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Could Trump Be The 1st U.S. President Charged With A Criminal Offense?

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross.

Now that Donald Trump is out of office and can't claim presidential immunity, he's facing two investigations into possible criminal conduct. One was opened last month by a county prosecutor in Georgia who's investigating Trump's efforts to change the state's election results. The larger investigation is being led by Manhattan's district attorney, Cyrus Vance Jr., who's looking into Trump's financial business practices, examining the possibility that Trump and The Trump Organization engaged in tax, banking and insurance fraud. If Trump is charged, he'd become the first former president charged with a criminal offense. He could end up doing prison time.

In a new article about this investigation published in The New Yorker, my guest Jane Mayer writes that this is one of the most significant legal showdowns in American history. It's about much more than a financial investigation; it's a stress test of the American justice system. Mayer is The New Yorker's chief Washington correspondent. Her article is published in the March 22 issue of the magazine. If you're looking forward on The New Yorker website, the title on the site is "Can Cyrus Vance, Jr., Nail Trump?"

Jane Mayer, welcome back to FRESH AIR. In what way is this investigation and would this trial, if it happens, be a stress test of the criminal justice system?

JANE MAYER: Well, one of the questions that's been posed by the Trump presidency is whether the president is, in some ways, above the law and beyond prosecution. The lawyers for President Trump when he was president argued that he was immune to sort of criminal prosecution. They literally argued that if he followed through on a boast that he made during the campaign in 2016 - that he could stand on Fifth Avenue and shoot someone and that it wouldn't hurt him - that is so, that that's true. They argued that he couldn't be prosecuted for that. And so this is, in some ways, a question of whether our president is above the law.

GROSS: You know, some people think, look; we should just move on. Like, Trump, his time is over. He's out of office. Let's focus on the present and the future. And I think some people are even divided in themselves. You know, part of them wants to move forward with a trial and really get to the bottom of what happened and see him face consequences, and the other part of their self is saying, let's just move on.

So you spoke to a bunch of people who think it is really important that we move forward with this investigation. What is their argument?

MAYER: Well, I mean, first, you know, I just want to say, I'm quite sympathetic to that ambiguity of this and - or ambivalence towards that question because, you know, I think there's a feeling that we don't want to become a kind of country that uses the courts and law to punish political opponents. And also, there's a feeling of, you know, time to move on; you don't want to be dragged into this forever and ever. And I was pretty ambivalent myself when I started this story. I really didn't know what I thought of the various competing arguments on this.

And as I kept reporting on it and speaking to experts on sort of rule-of-law issues and on democracy, I became more and more convinced by them that it's actually incredibly important that if Trump - and this hasn't been proven - but if Trump did commit crimes of some sort, even if they're kind of, you know, sort of ordinary business crimes, if he did, it's important that there not be a culture of impunity in this country, that there needs to be a message sent that there are consequences, no matter how rich and important you are, if you break the law, and that that message is more important almost than anything else when it comes to protecting democracy.

GROSS: Can you give us an overview of what Cyrus Vance Jr., the Manhattan DA, is looking into?

MAYER: So it began with one small thing. And people may remember this. There were - it's so obscure sounding. But during the 2016 presidential campaign, there were allegations that Trump paid off two women to stay quiet and drop their allegations that they had had affairs with him, extramarital affairs - one was the porn star Stormy Daniels - and that that money was paid by Trump's lawyer, Michael Cohen, at the time and then that Trump reimbursed him.

And the allegation was that - a couple things that were legal problems with that. One was the hush-money payoffs were described by the Trump organization as a legal expense, which is a fraudulent description of what was going on to cover it up. And the other was that, in some ways, it served as an illegal campaign contribution from Cohen because it helped cover up something for Trump's campaign. It was a gift to the candidate, and it was not declared, and it was larger than the law allowed, legally, the size of the contribution; the money was too much.

So Cohen, actually, was prosecuted for this, and he actually was convicted and is currently serving a three-year sentence. Meanwhile, when that prosecution took place, they described - it was the U.S. attorney's office in New York - described that Cohen was working with someone, a codefendant, who was described as individual No. 1, who had run for president and won. Clearly, it was a description of Trump.

