Chuck Todd is joined by Benjamin Wittes, editor-in-chief of Lawfare, to break down the widespread legal violations committed by the Trump administration during Donald Trump’s first three months in office.Chuck opens the episode by underscoring the gravity of the moment and why Trump appears to show little respect for the law or the authority of the courts.Ben Wittes then joins the conversation to discuss the constitutional amendments the administration may have violated, whether Trump is defying Supreme Court rulings, and what a potential legal showdown over his immigration policies could look like.They examine the administration’s targeting of law firms and universities, where institutional pressure could serve as a check on executive overreach, and whether lawsuits filed by state attorneys general stand a chance in court.Finally, they unpack Trump’s use of executive orders against his critics, why the U.S. is losing its reputation as a global “beacon of freedom,” and Ben shares one reason he still holds onto a sense of optimism.0:00 First 90 days of the Trump administration has been tumultuous 1:45 Congress is sitting on its hands2:45 The administration is slowing down routine investigations 4:00 This is a dangerous moment for the country5:30 Trump is “flooding the zone”8:15 There are legal ways to handle deportations but Trump isn’t interested9:30 They’ve violated amendments four through nine11:30 Trump left Biden a legal quagmire over the border, but Biden didn’t handle it well12:30 Prices will rise in the next 60-90 days 14:00 Incompetence has defined Trump’s administration thus far15:00 Administration is trending toward monarchy 16:45 Lindsey Graham has gone radio silent18:55 Benjamin Wittes joins the show! 21:10 Trump is violating multiple constitutional amendments 23:30 Is Trump violating the Supreme Court ruling? 25:55 Did the Supreme Court water down their ruling? 27:05 All 9 justices agreed on the premise 28:05 What would satisfy the court's order to "facilitate" the return of Abrego Garcia? 29:40 If Trump asked for the prisoner back, Bukele wouldn't say no 30:45 The White House is brazenly violating court orders 32:10 The administration is extorting law firms 36:45 How will Harvard's decision to fight back affect them? 38:35 Is the administration going out of their way to pick fights? 39:55 They're creating criminal impunity for allies 40:45 Administration is using civil litigation to target enemies 41:55 The government will pay more in damages than money saved by DOGE45:00 John Roberts is issuing rulings meant to avoid confrontation with Trump 46:25 SCOTUS justices are aware Trump is flaunting their ruling 48:45 Trump is putting tremendous stress on his own party 49:25 Are Trump's actions uniting SCOTUS against him? 52:25 What to make of the three liberal justices putting out a press release? 54:55 How alarmed are the six conservative justices? 56:05 Expectations for California's tariff lawsuit? 58:55 The president has civil immunity from defamation lawsuits 1:01:15 Targeting Krebs and Taylor are two of the most egregious acts so far 1:05:25 Trump 2.0 is an entirely different proposition 1:06:55 What authoritarian model does Trump most emulate? 1:07:55 Ben projected "Trump and Vance betrayed the country" on the Washington monument1:10:55 The beacon of freedom has been turned off1:12:25 Ben's hammock studio 1:14:15 Administration is targeting people the public doesn't care much about 1:16:05 The goal is to stop it from getting worse1:18:03 Showdown with SCOTUS looming?1:19:30 Chuck’s Nats rant - Fix the bullpen!(Timestamps may vary based on advertisements)
Chapter 1: What has the Trump administration done in its first 90 days?
Happy Monday and welcome to another week of the Trump administration. We are getting awfully close to the 100 day mark. And just to just to put this in perspective, think about how tumultuous this first 90 plus days has been on the American economy, on the American judicial system, on the American democracy, on foreign affairs. Just think about the things that have happened that we have.
Chapter 2: Why is Congress not taking action?
not had follow up on. I think about here as a D.C. person who uses National Airport a lot. I'll be honest with you. I'm still would like to know what happened the night that we had that deadly plane crash where a military helicopter was essentially got in the way of the landing of a commercial airliner. We've not gotten the after action report. There's not been the
The congressional investigations that you would expect yet. We really haven't had anything. And, you know, and part of this you can maybe chalk up to the news cycle. Part of it is the whole Trump administration's throw a thousand things at the wall and things get lost. And you sit there and it appears as if.
We only have the band that generically the media only has the bandwidth to do one story at a time. So when we were in the middle of the rescue operation, we got a lot of details on everything we could figure out in the 72 hours in and around that plane crash. But we haven't had any good reporting since. Congress, as usual, has been sitting on its hands.
I mean, look, we have an issue here where we have a very tumultuous period in American government and in American history. It's a busy executive branch and a busy judicial branch. The legislative branch is sitting on its hands. Doesn't appear to be doing anything other than figuring out how to not, at least the Republican majorities, not to alienate Donald Trump or Donald Trump's MAGA base.
Beyond that, It doesn't look like Congress is doing much. There's some rhetoric about things that they could be doing or should be doing. I think we're all waiting for the oversight hearing on Signalgate and exactly what did Pete Hegseth declassify to put on vulnerable private communication systems.
