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Transcript: The Rachel Maddow Show, September 28, 2020

Guest: Mary Trump

Summary

"The New York Times" obtained President Trump's tax information spanning more than two decades. "The News York Times" reports that Donald Trump's tax records show years of business struggles, financial losses, and that he paid no federal income taxes in the 10 of the last 15 years. Mary Trump, who is the niece of President Donald Trump and the author of "Too Much and Never Enough: How My Family Created the World's Most Dangerous Man," is interviewed.

Transcript

RACHEL MADDOW, MSNBC HOST: Good evening, Chris. Thanks, my friend. Much appreciated.

And thanks to you at home for joining us hour. Happy Monday. Happy to have you with us tonight.

Don't tell Lawrence O'Donnell that I told you, but I sort of said that I'd be low key about. But today is the ten-year anniversary of Lawrence's show. Today is the ten-year anniversary of "THE LAST WORD." Ten years. Nobody gets to be ten years old in this business.

On the occasion of that big celebratory birthday, you should know that Lawrence has a live interview tonight with the Democratic Party's vice presidential candidate, Senator Kamala Harris. That is happening live right after me, right after this show tonight. So you should plan now to stay on after me to watch that with Lawrence and Senator Harris.

Senator Harris, of course, will be debating Vice President Pence next week. That vice presidential debate is next Wednesday. But tomorrow, of course, is the first presidential debate between Trump and Biden.

I'll have more details for you a little later on this hour about what our coverage of that is going to be like tomorrow night. I will be anchoring right up to the start of the debate with my beloved colleagues Joy Reid and Nicolle Wallace. And then you'll be able to watch the whole thing live right here with us tomorrow night. Again, I'll have more on that for you later on this hour.

But the debates in this last lead-up to the election, we now know will coincide with the Republicans in the Senate trying to rush through the confirmation of a new hard, hard, hard-line, arch conservative Supreme Court nominee. The Republican plan is to try to confirm Amy Coney Barrett right before the election. I think they are hoping that they will excite their base and demoralize the Democratic base by doing that as close to the election as they can.

Democrats, though, are not conceding that this is a done deal. Vice President Biden this weekend urging Republican senators to not move the Barrett nomination forward, to not move any nomination forward until after voters have chosen who they want as the next president.

(BEGIN VIDEO CLIP)

JOE BIDEN (D), PRESIDENTIAL NOMINEE: I urge every senator to take a step back from the brink, take off the blinders, the politics for just one critical moment and stand up for the Constitution you swore to uphold. Just because you have the power to do something doesn't absolve you of your responsibility to do right by the American people. Uphold your constitutional duty. Summon your conscience.

(END VIDEO CLIP)

MADDOW: Summon your conscience. We shall see.

It would take two more Republican senators to side with Senators Collins and Murkowski in saying this nomination should wait until after the election. If two more Republican senators join with them in that, then this nomination, any nomination will wait until after the election. Democrats are pledging to do everything they can to stop any confirmation after the next president is inaugurated with public opinion polling on their side, the pressure on Republican senators is intense.

The elements that are trying to stop this nomination are getting some backup now from bold-face editorials like this one this weekend from "The Washington Post", headlined: The Senate should ignore Amy Coney Barrett's nomination. This editorial is not about Amy Coney Barrett. No matter whom President Trump had picked to fill the late Ruth Bader Ginsburg's Supreme Court seat, it would be the wrong choice because it is the wrong time. Senator Republicans should be disgusted at playing the role they are being asked to play.

The president himself has said he's counting on Judge Barrett's hurried confirmation so she can rule on what he appears to believe are the inevitable election disputes he will bring before the court. He has spoken in recent days about getting rid of the ballots and enlisting the court in stopping the Democrats' voting scam, arguing that he needs a ninth justice of his choosing to ensure the court rules his way.

The editorial board continues, quote, imagine the turmoil that would cause. A course hastily stacked with Trump nominees hands re-election to the president based to a degree on his view that some Americans' ballots should not count. Are there not four Republican senators, which is all it would take, with sufficient conscience or care for the country?

Are there not four Republican senators? That's "The Washington Post" editorial board this weekend.

The effort to delay any Supreme Court confirmation until after voters have chosen the next president will also get some additional backup, we now know, from a new women's march that is scheduled for Saturday, October 17th, in Washington, D.C. that means it will precede the election by about two weeks. That march will be aimed at trying to backstop these efforts to stop any Supreme Court nomination until after the inauguration.

It's all happening all at once, right? All news streams on stun, everything at the same time.