So the conviction described - the legal papers described that Cohen was working with Trump, yet Trump was not ever charged because he was considered to be immune, as president, from this kind of prosecution. So it's been hanging out there that Trump was never charged. So when he left office, this was hanging over him, and it was the beginning of an investigation into a number of other things.

GROSS: So what are some of the other things Vance is looking into?

MAYER: So if you look at the Cohen situation, in one way, it's about sort of fraudulent business practices, that these hush-money payments were described as legal payments and maybe deducted as a tax-deductible business expense, which would be a fraud. And in New York, that's a crime - New York state. And Vance has purview over New York state's legal, you know, code.

And so they started looking at that, but then at the same time, a number of other potential fraudulent activities that they are investigating by Trump and The Trump Organization that have to do with taking tax deductions, basically, for things that are not legitimate. And it's - mostly had to do with manipulating the value of his properties, so that he would exaggerate how much they were worth when he was trying to get bank loans and trying to get favorable insurance policies, and then he would devalue how much they were worth when he was paying his taxes, so he could keep his taxes low and get favorable loans. Those are the allegations they're looking into. And it could be on the order of many, many, many millions of dollars.

I mean, and - how do we know this? Because in part, The New York Times has revealed a tremendous amount about Trump's taxes. And The Times' reporting has been completely stunning. It's shown that while Trump has said that he's a billionaire many times over and making tons and tons of money, during his first year when he was president, he paid a grand total of something like $750 in federal income taxes - I mean, $750 total. And so he's obviously taking humongous losses. And in the previous 10 years or so, he paid very, very few taxes, and some of those years, no taxes at all, yet claim to be just humongous amounts of money. So what gives? Everybody wanted to know, how did he - you know, how did this magic take place in his taxes?

GROSS: One victory that Cyrus Vance has already scored is with the Supreme Court, because the Supreme Court ruled last month that Trump had to turn over his taxes and other financial records to this investigation. What's the importance of that decision, not only in this case, but as a precedent?

MAYER: Well, and so this has been this ferocious fight. For years, Trump has said he was going to make public his tax returns. But he said he couldn't because they were under audit. And so he's hidden them all of these years. And the prosecutors here, the Manhattan district attorney, Cyrus Vance Jr., tried to get a hold of Trump's tax returns so that he could see if there was fraud. And the reason it matters in a larger sense than even just the Trump case is that it's been a test of whether a president is above the law when it comes to cooperating with an investigation. And Trump's lawyers argued that he didn't need to comply with the subpoena from Vance's office and turn over these tax records.

This fight went all the way up to the Supreme Court, actually, twice. And Vance's lawyers just kept arguing that nobody's above the law and that Trump needed to comply with the subpoena. And eventually, after 18 months of wrangling over this, going through all the different layers of the courts and back down and up again, Vance's office won. They apparently mounted a tremendous argument in front of the Supreme Court. And the Supreme Court sided with the DA's office. And Trump was forced, finally, after 18 months, to turn over just millions of pages of records in digital form.

GROSS: What was the decision, the Supreme Court decision, based on?

MAYER: It was based on the idea that a president - even a president or a former president must comply with an investigation, that nobody is immune from just having to comply with the basic mechanics of the law.

GROSS: I think we need to take a short break here. So let me reintroduce you. If you're just joining us, my guest is Jane Mayer, chief Washington correspondent for The New Yorker. Her new article is about the Manhattan DA's criminal investigation into Donald Trump's financial business practices. We'll be right back. This is FRESH AIR.

(SOUNDBITE OF AMY RIGBY'S "PLAYING PITTSBURGH")

GROSS: This is FRESH AIR. Let's get back to my interview with Jane Mayer, chief Washington correspondent for The New Yorker. Her new article is about the criminal investigation into Donald Trump's financial business practices. The investigation is being led by Cyrus Vance Jr., the Manhattan DA who recently announced he'll be retiring at the end of this year. Mayer's article is in the March 22 edition of The New Yorker. It's also on the magazine's website under the title "Can Cyrus Vance, Jr., Nail Trump?"

