Can the Criminal Justice System Try an Ex-President Fairly?

Before I get into the specifics of exactly who is overseeing the federal trials of former President Donald Trump, can I just start out by acknowledging that America has always picked judges in pretty bizarre ways?

“In the old days, there was literally a wheel, and you would spin the wheel, and it would land on a certain judge, and that would be the judge to hear the case,” said Mark Joseph Stern, our resident expert on the courts here at Slate. He says courts ditched the whole wheel thing a little while back. “I think different courts use different procedures, and it’s generally electronic.” 

But still, the randomness remains. The goal is noble. Random assignments make it harder for the prosecution or the defense to curry favor with a person who controls their fate. But also?

“For regular criminal defendants in the system, it means that based on random chance, you might be assigned to a judge who decides to give you a really lenient sentence or you might be assigned to a judge who gives you an incredibly harsh one, and you have no control over it,” Stern said. “There is a huge amount of arbitrariness that’s built into it.”

And for special counsel Jack Smith, his wheel has landed on two very different jurists when it comes to prosecuting Donald Trump. In Florida, where Trump is charged with mishandling classified documents, Judge Aileen Cannon is overseeing the case. She’s new to the bench. A Trump appointee. In Washington, meanwhile, where Trump faces charges for his role in Jan. 6, Judge Tanya Chutkan is in charge. She’s got nearly a decade behind the gavel. She was appointed during the Obama years.

“It’s going to be like going from a frozen Chicago winter in Judge Cannon’s courtroom to the beach in Anguilla, in Judge Chutkan’s courtroom, in terms of how Jack Smith is treated,” Stern said. “What we’ve seen from Judge Cannon already suggests that she is really kind of angry with the government, unhappy with Jack Smith, not pleased with how this case has been handled so far and expressed in ways that I myself do not think are necessarily appropriate. Whereas with Judge Chutkan, she has, I think, dealt with both sides very fairly, and so it’s going to be whiplash for Jack Smith.”

On Tuesday’s episode of What Next, we took a deeper look at both of these judges—and why two of the most consequential trials in our country’s history could be decided in very different ways. Our conversation has been condensed and edited for clarity.

Mary Harris: Let’s go a little bit deeper into who these judges are and their biographies. Let’s start with Judge Aileen Cannon. This is the Florida judge overseeing the classified documents case. She’s pretty new, right? What do we know about her?

Mark Joseph Stern: Yeah, Judge Cannon is so new that she was appointed to the district court and assumed office while Donald Trump was planning the very coup at issue in the Jan. 6 case. She took office on Nov. 13, 2020, so Trump was already well into his plot to overturn the election by then. She was actually born in Colombia, so she is an immigrant, and she came to the United States relatively young. She was a corporate lawyer and then served as a federal prosecutor for some years, and I’ll say I was surprised by how many mistakes she’s already made.

What kind of mistakes do you mean?

In one case, during voir dire, which is when you’re picking the jury in a criminal case, she excluded the defendant’s family members from the courtroom, and that is crazy. The right to a public trial is guaranteed by both the First and Sixth amendments. It’s literally right there in the text of the Constitution. And the Supreme Court has ruled explicitly that that right attaches during voir dire because it’s a crucial phase of a criminal prosecution. And she kicked out the family of the defendant for no reason other than she alleged that there weren’t enough seats in the courtroom. When you have to choose between issuing an unconstitutional order and making some extra space in your courtroom, you choose the latter.

In another case, she forgot to swear in the jury. That might sound like a technicality, but it’s actually a really important part of this entire system.

It also just sounds really basic. 

Yeah, it’s fundamental. If you watch Law and Order, you know you have to swear in the jury for God’s sakes. And she’s only overseen four criminal trials from start to finish with a jury during her short time on the bench.

How has this lack of experience played out once she was handed the Trump case?

The worst part so far happened in 2022, at a much earlier stage of this case. After the FBI searched Mar-a-Lago for the classified documents, Donald Trump went to her court and asked her to essentially halt the investigation and prohibit the government from looking at the classified documents that it had seized. That is not something that is done. It’s a made-up idea that criminal defendants just don’t really get to do, yet she issued an order purporting to halt the investigation and prohibit the government from looking at these materials as part of a criminal investigation. That was the first time in the history of the American republic that a judge has purported to block an investigation into a criminal matter before an indictment. That had never happened before.