And you might have heard "The New York Times" got Trump's taxes. More than 20 years of Trump tax returns, finally, after all this time. In terms of how we got here, "The Times" had previously published three pages from Trump's taxes in 1995. Those three pages they received mysteriously, anonymously in the mail. That was in 2016 that they published those three pages. Those pages showed the president declaring huge financial losses from his failing business efforts like potentially more business losses than any other single taxpayer in the country that year.

Then in 2017, we published two pages from Donald Trump's 2005 taxes, two pages from his 2005 federal tax returns. Those two were obtained sort of mysteriously. They were mailed anonymously to reporter David Cay Johnston who then gave them to us to put on TV. Those two pages from the 2005 tax returns showed Trump paying a bunch of taxes that year, but no real detail explaining why.

Then the year after that, in 2018, "The Times" published an epic, multi-thousand word piece, an epic investigation into the financial history of the Trump family and the Trump family business based on financial and tax records that we later learned they had obtained from the president's niece, from Mary Trump. Mary Trump, of course, published a best-selling book this summer that was in part about her providing those family financial records to "The Times," which became the basis for that expose in "The Times," for which "Times" reporters won a Pulitzer Prize, and which led ultimately to Mary Trump filing a new lawsuit against her uncle, the president, for allegedly cheating her out of tens of millions of dollars worth of the inherited family fortune.

So, all of that had happened 2016, 2017, 2018. The book this summer from Mary Trump. The new lawsuit from Mary Trump about the family finances.

But now, what has just happened in "The Times," this is something different on an order of magnitude. From -- this -- from "The Times" right now, there's a reason elected Republicans in Washington have all been in hiding today, right? They have no idea what they're supposed to say about this. They are all under their respective rocks at this point because how are they going to explain this to the American people, particularly when so many of them are going to the American people are saying put me back in office alongside this president.

The reason we have a modern expectation that every president will show the public their tax returns is because of Nixon in 1973 when he was caught cheating on his taxes. Nixon was making 200 grand a year as president, but as the newspaper that got his tax returns put it in 1973, as the "Providence Journal Bulletin" in Rhode Island put it, President Nixon was paying in taxes at that time not what you would expect from a person making 200 grand a year. He was paying what you would expect from, quote, a wage earner with one exemption in the $7,000 a year income bracket. Nixon was making 200 grand. He paid taxes like he was making $7,000.

Nixon was found in that tax return that was anonymously mailed to that newspaper, Nixon was found to have paid a federal tax bill in 1970 of $792.81. That's it?

People were outraged. That's ridiculous. He's making 200 grand a year. He paid less than $800 in taxes while he was president?

Nixon immediately tried to quell the damage. He released I think it was four years of his tax returns publicly, and that turned out not to be an awesome idea because he was found to have, in fact, have weaseled out of his taxes on a much grander scale. It turned out he actually owed almost half a million dollars in back taxes, which he did end up having to pay, and that ended up being just one more thing driving Richard Nixon absolutely nuts and driving public opinion of him through the floor in the middle of the Watergate scandal.

But that debacle from Richard Nixon weaseling out of his taxes, that's why presidents have released their tax returns ever since. Because of that Nixon debacle, we expect presidents will not be allowed to hide stuff like that in their taxes anymore, that they will proactively show us their tax returns and let us see what they've got to hide, if anything.

Well, Donald Trump has broken that rule. If it weren't for "The New York Times" and their new reporting, President Trump would still be hiding his taxes. And now thanks to this new reporting from "The New York Times," we know President Trump paid even less than Richard Nixon did in federal income taxes. Even if you don't adjust for inflation between 1970 and now, Nixon paid more.

I mean Nixon paid, what was it, 780-something? Now we know the year he was elected in 2016, Trump paid $750 in federal income taxes. And again in 2017, that year he paid $750 in federal income taxes. That's it. The Biden campaign has already turned just that fact into a new ad contrasting what President Trump contributes to this country financially compared to what you contribute to this country financially, compared to a nurse, a teacher, a construction manager, a firefighter, basically anyone.

And, you know, I think that the American people have learned enough about how the rich rig the systems of this country in their favor to know that people expect now that rich people find ways not to pay taxes. I think the American people broadly expect that rich people will make the system work for them and come up with complex tax avoidance or tax evasion schemes.

But even though we have a sort of cynical expectation about that for rich people more broadly. What "The Times" has just revealed is Trump is doing something way different than even normal really rich people do. On average, we know what the richest .001 of pay in taxes now. If even Trump had just paid that, what the other mega rich people in the universe pay, he would have paid $400 million in taxes than what he actually paid.