So Cy Vance's office, his team now has access to an incredible amount of information about Trump. And who knows what they're going to find there. Do you think they might expand the investigation as they examine what are actually in these financial documents?

MAYER: I mean, they could very well. I mean, they're just crawling over these records. And, I mean, people have said to me that they run so many pages. Apparently, Trump, at some point, just with a single year's tax return, occupied a huge table on the 26th floor of the Trump Organization. I mean, his - he has incredibly complicated finances. And so it's hard to know what's in it. Vance's office is very buttoned up. He's a very correct kind of person, you know, so they're not a leaky ship over there. And it's hard to know what they will find in these tax returns. But they certainly finally have access to sort of the crown jewels of the Trump Organization.

GROSS: You report on where the Vance team has been storing the financial records that were released after the Supreme Court decision. Tell us about that.

MAYER: Well, yeah, as a reporter, I was trying to find out - OK, this is this momentous moment where the executive branch is forced to turn over just years of records that a local prosecutor's office, the district attorney in Manhattan, has been seeking. So I was - I wanted to sort of find out, what's the scene like where this gets turned over? And I imagined, you know, truckloads of boxes of documents and all of that sort of thing being turned over and, you know, driving up to the DA's office or something. That turned out to be completely wrong.

What this actually turned out to be is all of those records are on a - some kind of computer hard drive that it can be, you know, held in one hand. And they were handed over by the lawyers for Trump's accountants, a company called Mazars USA. And that accountant gave it to an assistant DA during a snowstorm. And the DA's office then, to protect this sought-after hard drive, put it inside something called the radio frequency isolation chamber in the Louis Lefkowitz State Office Building down in lower Manhattan. And it's this special room that is covered with sort of glimmering copper foil on the walls and is behind metal doors that stops all waves that - like radio waves that could tamper with digital evidence. And it kind of - it looks a little bit like Tutankhamen's tomb. Anyway, that is where this disk resides, apparently, at this point.

GROSS: Did you get a look at it?

MAYER: I did not. I looked at photographs of it. It's kind of amazing-looking. The walls look metallic. And they have these bolts that are soldered around it and then these gigantic metal doors that look like they belong in a bank vault.

GROSS: Did they build the room especially for this hard drive? Or did the room, this vault-like room, already exist?

MAYER: The room preexisted the hard drive. It's part of a very sophisticated cyber lab that the DA's office has that's the first of its kind for a local prosecutor in the country. It's a very unusual office. This - the Manhattan DA, they have many more resources than any ordinary prosecutor would.

GROSS: The investigation that Cyrus Vance Jr. is leading appears to be focused largely on Trump's business practices before taking office. What's the reason why the focus is before he became president?

MAYER: Well, I mean, these were the potential crimes that came to light as they began to probe the payoffs to Stormy Daniels during the 2016 campaign. And so it kind of grew organically from that. And in some ways, what I wondered as a reporter following this was, do sort of crimes of that nature, they seem - they may be big. They may be nothing. But they're - they don't have to do with his political performance, which is, you know, in some ways, makes them seem maybe kind of besides the point to opponents of Trump, but at the same time takes this out of the realm of politics, which is probably a good thing.

GROSS: If Trump is convicted, which in itself would be unprecedented, how realistic is it that he would actually face prison time?

MAYER: People I've talked to who know Trump, including - I think it was Barbara Res who was an engineer who worked with the Trump Organization and for a number of years. She said to me, he will never, ever serve time in prison. He would - she predicts that he would flee. And so do other people suggest that he would get out of the country. I don't - it's hard to know what to expect. But it's - for me, anyway, it's hard for me to contemplate him truly in an orange jumpsuit at, you know, Rikers Island.

GROSS: So as you point out in the article, if he's found guilty, he could be sent to prison. That is a possibility. But you're right that a felony conviction wouldn't disqualify Trump from a second term. And I was frankly astonished to read that. I mean, most people who have a felony conviction, it's really hard for them to get any kind of job. To think that with a felony conviction you could become president is, I think, astonishing.

