of blurring the lines between family and business, and, even in politics, what role does Ivanka Trump play in the Trump White House? What's her official position, title, portfolio?
We mentioned that Trump's tax bills were reduced by payments to Ivanka Trump. Could that potentially be a crime?
MARIOTTI: Yes, absolutely.
And I think a good way to explain it is, for example, you work at MSNBC. Could you imagine if, in addition to receiving your paycheck, you also got a separate paycheck through a company you own for doing additional work for MSNBC?
It's just -- it's weird, right? On its face, it seems odd. And the question is, did she do any legitimate work for that money? Sometimes, up to 20 percent of the value of a transaction is being returned to Ivanka Trump as a consulting fee.
And, on its face, it appears to be that she was getting money for doing something that wasn't actually work. So, if that is the case, that would be a, like we talked about before, false statement on his taxes.
MOHYELDIN: Let me pick up on another angle to this, Heather.
You have reported on Trump and Ivanka misleading real estate buyers in the past. Where does that fit into what we're learning now about all of this?
Well, this was very interesting to me, because when we were reporting that story a couple of years ago, we were very focused on the Panama property that bore Trump's name until recently. And in the process of that, people had talked about Ivanka picking out the drapes, picking out this -- some sort of decoration for the rooms, for the lobby.
So, her name did come up a lot related to that property with those sorts of choices. And I'm just super curious to find out whether this was one of those situations where she was being paid as a consultant, as well as being an employee.
MOHYELDIN: Renato, Michael Cohen testified in 2019 that Trump was inflating and deflating his assets. Watch this.
(BEGIN VIDEO CLIP)
MICHAEL COHEN, FORMER ATTORNEY/FIXER FOR DONALD TRUMP: Mr. Trump is a cheat. Trump inflated his total assets when it served his purposes, such as trying to be listed amongst the wealthiest people in "Forbes," and deflated his assets to reduce his real estate taxes.
(END VIDEO CLIP)
MOHYELDIN: Explain that to our viewers here.
If Trump did, in fact -- if true that he inflated or deflated based on what he needed for that moment, what crimes was Trump breaking?
MARIOTTI: Well, if he, for example, misstated the value of his assets in a tax return or in a statement to a financial institution to obtain a loan, that would be a crime.
And the tax returns, we already talked about what (AUDIO GAP) would be, a false statement in a tax return. But to a financial institution -- any false statement you make to a financial institution for purposes of getting a loan is a crime. It's a federal crime, a felony that's published -- that is punished with a very long prison sentence.
And so telling different stories to different people when it suits you can potentially get you in serious trouble.
MOHYELDIN: Heather, we talked about Seven Springs for a moment. I want to get your thoughts on this as well.
How does the highlight -- how does this highlight -- excuse me -- the Seven Springs dilemma that we're talking, about whether it is business, or, as it's listed on the Trump Organization, a family retreat, which means it is personal?
VOGELL: Right, exactly.
I mean, there was a lot in this story about what look like deductions that appear to be the sort of thing that you would expect potentially to pay out of your pocket, instead of charging it to your business.
And a property that you're using as a retreat for your family would be one you wouldn't expect to be charged as a business expense. So I think that there were other things too that came up, including some hairstyling, very high-cost, I think $70,000 for hairstyling when he was on "The Apprentice," $5,000, I think, for -- Ivanka for hair and makeup, things like that that I think that there are a lot of be (AUDIO GAP) about.
MOHYELDIN: Yes, a lot of unanswered questions going forward.
Heather Vogell, Renato Mariotti, thank you very much, both, for joining us this hour.
We got a lot more to come, including my very special interview with someone who has stared down President Trump in debates. She's going to offer how to beat him.
But, first, Neal Katyal is here on a potential new legal front in the Democrats' election night showdown with Trump.
(BEGIN VIDEO CLIP)
D. TRUMP: This is going to be a disaster. We're going to be counting ballots for the next two years.
And I don't want to end up in the Supreme Court. And I don't want to go back to Congress either, even though we have an advantage if we go back to Congress. We actually have an advantage. Oh, they're going to be thrilled to hear that.
(END VIDEO CLIP)
MOHYELDIN: So, that was Donald Trump referring to the rare possibility that the 2020 election might head to the House of Representatives if there's a tie in the Electoral College, making a point that, today, Speaker Nancy Pelosi basically confirmed, that Republicans hold the edge on that kind of vote, even though Democrats hold the majority of representatives in the House.
