Trump hit with Reckoning as Protests Trigger Legal Collapse

2 Apr 2026 · 25 min · 10 chapters

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In short

Legal AF special edition on No Kings Day protests and Democracy Forward’s litigation against the Trump administration, arguing “crowds, courage, and courts” are pressuring courts to enforce rights and slow unlawful actions.

Guests

Sky Perryman, founder and CEO of Democracy Forward (nonprofit legal organization). Background: leads an affirmative litigation effort; says Democracy Forward has filed hundreds of cases since inauguration and 700+ total cases nationwide against the executive branch.

Key claims

Mass protest participation (millions; “15–20% of the electorate”) strengthens court challenges. Federal judges are increasingly using contempt/show-cause tools against DOJ noncompliance. Supreme Court decisions affect a small share of cases; most impact comes from lower courts.

Notable examples

federal order restoring status for people using the CBP One app; upcoming birthright citizenship arguments (Cecilia Wang/ACLU); recent 8–1 Supreme Court decision on conversion therapy as First Amendment protection (Neil Gorsuch).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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The Impact of No Kings Day March

0:45 to 2:10

Discussion on the significance of the No Kings Day march and its implications for democracy.

“It's got almost 100 cases that have been filed just this term alone.”

Crowds, Courage, and Courts

2:10 to 4:30

Sky Perryman elaborates on how the public's engagement fuels legal battles.

“And so it was a really inspiring weekend for so many folks that were tuning in, watching, marching.”

Democracy Forward's Legal Efforts

4:30 to 7:40

Exploration of Democracy Forward's extensive legal actions against the Trump administration.

“Well, the courage and the crowds and people across the country, they fuel the fight in the courts.”

Big Win for Immigration Rights

7:40 to 9:02

Perryman shares a significant court victory restoring immigration status for many.

“But you've got some breaking news about in the immigration rights area that you can share with our audience along with some wins.”

Federal Judges and Their Challenges

9:02 to 11:10

Discussion on the evolving role of federal judges during the Trump administration.

“It hasn't done anything to actually tackle the hard issues we have around immigration policy in the country.”

Historical Context of Protest and Legal Action

11:10 to 14:04

Exploration of historical protests and their relation to current legal strategies.

“But in their second year, I think they're hitting their stride now.”

Historical Context of Protests

14:04 to 15:18

Learn about the historical significance of protests in American democracy and their necessity in current times.

“And I think that's actually what you see with the people.”

The Role of the Supreme Court

15:19 to 17:44

Explore the Supreme Court's history and its impact on American rights and the judicial system.

“robe, but in interviews, on panels, on things on legal AF, because I think they're also, as you said, encouraged about the support that's out there from the American people.”

Judicial System's Importance

17:45 to 19:33

Understand the significance of the broader judicial system beyond the Supreme Court and the ongoing reforms needed.

“And while the Supreme Court is the highest court in the land, as you mentioned, there's only a fraction of cases that go there.”

The Future of Democracy and Legal AF

19:34 to 20:10

Get insights into the future of democracy and learn about the Legal AF community and its impact.

“And we'll cover the birthright citizenship over on Legal AF.”
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Transcript

Automatic transcript. May contain errors.

0:00Michael Popok:Welcome to a special edition of Legal AF. We're coming off of that enthusiasm that has swept up the country. The No Kings Day march, more than nine or 10 million people hit the streets. That's the courage and crowd that's necessary to help the court cases that are going on all around the country against the Trump administration. And as the Democrats get ready for the midterms, we just came off a series of special elections where the Democrats are now 31-0 in flipping red seats to blue, including in some of the deepest, reddest parts of Florida. And now we've got to brief our audience, Sky Perryman of Democracy Forward, whose organization, a nonprofit legal organization, is fighting back against the Trump administration.