MAYER: We were all surprised, too, at The New Yorker. I have to say that several of us thought that it was among the requirements in the Constitution were that you couldn't be a convicted felon. It's not. It is not a bar to being elected president in this country. It could be a political problem. But it's not a legal problem.

GROSS: So after the Supreme Court decided in late February in favor of the investigation and decided that the investigation could get access to Trump's taxes and financial records, Cyrus Vance Jr., Manhattan's DA, told you that he was going to retire from that position at the end of the year, that he would not be running for reelection. This is an elected position. You are the one who broke the story. Were you astonished that you were in the middle of this story and it turns out that the head of the legal team is going to be leaving before the investigation is through?

MAYER: Yes. I mean, I was sitting on this information for a little while and waiting for the moment when Vance was ready to make it public. As I had, you know, interviewed him on background on that particular part, it was off the record. But I knew it as I was working on the story. And what he was waiting for before he made known that - before he was ready to announce that he was not going to run for another term, what he was waiting for was the Supreme Court to rule on the tax records, the Trump case. He was worried that if the court knew that he was leaving and some of his potential replacements came out and started slamming Trump, as they have, that it might alienate the conservative justices on the Supreme Court. So he was trying to keep it wrapped up until the court decided.

GROSS: Well, but will Vance have enough information to know whether Trump should be charged or not before the end of December when he resigns?

MAYER: They actually - from the reporting I've done, it seems they think they will know. And that was also some of the news that was in this piece is that they think they're going to wrap up this investigation and decide whether to charge or not within the next nine months and probably earlier.

GROSS: Then if they decide they are going to press charges, what happens after that?

MAYER: Well, I mean, the thing that's most complicated about this case and makes it really hard is that in order for this to be a criminal act, they have to prove that there was criminal intent, that Trump intended to break the law and knew what the law was. And that's going to be really hard because, you know, all you've got are these numbers on paper. How do you get at what his mindset was? And so for that reason, one of the things that would really make a difference in this case is if they could get a live witness to turn against him, someone who really knew how he was thinking about all of these issues, who would then explain it to a jury and convince them.

GROSS: Well, let's pick it up here after we take a short break. If you're just joining us, my guest is Jane Mayer. She's chief Washington correspondent for The New Yorker. Her new article is about the Manhattan DA's criminal investigation into Donald Trump's financial business practices. We'll be back after we take a short break. I'm Terry Gross. And this is FRESH AIR.

(SOUNDBITE OF TAYLOR HASKINS' "ALBERTO BALSALM")

GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to my interview with Jane Mayer, chief Washington correspondent for The New Yorker. Her new article is about the criminal investigation into Donald Trump's financial business practices, examining the possibility that Trump and The Trump Organization engaged in tax, banking and insurance fraud. If Trump is charged, he'd become the first former president charged with a criminal offense. The investigation is being led by Cyrus Vance Jr., Manhattan's district attorney, who announced last month that he'll be retiring at the end of the year.

The team investigating Donald Trump's financial business practices, from all that you've learned, is trying to flip a couple of people. Michael Cohen, Trump's former lawyer, has been cooperating with this investigation. They're trying to flip, from what you learned, Allen Weisselberg, who was Trump's chief financial - or The Trump Organization chief financial officer, who previously worked for Trump's father. So what would the significance be if they could flip Weisselberg?

MAYER: Oh, I mean, if there is a financial crime committed by Donald Trump, everybody says that Allen Weisselberg would know it. He has managed Trump's money flow throughout Trump's entire professional career and been right at his side. They have offices on the same corridor on the 26th floor of The Trump Organization, and he knows everything about the numbers. But so far, he is - he's the chief financial officer. That's his title. And so far, he is not cooperating. So from what I could tell, it seems that the prosecutors are looking for ways that they could pressure him into flipping on Trump.

GROSS: One of the ways they think they might be able to do that, according to your reporting, is to get at him through his two sons. What would that strategy look like?

