On Monday evening,
President Skye Perryman joined me for a live video chat in the app discussing President Donald Trump’s first 100 days — and the pushback that Democracy Forward and many others have brought to the courts.To watch other videos live when I host them, download the app:
In the first 100 days of this administration, I brought you 78 posts at Law Dork. It’s been a lot — for everyone — and I couldn’t do this without you. I am so grateful to all of you here for the community of more than 65,000 total subscribers at Law Dork. And, yes, I want to add a big thank you to the paid subscribers who make Law Dork possible.
As we have seen over these past months, informed coverage of the courts is essential.
As the next 100 days get under way — with June and its many key U.S. Supreme Court decisions right in the middle of that period — legal coverage will be all the more central to the national story. I look forward to continuing to bring my two decades of experience covering the Supreme Court and our legal system to my coverage here at Law Dork.
For now, watch — or, below, read — our conversation about the first 100 days and what Skye is watching for in the next 100 days.
This is a rough transcript provided for reader benefit.
LAW DORK: Well, I'm just going to get started, and we'll have more people joining us as we go on. We have the benefit of talking on the evening of the 99th day of the new Trump administration, with Sky Perryman, the head of democracy forward, who has been a key voice in court every day over the past 99 days. It feels like with with with dealing with what we what we've got here, and so what we're going to try to do over the next 30 minutes is, is break down, sort of where we started from, what happened, where we're going, and hopefully a little bit of what, what, what, Sky things we've learned. So, I mean, I guess just to start sky, I mean coming in to to this second Trump administration, you and I talked about democracy forward being, being ready for it. And what did, what did that entail? I think that that's something that, as as we got underway, that a lot of people want to know, like, what were people doing ahead of time? Like, what, what did you do to get ready?
SKYE PERRYMAN: Well, we knew from the first Trump administration and from what we've seen with right wing leaders in some states and communities across the country, that when an extreme movement or an extreme person tells you what they're going to do, you need to believe them. And so when we started in 2023 at the end of 2023 we saw the publication of Project 2025 much of that, as you know, Chris and you've covered, actually, was rehashing things that the former Trump administration had done or tried to do, and then there was new things on top of that. And then, of course, we have this ecosystem of far right legal organizations that have been trying to reverse people's rights in the courts, as opposed to protect people's rights in the courts that have a range of favorite hobby horses too. Our organization took all of that at democracy forward. We took sort of what was in Project 2025 what we had seen from the playbook with other far right organizations, and then what we knew from the first Trump administration, and developed a threat matrix about what would happen if the federal landscape regressed and if the Trump administration, you know, make it made a choice, which they've clearly chosen, to not govern on behalf of the national community, to not turn over a new leaf, but to really sort of accelerate what is a very extreme and, frankly, anti-democracy agenda.
So we put it all together, and then many of the things that the administration seeks to do are just flat out unlawful on their face. I mean, they almost gleefully brag about it in documents like Project 2025 and so we knew that we needed to develop some legal theories, start thinking about which people and communities would be harmed by certain things and what type of representation they would need in the courts. And so that's what we did. And then we worked with a lot of other organizations and launched an initiative that some of your listeners and readers know about, called Democracy 2025 which is really just a representation of all the groups that are on the front lines of civil society using the law to protect people's rights. And folks can learn more about that at Democracy 2025 dot org, or more on our website, at Democracy Forward. But, reading the stuff and taking it seriously. It wasn't just a political talking point, right? These were serious plans that needed to be taken seriously, and that's what we really sought to do.
LAW DORK: As it got underway, I mean, you and I had a chance to meet a little bit in and it already had, had sort of developed quickly in a in a different way than the first time around, because they, they did have Project 2025, and and just bluntly, I mean, they had already been in the White House once, and so they did know some of the corners — they weren't just running into the wall every day. In sort of that first month, what was the big sort of warning signs for you? How did you have to adjust your plan?