And she got called out for this.

Twice. Brutally slapped down by two very conservative panels on the 11th Circuit, who essentially accused her—correctly—of creating a totally different standard that applies exclusively to Donald J. Trump and said, “That’s not how we do law in this country.” You don’t get to seize this newfound power to shut down a criminal probe just because the guy in question happens to be Donald Trump. That’s not how it works.

Is it possible that Judge Cannon learned her lesson here? And I ask this because after she began weighing in on the Trump case more formally this summer, an analysis in the New York Times concluded that for now she’s the “jurist defenders have described—level-headed and not beholden to the man who appointed her” (Trump). It sounds like you disagree with that pretty firmly.

Well, yes, I disagree. Look, there hasn’t been a whole lot of action  so far. She hasn’t had a chance to rule on some of the most important motions that get filed before a trial begins. That’s when we discover if she is truly a real judge, or if she’s just a Donald Trump MAGA defender in robes. So, that New York Times piece struck me as egregiously premature, and frankly, some of her conduct already including a very recent order and some of her scheduling orders do not seem on the level to me and are sort of flashing warning signs that she is indeed the same judge who ran interference for Trump in 2022.

Let’s talk about Judge Tanya Chutkan. This is the D.C. judge overseeing the Jan. 6 case. What do we know about her? She’s been on the bench much longer.

That’s right. Tanya Chutkan was a Barack Obama appointee, and she also is an immigrant, like Judge Cannon. She was born in Jamaica. But her legal career was very different from Judge Cannon’s. She, after working in private practice, became a public defender. She was one of the relatively few public defenders who Barack Obama elevated to the federal bench. This was a big criticism of Obama, that he mostly elevated prosecutors and snubbed public defenders. It was a big deal that he chose her, and she was confirmed 95 to 0. And now she has been on the bench for about a decade, and she’s proved herself to be extremely competent, extremely efficient, very respectful to both sides, not the kind of judge to lose her temper

What do mean when you say that? Like, if you’re walking around the courthouse, what are people whispering about Judge Chutkan?

They’re whispering nothing, which is ideal. There are some characters on the district court here in D.C. She is not really an outsized ego or anything.

Judge Chutkan’s also been really involved with overseeing Jan. 6 cases, like the rioters that the DOJ has charged. When you look at her track record for other Jan. 6 cases, not the one against Trump, what does it tell you about her style and her approach?

Judge Chutkan is known as one of the more stringent sentencers in Jan. 6 cases. She has on several occasions issued sentences that are higher than what the prosecutors recommend. That’s not incredibly unusual. The sentencing guidelines are flexible, and judges issue on the higher end or even over what prosecutors want all the time.

But in some of these cases, the prosecutors weren’t even asking for jail time at all, right? And she’s like, Sorry, no, you go to jail.

That’s right. Now, it might not be for a very long time, but she has made a point of saying that this was an attack on democracy, that this was attack on our most basic institutions, and that the American people need to see the real-life consequences of engaging in this kind of violence. The fact that her sentences are on the higher end on this court can in part be attributed to the fact that there are some Donald Trump appointees on this court who really seem to view Jan. 6 as a lesser crime and are not handing down sentences that are nearly as stringent as what prosecutors are asking for.

And Judge Chutkan has previously ruled against Trump too, right?

Yes. Judge Chutkan handled this really important case from last year where Donald Trump was trying to block the release of a number of important documents relating to Jan. 6 that Congress wanted to get a hold of. He tried to assert executive privilege over them, even though he was, of course, no longer president. And Judge Chutkan blocked that request, allowed the documents to be released to Congress, and said, Presidents are not king, and Donald Trump isn’t even president, so he certainly has no right to block this release, especially when Joe Biden, who is president, said that he was fine with the documents turning over to Congress.

