Trump Runs into Four Straight Losses on Voting Takeover

29 Jun 2026 · 26 min · 12 chapters

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In short

Legal AF special edition on federal court fights against Donald Trump’s alleged election “takeover” efforts, focusing on (1) use of federal databases for voter/citizenship data, (2) mail-in ballot rules, and (3) litigation over the “JAN6 fund”/slush fund settlement and whether it’s moot or continues despite claims it’s “dead.”

Guests

Skye Perryman of Democracy Forward (advocacy org). Host: Michael (Legal AF).

Key claims

Courts are rejecting attempts to stonewall discovery; judges emphasize fraud-on-the-court and “voluntary cessation” not defeating review; DOJ filings are criticized for not swearing under oath that the fund ended; federal authority over elections is limited and states/legislatures lead.

Notable examples

District of Maryland (Judge Hollander) discovery order re DOGE accessing Social Security data and a voter-data agreement with a third party; Eastern District of Virginia (Judge Brinkema) rocket-docket discovery schedule blocking the fund; D.C. case blocking DHS SAVE database use to invalidate voters; Supreme Court term decisions on mail-in ballots and Justice Barrett’s warning about future presidential interference.

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

Chapters

Tap a time to open that second in VO

Supreme Court Decisions Impacting Elections

0:00 to 0:24

Discussion on recent Supreme Court rulings affecting mail-in ballots and election processes.

“TheSameMonday.com helping people worldwide getting work done faster and better.”

Supreme Court Decisions Impacting Elections

0:34 to 1:11

Discussion on recent Supreme Court rulings affecting mail-in ballots and election processes.

Trump's Election Database Controversy

1:11 to 2:06

Examining Trump's use of voter data databases for election takeover attempts.

“as the United States Supreme Court, I believe, just decided in their recent decision.”

Updates on Legal Cases Involving Voting Data

2:06 to 3:09

Updates on the legal case involving DOGE and its implications for voter data.

“testimony that she gave them the opportunity to submit.”

Federal Court's Stance on Voter Data Access

3:09 to 5:57

Detailed discussion on Judge Hollander's opinion regarding government access to voter data.

“Yeah, this is particularly interesting and I think a good development for everybody that should care on our 250th anniversary about the ability of people in this country to be able to vote and to use their voice.”

Implications of Fraud on the Court

5:57 to 7:39

Analyzing the potential fraud on the court regarding election funding and legal proceedings.

“When you hear Skye say there's some really good language in a case, what she means is that is either dicta or part of the holding that can be used in other cases, right, to advance that particular viewpoint.”

Judge Brinkema's Courtroom Decisions

7:39 to 12:18

Insight into Judge Brinkema's rulings on election funding and defendants' responses.

“They're, well, no, we're going to take another look now with the full panel about the inherent authority of federal judges to police misconduct and fraud on the court and other bad things in their presence.”

Data Collection and Voting Rights

12:18 to 14:00

Discussion on recent rulings against using personal data to disenfranchise voters.

“As the court explained during the hearing, Judge Brinkama wrote.”

Court Rulings on Voting Rights

14:00 to 14:27

Learn about recent court rulings impacting voting rights and election integrity.

“But the main thing is, and look, he has a confirmation hearing coming up.”

Reflecting on Independence and Voting

14:28 to 17:54

Discuss the significance of reflection on democracy as the 250th anniversary approaches.

“you have one about data and data collection that's in the District of Columbia.”
Show all 12 chapters

Taking Action for Democracy

17:55 to 21:00

Explore actions citizens can take to support democracy and voter engagement.

“And today is a great decision on that front.”

Supporting Democracy Forward

21:01 to 21:57

Find out how to get involved with Democracy Forward and support legal advocacy.

“We will make sure that doesn't happen, but we're going to need every single American along with us.”
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Transcript

Automatic transcript. May contain errors.

0:00This is a Monday.com ad. TheSameMonday.com helping people worldwide getting work done faster and better. TheSameMonday.com designed for every team and every industry. TheSameMonday.com with built-in AI. Scaling your work from day one. TheSameMonday.com that your team will actually love using. TheSameMonday.com with an easy and intuitive setup. Go to Monday.com and try it for free. Yes, TheSameMonday.com.