PERRYMAN: There were warning signs, and then there were good sign, signposting about strategies. So some of the warning signs and things that like weren't on the bingo card, even though we made a very extensive bingo card, was certainly the President's appointment of Elon Musk and. And the way in which DOGE was seeking to operate, it wasn't clear. In the transition we knew that DOGE was operating, at least as an unlawful Advisory Commission. At that time, it seemed like that there was plans to have it really advise the government. It was advising the government. It wasn't disclosing what it needed to disclose under the law. But as in the first days of the first days of the administration, we started seeing things that were much different than that, you know, breaking into federal buildings, seeking to take or access terabytes of data, federal data on Americans. So that was one big piece that we've now challenged and won many court orders regarding. But that was one piece that was not on that we had to adjust around.
And I think the other pieces is we knew that this was a administration that if they did what they said they were going to do, they were really going to try to weaponize the government against the people. That's everything from like the funding freezes we saw, to attacks on data and evidence to attacks on the civil service and retribution. I think what we didn't know was exactly the mechanisms they would do or how broad it would be early on. I mean, it really was this shock and awe, said, and we were able to adjust quickly. We got in on the funding freeze. We were able to get in in the first, you know, before it went into effect, and secure a nationwide order that remains in effect today, stopping that. We've been able to move but I think we knew we were going to need to move quickly. I think really experiencing how quickly that was is obviously something that requires some adjustment with the way in which Lawyers operate, right? Because we're not, you know, like I say democracy forward is powered by humans, not by AI. So, you know, really requires that we move fast, but we have been and we've been able to move fast and get in, you know, as much as possible.
LAW DORK: I mean, what in terms of like, the sort of breadth and scope of where they have have been moving, what sort of how, how do you think? Like, are there categories of litigation. Are there, like, how are you thinking about sort of like, what is the case against the Trump administration right now?
PERRYMAN: Yeah, I mean, I think there's like, three categories broadly of pushback litigation that's required to defend people's rights in this time.
One is the category of cases where the administration is really seeking to decimate or undermine the constitutional rights that people have, which, like the president, doesn't get to do that, but that's everything from birthright citizenship to some of the attempts, for instance, to restrict the First Amendment by telling people you can't say the word equity on a website, you know, or all these things. So that's one category.
One category is sort of, who and what is influencing the government, what the accountability, infrastructure, transparency ecosystem, is which they're seeking to attack. So that's what I would call, you know, our civil service litigation, the litigation against DOGE, the litigation against we're going to start seeing, just watch, we'll come back and talk about, we'll start seeing now at the agency level, appointments of people that either haven't gone through the right process, or advisory commissions that are not complying with transparency laws or efforts to sort of undermine the Freedom of Information Act, those types of things that's like, who and what gets to influence the government and what that transparency infrastructure is one.
And then the third category, which is sort of one that I think means a lot to people, is what I call the kitchen table category, right? The steps that the administration is taking across a range of issues and in a range of ways that are deeply harmful to the individual experience that Americans are having across the board every single day, you're going to go in and without any explanation at all and any authority at all, freeze all federal funding in the country, putting things like Meals on Wheels and head start in the balance, you're going to take Americans’ Social Security data, right, the data that, like we trust the government, where there's an implicit trust everybody's got a social security number, and do something with this personal data on individual Americans, that kitchen table, those kitchen table issues.
And then you have things like our case with the ACLU that you've covered a lot of the Alien Enemies Act case, or we're co-counseling with ACLU, and that's sort of both in category one and category right? Because they're seeking to sort of completely eviscerate due process. So he's seeking, with the stroke of a pen, to, you know, to invalidate constitutional rights. But then at the same time, that's a kitchen table issue, because if you can remove people from the country without any process at all, that doesn't bode well for any of us. And we're seeing the public opinion polls, including the ones over the weekend out of ABC News, really show that the people in America across the country are like getting this is a real threat. So those are the categories I see, and kind of I. I think that we're going to continue to just need to see volumes of litigation in all three of those categories.