I mean even compared to way the mega rich game the system, he is gaming that system like no one else. And the details are weird and damning and memorable. I mean, that year from which we got the two pages of his tax returns from 2005, we got two pages from David Cay Johnston, that showed, you'll recall, that he was paying a bunch of taxes. Turns out that year, 2005, was a huge anomaly in that he paid any taxes at all.

In 11 out of the past 18 years, President Trump paid $0 in federal income taxes, zero in 11 out of the past 18 years. In two of those years, he paid only $750 for the whole year.

He has radically, radically avoided paying taxes, and he has done it in part by declaring stuff as business expenses that are things that don't really seem like legit business expenses. For example, he deducted as a business expense the legal defense for Don Jr. in the Mueller investigation, which was mostly defending Don Jr. over him meeting with Russians during the campaign who were offering dirt on Hillary Clinton courtesy of the Russian government that they wanted Donald Trump to be able to use against Hillary Clinton in the campaign.

Well, tax law says you can't deduct business expenses -- you can't deduct as business expenses things that -- expenses that were accrued based upon your participation in a political campaign. But that does appear to be the type of expense this was for Don Jr. He nevertheless deducted it as a business expense from his taxes.

The president also deducted as a business expense from his taxes over $70,000 of hairstyling expenses for himself. Really? He also deducted almost $100,000 of hair and makeup expenses for his daughter, Ivanka. He also deducted as a business expense consulting fees that he appears to have paid to his daughter, Ivanka, even though consulting fees was supposed to go to independent consultants, and not to your own employees and executives like Ivanka Trump was in the Trump company.

And as "The Times" notes today, the IRS has pretty aggressively pursued other companies for breaking those rules. The tax records reported on by "The Times" show that the president has taken millions of dollars from foreign sources since he has been in the White House, including money from Turkey and from India and from the Philippines. Taking money from foreign sources is not supposed to be allowed clearly under the emoluments clause of the Constitution, but he has done that to the tune of millions of dollars.

When it comes to money from Russia, the tax documents reviewed by "The Times" show that Trump's Miss Universe, that pageant lost money regularly, basically every year, except for that year when the pageant was moved to Russia in 2013, somewhat inexplicably for what was otherwise a money-losing enterprise.

In 2013, a Russian billionaire close to the Kremlin offered to pay millions of dollars to put that pageant on that year in Moscow. That Russian oligarch himself lost his shirt on the thing. He lost millions of dollars himself, but millions of his dollars did end up in Donald Trump's pocket, making what was otherwise an unprofitable enterprise quite profitable for Donald Trump that year that the Russian oligarch was paying.

You'll recall this is sort of a pattern with the president. The Russian oligarch giving up millions of dollars so Trump could have a big payday with that pageant, that happened not long after another Russian oligarch appears to have wildly overpaid Mr. Trump for a Palm Beach, Florida, property that Trump marked up by tens of millions of dollars without doing much to it at all. That's the property that Michael Cohen says in his new book the president bragged was money in his pocket that had been personally approved by Russian President Vladimir Putin, who Trump believed controlled major spending by oligarchs abroad.

But the big story here, the big takeaway is really two things. First, it's that the president has avoided paying taxes to the tune of hundreds of millions of dollars over the years, and that is in part by declaring dubious business expenses. But it's mostly by him telling the IRS that his businesses are all massive failures.

I mean, on paper, in terms of what the president has reported to the IRS, the Trump corporation since the year 2000 has lost $134 million. According to the president, his golf courses since the year 2000 have collectively lost almost $316 million. He says that he's lost over $162 million on his Doral golf course alone, the one in Florida that he wanted to put the G-7 at.

At his D.C. hotel, in just the first two years of his presidency, the president told the IRS that hotel has lost over $55 million. I mean, that's the first of the two big-picture takeaways here that we might have guessed about how the president was conducting his business. But this shows it in black and white.

He has avoided paying hundreds of millions of dollars in taxes by telling the IRS that everything he touches fails, that all of his business dealings, all of his signature projects, his golf courses, his hotels and everything he tries to run with his name on it, it all has just failed catastrophically and it all fails every year. That's now in the record that has been exposed by "The Times." we can now see that in terms of "The Times'" account of his taxes.

And we can see how that story he's been telling the IRS diverges from what he's been telling us, the public. I mean, just look at 2018 alone. His financial disclosure from the White House, right, public-facing document -- his financial disclosure from the White House for 2018 said that he made at least $435 million that year. Well, his tax records show that he lost $47.4 million that year.