0:30Michael Popok:Welcome to a special edition of Legal AF. As the United States Supreme Court is wrapping up their term and dropping all of their decisions, it looks like this week, including about mail-in ballots, where the hard work continues to be done is at the district court level and the appellate court level below that. in particular about the use of databases created by the federal government to try to use them for a hostile takeover of federal elections, a place where the presidency has no role, as the United States Supreme Court, I believe, just decided in their recent decision. So you've got the hard work in the courts.

1:19Michael Popok:You've got this database fascination of Donald Trump to try to create these citizenship and voter data databases, which are the precursor to his attempted takeover of the election process, especially as we lead to the midterms. And then you've got the other thing, which is on everybody's mind as we lead into Todd Blanche's confirmation hearing in the middle of July, which is the slush fund, the creation of it. Numbers of – we have two courts in particular that are looking at the settlement, how it happened, the settlement agreement, the creation of the fund. And something very interesting happened down in the Eastern District of Virginia with Judge Brinkham's case in terms of her responding to something she never asked for.

2:05Michael Popok:which was a notice filed by the Department of Justice telling her to go pound sand about testimony that she gave them the opportunity to submit. When you tie all this together, what's the common denominator? Democracy Forward and Skye Perryman. Hi, Skye, how are you? Hey, it's good to see you. I'm good. Yeah, we're coming into the 4th of July weekend. I know you personally and your organization, as we are, are against the attempted hijack of the nation's birthday, which should be, as you said in one of your postings, it should be celebrating bringing Americans together, not using it as an attempt to line the pockets of Donald Trump and others.

2:46Michael Popok:And so as people descend on the nation's capital and start coming together and thinking about what it means to be an American and what it means to be a patriot, we've got these various decisions and accomplishments. Let's start with something that people may have forgotten about, but we haven't, which is this DOGE and DOGE data as it relates to voting. You have some new developments there. Yeah, this is particularly interesting and I think a good development for everybody that should care on our 250th anniversary about the ability of people in this country to be able to vote and to use their voice.

3:20This is out of the District of Maryland. And this is in our case, remember, where we've been representing retirees and large organizations who have been concerned about their members' social security data and the sensitivity of that data. And the concern, of course, is that DOGE, back in 2025, was engaged in unlawful efforts at the Social Security Administration to access the American people's data. That's what the case was initially about, and that's what the case is about. But what came out of the case was a hot potato revelation that the government actually withheld from the court for a period of months.

3:55They came into court and admitted that when Doge was at the Social Security Agency, they did, in fact, access American Social Security data. And a Doge team member signed a voter data agreement with a third-party organization that the government itself admits has been engaged in overturning state elections results. So that was the hot potato you and I have talked about that you covered. Well, we then aggressively moved for discovery in that case in order to learn more about what happened to our clients' data, especially as it concerns elections. The court issued that order to enable us to do what lawyers do, which is to get to the bottom of it.

4:37And the Department of Justice then went back into court and asked the judge to reconsider her order. Well, Judge Hollander issued a pretty lengthy opinion on Friday of last week. We can make sure you have it for the show notes. It's another one of these things. It's like worth a read for people that like to follow this, where she was very clear that she didn't know what she was doing when she granted the motion. She was not going to be reconsidering it, but she was clear about a few things. One, she really went at length in the opinion to talk about the concern that she has as a federal court about the administration's prior representations to her in the case and reminded everyone that courts have the ability to conduct fact finding and discovery when they have questions about candor with the tribunal and when they have questions about how the government's operating.

5:27But she didn't even have to do that because our requests, she found, were so clearly, you know, clearly relevant to those questions as well. There's some great language in the opinion about the concern with respect to the elections, with respect to voter privacy, And we are incredibly gratified that the court saw this attempt for what it was, which was another attempt by the administration to stonewall this information. And we will be pursuing discovery aggressively in that case in advance of the elections.

5:56Michael Popok:Well, let me unpack that a little bit from a lawyer to lawyer perspective. When you hear Skye say there's some really good language in a case, what she means is that is either dicta or part of the holding that can be used in other cases, right, to advance that particular viewpoint. Now it's not just Skye and her people briefing the issue. It's now a federal judge putting it in writing and then can be cited as precedent or as persuasive authority in future cases, right? Yes. And one of the main things here, and I'll tell you, you know, I've litigated a long time, litigated against the government a long time, occasionally had to seek discovery against the government even before the Trump administration, you know, in various disputes I would handle in corporate private practice.