MAYER: So he's got two boys, grown boys, and one of them works for a company called Ladder Capital, which is - has made many of the loans to Trump for his various projects. I think they've loaned something like $270 or $280 million. So there's a financial relationship between Ladder Capital and The Trump Organization. One son works there. The other Weisselberg son works directly for The Trump Organization, where he has managed the women's skating rink in Manhattan and the carousel in Manhattan and a couple other properties. They're New York City properties, where there's a contract with The Trump Organization to run them.

So both of these sons are potential pressure points. It looks like The Trump Organization has helped provide apartments to these sons. And it's unclear, if there was some kind of sweetheart deal there, whether the sons have fully declared whatever their financial deal was on these apartments. So that's something that the prosecutors are taking a very close look at. And if it's possible that they've got the sons in some kind of complicated mess, they could use that to try to flip the father.

GROSS: In other words, to make a deal - like, we won't prosecute your sons if you cooperate.

MAYER: That's right. I mean, I've talked to a lot of prosecutors for this story, and one of them said, you know, what you do is you take the chief financial officer and you say you've got 24 hours to decide whether you want your sons to go to jail or if you want to, you know, start talking - hardball.

GROSS: Yeah, very. Yeah. So you got a very interesting story from Weisselberg's former daughter-in-law. Tell us that story.

MAYER: Yes. Jennifer Weisselberg was married to Barry Weissenberg, the son of Alan. And Barry is the one who is - has been managing the skating rink and other properties. And she described - and has documents to back it up - that The Trump Organization gave her and her husband when they got married the free use of an apartment on Central Park South for seven years and that this was not, evidently, declared as any kind of compensation.

And what she said to me - and this was sort of her first big interview on the subject, though I would like to give credit also to Bloomberg News, which broke the story of this apartment originally - that in talking about it, she said, you know, what it is, is that Trump compensates people around him by giving them stuff. It's a form of control, she said, because people take the stuff and then - and if it's not declared as income, they have to do whatever Trump and The Trump Organization tells them, or else, you know, it gives them - gives him control over them. And that's what she felt happened with her husband, her former husband. She is now divorced from him.

GROSS: That by Trump giving him these key positions, that he had to follow what Trump wanted.

MAYER: Maybe - it's more that by The Trump Organization giving perks, like an apartment or help with tuition or cars, stuff like that that is sort of material goods, that it gets the people who work for him and who are around him indebted to him and in a position where they can't turn against him 'cause he's got control over them 'cause they've taken stuff from him.

And, you know, actually, it was a really interesting point, and it's one if you - people who know the history of Trump may remember that Wayne Barrett, who was a tremendous investigative reporter, who was really one of the best early reporters on the subject of Trump. When he was closing in on Trump on a number of tough stories, Trump met with him and said, you know, you need an apartment; you need to live in a better place. And Trump offered the investigative reporter, Wayne Barrett, an apartment. And, of course, Barrett turned it down, but it's an example of the same thing - he gives you stuff, and then he's got you. And that's the point that Jennifer Weisselberg made to me.

GROSS: She also told you a very interesting story about a shiva call. And shiva is the mourning period for Jewish people who've lost somebody in the immediate family, and as part of that mourning process, friends and family come and visit and, you know, kind of surround the bereaved. So what happened during this shiva call?

MAYER: Well, OK, and this was in the context of - she's trying to explain the relationship between Allen Weisselberg, the chief financial officer who the prosecutors want to get to turn against Trump, and his relationship with Trump. And it's of interest to the prosecutors because they're trying to figure out, how do we get this man to cooperate? And what she's describing is that her former father-in-law is just in the thrall of Trump, from her standpoint. He just worships Trump. And so it's going to be a pretty hard thing to turn him.

And so she described when she first met Trump. It was 1997, and she was attending this - the shiva for Allen Weisselberg's mother. And a limousine pulled up at the Weisselberg family house in Wantagh, Long Island. And Trump gets out of this limousine, looks around, and first thing he says is, this is where my chief financial officer lives? This is embarrassing. 'Cause it was sort of a modest house. So it starts like that.