Well, which is it? Did he make $435 million, or did he lose $47 million? Which is it? He told two different audiences two very different things about that same year.

He told the IRS he lost $47 million. Is that true? Is the president comfortable admitting that he lost all that money in 2018 and that he's been losing hundreds of millions of dollars for years?

Can he just shut up and eat that, right, now that everybody's going to be able to see the figures and see officially that his business empire is a terrible and consistent failure, or can his ego not take that? Will he feel obliged to disclaim what he's told the IRS? Will he feel obliged to claim publicly that, yeah, yeah, yeah, though losses are on paper in terms of what I told the IRS, but in reality, I really am makes hundreds of millions of dollars, I just told the IRS otherwise so I don't have to pay taxes on it? I mean his ego is going to drive him to say that.

But there's a problem. If he cops to that, the president is potentially showing the necessary intent and understanding of his actions to cross the line from obvious tax avoidance, which is legal, into obvious tax evasion, which is potentially a quite serious crime. So that's the first of the two big takeaways here. Can the president's ego endure the public knowing that what he says has happened to his business empire is catastrophe upon bankruptcy upon failure year after year after year? Or will he explain that away and thereby cop to a crime?

The second big takeaway here is that officially at least, the president appears to be up against the wall right now financially. As "The Times" puts it, they say clearly, quote, as the president wages a re-election campaign that polls say he is in danger of losing, his finances are under stress, beset by losses and hundreds of millions of dollars in debt coming due that he has personally guaranteed.

Quote, his tax records make clear that he's facing a battery of threats to his business and his own financial well-being.

Quote, over the past decade, he appears to have filled his cash flow gaps with a series of one-shots that may not be available again. In 2012, for example, he took out a $100 million mortgage on the commercial space in Trump Tower. He took nearly the entire amount as a cash payout, his tax records show. His company has paid more than $15 million in interest on that loan, but his company has paid nothing on the principal. That means the full $100 million mortgage is going to come due in 2022, which is only two years from now.

The president also has huge loans coming due for the Doral golf resort, $125 million owed there, and the Washington D.C. hotel. He owes $160 million there. Both of those businesses are struggling, so it's hard to believe that he'll be able to, say, refinance those loans in a way that makes any sense for his financial situation.

In all, the president, quote, is personally responsible for loans and other debts totally $421 million with most of it coming due within four years from now. Should he win re-election, his lenders could be placed in the unprecedented position of weighing whether to foreclose on a sitting president.

"The Times" calls this is a tightening financial vice. House Speaker Nancy Pelosi today calls it a national security issue, that the sitting president owes hundreds of millions of dollars to god knows who in loans that are coming due very shortly, loans that he appears to have no way to repay. What would a person in such dire straits do to get themselves out of that hole? What would a president do to get himself out of that hole?

Well, here's something to consider. Separate and apart from "The Times" obtaining these tax returns, this remarkable reporting that's likely to keep producing more and more news in the days ahead -- September and apart from that from "The Times"," we do have a new piece of help from history to help brace ourselves for the lengths this particular president might go to now that he appears to be in serious financial distress.

I mean judging from these years of tax records that have now been pieced together and scoured by "The Times," it seems like the last time Donald Trump was in financial straits this dire was in the late '80s and the early '90s when he, again, had run all of his business enterprises into the ground. He had taken huge loans he had no way to repay. He owed hundreds of millions of dollars, including a whole bunch of stuff he had personally guaranteed, meaning his creditors could come for his personal assets, his personal bank accounts, anything he owned personally in order to make good on those loans.

That's what's going on with him now it appears from these tax records. That also happened to him in the late '80s, early '90s.

Well, Mary Trump, the president's niece, who provided Trump family financial records to "The Times," as I mentioned, she's brought legal action against president Trump and other family members for them allegedly cheating her and her brother out of tens of millions of dollars in Trump family assets when it came to inheritance.

Well, alongside this "Times" reporting this weekend, this bombshell stuff from "The Times," this weekend, "The Washington Post" also reported that in 1990, the last time Donald Trump was in financial distress this severe, he had gone through six corporate bankruptcies. He owed hundreds of millions of dollars, including personally guaranteed loans. He was worried that his expected huge inheritance from his father when his father died would be seized by all his creditors as soon he was given that inheritance.

And so, in 1990, as detailed in "The Post" this weekend, Donald Trump sent an accountant and a lawyer to go see his father, to tell his father, quote, to immediately sign a document changing his will to benefit Donald Trump.