6:41And what has been amazing about where we are with the courts in this administration is that they have operated so irregularly and outside the bounds of anything that you would expect from a Department of Justice, that the case law is getting much stronger about sort of when you can get discovery against the government, including in an administrative procedure at case, which is one of the statutes at issue in this case. And so the judge, just for a practitioner's point, Judge Hollander did a great job collecting a lot of the authorities there, really walking through why it was appropriate in this case.

7:16And I think that is helpful for people that are also trying to get to the bottom of the government's, you know, attempts to bob and weave out of the truth here.

7:23Michael Popok:And in terms of fact-finding, I mean, right now, a federal appellate court en banc, 11 justice judges want to take a look at Chief Judge Boasberg's fact-finding on criminal contempt against this administration, having tossed a two-to-one panel that was in Trump's favor. They're, well, no, we're going to take another look now with the full panel about the inherent authority of federal judges to police misconduct and fraud on the court and other bad things in their presence. Because talk about anarchy. What kind of world would we live in if a federal judge was forced to turn a blind eye and couldn't do a darn thing about it, about people lying in their courtroom, adducing evidence that was invalid or corrupt, and let them get away with it, which allows us to turn now in Judge Brinkema's courtroom, just to switch gears for a minute.

8:21Michael Popok:You've got two judges, one in Judge Williams in Miami, who's conducting fact-finding about whether fraud on the court was committed, whether the settlement agreement that led to the JAN6 fund, the anti-weaponization fund that Todd Blanche announced and unilaterally amended the settlement agreement, whether that entire settlement and the creation of the fund is a product of a deceit on the court, of fraud on the court. That's what she's trying to get to the bottom of right now and has asked for effectively, has said, you better give me some testimony on this issue. She didn't get it. My gut is she's going to do an evidentiary hearing next about whether Donald Trump and his lawyers have defrauded the court, which takes us to Judge Brinkham.

9:07Michael Popok:You, your side, your democracy fork, it's a great ruling in the Floyd case in which the judge says, I'm going to indefinitely block the fund, the creation of it, the operation of it, the funding of it, while we get further along in the case. They run and said, Judge, it's moot. See, didn't you hear Todd Blanche just randomly at a congressional hearing say out loud that the thing is dead? Isn't that enough for you? And she said, no. She went to the same kind of law school, this guy that you and I went to, Contracts 101. We need the parties to the contract to tell me the settlement agreement is dead, not just one person giving some sort of testimony outside the courtroom.

9:46Michael Popok:So she said, here's your choice, right? Sky, you and I talked about it when you came on. You can either give me an affidavit, sworn testimony under oath from Todd Blanche, Scott Bessent, the Treasury Secretary, and I think Stan Woodward, the number three in the Department of Justice, or, which is your choice, and if you give me that and tell me that the thing is dead, you'll never see me again. Jurisdiction over, case over, okay? But if you don't, get ready and file your complaint or your answer to the complaint next month. And they don't do that. They file a whole nother thing. Why don't you tell the, why don't you tell, or what did they file?

10:23Michael Popok:And then what did Judge Brinkema respond when she got that filing? So as a practice point, you know, normally you don't just put these documents on file as this DOJ has done. I mean, they did the same thing. They put the transcript on file from a Judge Leon case where there was language that could have been interpreted as questioning Judge Brinkman's authority. I mean, that's, and, and, you know, it was not lost on her and she made a, she, she was clear about that in the hearing. And so they continue to just dig themselves a hole where they put these papers on file, almost, you know, really questioning the judges and their authority.

10:56So they, they essentially did not, which is the big headline for the American people, you know, did not swear under penalty of perjury that the fund was over, which was the whole thing. They could have gotten rid the whole thing probably with this court by just swearing to that. But they didn't do that and instead put a paper in. And instead of just saying, we're not, you know, we're not going to do this, they put a paper in insulting the judge, trying to argue in the case that they, you know, really that she had no authority to require this, a very circular paper. She responds, you know, classically calling that out, but also setting a schedule.

11:31And I think this is what we want everybody to understand. I mean, this thing has been set. There's going to be discovery. It's an aggressive schedule. We're in the Eastern District of Virginia. That's the rocket docket. And we're going to learn more. And we're going to pursue this case aggressively. And finally, you know, get a court order that not only indefinitely blocks the fund for the pendency of the case, but blocks the fund altogether. So that's our plans. But yeah, it's very interesting to see how this Department of Justice at every step lobs more papers into court. It's like, if you're in a hole, quit digging, you know, and they keep - Yeah, yeah.