We think we have the backstory as how the National Security Advisor put a reporter on that group, but we still don't know why. There was so much ease with which the secretary of defense shared what was classified information on that. We're still waiting for those hearings. We're still waiting for that investigation.
We know that Donald Trump fired so many inspector generals that it is slowing down investigations that would really be sort of routine. I mean, the fact of the matter is there's always issues that the government has to figure out what went wrong.
So Bob Gates, the former secretary of defense for George W. Bush and Barack Obama, once said once said that he tells presidents that on any given day, somebody is fucking up. And pardon my French there in your name, Mr. President. And he has said that to President Bush and he has said that to President Obama, meaning the federal government is so big.
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Chapter 3: How is the administration violating constitutional amendments?
That no matter how well it is run, how efficient things are, there is somebody making a mistake in your name, causing you at a minimum a political problem and a maximum a policy problem that impacts the public. And yet we seem to be almost paralyzed in our ability to. to deal in totality everything that's going on.
In many ways, I would argue the first 90 days of Donald Trump have been like demolition man, right? He is just trying to demolish norms all over the place. He is trying to, he is forcing the judiciary branch and trying to see how much executive power he can get the judiciary to essentially approve of or not stop.
And the way any administration works – this is why this is such a dangerous period in the history of this country because if this judiciary essentially allows some of these things to go, they become precedent. And what happens is future presidents take whatever minimum they have and then push even further. So this is why we're sitting here with –
Essentially vulnerable to one individual's belief on how the economy should work rather than having Congress make these decisions on tariffs. We're sitting here because the congressional branch handed all this power to the executive branch. It went back to not arguably this started with 9-11.
Actually, it started before then when more trade authority was being handed to the Clinton administration. Then 9-11, more national security authority got handed the executive branch. With Barack Obama, his party had full control of the trifecta. He got handed more executive power. Donald Trump grabbed more executive power the first term.
Joe Biden grabbed more and pushed the envelope with what he tried to do with student loans, which was another essentially executive branch power grab. And now, of course, this one, which is. really doesn't have any precedent, arguably, unless you go back to FDR and Lincoln, who did grab extra executive power under the guise of war. And those were actual wars.
Right now, we have these various emergencies that the president has declared in order to try to fast track deportations in this country, try to fast track trade authority in this country, try to fast track a few things here. So the point is,
He has done the Steve Bannon – taken Steve Bannon's advice, which is just essentially just flood the zone and try to knock your political opponents and make them woozy and only sort of pick one. And this is the cynical aspect of what the Trump administration is doing.
Ironically, if a Democratic administration were doing, I'm sure Stephen Miller would be filing all sorts of legal briefs to claim that this is an abuse of executive power. All he's doing is essentially testing the electric fence of executive power and pushing the envelope, pushing the envelope at the border, pushing the envelope when it comes to
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Chapter 4: Is there a legal showdown brewing with SCOTUS?
What what what say so a government should have over a private organization like the university, Harvard, pushing the envelope on on trade and tariff authority. And you have a Democratic Party that is divided in how to respond. Right.
You have some that are nervous about drawing a full line in the sand, for instance, when it comes to due process having to do with Kumar Garcia, the the accidentally deported. El Salvadoran migrant who is now sitting in a prison cell in El Salvador over on Friday. Chris Van Hollen, Democratic senator from Maryland, did meet with them. We saw that the El Salvador president tried to create a.
create some propaganda claiming they were sipping margaritas and sort of the absurdity of our of our information, of our misinformation ecosystem that we all now have to navigate these days. The fact that Chris Van Hollen had to spend Five minutes explaining, hey, look, if you notice, nobody took any sips out of this.
This was essentially the El Salvadoran government trying to create a warped picture of the situation. The most important piece of news, though, out of that meeting is the fact that Garcia is not in the more notorious prison that is nicknamed Seacott.
The fact that they put him in another prison, I think, tells you the El Salvadoran government is a bit nervous and the Trump administration is a bit nervous. So they want to make sure nothing happens to him physically. So if nothing else, the attention has probably kept him alive or at least kept him physically more safe than he would be if he were in that more notorious prison.
But the question I keep coming back to is there is a legal way to do this. But the Trump administration doesn't want to do it. They don't want to abide by a court order. They don't want to even get caught trying. They don't even want to fake it. They don't have the ambassador, you know, getting a meeting with the president of El Salvador and the president saying, sorry, we're not releasing him.
At least they could claim they were following the court order that said that the government had to facilitate and essentially make an effort. Give it the old college try, guys, to try to get him out. And they're not even doing that. They're not trying at all. And that's what you gotta ask yourself. Why aren't they doing that? Do they just think this is good politics for them?
Well, I do think that they believe that everything they've done so far, that individually, if Democrats try to push back on any one thing individually, they can somehow win an argument, at least have their base come up and help them own the libs. Right.