It's because the Constitution says that vote for a president is determined by state delegations in the House, not individual lawmakers. And, right now, Republicans represent the majority of House members from 26 states, Pelosi sending out a red alert, saying, this is yet another reason for Democrats to pick up seats in the House in November.
Joining me now is former acting U.S. Solicitor General Neal Katyal.
Neal, good to talk to you again, my friend.
Lots of people were surprised by this, because a lot of people thought it was based on the representation or the composition, if you will, of the House of Representatives.
Isn't it weird, though, how this vote would happen? Explain that to our viewers.
NEAL KATYAL, MSNBC LEGAL ANALYST: It is weird.
And it is so remarkable that we're talking about this, and this and all these other scenarios are usually unthinkable. And it's only thinkable now because of one fundamental thing, which is, Donald Trump doesn't care about the law. He doesn't care about rules. He doesn't care about institutions. He cares only for himself.
And so there's a fear that, if the election happens in November, he won't concede. And he's, in fact, intimated that, including in those clips that you were just playing.
Normal presidents concede. Starting in 1896, that's when the modern concession begins, with William Jennings Bryan, when he sent a telegram conceding. And that concession is not just about grace. It's about -- it's a profound act of democracy. It's about letting the country move on.
So what Trump is now talking about is this 12th Amendment gambit, which lays down the rules if there are not 270 clear electoral votes. And at that point, then, you have each state delegation conducting an internal election to decide the candidate.
And every state gets the same amount. Wyoming has about 600,000 people. They get the same vote in this as California, which has 70 times the population. So, Trump's right in one sense that the math may favor him a bit in this calculus.
But, boy, if that's the way a president wins, you have to really worry that it would tear the country apart, because it's profoundly anti-Democratic.
MOHYELDIN: Yes. I was going to...
KATYAL: And that's why we have not had that amendment kicked in.
MOHYELDIN: Yes, I was going to say, let's not forget that he is also a president who lost the popular vote by three million votes back in 2016. So, we could even see a similar scenario play out this time around.
Let me switch gears for a moment, Neal.
I want to talk to you about the Supreme Court. What do you think -- as the confirmation process of Judge Amy -- Amy Coney Barrett -- excuse me -- gets under way for the Supreme Court, what do you think the focus should be for Democrats as they begin to question her?
KATYAL: I think the focus has to be the transformational nature of this appointment and this kind of rush to jam her through, because the president's afraid he's going to lose in November.
I mean, it's only been 10 days since Justice Ginsburg passed away and we lost this giant in the law. And I think the Republicans are pretty clear in saying they want to rush her on the court because they want her there because of the Affordable Care Act and the vote to possibly strike it down.
They want her there to rule against Roe vs. Wade. Republican senators like Josh Hawley have said they won't even bother even listening to someone or confirming someone who's not adamantly against Roe vs. Wade. And he and others are fine with her.
So, I think the focus -- this is different than Justice Kavanaugh replacing Justice Kennedy or Justice Gorsuch replacing Justice Scalia. Those didn't change the matrix of the court fundamentally. Here, you have got one of the greatest and most powerful liberal justices, greatest thinkers, Ruth Bader Ginsburg, being replaced by someone who the Republicans themselves say that is deeply conservative.
So I think that's where the debate is going to be. It's not going to be, is she brilliant, is she nice? It's all that kind of stuff. She is those things. That's not where the relevant question in the hearings will be.
MOHYELDIN: If the math goes through as planned, she will get confirmed. Is there any effort or should there be an effort to try to get her to commit to recusing herself on issues involving this election if, in fact, it somehow ends up at the Supreme Court and she is confirmed?
KATYAL: I mean, refusals are done by independent individual justices.
Trying to extort something like that is going to get nowhere. So, I don't see that as plausible.
But I do think that the fact that the president has been going around saying in campaign rallies he needs her on the court because there may be an election dispute is really one of the most corrosive things I have ever heard a president say about our United States Supreme Court.
Those justices shouldn't be tarnished by Donald Trump's disrespect for the law and disrespect for the court. That's not the way our justices operate. And I find it reprehensible that he'd say something like that.
MOHYELDIN: Obviously, the way this is all playing out, the way Republicans are ramming this nomination through, as you outlined in such a short period of time, has a lot of people talking about how and whether or not there should be a reformation of the Supreme Court.
It's certainly something Democrats are calling for, including possibly term limits for the justices, even expanding the court from its current form of -- format of nine justices. What's your view on all that?
KATYAL: Well, there's two different proposals kicking around.
