‘Not the Way to Defend a White Collar Case’: How Trump Blew It

Donald Trump is a convicted felon.

His legal fight is not over, and his political campaign is ratcheting into high gear — but for now, the former president can’t deny that he’s been found guilty on all 34 guilty counts of falsifying business records in order to keep a porn star silent ahead of the 2016 election.

To explain how we got here and what’s coming next, Kyle Cheney, a senior legal affairs reporter at POLITICO, and Ankush Khardori, a senior staff writer and legal columnist for POLITICO Magazine, sat down for a very timely conversation on the Playbook Deep Dive podcast.

They discussed how Trump’s defense team may have repeatedly harmed its own case, how Trump’s conduct during the trial could influence Justice Juan Merchan’s sentence and Trump’s best hopes for an appeal.

This conversation has been edited for length and clarity by Deep Dive producer Kara Tabor and senior producer Alex Keeney. You can listen to the full Playbook Deep Dive podcast interview here: 

Kyle, you were inside the courthouse when the verdict was announced. Set the scene for us as the jury entered the room to deliver the news.

Kyle Cheney: The moment really started just before they came in, because everyone was packing up to go home for the day. There had been no word from the jury at all. And the judge, Juan Merchan, said, “We're going home. We're going to send the jury home at 4:30,” that they're not going to have a decision today.

He left to go check on them. And then he was gone for a while and we were all thinking,”What's taking so long?”

Suddenly he comes back and says, “Actually, we're not going home today. There's a verdict.”

So it was this kind of whiplash moment that I think added to the suspense and the drama of it, which was already high, of course. But then you had the jury come out and they confirmed they had reached their verdict.

Got it. Explain to people your vantage point, watching this unfold. 

Kyle Cheney: I was in the overflow room of the courthouse, which is where the majority of the press corps is situated. There are some people in the courtroom itself. But in fact, I actually prefer the overflow room because you have a screen where you can see Donald Trump's face. You can't see the jurors, but you can see Donald Trump. And so the biggest thing is, what's his reaction to this going to be?

And so you're hearing the judge address the jury and say “You've reached a verdict?”

They confirm that. And then they just went through very businesslike, orderly, one-by-one, count one guilty, count two guilty. And of course, the first one is the [big] moment, because it doesn't really matter what happened to the other 33 counts, though they all turned out to be guilty. You get the first one and you say, “He's a convicted felon now.” The power of that moment was immediate. And of course, you could feel it in the courthouse because it was so tense.

Wow. The advantage of that room you were in is that you have a line on to Trump's reaction. What was your memory of how he reacted and anything else you saw in the first seconds after they said “guilty”?

Kyle Cheney: Similar to the whiplash that we felt, even added to that was that Trump, moments before the judge came back and said there’s a verdict — he seemed in the best spirits we've seen him in the entire trial. He was laughing, talking very animatedly with his lawyers, but seemed happy. And I think in that moment, when they thought the jury was going home for the day, he was starting to maybe get a little hope that the jurors were not on the same page.

The abrupt change for him was also apparent when he suddenly went quiet and was not having this happy, animated conversation anymore. I think he was realizing what was coming. Immediately after the verdict, he didn't have a huge reaction. There was sort of, I think, a bit of a wince. He was staring intently at the jury as this verdict was being read.

Then after all 34 counts were read, he looked straight ahead and seemed to be sort of lost in a moment of thought, maybe contemplating what had just happened. Then the judge asked each individual juror to confirm that they agreed with the verdict. And so he looked back over at them and watched each one of them, and they all said, “Yes, we agree with that. That's the correct verdict.”

Fascinating. Alright, Ankush, let’s talk about the case itself. We're going to be as politics-free as a conversation like this can be, because I just don't think we know the political fallout here. So, how did the prosecution win this case? 

Ankush Khardori: It looks like they managed to win this case by persuading jurors that Michael Cohen was credible enough on the key elements of his testimony, including descriptions of some key conversations that he had with Trump, for which there were no other witnesses. And also by shoring up his testimony by sort of beating home this theme that he was being corroborated by documents and other witnesses, text messages, financial records and things like that. It wasn't entirely true that his testimony could be fully corroborated by other evidence in the case, but a lot of it could and that strategy looks like it paid off.

I don't think it's actually much of a surprise. Well, it is a surprise anytime you get a jury note. But the fact that they asked about circumstantial evidence in particular was a good sign for the prosecution because that was a key component of their case, which was presenting this as a story that just made logical sense and logically led to a conviction. I think that they had a pretty fulsome and consistent narrative that they sort of unspooled over the course of the trial. It had its gaps and weaknesses, in my estimation. But, it does appear to be the case that the jury accepted it.

