The Trump Administration Is on a Legal Losing Streak

Summary

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Podcast Summary: Bulwark Takes

Episode: The Trump Administration Is on a Legal Losing Streak
Date: July 24, 2026
Hosts: Sam Stein, Ben Parker
Topic: The Trump administration’s recent legal setbacks, overreach, and the broader implications for press freedom, civil liberties, and institutional resistance.

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Overview

This episode focuses on the Trump administration's growing string of legal defeats in high-profile cases concerning press freedom, civil rights, and governmental overreach. Sam Stein and Ben Parker discuss multiple recent losses, analyzing why the administration is repeatedly running afoul of the courts and what it means for the administration and its opposition. The hosts also reflect on the evolution of institutional resistance from early capitulation to a firmer, more effective legal pushback, and cap things off with a humorous look at performative loyalty among Trump’s allies.

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Key Discussion Points and Insights

1. Subpoenaing Journalists: Press Freedom Clash

[00:45 - 04:57]

• The Trump administration issued—and then abruptly withdrew—subpoenas aimed at forcing New York Times reporters (and their families) to reveal sources regarding leaks about security failings on Trump’s Qatari-gifted Air Force One.
• Courts generally consider subpoenas on journalists a "last resort" in leak investigations, as per the judge’s rebuke:

  "Subpoenas are the last step. Not the first step, but the last step."
  (Judge Aaron Submarine, as cited by Sam Stein, 03:09)

• Judge Aaron Submarine signaled he would have rejected the subpoenas, and the administration withdrew them to avoid a public court loss, especially with the White House Correspondents’ Dinner imminent.
• Insight: The hosts interpret the attempt as more about retribution and intimidation ("brushback"), not serious evidence-gathering:

  "I think it’s retribution. And the retribution against, you know, the evil, failing New York Times kind of itself failed because they didn’t actually get the subpoenas to go through."
  (Ben Parker, 04:06)

2. DoJ Demands for a ‘List of Jews’

[05:20 - 06:11]

• The Trump administration’s DOJ (via EEOC) requested the University of Pennsylvania provide a roster of Jewish-affiliated faculty, students, and organizations, framed as an anti-Semitism probe.
• UPenn refused and, after a prolonged legal fight, the administration quietly rescinded its demand, having obtained no protected information.
• The episode quotes the university’s statement emphasizing the importance of upholding employees’ rights and fighting discrimination.

3. Persistent Failures to Obtain State Voter Rolls

[06:11 - 07:53]

• The administration lost another court case (the 19th such loss, per the hosts) attempting to commandeer state voter rolls—this time, in Kentucky, and before a Trump-appointed judge.

  "A judge has ruled that the Trump administration cannot obtain a state’s voter rolls. This happened in Kentucky today. Notably, the judge in this case was a Trump appointee who said, no, you cannot have our state voter rolls."
  (Sam Stein, 06:27)

• Insight: Trump’s judicial appointees themselves are increasingly rejecting overreaching or poorly executed legal gambits.
• Hosts note that earlier in Trump's presidency, law firms and others would capitulate prematurely, but the growing willingness to litigate is producing results.

4. Reflections on Early Capitulation vs. Current Resistance

[07:53 - 09:18]

• The hosts recall how some institutions folded without a fight under early pressure (e.g., FBI Director Chris Wray’s resignation).
• With time, opponents have learned that legal resistance is possible—and often successful—because the administration lacks focus and resources to sustain so many fights.

  "The administration doesn't have the resources, the attention, the popularity, or frankly, the brain power to fight all these battles at once."
  (Ben Parker, 08:07)

• Even Trump-appointed judges now block unfounded initiatives.

5. Not All Legal Fights Reach the Supreme Court

[08:48 - 09:18]

• The Supreme Court has occasionally sided with the administration, but not all cases ascend that high—and many are lost in lower courts, even with friendly judges.

6. Performative Loyalty and ‘Applause Culture’

[10:18 - 14:37]

• Pivoting to a lighter note, the hosts parody the culture of servility at Trump events, describing an awkwardly long applause after a Trump speech that evokes comparisons to autocratic displays in "Stalinist Soviet Union" and "Castro’s Cuba."

  "We have like a very Kim Jong Un scene here where the clapping just does not stop. We're going to play the whole uncomfortable minute of clapping."
  (Sam Stein, 11:07)

• This segues into a reminiscence about the infamous "water bottle" mimicry incident with Mike Pence echoing Trump's gesture—emphasizing the “monkey see, monkey do” dynamic among top officials.