Donald Trump is certainly trying to make it look like Judge Chutkan is a partisan hack. In fact, he’s asked for his trial to be moved to West Virginia. Any chance of that actually happening?

No, certainly not. We can turn back to the Constitution here and see that it requires that criminal trials be held in the venue where the crime took place. There are extremely rare exceptions to that. Like, where it’s a super small town, and there was ubiquitous biased media coverage and 100 percent of potential jurors were irreparably tainted by this coverage. But that’s it. As a rule, you get tried where the crime took place. I’ll say that Trump’s efforts here, it’s not just about Judge Chutkan, it’s about the jury pool. He’s pointed out that the District of Columbia is majority Democratic, that more than 90 percent of voters chose Hillary Clinton and Joe Biden over Donald Trump. And so he’s claimed that that poses a total risk of bias that can’t be overcome, so the trial must be moved to get an impartial jury. But that’s not what impartial means when we’re talking about juries. It doesn’t mean that the jurors can’t have opinions or political leanings. So, all of that, all of those arguments, I don’t think they’re going to fly at this court, at the D.C. Circuit, or at the Supreme Court. I think this trial’s going to happen right here in the District of Columbia

This week, both of these judges, Aileen Cannon and Tanya Chutkan, issued rulings that showed just how different they may be as judges. Can you explain exactly what happened here?

Yeah, as folks may be aware, Donald Trump has a problem keeping his mouth shut when he is in legal peril.

He loves to post. He loves posting. 

Heroic levels of posting here. Not long after his arraignment in D.C. on Thursday, he posted on Truth Social, “If you go after me, I’m coming after you.”

Which is just a straight threat. Let’s be real.

Right, right. Whether it’s a true threat that could be prosecuted on its own, that’s a different question, but whether it’s quite obviously designed to intimidate Jack Smith, yeah, duh. Of course it is.

And at, like, 10 p.m. Jack Smith is like, “Hold it.”

Exactly. He turns around and files what’s known as a protective order, telling Judge Chutkan, “Hey, look, we as prosecutors have to turn over the evidence that we have to the defendant. A lot of that evidence, a lot of the materials that we have are super sensitive, and it seems to us that this defendant has a clear vendetta against us as prosecutors and is not someone we can trust to keep all of those highly sensitive materials to himself.” He poses a risk of releasing, revealing, leaking some of these materials to the world, which could have all kinds of negative downstream effects.

It’s sidestepping this free speech issue that Trump’s team likes to bring up a lot.

It reminds me a lot of how Jack Smith also declined to charge Trump with incitement to insurrection, which was very much open to him, which was advised by the Jan. 6 committee as a possible charge, which was the basis of Trump’s second impeachment. But Smith did not bring those charges almost certainly because he recognized that Republicans would claim this was an infringement on free speech, that he was criminalizing political speech by charging incitement. And so, he sidestepped that question by bringing these other charges that were rooted more clearly in conduct.

This whole episode has illustrated how Chutkan’s going to handle the case because Trump came in with his lawyers and said, “We need more time to respond to this. We don’t have time to respond over the weekend.” And Chutkan shut that down and said, “Absolutely not.” You better answer by Monday at 5 p.m. You do not need more time. This case is rolling along. This is going to be a speedy trial as required by law. So, answer this man, and I’ll issue an order, but you’re not going to run down the clock on me.

So, we have Judge Chutkan moving speedily along. Meanwhile, on Monday, Judge Aileen Cannon delivered a really different kind of order. What did she say?

This order is relevant to Donald Trump but specifically pertains to Walt Nauta, who is the Trump body man and assistant who was indicted alongside him in the Mar-a-Lago case. He famously was accused of taking documents from their storage area and secreting them away in the shower and bathroom at Mar-a-Lago so that investigators wouldn’t find them. And there’s a big problem here, which is that Nauta’s current lawyer, who’s named Stanley Woodward, represents people who are probably going to testify against Nauta at trial.

A little conflict of interest there.

It would be sort of like if you were a witness to a murder, and I represented you, and then I turned around and also represented the murderer.