One is an 18-year term for justices, which I think is a great idea. It's kind of weird, the way that there have been imbalances, of the last 18 justices, 14 appointed by Republican presidents, and Trump wants to make it 15 of 19.
And you have this kind of macabre spectacle of justices hanging on for a long period of time, in order to get a president who -- of the same political party who appointed them to be -- to be elected or something like that. It's just -- I don't think it's a good way to run things.
And then the other proposal kicking around is the idea of increasing the size of the Supreme Court, which I think is virtually inevitable if they do -- if the Republicans and President Trump do go in and install Judge Amy Coney Barrett as a justice on the Supreme Court.
I mean, it is so in fundamental tension with what they said in 2016. And paired up against the fact that they took that seat in 2016, I think it'll be -- I think that the Supreme Court will have 11, 13 or 15 justices on it as a result of what the Republicans are doing and the monkey games they're playing with our most treasured institution, the Supreme Court.
And I hate to see that, but I think it's inevitable.
MOHYELDIN: Yes, I think a lot of people would share your assessment.
Neal Katyal, thank you so much for giving us your perspective, as always. Appreciate it.
And, of course, for more of Neal's insight on all this, go to MSNBC.com/openingarguments.
Still to come, a former Trump Organization executive on THE BEAT speaking out about what she saw amid the uproar over his taxes.
Plus, on the eve of the first presidential debate, I'm going to talk to one of Trump's former debate stage opponents and what we can learn from that.
(BEGIN VIDEO CLIP)
D. TRUMP: What I have done is, I have used brilliantly the laws of the country, and not personally, just corporate.
And if you look at people like myself that are the highest levels of business, they use -- many of them have done it many, many times.
QUESTION: But did any average Americans pay the price, though, for that?
D. TRUMP: No, but I'm running a business. You have to understand, I'm running a business. I'm running a business for myself, for my company, for my employees, and for my family.
(END VIDEO CLIP)
MOHYELDIN: Donald Trump in 2016 talking about his use, or abuse, rather, of the tax code to prop up his businesses, an issue that's haunted him throughout his entire public life.
This new reporting from "The New York Times" undercutting his image as a financial whiz kid, which, by 2016, had begun to crumble. In fact, "The Times" reporting that "his financial condition some credence to the notion that his long-shot campaign was at least in part a gambit to reanimate the marketability of his name."
Joining me now is Barbara Res. She was an executive vice president at the Trump Organization.
Barbara, great to have you with us this hour.
Do these "New York Times" revelations match your experience working with Trump?
BARBARA RES, FORMER TRUMP ORGANIZATION EXECUTIVE VICE PRESIDENT: Well, you know, I didn't do the taxes.
But I did have a feeling about how he conducted himself. And they're a little surprising, I got to be honest with you. I didn't think that he would go to that extreme.
But I didn't think he would go the extremes that he's gone to in so many different areas, that it's -- it really shouldn't be a surprise.
MOHYELDIN: Do you think that he ran for president to try to reboot his business, as some have suggested, that he didn't seriously think he was going to win, but, in some ways, it would have made him more financially marketable in many ways?
I thought that from the beginning. First of all, I never thought that he wanted to be president. It's not -- it's not his nature to do that kind of work, to have to be responsible for other people, to answer to other people.
He's not like that. He likes to work when he feels like working. He says he's always working, but that's because he's a machine. He's always going. But I call it play work. I mean, I wish I could do what I want to do every moment of the day. And that's what he does.
And he -- president, no, I don't think he would dream of it. But he did turn the presidency into what he's used to in terms of work ethic.
MOHYELDIN: I'm curious to get your thoughts on the reporting by "The New York Times" that Trump paid his children through his companies and then deducted the cost as a business expense.
Does that surprise you?
RES: No, especially after having read that wonderful report they did about Fred Trump and how he funneled money to his children by creating this make-believe maintenance organization, and letting them get all the proceeds it, and running up the cost of maintenance in his different apartment buildings at the same time.
No, it didn't surprise me, no. And we're not going to look at Ivanka's returns, are we? I mean, it's these -- nonsense about $70,000 of hairstyling and things like that. You are supposed to deduct reasonable expenses.
MOHYELDIN: We have been talking about the two bombshells of this report.
The one aspect is how much he's paid, the $750. That really has more to do with the politics, how viewers and voters may consider it. But then there's the issue of the debt and the implications of that for our national security and the leverage the people who actually loaned him the money have over him.