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Notable Quotes & Memorable Moments

• Subpoenas as Retaliation:

  "Wouldn’t it be better for Rich? I mean... it could be like a brushback kind of thing. But if they... I think it’s, I’m just speculating here."
  (Ben Parker, 03:54)

• Legal Overreach Failing:

  "If you actually fight this thing, the administration doesn’t have the resources, the attention, the popularity, or frankly, the brain power to fight all of these battles at once."
  (Ben Parker, 08:07)

• Performative Applause:

  "That is the kind of thing you hear about happening in like Stalinist Soviet Union. Right. And like, you know, Castro’s Cuba is that [Fidel] gives a four hour address... and people just like, they don’t want to be the first one to stop clapping."
  (Ben Parker, 13:00)

• Monkey See, Monkey Do:

  "It reminded me. Do you remember the famous Mike Pence moment with the water bottle?... That is wild."
  (Sam Stein & Ben Parker, 13:15 - 14:35)

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Timestamps for Key Segments

• [00:45] Sam Stein and Ben Parker kick off: Background on the New York Times subpoenas.
• [01:36] Legal protocols around journalist subpoenas.
• [03:09] Judge’s rebuke and the administration’s retreat.
• [05:20] DoJ’s failed demand for a University of Pennsylvania “list of Jews.”
• [06:11] Rulings blocking access to state voter rolls.
• [08:07] Institutional resistance and the administration’s lack of resources.
• [10:18] Awkwardly long applause for Trump at a public event.
• [13:15] Recollection of the Pence water bottle mimicry moment.

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Takeaways

• The Trump administration is repeatedly failing in major legal initiatives—often due to procedural recklessness and overreach.
• Even Trump-appointed judges and previously pliable institutions are now resisting, with legal victories for press freedom and privacy rights stacking up.
• While Trump’s base and some institutions still engage in performative loyalty, the courts and key sectors of civil society are increasingly asserting themselves, underscoring the limits of executive power.
• The episode balances serious discussion of civil liberties and institutional pushback with satirical takes on sycophantic behavior in Trump’s orbit.

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For Listeners New to the Podcast

This episode is essential listening—or reading—for those wanting a sharp, irreverent, and well-informed rundown of how courts, universities, and state officials are pushing back against executive overreach, with plenty of inside-baseball anecdotes, humor, and righteous skepticism.

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Transcript

[Monday.com Narrator]

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[Sam Stein]

Hey everybody, it's me, Sam Stein managing out the book. I'm here with my partner in crime, Ben Parker. What's up buddy?

[Ben Parker]

Don't say partner in crime. The administration's gonna take that seriously and try to subpoena us?

[Sam Stein]

Depends on the crime. We're talk talking now because breaking news just a little while ago recording around like 4pm on Thursday, the government has withdrawn the subpoenas it had issued to reporters of the New York Times. Three reporters trying to compel them to testify about their sources for articles they wrote about the lack security features on President Donald Trump's new Qatari gifted Air Force One, which he says is being put out of commission for a little bit to get what he called maxed out. But really that just means that they don't have the proper security on this thing. The news though is that they withdrew the subpoena. So Ben, get us up to speed what's going on here?

[Ben Parker]

Yeah, so I mean the government has always had legally the authority to subpoena journalists when there's classified national security information that gets leaked and traditionally they don't. There are a few reasons for this. One of them is, you know, it's got some first amendment implications. The other one is some. Yeah, the other one is the government would, you know, honestly most of the time rather have a good relationship with the press than then like constantly be hounding them with subpoenas and you know, maybe criminal investigations and stuff. And so usually it's the people who are leaking the information rather than the journalists who are at the end of the criminal investigation process. The Trump administration decided, nope, we're going to we're going to subpoena not only these journalists, but also apparently their family members. Until the court said, like, hey, why don't you slow down, take a beat and try, like, saying please first. It's not, it's not illegal for them to bring these subpoenas. They could try again after they go through some other process. But it is like, hey, guys, slow your roll here a little bit.

[Unidentified Commentator]

Right.

[Sam Stein]

You're supposed to exhaust other processes to try to investigate the leak of that information before going to the subpoena. They did not. I'll just read from the Associated Press. The withdrawals in the US District Court followed a remarkable back and forth between a visibly irritated Judge Aaron Submarine and government attorneys. They come at a time when the Trump admin is vigorously going after news organizations who's reporting coverage it doesn't like. The judge said he otherwise would have granted the newspaper's request to reject the subpoenas because laws and regulations pertaining to subpoenas served on journalists maintain that they should be issued as a last resort in investigation. This is what judge said, quote, subpoenas are the last step. Not the first step, but the last step. That does seem to be the case, which makes me think that I wouldn't rule out them coming back to doing the subpoenas.

[Ben Parker]

Yeah, I mean, it's possible, but it's yet another one of these cases where the Trump administration could have done more damage if they'd been a little more competent and honestly, a little more. A little more careful with their procedure and just dotted their eyes and crossed their T's instead of going straight for the maximum amount of retribution against their enemies as quickly as possible.

[Sam Stein]

Unless their goal was not to actually get the records, but to throw just a pitch iron inside.