And so, Smith came in and asked for a hearing in the 11th Circuit—it’s called a Garcia hearing—just so that the court could hear about this conflict of interest and decide whether Nauta could waive concerns about this or whether there needed to be further steps taken, including potentially an independent counsel

How did the judge respond when this was brought to her?

This is just incredible to me. She comes in and first she says, “OK, well, you filed all of this supplementary material that’s classified or secret or incredibly sensitive. You filed that with me under seal, but I don’t think you should have done that. So I’m going to strike it all.” So she’s saying you didn’t justify keeping this under seal even though it pertains to an ongoing grand jury investigation, which is, just again, very odd. If you hate the government always in these cases, then you’re like, “Yeah, stick it to the feds. Make ’em say more.” I understand that perspective, but it’s just very weird to say you have to prove why this secret stuff should be kept secret.

But the second thing she did, which I think is even weirder, is that she noted that these witnesses are testifying in a grand jury that’s in D.C. She said, “Oh, I see you’ve got this grand jury in D.C. that’s still looking into the classified documents case, and I don’t like that. And so, because I’ve noticed that you’re doing this, I am going to force you to now file a kind of jump-scare motion explaining why you are allowing this proceeding to continue to investigate matters pertinent to my case.”

It seems like she is maybe running down the clock, which everyone knows is Donald Trump’s No. 1 legal strategy that he’s used to great effect in the past. It really feels to me like she is building in a ton of buffer time in between each filing. And that disincentivizes Jack Smith from filing further motions because every time he makes a request to Judge Cannon, it’s going to become a monthlong odyssey that poses the very real risk, as we draw closer to the new year, of pushing this trial even further back. And if it goes much further back, then eventually Judge Cannon says, “Well, now we’re too close to the 2024 election, and we have to wait,” and if Trump wins, we know what happens after that.

Are judges more partisan than they used to be? Or is it just that we’re seeing it more now?

First of all, we’ve never really had a case like this. This is uncharted territory, and so, we’ve never had the opportunity to see how federal judges will behave themselves when the president who appointed them is facing prison time. That is the main difference between this and every other prosecution that’s ever occurred in the United States.

But I also think that, yeah, the way we’ve begun to select judges, especially on the right, specifically with Donald Trump, was to say, “OK, Federalist Society, send me your most extreme ideological conservatives, and I will put them on the federal judiciary.” So, I do think every aspect of the judiciary is becoming more politicized, and this is maybe the chickens coming home to roost with Judge Cannon overseeing a case that she’s not qualified to handle and on which she seems to have a very strong bias.

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But if progressives like you don’t trust Cannon and conservatives don’t trust Chutkan, what does that mean for the outcome here?

Well, frankly, I fear that if Donald Trump is either acquitted or if Cannon throws out the case or does whatever she can to ensure that Trump gets off scot-free, that everyone on the left is going to be like, “This was an unfair trial.” If Judge Chutkan comes in and does her level best to conduct a fair trial and does everything right and is the consummate professional, and Donald Trump does get prison time, everyone on the right is going to say, “This wasn’t a fair trial. This was an incredibly biased, partisan witch hunt against Donald Trump.” There’s an integrity gap between how the two parties are treating the judicial system at this moment with regard to these cases, and it’s going to be impossible to get everybody on board. It’s almost certain that one of them will go up to the Supreme Court, and I’m kind of scared to imagine what happens either way when the Supreme Court hands down a decision that either lets off Trump from consequences for Jan. 6 or holds him to the laws that Smith has charged him under and says, “Yes, this is a legitimate prosecution.”

One way or the other, there’s going to be an incredibly fiery response that’s not going to be great for the Supreme Court, that’s not going to be good for the judiciary. But this is what Republicans said would happen when they refused to remove Trump from office and disqualify him from running for president again. Mitch McConnell went up on the Senate floor and said, “We’ll, let the criminal system handle this.” Well, that’s where we are. The criminal system is handling it, and we’ll just have to see whether the criminal system has the capacity to do so or whether it’s all going to come toppling down under the weight of a totally unprecedented and kind of frightening prosecution. The whole legal system floats on our collective belief that it’s real. And if we stop believing that, I’m not sure what happens next, but I’m not looking forward to learning.


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