How the Supreme Court Defeated Trump

A conservative court watcher explains why the president has failed to bend the judicial branch to his will.

Hosted by Ross Douthat

Produced by Sophia Alvarez Boyd

Mr. Douthat is a columnist and the host of the “Interesting Times” podcast.

President Trump has been testing the limits of presidential power since he returned to office — from his assertion of total control over federal agencies, to now his undeclared war with Iran.

But so far, many of Trump’s most aggressive moves have ended in defeat — usually in the courts, and increasingly at the Supreme Court. And it may be that the key revelation of his second term is that the judicial branch is the real power center in American democracy right now.

That’s the argument of this week’s guest, Sarah Isgur, a conservative court watcher, a lawyer, and the author of the new book, “Last Branch Standing.” I wanted to talk to her about Trump’s power grabs, the internal politics of the Supreme Court, and whether we should be reassured or troubled that it takes an imperial judiciary to counter an imperial presidency, with Congress increasingly out of the picture.

How the Supreme Court Defeated Trump

Below is an edited transcript of an episode of “Interesting Times.” We recommend listening to it in its original form for the full effect. You can do so using the player above or on the NYTimes app, Apple, Spotify, Amazon Music, YouTube, iHeartRadio or wherever you get your podcasts.

Ross Douthat: Sarah Isgur, welcome to Interesting Times.

Sarah Isgur: Thanks for having me.

Douthat: So we’re going to talk about the Supreme Court, the divisions within the court, its influence over American politics, and the future of the Constitution. We’re going to get to some big questions, but we’re going to start where all things must start, with President Donald J. Trump and executive power.

We’re about a year and a few months into the second Trump administration, and in the first three to six months of the administration, all anyone wanted to talk about with constitutional questions was just how much power his administration was consolidating in all kinds of different domains.

And I want to give you a chance to talk about where that revolution stands. How successful has his attempt been to remake the presidency’s powers?

Isgur: There’s very little that Donald Trump has done — in fact, I’m hard pressed to think of anything — that is wholly unique. What Donald Trump has done is turned the amp up to 11 on places that his predecessors had built on in the past.

On the one hand, we can go back to Obama’s “pen and phone” moment.

Archival clip of Barack Obama: I’ve got a pen and I’ve got a phone. And I can use that pen to sign executive orders and take executive actions and administrative actions that move the ball forward.

Archival clip of Barack Obama: I’ve got a pen and I’ve got a phone. And I can use that pen to sign executive orders and take executive actions and administrative actions that move the ball forward.

In a lot of ways, you can see Trump using a much bigger pen and a much bigger phone and really having done all of government by executive action.

In another lens, you could go all the way back to the progressive era, to Teddy Roosevelt and Woodrow Wilson, where they think Congress is a bunch of dumb-dumbs coming from wherever, saying: What if we did government by experts in the executive branch? And instead of having Congress decide this, we’ll have the smartest people, because there are right and wrong answers. And instead of representative democracy that’s so passé, we will basically have this constitutional revolution and move power from Congress over to the executive branch?

In another sense, Trump is the end point of this hundred-year experiment that we’ve been running, of, “Meh, let’s just have the presidency do it all.”

Douthat: So it’s the endpoint. Where are we ending? What has Trump actually succeeded in claiming, and where have his claims fallen short or not achieved as much as it looked like they might?

Isgur: I say it’s an endpoint because it has so obviously failed. He has failed to implement any of his major policy initiatives through executive order in any realistic sense. Think about the Alien Enemies Act, federalizing the National Guard, worldwide tariffs, birthright citizenship. These are the main pillars of Donald Trump’s policy presidency, the substantive aspects of it. And they’ve all failed, with the exception of birthright citizenship, which is going to [fail].

Douthat: What about Trump’s campaign for what you might call legal retribution against his enemies? This is another area where there was a lot of aggressive movement. And who is an enemy? You could define that to include the goal of prosecuting James Comey. You could define it to include the president’s campaigns against universities and against law firms. Where does that particular campaign stand?

And again, we’re talking a few weeks after Trump fired his attorney general, Pam Bondi, which seemed to be primarily related to the Jeffrey Epstein story, like all things are ultimately. But it was also this sense that she had been in charge of conducting this campaign, and the campaign was not going well. But how do you assess that campaign after a year or so?

Isgur: Legally, it has failed, at every turn. You can’t point to success in the retribution campaign. And by the way, my list, I think, looks identical to yours. It’s not just the individual — it’s the entities as well.

That being said, politically, I think it’s been very successful. I don’t think Trump cares that much about losing in court. I think probably he’s pretty satisfied with that, which —

Douthat: Do you think so? I guess I looked at the Bondi firing and I said, “Oh, even though she was willing to do all these things for Trump, he still wasn’t satisfied.” My sense is that maybe he would’ve been satisfied if just one presidential enemy had been convicted.

Isgur: Well, let’s say this: There’s a way to lose competently, and there’s a way to lose incompetently. I think President Trump doesn’t like displays of incompetence. They’re going to lose those cases no matter who the prosecutor is.

But culturally, I mean, we’re sitting here talking about it. I think we can all point to areas that has affected. Universities are a great example, by the way — all sorts of university changes are downstream from this effort.

I focus on law stuff, but it’s obvious to me that the legal part is just a very small part of the cultural aspect of the retribution campaign. So I don’t know, we’ll see what’s next. But the good news is that legally, none of it has worked.

Douthat: Look forward for a minute. What about the liberal anxiety heading into the midterms around elections and election power? This, too, is an area where Trump has threatened to or put out executive orders suggesting federal takeovers of election law. Does that follow the same pattern that you’ve just described, where it only works on paper?