And the next thing that happens is Trump comes in to the shiva, where the the bereaved are and, you know, paying their respects to the family, and instead of being supportive, what Trump does is he takes out pictures of nude women that had been on a yacht that he'd had recently and starts passing around pictures of these nude women. And then he turns and starts hitting on Jennifer Weisselberg, who is the - at that point dating Weisselberg's son. They're not yet married.

And what Jennifer Weisselberg said to me was, that far from defending her and standing up to Trump, that Allen Weisselberg just sort of tried to please the boss, laugh it off, sort of egg him on in some ways. And so you get to see from that that Weisselberg is very much in Trump's shadow and sort of playing up to the boss, even at his own mother's memorial service.

GROSS: Is there anyone else that the prosecutors are trying to flip?

MAYER: I mean, I think that there's probably a panoply of people on the inside who they're working on.

GROSS: (Laughter) Right.

MAYER: But the Weisselbergs seem to be front and center right now. And the other thing that's going on right now is that the prosecutors have been talking extensively to Michael Cohen, the former lawyer to Trump. And they've already interviewed him seven times. From what I understand, they've got a date to do it on an eighth time. And he is being very forthcoming and knows quite a lot. The problem with Michael Cohen - and I think he's quite willing to testify against Trump and would be, you know, willing to go in front of a jury - but the problem with him is that he has been convicted of a felony and has admitted lying to Congress. So his credibility isn't perfect.

GROSS: But his insight is real. I mean, you interviewed him before the election, before the 2020 election. And he's...

MAYER: I have to say, of the - yes.

GROSS: (Laughter).

MAYER: Of the people that I interviewed about what might happen and how Trump might deal with losing the election - this was right before the election - nobody was more on target and seemed to understand Trump better than Michael Cohen. I mean, he worked closely with him for many years, and he has really got Trump's number. And he was the one who predicted that if Trump lost the election, he would never concede. He said, he'll never concede, that he would claim fraud and never drop it - never, ever, ever. And of course, it's proved completely prescient.

GROSS: Well, Michael Cohen thinks that Trump's children are also under legal scrutiny, including Ivanka. What is she under scrutiny for?

MAYER: She's under scrutiny for something that The New York Times has exposed, which is that at the same time that she was collecting a salary as an employee of The Trump Organization, she was also being paid over $700,000 in consulting fees by The Trump Organization for essentially the same project. And so, you know, usually you are either an employee or you are a consultant, but not both.

GROSS: Is that against the law?

MAYER: Well, what could be against the law is that The Trump Organization declared the consulting fees tax-deductible business expense and treated it not like salary. That could be a fraud. If - anything where you lie purposefully on your taxes is potentially a crime.

GROSS: So I think the Manhattan DA investigation is looking into that, but so is the New York state attorney general, Letitia James. So what's the difference between those two investigations into Ivanka Trump and the consultancy fee?

MAYER: They do overlap in terms of the specific areas they're looking at, of potential misbehavior by Trump and The Trump Organization. But so far, Letitia James is - has a civil investigation. She's looking at civil damages, whereas the DA is really doing the criminal investigation.

GROSS: Let me take another break here, and then we'll talk some more. If you're just joining us, my guest is Jane Mayer, chief Washington correspondent for The New Yorker. Her new article is about the Manhattan DA's criminal investigation into Donald Trump's financial business practices. We'll be right back. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. Let's get back to my interview with Jane Mayer, chief Washington correspondent for The New Yorker. Her new article is about the criminal investigation into Donald Trump's financial business practices. The investigation is being led by Cyrus Vance Jr., the Manhattan DA who recently announced he'll retire at the end of this year. Mayer's article is in the March 22 issue of The New Yorker. It's also on the magazine's website, under the title "Can Cyrus Vance, Jr., Nail Trump?"

Deutsche Bank was Trump's biggest lender. And to what extent is Deutsche Bank cooperating with the investigation and talking about the loans that they made to Trump and whatever they know about Trump's finances?