0:52Michael Popok:It's got almost 100 cases that have been filed just this term alone. And we've got some breaking news about some wins there. I want to bring in Sky Perryman, the founder and CEO of Democracy Forward. How are you, Sky? Great to see you. How are you? I'm doing great. And our audience loves the slogan that's always up on your website. We go to court for people and democracy. But you saw some fantastic things. I know that you went to No King's Day and marches in the D.C. area and virtualed in to the flagship one in Minnesota. What did you see in the crowds and courage of the American people on the streets this time around for No King's Day?

1:35It's really amazing. I mean, you see over 8 million people across the country. And we saw people of all generations, all backgrounds here in Washington, marching people from across the country. But you also saw that across the country. My hometown of Waco, Texas, which is kind of a red area, right? You see even activated people in red areas and swing areas across the country. people all united together saying, we're going to be here together, no kings. What is this administration doing? And we're not going to allow this administration to take our democracy down without hearing from the people.

2:11And so it was a really inspiring weekend for so many folks that were tuning in, watching, marching.

2:18Michael Popok:Let me show a clip that Democracy Forward has up on its social media, sort of a compilation of, I don't want to say the best of No Kings Day, but just to frame it here. When you add up all of the marches, the 55-01s, the hands-off, the third No King's Day, you're talking about 15 to 20 percent of the electorate hitting the streets. This isn't just the Trump derangement syndrome therapy session that the Trump administration calls it. These are voters. These are Americans. It's historic. It's historic. And so let's play the clip that's up on the social media for Democracy Forward. This is what democracy looks like.

2:57Michael Popok:This is what democracy looks like. The constitution in this country does not defend itself. It has to be defended by people. Today is a movement. Let it be a reminder, a reminder that progress is real, a reminder that sacrifice brought us this far, a reminder that the job is not finished. What are you willing to do to be a part of the change that we are overdue and that we absolutely deserve? Engage in small acts of resistance. Join the big movements. Share information. It has been very inspiring to see how many people are taking to the streets and just the clear message of no kings. The American people are not going to let their democracy go down without a fight.

3:44And we stand today because we are rising in solidarity. We are standing today because we are clear that the power belongs to the people.

3:59And from your perspective, Sky, how important is when our audience takes to the streets,

4:09Michael Popok:when they participate in these events, when as Rob Bonta and Chris Mays, our great attorneys general from California and Arizona call it, crowds, courage, and courts, the three C's that are important right now. We just saw crowds and courage in the streets that you observed. How does that help you in the courts? Then we'll turn to some recent amazing victories for Democracy Forward. Well, the courage and the crowds and people across the country, they fuel the fight in the courts. We've always viewed the court cases that we have the privilege of filing, and we have filed hundreds of them since inauguration.

4:45And there have been over 700 total cases across the country, which is the largest and most successful affirmative litigation effort against an executive branch in U.S. history. But we've always viewed the courts as a way for people to make their voice heard. You heard me on the clip that you just played. The Constitution doesn't defend itself. It's a piece of paper. The way we defend our Constitution is by using our constitutional rights. That includes the right to protest and march and assemble and use our voices. It also includes our ability to go to court and to challenge our government when they are violating our rights.

5:20And so we really see what we have seen in the courts from nearly day one with people across the country stepping forward to file these cases, not necessarily powerful institutions, but people doing that when powerful institutions have pulled back, when Donald Trump has said at the White House he wants to threaten everybody that files a lawsuit, people haven't been deterred. And that's why you have this tremendous legal effort that has served as a guardrail. And you're seeing people aren't deterred either by the historic numbers that we're seeing in these activations and no kings protests and a range of other mobilizations across the country.

5:54So, you know, the tide is turning. The tide is turning on this administration. They never had the support of people on the issues. They had political support from the prior election for various reasons, in part because so many Americans didn't vote, were apathetic, didn't believe the system was delivering for them, and it wasn't. We're not going to make excuses for that. But now you see the tide is turning. And this administration, this administration is really has lost so much support.