Let me play for you and our viewers something Ivanka Trump said 20 years ago talking about her father and debt.
(BEGIN VIDEO CLIP)
IVANKA TRUMP, ASSISTANT TO PRESIDENT TRUMP: I remember once my father and I were walking down Fifth Avenue, and there was a homeless person sitting -- sitting right outside of Trump Tower.
And I remember my father pointing to him and saying, "That guy has $8 billion more than me," because he was in such extreme debt at that point.
And you're thinking, what are you -- what are you talking about?
(END VIDEO CLIP)
MOHYELDIN: Your thoughts on that, Barbara?
RES: I'm surprised that she was such a good liar 20 years ago. I mean, maybe that is why she's raised it to an art form.
I have heard that story 100 times from his wife, this wife and that wife and the other wife all walking down the street with him. Now it's Ivanka.
He was in debt for a lot of money. There's no question about that. And the banks saved him. The banks had to save him, because he was too big to fail. And if he lost -- if they lost him on all these different projects that he was working on, especially the West Side yards, they'd have a piece of property that they would sell at a bargain basement price, and lose a lot of money, whereas, with him, they were developing it.
And they believed that he could get approvals. And he ultimately did. Then it would be worth something, worth probably as much as the debt that was carried on it. So that's why they kept him alive, basically.
MOHYELDIN: Yes, interesting.
All right, Barbara Res, thank you so much for joining us this hour. I appreciate your time, as always.
RES: Thank you.
MOHYELDIN: Up next: a special guest, one of the few people alive who's actually gone against Donald Trump in a presidential debate; and what Kamala Harris said today about Trump's Supreme Court pick.
MOHYELDIN: Donald Trump's tax record will surely be a key part of tomorrow's first presidential debate with Joe Biden, one of the most anticipated and most important debates in American political history.
"The New York Times" supplying new details for suspicions about his business dealings, suspicions that also haunted him in the 2016 GOP primary debates.
(BEGIN VIDEO CLIP)
D. TRUMP: But you wouldn't know anything about it because you're a lousy businessman.
SEN. MARCO RUBIO (R-FL): Well, I don't know anything about bankrupting four companies. You've bankrupted...
D. TRUMP: No, I -- and you know why? You know why?
(CHEERING AND APPLAUSE)
RUBIO: I don't know anything about...
D. TRUMP: You know why?
I took $1 million and I turned into $10 billion.
RUBIO: Oh, OK, $1 million.
D. TRUMP: I borrowed $1 million...
RUBIO: Better release your tax returns, so we can see how much money he made.
(END VIDEO CLIP)
MOHYELDIN: And my next guest, Carly Fiorina, came to those same debates armed with her own successful business record, which she turned on Trump.
(BEGIN VIDEO CLIP)
CARLY FIORINA, FORMER HEWLETT-PACKARD CEO: There are a lot of us Americans who believe that we are going to have trouble someday paying back the interest on our debt, because politicians have run up mountains of debt using other people's money.
That is, in fact, precisely the way you ran your casinos. You ran up mountains of debt, as well as losses, using other people's money, and you were forced to file for bankruptcy not once...
D. TRUMP: I never filed for bankruptcy.
FIORINA: ... not twice, four times, a record four times.
Why should we trust you to manage the finances...
D. TRUMP: I will tell you why. It's very simple.
FIORINA: of this nation?
(END VIDEO CLIP)
MOHYELDIN: All right, joining me now is the aforementioned Carly Fiorina, former Republican presidential candidate.
Great to have you with us.
MOHYELDIN: So, you are one of the few who has actually debated then candidate Trump.
How would you use these "New York Times" revelations against Trump in a debate, if you were the Biden campaign?
FIORINA: Well, I would use them, but I would use them carefully.
And I say that because while, of course, the media is fascinated by this story, as am I personally, because it confirms my suspicions that he's never been a businessman -- he's always been an entertainer, and he's in a great deal of financial distress, it turns out.
But I say use them carefully, because the vast majority of Americans may not be following this closely. And what they really need to see from Joe Biden is how he is going to improve their lives, whether it's with regard to COVID, or their job, or their health care, or the fact that they're still homeschooling their kids because they can't go back to school.
So, of course, he needs to deal with it. The fact that Trump paid literally no taxes, it would appear, federal income taxes for 10 years, is certainly -- most Americans would consider that unfair, if nothing else.