Isgur: Totally. He puts out this executive order about mail-in ballots, and the Constitution quite clearly says that states control their elections, subject to regulations by Congress.

So once again, we’re back to the same question that we’ve been at, through the Obama administration, through the Biden administration, through the Trump administration: A president wants to do something, can’t get it done with Congress, so they go find some vague old statute and they’re like, “Oh, Congress gave me this power decades ago. Don’t worry too much about it.” He signs an executive order, and then of course the whole thing winds up in court.

The difference for Trump is that the old statutes that he’s finding are less persuasive and even harder to justify. And I think his election executive order that he did was even flimsier on paper than a lot of these others.

But again, I hope it shows people we don’t want government by executive order. Either the court will say, “The president doesn’t have the power to do that,” or more likely, the next guy will get rid of it on day one.

Think about climate change: Obama had his clean power plan. Trump repealed it. Biden came into office. He didn’t just put Obama’s plan back into effect — he has his own. And then Trump came back into office.

This is no way to run a railroad. We take one step forward, we take one step back, we take one step forward, we take one step back. We’re just dancing at this point.

Douthat: But I mean, the biggest reason, though, that you think it’s reached this endpoint, this failure, is that the Supreme Court — the courts generally, but the Supreme Court in particular — have said no repeatedly.

Isgur: Over and over again.

Douthat: And this is the difference between where we are now, versus where we were a year ago: We have a lot of concrete examples of the Supreme Court saying no to Trump.

Can you put those together with the cases where the Supreme Court has said yes to Trump on executive power, of which there have also been a lot? And those got a lot of attention early on. Is there a coherent Supreme Court approach to the Trump administration that makes sense of the range of decisions that we’ve had?

Isgur: Yes. Again, the wins that Trump has had have all been on that emergency docket, interim docket, shadow docket — whatever we’re calling it.

So the wins have been: What will the status quo be while this case is working its way through? Does the policy go into effect, or does the policy not go into effect while we decide whether the policy is constitutional?

Biden had fewer of these executive orders, so there were just fewer of these emergency cases. And he would win one on the interim docket but lose it in the end, and vice versa. So there’s nothing particularly new, and those interim decisions can be quite messy.

It’s very important to understand the denominator for Trump. At one point there were these blaring headlines that Trump had won 17 cases in a row, but they choose which cases they appeal. There had been more than 100 that they did not appeal. They just took the L and lost. So as a percentage, Donald Trump isn’t actually doing that well, even on those.

But the conservative legal movement has long had this idea that independent agencies are not a thing. You can go back to Justice Kavanaugh’s writings as a baby circuit judge, where he talks about the problem of presidents running on what they’re going to do with the economy and then getting into office and realizing they actually have no say over all these parts of the economy.

As a result, you’ve created redundancies in the executive branch where parts of the Department of Justice do the exact same thing as the Federal Trade Commission. The difference is the president controls the lawyers in the Department of Justice, in a way he doesn’t control the Federal Trade CommissionIf you’re a corporation or even a person trying not to break the law, you’re just in a total mess. There’s no political accountability that has long existed out there.

What has happened is Donald Trump is actually willing to test the waters in it. So of course, he’s winning on those things because conservatives have been writing about them for decades.

And what’s funny is, before that, it was liberals writing about them as well.

Douthat: You mean that when liberals were more likely to win the presidency, there was more scholarship — liberal scholarship — arguing: Wouldn’t it be nice if the president had more control over all his independent agencies?

Isgur: Right. I mean, Chevron doctrine, this idea that courts just defer to whatever the agency thinks its own power is, was Scalia. That was a conservative thing. And now conservatives are like, “Ugh, Chevron deference — blech.” So, things evolve over time, I guess.

Douthat: Right. Coalitions shift. Yes, I’ve noticed that. So basically, the court’s understanding of presidential power is, as you’re describing it: Maximal presidential freedom, in terms of what federal agencies and elements of the executive branch are told to do. And then, limits are where?

Isgur: Maximal presidential freedom within the executive branch and minimal presidential freedom vis-à-vis Congress.

And it’s funny — the court decides these individual questions and cases, but there’s also these larger trends. Because they decide what cases they take, they can almost be on multiyear journeys or projects.

Douthat: Sculpting anew.

Isgur: Yes, yes. And so it matters where they think the constitutional problems are emerging.

For a long time, the problems that I think they felt were emerging were coming from Congress having too much power vis-à-vis the states, like the commerce clause issue. So in the ’90s, you see the court starts saying: No, no, no, no, no. Congress is of limited powers. And just because Congress wants to do it doesn’t mean it can. Some things are reserved to the states, and the federal government doesn’t have any say.

By the time you get to the Roberts court, the problem seems to be emerging from somewhere else. It’s not that Congress is doing too much, it’s that Congress is doing too little. So now you see the court on this 20-year journey to try to reign in the president. Think of it like little siblings, and the big sibling is sitting on the little one and he can’t breathe. The court is trying to get the president to stop sitting on Congress.

They can’t make Congress do its job, but they can hope that if it’s very clear that the president cannot solve these problems — if a president runs on student loan debt forgiveness, and there’s a bill pending in Congress and it doesn’t pass — and the president just does it by executive order, you’re not going to have Congress try to pass bills anymore. If one side knows they can get everything they want through executive order, they don’t need to compromise.

And so the court has been involved in this multidecade process to say: “Nope. You cannot do it that way. You must go back to the........

© The New York Times