Kyle, anything to add to that view? 

Kyle Cheney: In addition, I think in the closing argument, they did a good job of yes, shoring up Cohen's credibility, but also talking about how it was kind of, in a weird way, beside the point — that there was so much corroborative evidence and documents that they should focus on. And then, as Ankush pointed out, the inferences they could draw, even just from the stuff that was independent of Cohen, that they could reach a conviction without needing too much of Cohen. And I thought — whether you buy that or not, because I actually think there were some aspects of the case that only Cohen could speak to — it was persuasive in the closing argument, and I think may have been effective with the jury.

This speaks to what both of you just said, there was this moment where the jurors asked Justice Merchan to repeat his rain analogy. And that seemed to be a good clue about where this was going. Either of you want to explain what I'm talking about and its significance in hindsight? 

Ankush Khardori: There are a variety of these very common metaphors that judges use to explain circumstantial evidence and inferences. Rain is one. I don't know exactly how to formulate it but —

I think it was basically, “If you wake up and you don't see rain, but you see people with umbrellas and it's wet outside and they're wearing rain gear, a fair inference is that it rained overnight.” 

Ankush Khardori: Or like, “You wake up and you see snow on the ground, a fair inference is that it snowed overnight.” There are a bunch of these.

So this is common? 

Ankush Khardori: It is very common.

And so this was a sign that the jury was trying to make those inferences with the evidence that didn't require the Michael Cohen testimony?

Ankush Khardori: I mean, that's what I drew from it. And look, we don't know how many people had the question. For all we know, it was one juror who had the question and the other jurors were happy to put it to the judge in hopes that —

Right, you don't have to be unanimous on the question that goes to the judge. 

Ankush Khardori: Correct. I did think it was a good sign for the prosecution. Obviously in hindsight it's easy to say that, so I don't really want to oversell it. But it did seem to be a positive indicator.

Kyle Cheney: The point you make, Ankush, is interesting, too, because I think there was so much psychoanalysis of the jurors and every little word of the question is, “What does this mean?” And you saw a lot of the pro-Trump people saying, “Oh, that question is good for Trump because it means someone is confused about the instructions or maybe not buying that they can make these inferences, so therefore, the other jurors said, “Hey, let's give the instruction again to try to convince this person … ”

Yeah, it's a holdout. 

Kyle Cheney: Right. In hindsight, I think that analysis is correct. But in the moment, we're saying, “Is that because someone's saying they can't make the inference and therefore is holding out?” Maybe that was true. Maybe there were a couple of jurors who said, “I'm a little uncomfortable about that.” And they said, “We'll show you. We'll read the instructions again and you'll see that you can do it.”

Ankush, this is a subject that's near and dear to your heart, I believe. And that is: How did the defense blow this?

Ankush Khardori: Alright. I think that, again, hindsight is 20-20, so I don't want to oversell this. This is actually very similar to the end of a political campaign where everybody retroactively decides that the winner was a genius the whole time, and that the loser was destined to lose the whole time.

Totally. 

Ankush Khardori: The same thing happens in a trial, too. So I don't want to oversell it. But I do think even in the moment, as the pretrial proceedings and the trial proceedings unfolded, there were just some very conspicuous missteps.

In the run-up to the trial, they just could not stop talking in their court filings about how they thought that Donald Trump was being persecuted by the Democrats and the Biden administration. That was for public consumption, obviously. But it went to the judge, too. And it made all of their briefs weaker and easier to set to the side. Also, this was a complicated case with lots of intricate pieces that provided some novel legal issues. I never felt like the defense's briefs did a particularly effective job of explaining just how much there was in the way of new prosecutorial imagination, if you will, not to suggest that it was inappropriate or anything. But a lot of this was untested in the architecture of the legal case.

Then as we got to the trial, you know, I did a whole column on this. It was just completely idiotic. For Todd Blanche, Trump's lead counsel, to deny that Trump had had a sexual encounter with Stormy Daniels, they were just asking to get beaten over the head with her testimony. That's exactly what happened

Throughout, there were also these cross-examinations of every single witness. Again, this is a very Trumpian strategy. You just have to attack everything, deny everything. And the early witnesses — take someone like Keith Davidson, who was Stormy Daniels’ lawyer. He had no contact with Trump. His dealings were all through Michael Cohen. So, the cross of him could have been: “How many times did you talk to Donald Trump? OK, zero? Thanks.” Or some variation on that.