12:07Michael Popok:And another metaphor, the rake stepping, the consular stepping, they did not, again, they did not have to file that piece of paper. Here's what the judge said when she got the piece of paper, that the defendants have refused to accord a genuine degree of trustworthiness to their representations about the fund not going forward is particularly concerning because of the president's consistent support for the fund and Acting Attorney General Blanche's acknowledgement that the fund remains important using the same video clip of his testimony. Although Acting Attorney General Blanche reiterated several times during his testimony that the fund was not going forward, when asked whether he would issue a new memo rescinding it, he said, I'm not committing to putting anything in writing as I said it over and over again.

12:56Michael Popok:As the court explained during the hearing, Judge Brinkama wrote. A civil suit does not necessarily become mute when the defendants agree to stop the conduct at issue in the litigation. Under the voluntary cessation exception to the mootness doctrine, a party should not be able to evade judicial review or defeat a judgment by temporarily altering questionable behavior, especially as she observes when they're a reluctant, they reluctantly give up the bad conduct. Well, I don't really want to do it. I'm going to have to do it. No, you're not going to get out from under a court jurisdiction as a result.

13:35Michael Popok:Now, and as you said, set a very aggressive briefing schedule. It's all timing out to fall right around the time that Todd Blanche is going to have to testify. I mean, put this in context for us, Sky. You just had Judge Emmett Sullivan in Katie Fang's case rule that Todd Blanche conceded that he violated the Epstein Transparency Act by not properly defending himself in any filing before that particular court. Another example of them digging holes. Yeah. I mean, it's unbelievable. But the main thing is, and look, he has a confirmation hearing coming up. And so I'm sure Congress is going to have a lot of questions.

14:19Senate will have a lot of questions about, you know, how can you come in here and say one thing and then you refuse to say another to the court. So we'll be popping our popcorn for that as well.

14:27Michael Popok:Yeah. And then lastly, you have one about data and data collection that's in the District of Columbia. I just did a report on Judge Talwani making her ruling on behalf of 23 attorneys general in California, leading the way there about, no, you're not going to use the Postal Service and Social Security Administration on citizenship database, and then try to use that to deny the right to vote or the delivery of a ballot. Talk about how your case fits in with that. Yeah. So last week, let me just take a step back, and it's a Monday we're recording this. Like last week, the president just lost across the board on all of these initiatives in the district courts around his scheme to either federalize or otherwise interfere with the election.

15:11So you have this great win for the state AGs on the Postal Service. Of course, right as the postmaster generals at Congress saying, you know, we're not going to deliver ballots. Federal court says that that's not a thing. Yes, you are. Here's the court order. We are litigating a case alongside our friends and partners at Crewe and the Fair Election Center on behalf of the League of Women Voters that has been really after blocking improper attempts to take Americans' data that exist in parts across the federal government, consolidate that, and then use this SAVE database that is at DHS to try to invalidate voters from voter rolls, eligible voters from rolls.

15:51A very lengthy opinion out of the district court in D.C., making it very clear that it is unlawful and issuing a preliminary injunction there. The government has appealed that but has not moved for a stay. So right now they cannot be using the SAVE database at DHS to try to remove voters or compare voters on rolls, which is really important. And then there was another, you know, great win last week out of the federal courts. Another federal court says that they don't, that states don't have to give over voter data, which has been a series of losses for Donald Trump over the past year. And so all of that, and then today, of course, we're talking as the Supreme Court has made clear that mail-in ballots can be counted if they're postmarked correctly.

16:36Michael Popok:And one other thing on that, as where you and I are digging through that decision, language in there by Justice Barrett, which suggests that any other future effort by a president of the United States to try to interfere with on the grounds of voter protection or integrity is not going to be met with five votes in his favor. She said it's the legislature's state first and then Congress. I mean, there's nothing. I mean, we're at 250, right? So let's talk about 250. You know, the people that overthrew a king did not give the president of the United States, I mean, you know, they do the Declaration of Independence.

17:19About a decade later, you get the constitution. Like the people that literally fought a monarchy and overthrew a King did not give the president of the United States any authority to engage in elections. And the constitution is quite clear about that. The only federal authority really is Congress. And it's even a limited authority because this is really a state and local issue. So I think that's encouraging as we look at all of these initiatives that are making their way through the courts, all of the initiatives that the administration will likely appeal as we win. We have been confident since day one that we will be able to win on these cases that the president doesn't have legal basis for what he's trying to do.