Quote, it was a fragile moment for the senior Trump, who was 85 years old and had built a real estate empire worth hundreds of millions of dollars. He would soon be diagnosed with cognitive problems, such as being unable to recall things he was told 30 minutes earlier or remember his birth date according to his medical records. Trump's father was 85 years old at the time. He was about to be diagnosed with significant cognitive impairment, and that's when Trump to him and said, sign over the estate to me.

The president's brother, Robert, gave a sworn deposition in a lawsuit over that will that in 1990 when Donald Trump was in financial distress and he tried to push his dad into signing over control of his whole estate to him, Robert testified in that deposition that his father, his and Donald's father was in, quote, notable decline cognitively starting that year. But Trump went to him anyway to try to get him to redo his will, to help Trump out because he was in dire straits.

Mary Trump has now released recordings of her aunt, the president's sister, talking about that incident.

(BEGIN AUDIO CLIP)

MARYANNE TRUMP BARRY: I still have all the papers -- my contemporaneous handwritten notes of what -- John -- I look at this. I don't know this trust and estate, I've done criminal (INAUDIBLE) mostly, but not this. I show it to John, he says, holy (EXPLETIVE DELETED). He was basically taking the whole estate and giving it to Donald. And he would be our, you know, if you want to get a cup of coffee, Donald, may I have 50 cents? You know, I'm exaggerating, but no.

Now, he was also in bankruptcy, several bankruptcies. Holy (EXPLETIVE DELETED), John got a new lawyer in the next day, and that codicil was never signed. Dad was in dementia at that point, you know so --

(END AUDIO CLIP)

MADDOW: So Trump family medical records and tax records and these recordings of the Trump family talking about their financial history, all this stuff is making its way into the press the day before the first presidential debate. And so, now, we know that apparently the president owes hundreds of millions of dollars in loans to God knows whom, loans that he has personally guaranteed that are all coming due very soon, and that he has no obvious way to pay back.

We now know that the last time that happened to him, he wasn't president, but he did have a father sliding into dementia from whom he apparently tried to hijack the family fortune. This time his father's gone, and he's squandered the family fortune. But instead in his desperation, he's got us, the American people.

And he's got the powers of the federal government. And he's got an election coming up soon by which he will try to stay in office, which happens to offer him immunity from prosecution as long as he's in power, and which might conceivably cow his creditors into not seizing everything he owns.

So how far do you think he'd go to hold on to power in this context? What could possibly go wrong for us as a country? How is a person with liabilities like this in the presidency in the first place? My god.

(COMMERCIAL BREAK)

MADDOW: So, "The New York Times" broke this story yesterday, 20 years of the president's tax returns, with a whole bunch of very newsy, very important revelations like the president having over $400 million in personally guaranteed debts that he needs to pay back in the next four years, with what appears to be no way for him to meet those obligations. I mean, you couldn't get the lowest level security clearance from the federal government with that kind of liability hanging over you, but here he is president.

"The Times'" previous Pulitzer Prize-winning reporting on the president's financial and tax history was based on documents we later learned but provided to them by Mary Trump, the president's niece.

Well, tonight, Mary Trump says that she is not the source of the documents for this latest reporting of "The Times." "The Times" says in their piece that they received the documents from somebody who held them legally. They say they're not releasing the underlying documents, the tax returns themselves, in order to protect the anonymity of their source.

That means that nobody else, including MSNBC and NBC News, have seen the raw documents, only "The Times" have seen this. But the reporting itself is remarkable.

Joining us now is Mary L. Trump, who is the niece of President Donald Trump. She's the author of "Too Much and Never Enough: How My Family Created the World's Most Dangerous Man."

Mary, it's really nice to see you. Thank you very much for making time to be here tonight.

MARY TRUMP, AUTHOR, "TOO MUCH AND NEVER ENOUGH": Thanks so much. I'm really happy to be here, Rachel.

MADDOW: So, there's a bunch of things going on here at once. I feel like the new revelations in "The Washington Post" about what your uncle did when he -- the last time we knew he was in dire straits, financial straits this dire, when he tried to go to his father. He was in decline, he tried to get him to change his will -- I feel like that is a scary piece of foreshadowing, more reason to worry about what he might do now that he's president, and he appears to be sliding back into financial straits that dire.

Do you see a parallel there?

MARY TRUMP: Yeah, unfortunately, it's a parallel in a long series of parallels, that for reasons I'm still grappling with, a lot of people have either chosen to ignore or to take advantage of.

But you asked exactly the right question and it's not what a theoretical president would do. It's what Donald would do in the situation and we know.