Instead, it was like this whole thing about how he's a sleaze merchant and potentially extorted Trump and all that. That may be good for political theater, but it is not the way to defend a white collar case, which usually requires a very strategic judgment about what to contest and what not to contest. And then we get to the cross of Michael Cohen, which I think was always sort of the main event in this case. I've never seen a government witness in any serious criminal prosecution with this much material for a defense lawyer to work with as Michael Cohen.

Really? I mean, people talk about Sammy "the Bull" Gravano putting away John Gotti. He was a murderer. Worse than that kind of criminal?

Ankush Khardori: I mean in white collar cases.

Fair enough. 

Ankush Khardori: But he's lied to so many people. He’s lied to every branch of the federal government. He lied to his banks. He lied to the IRS. He just provided an extraordinary amount of fodder for a defense lawyer. Obviously he's had reams of material in the form of podcast and television interviews that could have been used across him. And some of that was, at least the podcast stuff.

The cross itself, on paper, I thought Blanche actually did a good job of extracting some key points. And particularly, there's no denying whatever the result was, the cross on the call to Keith Schiller and the revelation that it may have been about a 14-year-old kid harassing Michael Cohen, rather than Michael Cohen apprising Donald Trump about Stormy Daniels — that is an excellent cross-examination moment, despite the fact that they lost the case.

He pulled out that material. But I heard from people who were in the courtroom that it was not landing because Blanche was all over the place. He didn't moderate his tone very well. You can see this on paper, too, but it jumped around in time and even thematically. And you have to pick one if you want jurors to follow what you're doing. A cross examination either needs to move thematically or temporally or some combination thereof.

So then we get to the closing arguments. And the column I did prior to the closing, what I truly believe, was that this case could actually come down to the closing arguments. Because had the defense really rearranged all the material from Cohen's cross and jettisoned some of their silly mistakes, like denying the encounter with Stormy Daniels, they could have put together a very, very good closing.

And then the closing. You know, I hate to beat down on the losing party here, but the closing was bad. It was really bad. And the scuttlebutt going around among the legal analysts and commentators for the last week or two: The closing sort of solidified that Todd Blanche did not do his best work on this case, and that another set of lawyers plausibly could have gotten Trump off.

Listen to this episode of Playbook Deep Dive on Apple, Spotify, or wherever you get your podcasts.

I want to ask Kyle about the complicated jury instructions that confused everyone earlier this week and gave the jurors these multiple options that people on the right found infuriating. Could you just explain that for us, Kyle?

Kyle Cheney: Sure. I think it is a fair criticism of this case overall that they relied on this law that has so many layers and is somewhat untested in the way that it was used against Trump. That will be a matter on appeal and it may be a serious appeal. But the prosecutors had to show that Trump falsified the business records in the commission of another crime.

So in other words, he broke New York election law, but by one of these three methods?

Kyle Cheney: Right. There's a kind of a menu of ways in which the jury could have found that he attempted to do that or intended to do that.

And the jurors did not have to agree on which method?

Kyle Cheney: And that's what became the firestorm on the right because everyone is very familiar with the concept of jury unanimity to convict someone of a criminal offense and to potentially take away their liberty. It's got to be overwhelming. And that's true.

And the judge was very clear. You need to unanimously agree that he falsified records. You need to unanimously agree that he violated New York state campaign finance law. What you don't need to unanimously agree on is how he attempted to violate New York state campaign finance law. There are several different ways the prosecutors offered to show that Trump attempted to do or intended to do that.

At the end of all this, Justice Juan Merchan set sentencing for July 11. That's four days before the Republican National Convention starts in Milwaukee. Let's distill everything we know about sentencing and what the range of options are here. 

The conventional wisdom I see among the legal analysts is on one side, “Oh, it's a class E felony in New York. That's minor. And most of the time, there's no jail time.” On the flip side, Trump was found to be in contempt of court 10 times during this trial. He was found guilty on all 34 counts. It doesn't seem like he's likely to show much remorse. And that weighs more toward the side of a stronger sentencing. What's your view of all this?

Ankush Khardori: I think that is correct. First of all, the maximum sentence on a charge that he's been convicted of is four years per count. They're not going to stack. So, I would think the judge would be thinking about this as a maximum four-year term of imprisonment.

Not 4-times-34?

Ankush Khardori: No. For a first-time offender in New York, where white collar defendants are treated pretty well by sentencing judges — and Trump has a history of serving as U.S. president, which is not nothing by any means — he would have a very good case for probation in the ordinary course. Or potentially getting off with some combination of probation and fines or something like that.