17:53And this has been a really good, last week was a great week on that front. And today is a great decision on that front.

17:58Michael Popok:So lastly, Sky, you and I are very good, I think, at the end at getting our overlapping audiences sort of geeked up to do great things as Americans. And we've got the 250th anniversary birthday coming up. We've got the resistance against letting Donald Trump hijack it. And I've been talking about how important it is for people individually and collectively to do their bit towards counter-programming to celebrate the 4th of July, that long weekend, the right way. What can you suggest in terms of counter-programming for the upcoming weekend? Well, first of all, I mean, make sure your voter registration is active.

18:40And that is not a box checking exercise. And this is not some just performative list. This is something we all need to be doing. You can go to vote.org, you can go to vote411, but make sure that you know that your voter registration is in order, that your community's voter registration is in order. If you've got adult children, if you've got friends and family members, whoever's coming over for your barbecue, have a laptop or something set up or put some sign out, have you checked your registration. That's one of the main things we need people to do right now is to make sure that they, put on your own mask first, right?

19:14Make sure they are ready and prepared and can vote. The second thing I think is to really do the reflection that we hopefully will do as a nation on this 250th anniversary. Our founders fought against a tyrant and they were not perfect people. And the promises that were made in the Declaration of Independence fell far short of being realized for all people. And we know that. But these were people that knew what tyranny was when they saw it, wrote it out in the Declaration of Independence. Compare that list to what you're seeing from this administration and see where you get, because it is a stark, it's a real on all fours comparison when you see what they were protesting against, what they were fighting against, and what we are seeing from this administration.

20:03And then do some reflection about the courage and communities that we have to have in this moment. At the end of that Declaration of Independence, at the end of it, these are people that signed their name to a document that they would have been charged with treason had the Revolutionary War not been won. And it was not clear that it was going to be won, and it would take years before it was won. And at the end of that declaration, they say that they pledged to each other, themselves, their mutual honor. They were putting their lives in each other's hands, even people that didn't get along, and all uniting behind this notion of a promise of democracy, a promise that would take a long time to achieve that we're still trying to achieve.

20:42I think we need to reflect on that. And this is a time that if we've ever thought that it was just like easy to achieve freedom or easy to make these promises a reality for all people, it's never been easy for any generation. And this is our generation's moment. So I think some of that reflection is very helpful. Match with action, which the first start of that is the voting. And then, of course, We're going to have a lot of actions we need you to take over the summer and into the fall as we get to the midterms and as we have an administration and many state governments that are going to seek to prevent the American people from their voices being heard.

21:13We will make sure that doesn't happen, but we're going to need every single American along with us.

21:17Michael Popok:And our audience wants to support you every time you're on here, every time you're talking about. No, seriously. And Democracy Forward. How can they do that? Yeah, democracyforward.org. Go to our website. We have a donate button if you want to donate. That is what enables us to represent everyone free of charge. We also have a get involved button that has a lot of these activities that you can do. Hosting a dinner for democracy, how to have conversations at your 4th of July barbecue, what your rights are in all of these different ways. And so get engaged with some of our programming and we'll come on after the 4th and talk about more winning.

21:49Michael Popok:Fantastic. I'm so glad you're here. Sky Perryman for Democracy Forward here on Legal AF and getting us all sort of geeked up. I am now for the Fourth of July weekend and what we can do to protect our democracy, to support Legal AF and an independent democracy channel. Hit the free subscribe button until our next report. This is Michael. Can't get your fill of Legal AF? 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.

22:28Michael Popok: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.

22:47Ryan Reynolds here from Mint Mobile, with a message for everyone paying big wireless way too much. Please, for the love of everything good in this world, stop. With Mint, you can get premium wireless for just$15 a month. Of course, if you enjoy overpaying, no judgments, but that's weird. Okay, one judgment. Anyway, give it a try at mintmobile.com slash switch. Upfront payment of$45 for three-month plan, equivalent to$15 per month required. Intro rate first three months only. Then full price plan options available. Taxes and fees extra. See full terms at mintmobile.com.

From the publisher

Popok is joined by Democracy Forward leader Skye Perryman for exclusive briefing on the success in the last week to defeat Trump's attempt to undermine confidence in voting and take over voting in the Courts all the way to the US Supreme Court.

https://democracyforward.org/

https://www.vote.org/

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