MADDOW: In terms of what "The Times" has reported today. Obviously, in 2018, they had that huge expose that you later explained in your book was based in part on documents from you.

Now, this is new reporting. They've been able to access 20 years of tax returns and that nobody has ever seen before and that nobody except them has seen.

How is this -- what they're reporting -- comport with what you understood about your uncle's financial history, about your family's financial history? Did this open big new avenues of understanding for you or is this in keeping of what you expected?

MARY TRUMP: It's in keeping with what I would -- what I expected because, again, unfortunately, nothing Donald has done in the last five years has surprised me. But that doesn't mean it's not horrifying, and it doesn't mean it isn't necessary, you know?

As usual, Susanne Craig and Russ Buettner have just been extraordinarily brilliant in their reporting, I believe every word of it, and also, hat tip to Mr. McIntire whom I don't know. But laying out this way is very important for the American people because it's one thing for me to have an opinion or for me to say I'm not surprised, it's all part of a pattern, and, you know, just by your own brilliance synthesis and connecting of dots, people like to see proof and numbers.

I mean, it's is interesting how that $750 number has resonated so strongly with American taxpayers, even though I don't think it's the most important aspect of the article. I think the national security threat is infinitely more important. But if it helps people connect to the story and if it's -- if it's an end road to understanding this fairly complex tax information, I'm all for it. .

MADDOW: Mary, the presidential debate, the first debate is tomorrow between your uncle and former Vice President Joe Biden. Obviously, this is going to be -- I don't know if this would be the basis for questions, but it's clearly an important part of the backdrop for the news heading into this debate.

It strikes me that the -- your uncle's ego around financial issues, the way he likes to sort of perform this sort of pageant of success and never having any sorts of failures might be a weak point for him in the debate on this if Vice President Biden wanted to try to pin him on this issue. I -- I mean, you know his brain better than anybody else I've talked to.

Do you think that he will cop to the fact that his businesses, at least on paper, at least according to the IRS filings, appear to be massive failures, or do you think that he might try to explain that away as something he did just to avoid taxes? Which, of course, would provide its own form of risk for him in terms of potential future prosecution.

MARY TRUMP: He's in a bit of a vine, is he?

I hope that this is a major topic of the debate. Honestly, for people to ignore this and ask him about his policy position or his corrupt Supreme Court nomination is once again to legitimize him.

This is a topic that cannot be let go. It can't be ignored. It has to be hammered on, because if he's just asked once, you're right, his ego will kick in, but he'll spin it in a way that makes it seem like it was the smart thing to do as he said in 2016.

But, if he goes there, because obviously, you know, nobody is going to be able to prove criminality on the debate stage. But, you know, it's one thing to be a private citizen and not pay taxes because you're, quote/unquote, smart. It's another to do it as a leader of a country you're supposed to be protecting and caring about, it's deeply unpatriotic. And it needs to be seen at least in those terms right now and we'll deal with the rest later.

MADDOW: Mary Trump, the niece of President Donald Trump, the author of "Too Much and Never Enough: How Family Created the World's Most Dangerous Man" -- Mary, I am looking forward to talking to you after -- after the debate tomorrow. I know it's going to be -- I feel sort of a sense of foreboding and also, I can't wait to see it.

MARY TRUMP: Yeah, I'm with you.

MADDOW: All right. Thank you.

All right. Still ahead tonight, we are going to be speaking with somebody who had more of a chance than almost anybody on Earth to actually investigate the president's finances with subpoena power and all the rest of it, except he was told to stop. He has written a remarkable new book about it and he joins us for his first TV interview about that book, next.

Stay with us.

(COMMERCIAL BREAK)

MADDOW: This is from page 146. Quote, I had arrived at the special counsel's office expecting to conduct a rigorous financial probe. There was no shortage of intriguing threads to pull on when it came to Donald Trump and the Trump Organization. Tax fraud, foreign bribery, election fraud, bank fraud.

But our office was put on notice by the White House early on that engaging in such a broad-based financial investigation might lead to our firing. This is from a new book that comes out tomorrow which is called "Where Law Ends: Inside the Mueller Investigation," in which lead Mueller prosecutor Andrew Weissmann explains how and why the special counsel's office failed to investigate, among other things, the president's finances, really anything about the president's finances.

This is how Weissmann describes what happened when his fellow prosecutor in the Mueller team Jeannie Rhee wanted to subpoena the Trump Organization for emails about the Trump Tower Moscow project, which the president kept secret throughout the 2016 campaign.