But to me at least, the factor that I think is the wild card here is his own behavior during the trial. And I'm sure we're going to see more of it after.

We saw it immediately after the verdict.

Ankush Khardori: Yeah. I mean, he used every single day to rail against the judge and the case. And that's all well and good fine, rail away. But it was extremely dishonest claiming that the case was orchestrated by the Biden White House, that it was political enemies coming after him. That undermines the New York criminal justice system. And it undermines the integrity of the proceedings. I'm sure there are plenty of people who are happy for that to have happened. But I guarantee you the judge was not happy for that to have happened. And one of the things he's supposed to do is to guard the integrity of the legal system, the court proceedings and to promote respect for the law.

I don't know what he'll do, obviously, in terms of actually rendering a sentence. But if I were him, that part of it would give me a very serious pause, because I would be thinking, “It's all well and good that he was convicted on this. We don't usually give people prison time, that’s very, very significant and important. But how can we let someone just treat the justice system this way?”

I literally cannot think of a precursor for the way in which Trump behaved. We'd have to go to mobsters, I guess. But even them, they don't get every day to speak to the national media and have their words broadcast around the country. That's what Trump did.

They often listen to their lawyers. Kyle, what do you think? Is Trump going to go to jail?

Kyle Cheney: One factor here too is over the next few weeks, we're going to see a bunch of filings and submissions, including from the DA, recommending a sentence. And Trump will actually have to sit for a probation interview with a probation official, who will also contribute to the potential recommended sentence.

So Ankush, the appeals can start after sentencing. What does that process look like? Is it likely that if he is sentenced — even if it's to community service or home confinement — is it very likely that that would be suspended during an appeal, or is that an open question?

Ankush Khardori: So the process would follow a fairly standard process of just [going] through first the Appellate Division, which is the intermediate court in New York, and then, potentially up through the Court of Appeals, and it would be briefs and potentially oral arguments at the judge's discretion. I would imagine there would be oral arguments. In terms of whether or not he would be allowed to suspend his sentence pending appeal, I'm sure he will ask. I do not know if it will be granted.

I do think he would have a pretty good argument under the circumstances, simply because there are some novel legal issues here, and that tends to be the best argument for defendants to stay out pending appeal, which is to say, you don't quite know how this is going to resolve itself, and particularly when the sentence might be significantly shorter than the time it would take for the appeal to run. I think he'll have a pretty good argument in this case, but I don't know how it'll unfold.

Kyle, what do you think the best avenues for an appeal are? Ankush, feel free to jump in as well.

Kyle Cheney: There are a couple. I think one is what we talked about earlier, which is that they're going to challenge this idea that the jury could choose from that menu of choices to decide how Trump violated campaign finance law [and it didn’t have to be] unanimous. They'll say that that's a violation of Supreme Court precedent. Ankush may have a better grasp on whether that's even plausible. But I think that's talking point 1 for them on appeal.

Then I think there's also going to be some question about some of the testimony that came in from Stormy Daniels and whether it was prejudicial in the sense that it wasn't related to the actual crime itself. Even the judge got upset at a couple points when the prosecutors kept eliciting testimony from her that was really salacious. It's sort of fortuitous for Trump that the high court in New York ruled that Harvey Weinstein should be retried in part because his trial was prejudiced by similar evidence coming in that shouldn't have come in that may have been inflammatory. I don't think these are analogous cases in any respect, but Trump's people are very well aware of that ruling and might point to it to say Stormy Daniels’ testimony was so prejudicial he should get a new trial at least.

Ankush Khardori: I agree with Kyle. It does seem to be some of the avenues that they're pursuing. They don't sound terribly promising to me, those particular two. I'll take them one at a time.

The structure of the decision-making that the jury did here — is he guilty of this offense and providing multiple means by which you could reach that conclusion without the jurors having to agree — is extremely common in criminal cases and particularly conspiracy cases. I would be surprised if that had legs legally. But New York courts can surprise from time to time. I do understand why Trump and his supporters have tried to mislead the public into thinking that this is unusual because it sounds counterintuitive, but it's in fact quite common in the criminal system.

As for the analogy to the Weinstein case, I completely agree with Kyle. There are significant differences. The most obvious one, which I think just is the whole ballgame to me at least, is that the Weinstein conviction was overturned because there was testimony from women accusing Weinstein of misconduct that had not been charged in the case, meaning it was extrinsic to the charges that have actually been brought. In this case, we're not talking about a totally different witness being allowed to testify about some other event. We're talking about a single witness potentially offering some extraneous details, which is very different in kind.