Just notice the sort of demagogic rhetoric that that the White House has been using having to do with Kilmar Garcia, that the fact that anybody questioning whether they followed the law or In in in in deporting him and giving him due process, which I promise you they did not. By my count, you'll hear this in the interview with Ben Wittes.
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Chapter 5: What are the implications of Trump's executive orders?
Chapter 6: How are law firms and universities being targeted?
There was absolutely an ideological brick wall that Mayorkas ran into during the Ron Klain era of of the White House. And then when that went from Klain to Zients, the thing that changed the most, if you actually look at. border policy, that was the biggest dramatic change.
So I don't want to sit here and say that the Democrats didn't help create the mess at the border and certainly didn't do enough that could be done. Donald Trump left them a legal quagmire when he left office during the COVID era at the border. But it's not as if the Biden administration managed it very well in the first two years. They did get their arms around it eventually.
But it was after there was a new chief of staff and after, frankly, it had already become a political problem. So the Trump folks just believe that if they can just make this an immigration issue, first of all, notice what we're not talking about tariffs. We're not talking about the economic disaster that is coming. Now, this is a bit of a lagging indicator, right?
All of the current economic figures that have been coming out are what's happened in the previous 30 days or the previous 60 days or the previous 90 days. The fact is we're going to start to see a rise in prices probably in the next 60 to 90 days. You're not seeing them right in the moment, right? Because plenty of American companies have inventory that they got in before the tariffs hit.
So prices are only just now starting to creep up. And that, of course, will then start this spiral that could get really ugly for a while. Rising prices, inflation, stagnant wages, layoffs. You can see where this is headed. But in the short term, as all the focus has been on. On the one issue, because apparently only one issue can be done at a time.
There's been this debate in the Democratic Party about whether how hard they should go. You have had Gavin Newsom, who sees the Kilmar Garcia story as a distraction. You have others that say if you don't draw a line in the stands somewhere, then what's the point of being a political party? You're in the opposition.
The fact of the matter is I do think the party needs to figure out how to have one message. And I think the chaos message. which worked in the first administration, right? The fact is the public doesn't like the chaos. Individual goals that Donald Trump has outlined are things the public would like to see, right? A safe and secure border, more manufacturing jobs in America.
But how he's gone about doing it, upending the world economy, upending due process and the rule of law, that isn't what the public wants. They don't like how this is being done. And the political opposition, I don't think, has done a good enough job sort of framing this as that as incompetency, because ultimately that's what this has been complete and utter incompetence on the tariffs.
If you wanted to do this, there was a more systematic way to do this on the border. If you wanted to do this, there was a more systematic way to do this. But ultimately, the only conclusion one can come to is – it looks like the conclusion that our friends at National Review came to over the weekend.
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Chapter 7: What does the future hold for Trump's legal battles?
Chapter 8: Are Trump's actions uniting the Supreme Court against him?
One of the patterns to Lindsey Graham in particular, if you want to know, when he can't defend what Donald Trump is doing, he goes radio silent. Completely radio silent. He has sort of two versions of it. Sometimes what he does is he doesn't defend the actions, but he defends the goals. But this is a guy who was in the JAG Corps in the military. I think actually does care about the rule of law.
And I think is probably, I would like to think, I don't know if he's personally outraged by how this administration is dealing with the rule of law. But it's clear he's not supportive of it. Because it is crickets. You don't see him anywhere. You don't see him.
This is a guy who knows his state has benefited from an open and free market economy with a company like BMW and Mercedes, both, I believe, with plants in South Carolina. And here's a guy who actually seems to care about the rule of law. And clearly this administration right now doesn't care if it's following the rule of law.
So you can see sometimes by the lack of positive affirmation from some of these folks that if they can't defend it, they're staying silent. Because as Lisa Murkowski admitted last week, Speaking out comes with a threat of retaliation. And that is something that many Republicans are very, very nervous about. All right. I'm going to sneak in a break.
When we come back, my conversation with Ben Wittes as we try to understand exactly if there is any actual legal strategy behind what the executive branch is up to or if this is all lawsuits that are designed for maximum political advantage and or pain. Thank you.
And joining me now is the editor-in-chief of Lawfare, which is a publication that's devoted to legal issues having to do with national security. But these days, the definition, at least what the White House uses for national security, keeps broadening, which means in many ways, I'm going to be counting on Ben Wittes here to be our...
our tour guide in understanding, frankly, all of the legal fights that the Trump administration has decided to take on, whether it's we'll concentrate first and foremost on the on the immigration case. But I'm hoping to tap into Ben's nimble, legal mind on all sorts of things, including what's going on with Harvard and thus far. Ben, what is good to see you, sir?
Great to see you. It's been a while.
It has been a while back when both you and I took financial rewards from NBC. It might be one way to put it. But yeah. one thing you can't be upset about is that donald trump is giving lawfare plenty of material to i mean and i guess he's made uh people paying attention to the law great again not
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