From page 260, quote: Mueller's chief of staff Aaron Zebley and Jim Quarles, the prosecutor leading the obstruction investigation, knew that making a move like this would get back to the White House and there could be consequences. And sure enough, Aaron Zebley eventually told Jeanie to stand down in her pursuit of Trump tower Moscow emails. He said that Mueller agreed with him, that this was not worth the potential blowback. We were still negotiating with the White House to get an interview, and once again, Aaron claimed this would hurt that negotiation.

For Jeannie, this directive was the last straw. We shut the door to her office and had the mother of all bitch sessions. So what, she railed. Better to get fired than to voluntarily pull our punches.

All I could do was reiterate her point in various different ways and with rising amounts of ire and profanity. From then on, better to get fired was the refrain we tossed back and forth every time we sensed our office pulling back from our mission. We both knew that the lack of follow-up here meant that any chance we had of ever performing a classic financial investigation to assess Trump's ties to Russia and motive -- excuse me -- and mode of evidence was dead. Needless to say this meant that Trump's tax returns were out of bounds.

In the end, Weissmann says, we would fail to conduct a full investigation, and we never got an interview with the president. In the end, the wrongdoing we found in the areas in which we chose to look, particularly in the one Russian financial deal we examined as a result of Cohen's cooperation, left me with a deeply unsatisfying feeling about what else was out there that we did not examine. The inability to chase down all financial leads or to examine all crimes gnawed at me, and it still does.

That's from the new book by lead Robert Mueller prosecutor Andrew Weissmann. It comes out tomorrow. It is the first real unvarnished look we've had inside the Mueller investigation from someone who was there from day one till the end.

Andrew Weissmann is not shy about describing where he thinks their investigation fell short, particularly on the issue of following the money. Now that we've got this "New York Times" report on all of the unexploded bombs that are inside Trump's taxes, that reporters have been able to find even though prosecutors didn't go looking for it, we've got Andrew Weissmann joining us next here live.

Stay with us.

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MADDOW: It's the fall of 2018. Andrew Weissmann is in a meeting, arguing his case to Robert Mueller.

Weissmann writes, quote: The way I saw it, our office had a mandate to conduct a thorough investigation and we needed to be appropriately aggressive in order to fulfill it. I'm concerned about the precedent we're sitting, I began. What are we saying to future presidents and future investigators who will have our decision thrown in their face? If we don't subpoena the president in this investigation, how can other justify the need to do so? The facts warrant it. If taking our shot with a subpoena leads to our getting fired, so be it, I concluded.

Mueller sat patiently through all of this, nodding but offering no reaction, no indication of whether it was affecting his thinking. This, I knew, was not a good sign. The meeting ended unceremoniously shortly after I'd concluded my soliloquy. It was clear a decision had been made, and that the rest of us were simply late in recognizing that and accepting it.

As much as we respected Mueller and understood that his decisions were governed by his sense of duty and right and wrong, we also knew how each of us would have proceeded if we'd been in charge.

It just didn't sit right. We were left feeling like we had let down the American public, who were counting on us to give it our all.

Andrew Weissmann, one of the lead prosecutors for special counsel Mueller, he headed up the prosecution of Paul Manafort. His book is called "Where Law Ends: Inside the Mueller Investigation." It is on sale tomorrow.

Andrew, thank you for being here.

ANDREW WEISSMANN, AUTHOR, "WHERE LAW ENDS: INSIDE THE MUELLER INVESTIGATION": Nice to be here, Rachel.

MADDOW: This is a heartbreaking book. This was not the book that I expected to read, and your sort of rending of garments and your regret about what wasn't done feels terrible. I mean, the book is beautifully written, and I learned a ton, and I'm sort of gutted.

Did you know it was going to do this to me?

WEISSMANN: Well, it did it to me also. It was a very hard book to write, but I really thought it was necessary for me to be as candid as possible about the things that we did right and the things that I thought we could have done better. I do think one thing that's certainly relevant to "The New York Times" story that you've been reporting on is just how much the White House did not want us to do a financial investigation.

In the book, I tell the story of our issuing a grand jury subpoena to Deutsche Bank. It turned out that grand jury subpoena was for Paul Manafort, but the White House got wind of the fact that we issued that grand jury subpoena and called up and demanded to know whether we were doing a financial investigation of the president. That was a red line.

And at that early stage in the investigation where there was this sword of Damocles over us as to whether we were going to be fired from one day to the next, the decision was made better to let the investigation go forward and put the financial investigation on hold.

The issue I have is that that decision was not revisited and that we really should have done the financial investigation. And many of the questions that people have from "The New York Times" reporting would have been answered.

