Just How Much Legal Trouble Is Trump In?

An update on the many investigations into the president’s business interests.

Trump stands on the steps of Air Force One, clapping and smiling.
President Donald Trump at Wilmington International Airport in Wilmington, North Carolina, on Wednesday. Mandel Ngan/AFP via Getty Images

Subscribe to What Next on Apple Podcasts for the full episode.

You could be forgiven for losing track of all the investigations into President Donald Trump’s business—there are just so many of them. They take a long time, they’re complex, and there’s no linear story structure. The latest salvo came from the New York State Attorney General’s Office, which is investigating whether Trump’s company improperly inflated the value of its assets to get tax benefits and loans. But how close are we to the truth? On Thursday’s episode of What Next, I checked in with David Fahrenthold, a Pulitzer Prize–winning investigative reporter at the Washington Post, to find out what we know and still don’t know about the Trump Organization and its finances. Our conversation has been condensed and edited for clarity.

Ray Suarez: You’ve been piecing together the Trump family business for years now. Are you getting closer to a complete picture of its interests and operations?

David Fahrenthold: Closer is the key word. We know a lot more about the state of its businesses, its business partners, the pressures it’s under, and its business with the federal government than we did when we started. But in many ways it’s still a black box. There’s still a lot I don’t know.

The Trump Organization is facing a level of legal scrutiny that it really has never faced before. It has always sort of skated by, both because Trump was so difficult to deal with—he was so contentious when you went after him as an investigator—and because it wasn’t very big. None of its balance sheets were ever that big, and so people didn’t feel like it was worth the trouble. Now, that’s changed. It’s facing some pretty serious investigations, and that could cost it a lot of money in legal fees, but it could also bring some significant damages, and, perhaps most importantly, it could crack open this black box of a company in a way that we really have not seen before.

The president and his family have lost a fair number of rounds in various federal courts, but there’s been no payoff, no “aha” moment of here’s the final thing, the missing key to understanding a lot of other things. Do you feel like you have a better handle on this? Are there little details that leak out in these wins and losses and ties where you find things out almost by accident?

Generally, no. What’s happened so far is sort of procedural wrangling that doesn’t tell you anything at all about the underlying questions: How much foreign money has gone to the Trump hotel in D.C.? Did Trump break the law with the way his company handled the Stormy Daniels payments? There’s been a lot of talk about that—who gets to look at those documents and what they might say. But we haven’t learned anything about what they actually do say. To be honest, the most revelatory document we’ve gotten was the one thing that’s been filed by the New York attorney general’s office, which at least laid out the specific cases that the New York attorney general is interested in. It’s interested in a few different properties where Trump allegedly inflated the value of his properties. That’s not the biggest offense, but at least we know now which properties they’re interested in, and we can go dig into what Trump has said about those values. Everything else has been a very frustrating but I guess illuminating course in how you can use the legal system to delay accountability.

These would be knotty legal and business problems for any business anywhere at any time. But here we have crossing jurisdictional boundaries—the president is the head of the executive branch of the United States and holds a position in a private business headquartered in the state of New York. And while there’s a lot of ink being spilled about who can accuse him of what, where, and when, it seems like even after 3½ years, none of this has been nailed down.

No. One thing I’ve learned about Trump and about the country is that Trump has always exploited honor systems. He’s always looked for places where people obey the law not because they have to but because it’s seen as the right thing to do. They don’t want to go against social convention, and so they follow the rules—but when you break the law, it’s not like a cop steps out from behind a pillar and arrests you. He takes advantage of that. When he finds a place where there’s an honor system, he exploits it. He does what the honor system doesn’t expect. And he often gets a huge advantage out of that. He did that in his business often. He did it at his charity—he didn’t follow charity rules, and he took advantage of the fact that the charity system takes a long time to catch up with you if you do that.