[Ben Parker]

Yeah, I guess. But if they had, I mean, wouldn't it be better for Rich? I mean, you're right. It could be like a brushback kind of thing. But if they. I think it's, I'm just speculating here.

[Sam Stein]

You think it's retribution?

[Ben Parker]

I think it's retribution. And the retribution against, you know, the evil, failing New York Times kind of itself failed because they didn't actually get the subpoenas to go through. They, you know, they got slapped out a little bit.

[Sam Stein]

Yeah, No, I, we got to point out the context here. Not that this factored into his decision whatsoever. I mean, it's very clear that the reason they unilaterally withdrew these subpoenas because they were going to lose and they didn't want the embarrassment. But this is Coming literally one day before the White House correspondents makeup dinner. It's supposed to be Friday night. Obviously the first one got painfully disrupted as a wannabe assassin barged in with a gun. Thankfully, nothing happened, but they are making up the dinner on Friday and Trump is supposed to be there and give a speech. And it would have been and still is pretty odd to have him at the dais as you celebrate the First Amendment while his administration is doing shit like this.

[Ben Parker]

Yeah, I do wonder what he's going to say. He's going to praise the First Amendment, talk about how important it is.

[Monday.com Narrator]

No, I'm not.

[Sam Stein]

You hold me to account and I appreciate that. No, that's definitely not going to happen. You in our slacks have been pointing out that this is a string of Ls that the administration has suffered. And just today there's two others. But what was. Can you elaborate a little bit on that?

[Ben Parker]

Yeah. The other one was again, another thing. The administration was forced, after a long legal battle, to quietly retract. You may remember this was in the deluge of like 2025, Trump administration craziness. They had asked the University of Pennsylvania for a list of all of its Jews. Basically they said, I'm not going to do the voice, I'm not going to do a German accent, I promise. They said, we're investigating anti Semitism. Would you please give us a list of all of your Jew, all of your faculty in the Jewish studies program, all of your Jewish cultural rel. Whatever organizations, and all of the people who belong to those organizations, please give the government a list of your Jews. And the school, to its credit, said no. So after a long fight, the administration has said, okay, we are no longer requesting a list of your Jews. Thank you very much.

[Sam Stein]

Jesus, so dark. I'll read the statement from you, Penn, about this quote. With the support of many members of the community who have stood with Penn throughout the university has been able to protect its employees rights. And none of the subpoenaed personal contact disclosed. Penn remains committed to fighting anti Semitism and all other forms of discrimination to ensure everyone it serves can learn, work and thrive. Noted that they never actually provided any of the subpoenaed personal contact information. The. The office that is housing the doj, which is the Equal Employment Opportunity Commission, did not comment for this, for that story. So, yeah, I, I mean the other one that I was going to point out, which is not the same as this, but it's, it's kind of, I count it as a loss is that for I believe the 19th time. I'm pretty sure it's the 19th time. Yeah, yeah, the 19th time. A judge has ruled that the Trump administration cannot obtain a state's voter rolls. This happened in Kentucky today. Notably, the judge in this case was a Trump appointee who said, no, you cannot have our state voter rolls. If I, if It's not the 19th time, I apologize. You can correct me in the comments. But this is just like, it's a remarkable string of losses. And it got me thinking about how. It got me thinking back to the early days of the administration when, like, the instinct was capitulation when faced with these things, and how the biggest capitulators were the law firms, ironically. Yeah, the ones who are the most perfectly suited to fight these things in court. They were the ones that just laid down quickly. And now those firms obviously are finding out that they just invited a whole host of trouble for themselves.

[Ben Parker]

Yeah, no, I totally agree. I remember the. It all got started even before Trump got inaugurated. Do you remember when FBI Director Chris Wray resigned?

[Sam Stein]

Yes, of course.

[Ben Parker]

Yeah.

[Sam Stein]

He was just like, I don't want to get fired. I'll just get out of here. Right?

[Ben Parker]

Like, I still got time left in my 10 year term. But, you know, I'll, I'll, I'll just, I'll just, you know, tuck my tail between my legs and go home and let Kash Patel take over. And it was like, what the hell are you doing, man? And now people, it's taken us like a year. People are like, oh, wait, if you actually fight this thing, the administration doesn't have the resources, the attention, the popularity, or frankly, the brain power to fight all of these battles at once. Like, yeah, there are some victories piling up here for the anti Trump opposition.

[Sam Stein]

It's funny to think about that time period, and I can't recall precisely, but maybe there was just this assumption that the courts wouldn't, wouldn't uphold the law, or that the Trump administration maybe wouldn't have respected the court rulings and you might as well just get out of the way.

[Ben Parker]

Yeah, I think that's right. And, you know, I think we have seen some cases in which the Supreme Court has, shall we say, gotten creative with some interpretations that let the Trump administration do things that prior administrations couldn't do or that let Trump do crimes that other people can't do. But not every case goes to the Supreme Court. Actually, Trump's record at the Supreme Court isn't fantastic. It's better than we want it to be.