LAW DORK: Just to roadmap for people, I think that people are, are really interested in the doge litigation and the alien enemies act litigation. And I'd like to talk a little bit about about that. I mean, the the DOGE litigation, I think we saw sort of a wild, sort of breaking now, today, news today that like that in the challenge to the Consumer Financial Protection Bureau's agency wide RIF that sort of the DC Circuit had somewhat allowed it to go forward, and as long as there was, like, a particularized assessment, and then, like, four days later, they tried to riff 90% of the agency, and we just got a ruling today from that included judge Katsas basically switching sides and saying, No, we're going to put firings on hold until the DC Crcuit can decide this, not even waiting for Judge Amy Berman Jackson at the district court to deal with it. I mean, how much of what DOGE is doing, one is illegal, and two is is actually sort of like shooting the Trump administration in their own foot?
PERRYMAN: Let me just say this thing that happened today, and frankly, what's happened on Alien Enemies Act and a range of other things, shows you that the gamble that the administration is trying to make to thumb their nose at the courts is not paying off for them. I mean, they are hurting themselves when just being silent and kind of following the court order would do them far better, right? And so I just want to point that out, because we're seeing that across the board, where they're just not they're seeking to undermine what judges, even judges that are kind of ruling for them in a little bit, is really turning off the judiciary. Of course, it's a violation of the rule, while we know American people are very concerned about that, but to your point on DOGE, I again, think this is a place where they cannot get out of their own way. I mean, they have much of what they have done is unlawful, especially when you know they're not even being clear about what they are doing. So judges are highly skeptical of that, and we've had some judges that haven't issued emergency orders immediately, but have called and said, like, but you can take depositions, or we want to hear testimony, because nobody thinks the government is just to do stuff and not explain to a court or to the people what they're doing.
I think the DOGE cases really are kind of threefold. There's the data cases, which is, what are they doing with data? Are they authorized to access it? What are they doing with it? Have people been vetted, have protocols been followed? Is the Privacy Act being violated, which, in our cases, many times it is. Then there's the sort of “we're going to take a sledgehammer to the civil service,” which they're trying to do in part through DOGE, that's the RIF cases, or even these agency decimation cases. Much of that is not lawful either, because Congress set up these agencies to do certain things. And you're seeing, you're seeing, we're in the USAID case. We're watching the CFPB case very closely. We're in the Department of Ed case. We represent, you know, doing some of the smaller agencies too, you see that. And then there's this transparency piece around DOGE, which is that, like, from day to day, the President, you know, is, should Elon Musk have been appointed and confirmed by the Senate? What is the role of Musk? What is the role of the people that are there, that transparency piece? So I think there's like three of three categories. And in many instances, we've not seen federal courts say that anything DOGE is doing is quote, unquote, lawful. We have seen some of them be willing to sort of let DOGE operate a little bit while they explore, and then others that feel like they have to block it because of this right, because of this irreparable harm.
LAW DORK: And, I mean, this is sort of a big picture question: Let's just bite the bullet. I think there's a lot of concern that to the extent that there are court rulings, that the Supreme Court isn't going to go along with it, that when they get to the Supreme Court, it's not going to go well, I have my thoughts on that. I'd love to hear how is it that you're thinking about the Supreme Court? What concerns do you have about the Supreme Court? Do you think that they are ultimately going to stand up to Trump or not?
PERRYMAN: Well, I think that every day that this administration makes a decision, which is that made a number of instances to contend that court orders are optional or that the judicial process is a nuisance to them, is not a good day for them, including at the Supreme Court. So let me just that and say that I think that they're exposing and showing themselves in these first 100 days for what they are in a way that is really undeniable, even to judges that the President himself has appointed or supported in the past, and so I think, as a piece of what we have to say, Whatever one might have thought the way the cookie might crumble at the Supreme Court a few months ago, we do have, to some degree, I think, somewhat of a changed picture, because this administration has chosen to really take, like I said, a gamble that I wouldn't be taking, to just stare down the judiciary as if that is if we don't operate in a in a country where there are checks and balances, and where the executive that said, this is a Supreme Court that in large part was shaped and really by Donald Trump's first presidency, as we know and as you've written about.