6:21Michael Popok:Yeah, and we have the new reporting that Donald Trump, advised by his closest advisor, Susie Wiles, the chief of staff, and his wife, Melania, believe that their mass immigration deportation program led by Stephen Miller has been a loser for not only America, but for Donald Trump's electoral fortunes. And there's rumors out there that Stephen Miller's time in the administration is maybe coming to an end soon. One of the many, if we're to categorize the hundreds of cases that Democracy Forward's been handling, I'm just going to do a rough cut and then you can fill in the blanks there. It has to do with cutting off of funding to the American people, immigration rights, including due process, right to counsel, voting, including using Department of Homeland Security and ICE to scare people out of voting.

7:13Michael Popok:I mean, there's many other things, gender affirming care and that type of thing. But for me, that seems to be where a lot of your cases are coming. We're coming up to the number I predicted at the start of the administration. I said, if we don't see 4 ,000 cases filed by the end, and that's not even including the writ of habeas corpus. No, no. If you add those, I mean, we're already in the thousands. We hit my number already. Yeah. You know, I was like 1 ,000, the first administration, 4 ,000, this administration. We're certainly well on our way. But you've got some breaking news about in the immigration rights area that you can share with our audience along with some wins.

7:49Michael Popok:I mean, you know, I'd love to have you on every day, but we'd have to have you on every day to talk about Democracy Forwards wins for democracy and people in the courtrooms. Why don't you share with our audience what's happened recently? Well, just as we were getting on, so I'm really excited to get to share this. You're the first person I've talked to about it. We received a federal court order that is going to restore status to individuals who are using the CBP1 app for their immigration. And so you'll recall, this is a program that the Biden administration put in place. These people have been doing everything they were supposed to do, filled out the right paperwork, showed up to the right hearings, were waiting for their status.

8:34and the administration had deprived all of the people who utilize the CBP1 app of, tried to deprive all of them of their status, of their ability to continue to move through the immigration system. A federal court has said that is unlawful. We know it was manifestly unfair and un-American, but a federal court has said that is unlawful. And so everybody we represent a big class is going to have their status restored. So this is a big day and a good win. And really, I think, hopefully shows people that, as you said, this administration's agenda, I refuse to even call it an immigration agenda anymore.

9:10It's a power grab agenda. It hasn't done anything to actually tackle the hard issues we have around immigration policy in the country. It's just been a cruel agenda. And the administration has faced many setbacks. And of course, later this week, we're going to have the birthright citizenship argument. Cecilia Wang at the ACLU will be making those arguments. And I think the administration is going to face another big setback there as well, because they continue to operate in ways that are so unlawful and so harmful. So we're really excited here today at Democracy Forward, people outside the hall, very excited about this win.

9:43And then we've received a number of positive court orders over the past week alone. I mean, a judge that was appointed by President Trump himself at Whipple in Minneapolis continuing to affirm our bid to make sure that people can access their lawyers and access counsel and holding the government to account for its, you know, its performative compliance with the court orders. that we've won while it's still continuing to skirt it. You have them calling the government out for misstatements, misquotes, potentially the misuse of AI in the courtroom. All this from a judge that President Trump himself appointed.

10:21And so we want people to know is that the litigation's working. It's buying time. It's enabling people to use their voice. And you can see that it's motivating people because of all the historic crowds we just joined this last weekend at No Kings.

10:36Michael Popok:Absolutely. And listen, judges are people too, and they see the crowds. I think in the first, this is my opinion, I'll get your view on it. First year, federal judges, you know, listen, they were knocked to the canvas and trying to figure out what was in their tool. They didn't expect the defiance. They didn't expect the Department of Justice to be so disrespectful, both in making arguments that had no merit and disregarding orders. We know why, because people like Stephen Miller and Donald Trump was telling Department of Justice to disregard federal court orders. But in their second year, I think they're hitting their stride now.

11:18Michael Popok:And I think they are empowered by what they're seeing as this wave of democracy and support for our values in the streets and around the world. And now we're seeing federal judges that are not shy about contempt, not shy about having the Department of Justice do an audit on itself about how many orders they have violated, and then taking steps or order to show cause to force Trump administration officials to take the stand under oath. They're coming up with new and creative ways against a defiant and lawless Trump administration, right? Yes. I mean, I think that the federal courts, the federal judges, I mean, first of all, I just want to say they've been incredibly courageous.