The issues that I think actually might have some legs are the issues surrounding the interaction between New York and federal law. Let's say that for instance, the crime that elevated this from a misdemeanor to a felony was this New York state law that prohibits promoting the election of someone through unlawful means. The unlawful means included potential violations of federal campaign and finance law. Is that a permissible object of a New York criminal statute of that nature? Can that object of that statute be a federal offense, or does that overlap with federal jurisdiction in the area and campaign finance law more generally?

That is an actual intricate issue that I don't think is particularly well resolved in New York courts. And also this question of what does it mean to have the intent to commit another crime? That was hotly contested in the run up to the jury instructions. That is an area where there was really not much guidance for the parties to work with in terms of figuring how to instruct the jury and that can be an area of vulnerability on appeal as a result.

Now that Donald Trump is a convicted felon, what are all the ways in which being a convicted felon will affect his life? From his ability to vote to any other kind of restrictions like what it might mean for the other three cases that are still ongoing. Without asking you the political question that we're all going to be debating over the next few weeks in terms of what this means for the election, what does it mean to be a convicted felon for him?

Kyle Cheney: I think being a convicted felon for Trump is going to mean something different than it would for most people in the world, and a lot of things are.

It's going to mean he's going to raise a lot of money.

Kyle Cheney: Right. Exactly. I got a text message while we're on this podcast talking about, “I'm a political prisoner. Donate here.” I think they'll make hay out of this for a while, in part because of what we just talked about. There's a good chance the sentence will be suspended pending appeal and he may not feel a real consequence from this for quite a while. That said, he's not going to be the typical convicted felon who has too many restrictions on his travel or his movements.

I'm very curious how they factor in — because the court system is not supposed to factor in the political side of things — whether they account for the fact that he'll be in the home stretch of a campaign when his sentence is supposed to be effectuated and that actually trying to sentence him to prison in that moment might have bigger repercussions than just putting someone in jail.

Ankush Khardori: I totally agree with Kyle. In the ordinary course, you know, there might be some collateral effects in terms of his ability to vote in Florida. And other than that, what does it mean to be a felon? Well, it's usually harder to get a job if you're looking for a job, but he's not going to have that problem. It's supposed to be a huge stigma and an embarrassing thing, but we'll see if that is the case here. Certainly he's not going to present himself as someone who's suffered some actual stigma. And I agree with Kyle, I wouldn't expect too much in the way of any types of restrictions on his movements or any sort of particularly onerous conditions on him, but we'll see.

It may be that if the judge decides to sentence him to some form of probation that he does impose or attempt to impose some constraints along those lines in order to sort of make it a little bit more burdensome than probation might ordinarily be. But the practical effects, I agree with Kyle. I don't think those are going to materialize — at least the worst ones — just yet and not until the appeals process plays out and if he's in office when that happens, I don't think there will really be any effect.

Kyle Cheney: I think it goes away [if he’s elected president]. I was just going to make that point that I think there's a constitutional argument that constraints put on him by a state court would be unconstitutional while he's president. He has duties to the country that require him to be uninhibited and unshackled from certain restrictions that probation might impose, and they would supersede any interest a state might have in effectuating its sentence immediately. In Georgia, Trump said if he's elected, the trials there should be postponed until 2029. I think they'd make a similar argument for the effectuation of a sentence in New York.

Ankush Khardori: Yeah. And I would say I know a lot of people like to fantasize — and I don't mean that pejoratively, but sincerely — about like, “Oh, could he be president from prison?” That would be bad for the country. Whatever one thinks about Donald Trump, like him or dislike him, his worst impulses would just get worse if he had to serve as a president from prison. That is not going to happen.

Yeah. Doesn't seem like a good thing.

Ankush Khardori: Exactly. It'd be bad for all of us.

Kyle Cheney: I mean, the president has to conduct foreign policy. That means going around and meeting world leaders. You can't do that from jail.

Ankush Khardori: I was going to say, are they going to set up a Situation Room down the hall in Rikers or something? I just think that's practically inconceivable and the legal argument that Kyle sketched out is I think the one that would be the principal one.

So not completely out of the realm of possibility that the Supreme Court has to think through an issue like this at some point in the near future. 

Ankush Khardori: Actually, it's plausible that Trump tries to take it from the New York state court system if he loses in the Court of Appeals to even the Supreme Court. There's a lot of string left to play here. We're not dwelling on the politics here, but November is really going to be crucial in terms of whether and to what extent this process really plays out to its natural conclusion.

Listen to this episode of Playbook Deep Dive on Apple, Spotify, or wherever you get your podcasts.