And so I think there are several areas where the administration is certainly thinking that the court will side with it, along the lines on some immigration issues, potentially on civil rights, diversity equity, inclusion issues, maybe some executive power issues. And so we're going to have to see how that plays out. But what we've been seeing is that in a number of cases, judges, who you might not think were as aligned with some of maybe even not the underlying policies, or the opposition to the underlying policies, are really concerned about the lawless way in which the administration's operating, including in like, not following basic procedures. I mean, on the funding freeze case is one example. Everybody wanted to talk about empowerment, and that's a constitutional issue, but in the funding freeze they just flat out violated other protections, including the protection against arbitrary and capricious government that's in the Administrative Procedure Act.
So I think that, like some of these things, we're going to have to see how they tee up. But I I wouldn't count the court out on some of them. That said, we also don't have rose colored glasses about the environment that we're the environment that we're in. But certainly the administration thought, and I think this was a bad, just a bad fight for them to pick, that they were just going to get to the Supreme Court, and the Supreme Court was going to rubber stamp everything, and so they could just play Whack a Mole up and down the federal court system. And you've seen the district courts and the appellate courts and even the Supreme Court have something very strong to say against — that we follow court orders, even district court orders, in this country. And I think that might influence to some degree what the Supremes end up doing on some of the merits.
LAW DORK: I think, I mean, I definitely think that that the Katsas example is a good example from today, obviously. I mean the fact that over the course of, and it's in this case for the CFPB, that he literally had a ruling earlier in the month where they were allowing a RIF if there was a particularized assessment. And then today, he was like, No, we're holding off. And then you saw a similar thing with the alien enemies act or not the alien enemies act with, with Kilmar Abrego Garcia, with the fact, with Judge Wilkinson, who, initially, when the Fourth Circuit was was up on The say he wrote a concurrence, saying, basically, kind still siding against the administration, but sort of like chastising his colleagues and saying, my colleagues think this is an easy case, but I think it's a complex issue, and then you fast forward after the administration's own behavior, and he wrote that blistering opinion saying this, this is a very clear case —
PERRYMAN: And just every American should read.
LAW DORK: Moving over to the Alien Enemies Act. I mean, I think the Alien Enemies Act is, is sort of this administration's version of the travel ban, in terms of something that they bit off more than they could chew, they thought that they were going to have an easy way with it, because it was something that they could claim was a clear presidential power, and yet they've sort of gotten pushback at every turn. And I think you can give us some insights into sort of like, how that pushback happened from from morning one with the filing that we all woke up to on on March 15.
PERRYMAN: It was a late night. It was a late night, but there have been many late nights around here with our partners. But look, this was an issue. I you know, the story of this case, and we'll have to see how things turn out. And I really, you know, I will tell you we hope every single day, and are working every single day to see if there's any way that our clients who were unlawfully removed will be able to be back, and then, of course, to protect people from this horrific situation.
LAW DORK: If people haven't read it the obviously, the amended complaint and the amended preliminary injunction does ask for the people who were taken to El Salvador to be brought back, to get the process that they were not given the first time.
PERRYMAN: I'll just say from the you know, this is one of those cases that when it's all said and done, I mean, the President started announcing and gleefully bragging in the Great Hall of the Department of Justice, right? That's what we have to remember about March 15, is you have that Department of Justice speech. And in his public remarks, he starts saying, and your people are going to wake up in the next morning and they're going to see what we did. That's what he said. He said it would be a beautiful thing, and they're what we did. And so that just smells like, right? And we know based on public reporting and based on the President's own statements, his associates, own statements that they wanted to put in place, which he did, of course, in the dead of night. Not publicly, you know, not publicly, publicizing it until the next day, the alien enemies Act, which is a wartime power that has only been used in World War One, the war of 1812, and World War Two. And then on top of that, deprived people of process that even that act requires, which is when you have, you know, DC Circuit Judge Millett saying we gave people accused of being Nazis in this country more process in World War Two than what this president and his administration has afforded here when we're not even at war, right? And so, the ability to get into court that day, on behalf of our five clients, we had actually asked, of course, for class certification, which Judge Boasberg provisionally issued later in the day. That was the very infamous hearing where it was clear he issued relief. The government didn't want to follow his order. Didn't turn the planes around.