12:02They are doing their job. And there are lots of people in this country that are facing far more threats. So I don't want to minimize the threats that people, communities of color, immigrants, so many communities across the country, the LGBTQ community are facing right now. But the federal judges have been facing a lot of threats as well, with the president specifically targeting them and their families. And you see them continuing to interpret the law, to write their opinions, to, you know, not, you know, without regard to the politics of the moment, write their opinions and say what they need to say, including if it's someone that President Trump himself appointed, which is what we've seen in a number of our cases.

12:40But I do think initially they struggled with two things. I think the court struggled with the speed at which the administration was operating. I mean, we were ready for the speed at Democracy Forward. We got into court early. You know, we read Project 2025. We took it seriously. The state AGs did the same thing. But I think the courts initially were like, how do you know the administration is going to do this if Doge is at the door of the Department of Labor? And so it took them a minute, I think, to really see the speed at which it's operating. And they've been able to move much quicker as time has moved on.

13:12So that was sort of one area. And then the other area is, you know, you learn about lack of compliance in law school. I mean, these are kind of academic things that you learn about. But I was talking to some lawyers the other day that have like civil practices and criminal practices that are not really focused on government action. And it's like, you might have one case your entire career, an entire career of a 40, 45 career where you're litigating a contempt issue. I mean, that's just not something that lawyers do every day. And so I think that the federal courts, too, I mean, we as lawyers had to at first it's like, do you really go in and make a big deal about this?

13:45I mean, what's going on? Maybe it's a mistake. No, the federal courts are now seeing that the government doesn't have that present what we call that presumption of regularity. And so it's been inspiring to see the courts adjust using the tools that are their tools. They're not making up new tools or not finding new tools, but we're having to we're having to build our muscle. It's a muscle memory. And I think that's actually what you see with the people. I mean, these are not new tools. I mean, mass demonstrations, direct nonviolent action to overcome big barriers to our freedom. Those have been the tools that movements in this country, that people in this country have used.

14:18But the American people needed to, you know, remember those tools and kind of work out a little bit. And I think that's what you see with these demonstrations that are building and building and building. And we're going to need it because he's coming straight for the elections. We're going to need it.

14:31Michael Popok:Absolutely. So the anti-war protests, civil rights protests, and we're looking back and we're standing on the shoulders of that and realizing, no, we have to we have to take to the streets. As to the federal judges, you're exactly on point. I've been doing this for 35 years. I've had one contempt proceeding I had to deal with with somebody on the other side. Right. I mean. And judges didn't, you know, judges didn't sit. You were doing tabletop exercises and learning as we were about Project 2025. Judges weren't doing that in a judge school about what do we think is coming up next week? Yeah, they weren't doing that.

15:05Michael Popok:And so it's been really heartening to see. And we've we've platformed a number of federal judges who are doing something extraordinary and courageous. They're speaking out as sitting federal judges, not even waiting till retirement. They're speaking out now about the Trump administration, not just wearing their black robe, but in interviews, on panels, on things on legal AF, because I think they're also, as you said, encouraged about the support that's out there from the American people. Let me turn quickly here at the end about the United States Supreme Court, because one One of the things I've found from our audience, understandably so, so much information, is that they tend to focus on the important cases, and I'm not minimizing them, at the United States Supreme Court.

15:52Michael Popok:The 70 cases or even the 10 cases at the Supreme Court, and not the thousands of cases that really affect their life and what we consider to be our constitutional republic. And so we've got a series of cases, you know, as we lead into birthright citizenship as an oral argument tomorrow, and we'll be having that as a live feed on Legal AF. You know, we got an opinion just today as you and I came on the air about gender affirming. Yes, 8-1. 8-1. Right, right. About, you know, conversion therapy. You know, yeah, conversion therapy. Now, you know, licensed therapists can try to convert people, you know, and use that kind of voodoo on people's minds about what their gender identity is.