MADDOW: In a normal prosecution that doesn't involve the president, when a suspect or a target of an investigation tells you some things are red line, don't go there, usually wouldn't you take that as an indication that that's where the crime is and that's why they don't want you to look there?

WEISSMANN: That would be a red flag. Usually when someone's saying don't look there, as a prosecutor, you want to look there. And also, it's completely abnormal to be investigating somebody who has the power to pull the plug on your investigation.

So it's important to remember that for 22 months, we did not know from one day to the next whether we would have a job the next day. So it was an extremely unusual situation.

MADDOW: That said, I feel like you would have all had -- you would have not had the jobs that you had working on the special counsel's investigation, but you would have all had jobs. You would have all gone back to whatever it was you were doing before you were seconded to this investigation.

I guess the thing that I didn't -- the thing that I still feel like I don't understand and maybe I just am not a lawyer, and I've never worked at the Justice Department, and I can't empathize for those reasons. But it just feels to me like getting fired was not a fate worse than death. If you'd been fired because you did something that angered the president, you could all then say, this is why we were fired, and then other investigators, potentially even a subsequent special counsel, would know that you hit the land mine, that you stood on something that exploded, and that's why you were all fired. There would have been -- just as after the Saturday night massacre in Watergate, there would have been a reason and a way to follow up on what happened to you guys if you pushed too hard.

WEISSMANN: Rachel, I completely agree with you. That is a decision I think that we should have made, whether it came to subpoenaing the president, whether it came to doing a financial investigation. There's absolutely nothing wrong with being fired for doing your job, and I think that's a line we -- we had an obligation to the public to do that.

MADDOW: Andrew, let me ask you about something that emerged over the course of the Manafort investigation which you were sort of team leader on, and that was the issue about Manafort's contact with Konstantin Kilimnik. In your report, he was described, and in court he was described as somebody who was tied to Russian intelligence. Senate intelligence committee later came out and said bluntly, he's a Russian intelligence officer. I want to ask you about those different -- those different ways of describing Kilimnik and whether that was sort of a pulled punch or whether you think the intelligence committee actually came up with something other than what you guys had.

But also what you take -- what you think the people -- the American people should take away in terms of the seriousness of this incident in which Manafort was providing Kilimnik with all of this internal polling data, strategic data about the campaign, while Manafort was serving as Trump's campaign chair.

WEISSMANN: So I'm not sure whether the Senate Intel Committee came up with new evidence. There was a lot of debate about the team, that is, my team wanted to have a classified appendix to the report that put in information that would supplement our information about Konstantin Kilimnik. So it could very well be that that information is what guided the bipartisan Senate report.

I think what people need to understand that's remarkable is that Paul Manafort, during the presidential campaign in June, July, August of 2016, was sharing Trump campaign polling data with Konstantin Kilimnik who has been identified as a Russian asset. He met with him in person on August 2nd and described for him the state of the campaign. He described the state of play in so-called battleground states, of which one of the battleground states he described was Wisconsin, which I don't think people generally thought of that way.

So there was a lot of private information going to a Russian intelligence officer, which, of course, is remarkable.

MADDOW: At the same time that the Russian intelligence was mounting an effort to make sure that candidate got elected and doing so with some level of skill and detail.

WEISSMANN: Yes and --

MADDOW: It's a remarkable story that still is not told. Sorry. Go ahead.

WEISSMANN: I was going to say, you know, tying it back to what we learned from "The New York Times" yesterday, if you remember, Eric Trump in 2014 made the statement that the Trump Organization did not rely on American banks because they got plenty of funding from Russia. So the outstanding question and the question that we, I think, really did drop the ball on is the 400 or so million dollars that the president has in debt. Who does he owe that money to?

We have some inkling from Eric Trump as to one possible answer to that.

MADDOW: The book is called "Where Law Ends: Inside the Mueller Investigation." It is on sale as of tomorrow.

Andrew Weissmann, thank you so much for your time tonight. It's really good to have you here. Congratulations on the book.

WEISSMANN: Thank you very much.

MADDOW: We'll be right back. Stay with us.

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MADDOW: That's going to do it for me tonight. I'll see you again tomorrow for our debate coverage.

But right now, it's time for "THE LAST WORD WITH LAWRENCE O'DONNELL". "THE LAST WORD" celebrating it's 10th anniversary as a show. Don't tell Lawrence I reminded you. Lawrence has -- have a big guest joining him tonight, vice presidential candidate Kamala Harris.

Oh, good evening, Lawrence. Didn't know you were there.

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

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