But I think Joe Biden needs to stay in control of this debate. And what I mean by that is, he has to decide, what is -- what are the points that he wants to get across about himself? He needs to look presidential, act presidential, behave presidentially, and he can't get into too much of a mud fight with Donald Trump, because that's what Donald Trump wants, in fact.
MOHYELDIN: What do you think?
And you just pointed out that you're very fascinated and interested in these reports, just as the media is. What do you think of how Trump runs his businesses, based on what you have learned from "The New York Times"' reporting?
FIORINA: Well, you know, I was reminded today, reading this report, of being asked in 2015, if I had only one word to use to describe Donald Trump, what would it be? And my answer was entertainer.
And the journalist said, oh, don't you mean businessman? I said, no, he's a lousy businessman. I mean, we knew enough then to know he was a lousy businessman.
What we now know is that he has actually presided over a lot of financial distress, and that he is facing a lot of personal financial liability. And so, obviously, that demonstrates that this is not a guy who understands how to manage things successfully.
We knew that with four bankruptcies in a row, but now we know it at a level of detail, I think, that's quite surprising, actually.
MOHYELDIN: Let me play for you how Joe Biden talked about his debate plans in an interview with my colleague Stephanie Ruhle. Watch this.
(BEGIN VIDEO CLIP)
JOSEPH BIDEN (D), PRESIDENTIAL CANDIDATE: Look, the people know the president's a liar. I mean, they know that. It's not like it's going to come as a surprise to them.
And so I'm prepared to go out and make my case as to why I think he's failed and why I think the answers I have to proceed will help the American people on the American economy and make us safer internationally.
It is going to be difficult. I know the -- I mean, my guess is, it's going to be just trade attack. They're going to be mostly personal.
That's the only thing he knows how to do. He doesn't know how to debate the facts because he's not that smart.
(END VIDEO CLIP)
MOHYELDIN: What are your thoughts about that assessment?
Obviously, President Trump, as Joe Biden said there, lies, he's not going to stick to the facts, he will make things up, he may not be grounded in truth, he may make the attacks personal.
What does Joe Biden has to do? What does the moderator in this debate have to do, you think?
FIORINA: Well, I think Chris Wallace has demonstrated in previous interviews with the president that he's willing to hold people accountable for the facts, and I'm sure he will do that in a fair and balanced way.
But I think Biden is exactly right. Trump tries to control the airspace, and he has succeeded in controlling the airspace, as he did in the 2016 primaries, by being outrageous, controversial, insulting, by hurling amazing statements that people fall over themselves trying to correct.
And Joe Biden can't let him control the airspace. And so part of Joe Biden's job, I think, is to let Trump be Trump. Maybe there's a moment where he can have a Reaganesque, "There you go again," because the more people see Donald Trump, the more he reinforces what they think of him.
And so don't try and control Donald Trump, but don't let Donald Trump control you either.
Joe Biden has to stay in charge of his own message.
MOHYELDIN: All right, very important advice there from Carly Fiorina.
Thank you so much for joining us this hour. Appreciate your insights.
FIORINA: Thanks for having me.
And be sure to tune in to MSNBC for the full debate coverage starting tomorrow night at 8:00 p.m. Eastern time.
We're going to be right back with new comments from Kamala Harris on Trump's Supreme Court pick.
Stay with us.
MOHYELDIN: Tomorrow, Donald Trump's nominee for the Supreme Court, Judge Amy Coney Barrett, will head to Capitol Hill to begin meetings with GOP senators.
Judiciary Committee Chairman Lindsey Graham saying that he will hold the first vote on her nomination on October 22. That is just 12 days before the election.
Vice presidential candidate Kamala Harris addressed that quick timeline today.
(BEGIN VIDEO CLIP)
HARRIS: We're in the middle of an election.
President Trump and his party don't care. They just want to jam this nomination through as fast as they can. It's called raw power.
We will not let the infection that President Trump has injected into the presidency and into Congress spread to the United States Supreme Court.
(END VIDEO CLIP)
MOHYELDIN: All right, that does it for me.
Ari will be back here tomorrow night at 6:00 p.m. Eastern.
A reminder for tonight: Democratic vice presidential nominee Kamala Harris will join my colleague Lawrence O'Donnell at 10:00 p.m. Eastern. You do not want to miss that.
And, of course, you can catch me back here tomorrow at 3:00 p.m. Eastern.
"THE REIDOUT" with my friend Joy Reid starts right now.
THIS IS A RUSH TRANSCRIPT. THIS COPY MAY NOT BE IN ITS FINAL FORM AND MAY BE UPDATED.END
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