MAYER: Deutsche Bank is fully cooperating, it sounds like, and so is the insurance company, Aon, that Trump dealt with. So you have the sense that Trump is surrounded by organizations that he has done business with who are turning against him. The feeling is that - sort of that things are closing in on him.

GROSS: So as you point out, Trump has survived two impeachments, the investigation by special counsel Robert Mueller, half-a-dozen bankruptcies, 26 accusations of sexual misconduct and an estimated 4,000 lawsuits. And, you know, he served as president for four years. These investigations, these accusations, did not stand in the way of his becoming president. Of course, some of them happened after he was president. That didn't stop him from continuing to be president. Is there a chance that he'll actually lose this one? Because this would be big. Like we said, this would be - if he loses, he would be the first former American president to be convicted of criminal charges.

MAYER: Oh, I think there's absolutely a chance that he could face serious charges and be convicted. I mean, this is no joke. This is - you know, as Michael Cohen says, this is the investigation that keeps him up at night. At the same time, I think it has to be said, as you point out, he has been terrifically, you could say, either lucky or wily or, you know, choose your adjective. He has gotten away with everything he's gotten away with with great skill. And there's a quote in this story from Preet Bharara, the former U.S. attorney for the Southern District of New York, who says this case is not a slam dunk, it's not an easy case, and nobody should think that it is. And part of the reason that it's hard is the way that Trump has always behaved.

His mentor on legal issues early on was Roy Cohn who was sort of a notorious fixer, and later in life, a lawyer to the mob characters in New York. And and Roy Cohn taught Trump leave no fingerprints and Trump really doesn't. It's interesting. He doesn't use email, which is often how prosecutors get people. He doesn't have a private email address even. When he texts people, he asks his assistants to text them from their phones. He doesn't have a computer that he keeps on his desk. He writes very little down, and when he issues orders, he often does it very indirectly. And I interviewed a number of people who described how you know what he wants, but he doesn't say it outright. And so he's very, very good at protecting himself.

GROSS: Who are some of the people on Vance's team, and what does that tell you about the legal strategy?

MAYER: The biggest change that's taken place on Vance's team is he has brought in a man named Mark Pomerantz, who is a really highly regarded and seasoned lawyer in New York, to be - he swore him in as a special assistant district attorney a little more than a month ago. And Pomerantz had been the head of the criminal division, prosecuting crimes for the Southern District of New York and the federal prosecutors. And since then, he has also been for about 20 years one of the top defense lawyers for white collar crime in New York. And as such, he's just seen as someone who's just a real pro. He has a terrific reputation. And he has apparently taken up a notch the investigation into Trump. He's got a really good idea how to go after this whole thing. And people say they can feel the difference. It's like night and day.

GROSS: Why would you hire somebody who defended white collar crime to help prosecute white collar crime?

MAYER: Good question. But apparently, what the answer is is that he understands all the holes through which a potential white collar criminal might escape. He knows how to close the hatches. And so he's just very good at seeing it from both directions, from the prosecutor and from the defense side. And so, you know, people think that he's just - he's going to stay on even after Vance leaves and provide some continuity to the office and to the investigation, no matter who comes on to replace Vance too.

GROSS: I think we need to take a short break here, so let me reintroduce you. If you're just joining us, my guest is Jane Mayer, chief Washington correspondent for The New Yorker. Her new article is about the Manhattan DA's criminal investigation into Donald Trump's financial business practices. We'll be right back. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. Let's get back to my interview with Jane Mayer, chief Washington correspondent for The New Yorker. Her new article is about the criminal investigation into Donald Trump's financial business practices. The investigation is being led by Cyrus Vance Jr., the Manhattan DA who recently announced he'll be retiring at the end of this year. Mayer's article is in the March 22 edition of The New Yorker. It's also on the magazine's website under the title, "Can Cyrus Vance, Jr., Nail Trump?"

In addition to all the investigations Trump is facing, he's also in financial trouble. Tell us a little bit about the kind of debt that he owes now and why he owes so much.