But being able to get in early and to expose and show to the American people, who are fundamentally fair-minded people, what was happening really turned the tables. And then you have the fact that a judge issues an order, and the administration gleefully over social media with a number of these like, you know, officials like the Secretary of State, almost bragging about the fact that they somehow felt as if they could avoid the court order, that there's no place for that in America. I mean, the public polling is clear. People disagree on a lot of things. They may not even like courts, but over 80% of people in poll after poll believe you follow court orders in this country. And so I think it was a real turning point where the administration wanted a made for TV moment. They wanted to be able to be able to label people as gang members. Of course, they hadn't given anybody any process. If they're confident, don't avoid the process. Go through the process. What has happened now is, I think the American people, including people who don't follow this stuff day in and day out, are starting to see really what's at stake, and as as harmful as it is for the people that have suffered under this lack of process, I do think that what has happened and what is happening in the national conversation can provide us some amount of hope that the American people are getting to a point to say enough is enough of this. And we saw that in the opinion polls over the weekend, where people saying, yeah, they're concerned about the economy, but they're also really concerned about the rule of law and due process, because it just doesn't sit right with people that the president can [do this].
LAW DORK: We're sort of coming up on a close here. I guess two things, what are you going to be paying attention to most over the next month, and what do, what do you want other people to be paying attention to? What, what should, should the people watching be paying attention to?
PERRYMAN: I'm going to be paying attention to with the administration. I think we've got to start looking at the federal agencies, because this 100 days has been shock and awe. What's the President going to sign? What's do? What's Elon Musk going to tweet about? All that violates, loss, deeply harmful. We got to get into court. But what you're going to see now is a range of agency officials, they're taking their positions and array things that will happen that are not headline news, but that nevertheless are unlawful and harmful and will affect millions of people if they're not detected and stopped. So that's everything from pulling back policies without providing appropriate public comment or explanation. It's everything from trying to manipulate data and evidence sources or put these people on commissions that shouldn't be there without transparency laws, so we're going to be really taking a look at that. That's one of our signature things that Democracy Forward is to make sure that we're not letting the shiny objects, so to speak, distract from some of the real harm to people that that there is legal recourse for if you get into court.
And I think what I love for everyone else to pay attention to is to watch the pace of litigation. And don't just look at the lawyers in the legal argument, but look at that heading of the complaint and who is showing up into court, because when I look at it even today, it tells a very hopeful story about this country, even though we're in a very difficult situation because we have represented Baptist and Quakers and Republicans who have been fired by the President and veterans and school teachers and conservationists and nonprofits who never thought they were ever going to go to court, and the American Bar Association and small businesses and on and on and on and almost in that picture that's painted from the top of the docket, you can see the chorus of the American people saying, Not on our watch. Are we going to allow this to happen? We get to initiate litigation, and we're going to do it to defend our rights. And I think paying attention to that over the next 100 days, who else comes in to the fray. We're representing some law students, right? Because the law firms weren't going to challenge something unlawful that the EEOC does. So now the law students are doing it. Who else comes into the fray? What can that tell us about our country, and what does that tell us about the path forward? I think that's something to definitely watch. And then, of course, everyone reads you, and we'll get your great reporting and commentary as the cases start coming down.
LAW DORK: Well, we will certainly be paying attention, and I will be eagerly awaiting the the next filing from from you all, because certainly Democracy Forward has has been one of the the front organizations over the past 100 days, and so I really appreciate you giving us some time today to talk about where we're at and where we're going.
PERRYMAN: Thank you so much. It's always good to see you, and we'll talk soon. Thanks.
LAW DORK: Bye.
Share this post