And what we’ve found is that the presidency is an honor system. On purpose, we did not write a lot of laws that govern the presidency because that’s supposed to be held by a person of honor who will follow honor systems about not mixing government and private business, not mixing government and politics. And Trump has again taken advantage of that. There’s so many cases in which he said, I know it says I can’t do this or other people haven’t done this, but I’m going to do it. Try and stop me. I’ll see you in two years. What we’ve seen in all these court cases is that that worked. And also that Trump’s opponents, the Democrats in Congress and people in law enforcement, didn’t understand whom they were dealing with. Often they sort of seemed to expect that Trump would follow the honor systems, even when his whole life had shown that he would not.

Are Trump’s kids on the hook in any important way?

I think they could be. The New York attorney general’s case mentions Eric Trump specifically—he’s linked to a couple of transactions they’re interested in. Trump’s approach only works for a while, and sometimes that’s enough. I mean, think about how well it worked for him in 2016: It got him elected president. But eventually it comes down on him. That happened with the Trump Foundation. It happened with Trump University. Eventually the system stirs to life and comes after him. So he and the whole organization could be in that position next year if Trump loses. He will finally have the honor system catch up to him, the kids and Trump. If he’s reelected, though, he may get a protection from it that will last long enough to effectively be permanent.

Often in a story there is a sort of nexus fact, a knot that, once you untie it, a lot of other things loosen up. In this beat over the years, has there been a great white whale fact or document or piece of data that you’re still trying to get your hands on?

Yeah, certainly. In Trump’s case, there’d be a lot of them. Tax returns would obviously be a clue to solve a lot of different mysteries. But I’ll just tell you about one of them—it’s my sort of favorite mystery. Trump says, on his financial statements that he has to file as president, he owes a loan of more than $50 million to a company called Chicago Unit Acquisition LLC. Now, Chicago Unit Acquisition LLC is basically a shell company. It has no employees, has no offices, and its headquarters is Trump Tower. Trump owns it, so he owes a $50 million–plus loan to himself. Now, why would you do that? He says it started in 2012 and has to do with Trump’s hotel in Chicago. And so one of the things we’re trying to figure out is whose loan is that? How did he get it? What would be the tax benefits to doing that? And even more intriguing, the only thing Trump has said about that loan is that he bought his own loan back from his creditors. I can’t find any evidence that’s true. So that wouldn’t be the key to all of his finances, but if I could understand what happened there, I’d at least unlock a pretty important portion of his finances. And I think the New York attorney general has zeroed in on the same thing. I have a faint hope that that office, because it has subpoena power, will figure it out before I do.

Are there things you’re starting to suspect you may never find out?

I’m sure there are a lot of mysteries about his finances that we won’t know this year or next year, maybe ever. So certainly I worry about that. In Trump’s case, it will be interesting to see if he does lose in November to Joe Biden and becomes a private citizen in 2021. Will the zest for prosecuting him or investigating him go away completely just because, for purely partisan reasons, the Trump Republican Party has no other leader? There’s no other person ready to step in. Trump is the Republican Party, and he will still be in 2021. Even if he loses, Trump will still be the most important figure in Republican politics and a huge thorn in the side of Joe Biden if Joe Biden is president. So I wonder if the zeal to investigate him will disappear, especially because there are so many questions that Trump has managed to run the clock out on that are still standing.

It has surfaced that the Trump administration is preparing a dossier on you. It must be a little bit of a shiver to find out that, with the tremendous power of the presidency, they’re mad at you.

Yeah. I suppose that’s true. I mean, I definitely have had presidencies mad at me before. What the dossier threat was, at least the way they phrased it, was not like “we’re out to get you“—it’s that “we’re out to show that your stories are false.” Now, if they think our stories are wrong, I want to know. We ask them a bunch of questions before the story runs and give them a chance to comment on everything, but if they still think something’s wrong, they’ve got to tell us. That’s true for presidents. It’s true for anybody. And they haven’t. There’s been no challenge to anything we wrote in the particular story that that’s in response to, or in any other story this year. So if they want to come to us and say our stories are wrong, we are all ears. But that has not happened.

Subscribe to What Next on Apple Podcasts

Get more news from Mary Harris every weekday.