MAYER: Trump is under a lot of financial pressure. If you step back and take a look at the situation, he has debts coming due of hundreds of millions of dollars worth of debts coming due at this point. And he also - he's had this long-running tax audit where he took hundreds of millions of dollars in losses that he claimed that the IRS is challenging. Together, these - sort of a double pincher of financial pressure coming at him that look fairly, I mean, really quite serious. So he's got a lot of financial pressures.

We've seen recently, though, he's discovered a new way to raise money. He's been soliciting contributions for his election defense fund. And he's positioning himself also to be a kingmaker in Republican politics and potentially run again himself. So he's set up a number of sort of campaign vehicles and organizations that people can contribute to. And he's taking in millions and millions of dollars that way.

GROSS: And that's money that might have been going to the Republican National Committee if it wasn't going to Trump. It's creating a bit of a rift in the Republican Party, even though I think a lot of Republicans aren't admitting that.

MAYER: I think you're absolutely right about that. I mean, he is just a magnet for money.

GROSS: So, you know, getting back to the fact that Cyrus Vance is retiring at the end of the year during this ongoing investigation. You describe this investigation as the most significant legal showdown in American history. So why is Vance leaving before he finishes it?

MAYER: Well, I thought that was pretty mysterious, too. He's 66 years old. He's already served three terms. They are four-year terms. And he had made up his mind before the Trump case, really, that he felt that he'd done a lot of what he set out to do. And I think, you know, he said it turned out to be harder than he thought it would be. He's taken a lot of criticism. He's had a hard time turning the culture of the office around.

Attitudes towards criminal justice have changed a lot during the period that he's been there, so that there's now much more emphasis on racial justice and fairness. And he's tried to push the office in that direction, but it hasn't gone fast enough in the eyes of many critics. So I think he - you know, he says that he felt that his predecessor, the famous Robert Morgenthau, who was in that job for 35 years, he thinks Morgenthau stayed too long. And he thinks the next generation should take a shot at it.

GROSS: It's still surprising that he'd leave in the middle of such an investigation. But I guess if he stayed, it would be another four years?

MAYER: It would be another four years, though, of course, he could always resign partway through it. I mean, many people, many lawyers would regard this as the case of a lifetime. I think that Vance feels that having taken the president up to the Supreme Court twice and won is already a tremendous victory. And I think he very much wants to make the decision about whether to charge the former president. But he's not known as a prosecutor who has a big killer instinct. He's known as being sort of earnest almost to a fault. And so I think this is an example of that.

GROSS: Do you think that Vance's leaving will weaken or jeopardize the case in any way?

MAYER: I mean, I think the answer is unknown, but I certainly think it throws a lot of questions into it. A lot depends on who takes over after him and whether this team, including Mark Pomerantz, stays on. You know, the sense is that the investigation is in good hands right now, very serious and apolitical and professional hands. And, you know, it's a bit of a question mark what happens next.

GROSS: Jane Mayer, thank you so much for coming back to our show. It's always such a pleasure to talk with you.

MAYER: So great to be with you, Terry.

GROSS: Jane Mayer is the chief Washington correspondent at The New Yorker. Her article about the criminal investigation into Donald Trump's finances, "Trump In The Crosshairs," is in the March 22 issue of The New Yorker on the magazine's website. It's titled "Can Cyrus Vance, Jr., Nail Trump?"

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FRESH AIR's executive producer is Danny Miller. Our technical director and engineer is Audrey Bentham. Our interviews and reviews are produced and edited by Amy Salit, Phyllis Myers, Roberta Shorrock, Sam Briger, Lauren Krenzel, Heidi Saman, Ann Marie Baldonado, Thea Chaloner, Seth Kelley and Kayla Lattimore. Our associate producer of digital media is Molly Seavy-Nesper. Therese Madden directed today's show.

We're happy to end today's show with some great news from our film critic, Justin Chang. His wife just had a baby. Congratulations from all of us at FRESH AIR. I'm Terry Gross. Transcript provided by NPR, Copyright NPR.