16:34Michael Popok:And that went eight to one as a First Amendment right that couldn't be regulated against, written by Neil Gorsuch. Talk, touch on whatever you like about the Supreme Court, including birthright citizenship, but how you see that and some despondency among our audience about hearing about the Supreme Court rulings and thinking all is not. We understand the despondency. I mean, and the Supreme Court, as we know, in a range of decisions over the past few years, and you can look back through history and find that there are many times throughout history, has not consistently been protecting the rights of all Americans.

17:12And you can see that with big, high-profile cases like Dobbs. You can see that with smaller things that are on the shadow docket that also have a range of implications for people and communities. But first of all, let me be very clear. This president is not going to win 100 % of the time at the Supreme Court. He hasn't been winning 100 % of the time at the Supreme Court. And he's going to face significant, significant, significant hurdles there, even given the politics of the court. And we're going to continue to see that. And you heard it here first. But the second piece of this is the court system is a system.

17:48The judicial system is a system. And while the Supreme Court is the highest court in the land, as you mentioned, there's only a fraction of cases that go there. Of those 700 plus cases that we and others have brought against the Trump administration, less than 5 % have or will go to the Supreme Court, including with the administration's desire to go to the Supreme Court all the time on the shadow docket and in this accelerated pace. And so what we're encouraging people to do is to look at it as an overall system. Susie Wiles, Stephen Miller, Donald Trump, they will all admit, and they have, that the courts and the judiciary in this country have been slowing and stopping some of their most priority items.

18:30Slowing, buying time, exposing. That's the work of the court system. It may not be the work of the Supreme Court, but that is what this judicial system has done. Now, as we look forward to the future, the American people have power to insist on reforms to any institution that is not serving the American people, not serving our constitutional rights. And so I think that there are going to be important conversations and work to do as we move out of this moment, when we get to move out of this moment, to help restore the American people's trust in our judicial system, in our Department of Justice, but also in our Supreme Court.

19:04Things like an enforceable code of ethics. This should not be some radical proposal. I mean, the Supreme Court needs to operate with an enforceable code of ethics. There are many reforms that people can demand as we get to a new moment. But I will say that, you know, if you take a look at it overall, it is the courts and it's the people that have been pushing back. And that's precisely why the president has threatened lawyers and judges is because it's working so, so much. So it may not feel that way on a day-to-day basis, but that's a bit of hope for people and a bit of dose of reality as to what we're seeing.

19:39Michael Popok:Absolutely. And we'll cover the birthright citizenship over on Legal AF. Love to have you back, Skye. Great. To talk about, like, on an hourly basis. I mean, this is where democracy is going. I mean, every day. Yes, yes, yes. Right. Okay, well, thank you so much. Thank you. Congratulations to your team of phenomenal lawyers and what they're accomplishing for our public. You're on Legal AF YouTube channel. Take a moment, hit the free subscribe button, especially. That's your way to vote for this type of content. Sky Perryman of Democracy Forward. Thanks for being on board. Thank you. Can't get your fill of Legal AF?

20:13Michael Popok:Me neither. That's why we formed the Legal AF Substack. Every time we mention something in a hot take, whether it's a court filing or a oral argument, come over to the Substack. You'll find the court filing and the oral argument there, including a daily roundup that I do call, wait for it, Morning AF. What else? All the other contributors from Legal AF are there as well. We got some new reporting. We got interviews. We got ad-free versions of the podcast and hot takes. Where? Legal AF on Substack. Come over now to free subscribe. We have the tech to get food delivered in 15 minutes, but we all have horror stories about buying tickets.

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From the publisher

When 20 percent of Americans use their courage to take to the streets to protest Trump, it also impacts what happens in the thousands of cases filed so far against the Trump Administration. Popok is joined by Skye Perryman of Democracy Forward to exclusively brief on a new big win against Trump and why crowds and protests matter.

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