[Sam Stein]

But, yeah, he can't win he's had some losses. He's had some losses for sure.

[Ben Parker]

A lot of these Trump appointments, appointed judges from his first term, are the ones smacking down what he's doing now because they're sort of pre Trump, you know, Fed Soc or Federalist Society types. And they're saying like, no, you can't just like take a state's voter rolls. Like, what the hell are you talking about?

[Monday.com Narrator]

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[Sam Stein]

All right, let's leave on a funny note. This happened today, totally different. I'm going to try to connect the two. While the courts are, while there have been a string of losses for Trump and the courts do seem to be holding in key venues and you cannot just proactively subpoena reporters, notebooks and all that stuff. There are a group of people who still are going to acquiesce and bow down and play good soldier to the dear leader. That happened today at a stop that Trump was talking about rebates among a bunch of different business leaders. I guess some politicians were there people going like rebates.

[Ben Parker]

That really is a crowd pleaser. Rebates. Who doesn't love.

[Sam Stein]

Did you watch the speech? Obviously it was, it was like portions were about rebates and then some of it was about like Shohei Ohtani. It was like it was all, it was all over the, it was classically Trump, a little bit of Iran sprinkled in there and all this stuff. Anyways, after he leaves, after he's done, he hasn't left after he's done. We have like a very Kim Jong Un scene here where the clapping just does not stop. We're going to play the whole uncomfortable minute of clapping. It just keeps going.

[Ben Parker]

That died out a little bit. Oh, we're still going.

[Sam Stein]

No, and this guy.

[Monday.com Narrator]

Yeah.

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At the end.

[Sam Stein]

Yep, keep going. He's there.

[Ben Parker]

Oh, oh. Not done yet. But still more

[Sam Stein]

and almost. It reminded me of when Longwell enters the room at one of our editorial meetings.

[Ben Parker]

Yeah, that's exactly what happens. Were they expecting Shohei audience Tani to come out? Is that what they thought?

[Sam Stein]

Like, I don't think so.

[Unidentified Commentator]

They.

[Sam Stein]

He did say he did have this big wind up about Shohei coming to the White House and how great a pitcher and Hillary was. But no, they did not expect Shohei to come out. And it was not about rebates, it was about ratepayers. I don't know why I thought it was about rebates. And I don't even know what the hell. But it's an extended. Extended applause for the man.

[Ben Parker]

Yeah. I mean, that is the kind of thing you hear about happening in like Stalinist Soviet Union. Right. And like, you know, Castro's Cuba is that he gives a four hour address, which by the way, I think Trump would love to do on the National Mall. And people just like, they don't want to be the first one to stop clapping.

[Sam Stein]

It reminded me. Do you remember the famous Mike Pence moment with the water bottle? Do you remember that one with the water bottle? Oh, you don't mind the water bottle.

[Unidentified Commentator]

Sort of what happened here. And brings to mind that old saying, monkey see, monkey do. President Donald Trump, Vice President Mike Pence, disaster officials with FEMA meeting in Washington yesterday, briefing on the 2018 hurricane season. So fine, you know, the proper. Here's the video getting a lot of attention. Look at the president. He puts his water bottle.

[Ben Parker]

He just moves the water bottle. So does the vice versa.

[Unidentified Commentator]

Why? So watch this again. He's like, gotta get this water bottle off the table.

[Ryan]

Why?

[Ben Parker]

Why are they moving their water bottles?

[Sam Stein]

Is there like a camera shot?

[Unidentified Commentator]

My thought would be that you're expecting

[Ben Parker]

a phone, maybe like an aide said he'd get those out of the shot or something.

[Unidentified Commentator]

Well, and you know how people kind of freak out about water bottles instead of reusable water bottles? Maybe that was the thought.

[Ben Parker]

That's definitely not it. No, no, no. Okay.

[Monday.com Narrator]

All right.

[Sam Stein]

What do you think happened here? Because there's other water bottles on the table.

[Ben Parker]

No. So they're half right. Trump definitely cares about the shot and he just wants him with his name card and, you know, whatever. And so he's moving the water bottle out of the shot and Pence just goes, yeah, I hate water bottles too. Whatever. It totally is like yeah f water bottles. We all hate water bottles.

[Sam Stein]

It just felt.

[Unidentified Commentator]

Wow.

[Ben Parker]

That is wild.

[Sam Stein]

Oh my God.

[Unidentified Commentator]

Yeah.

[Sam Stein]

That was such a great moment. Those were the great days. TRUMP 10 all right, if you like this stuff, if you like this conversation, subscribe to the Bulwark. You should check out our site. It's kind of going through a rebrand right now. Just check it out. Take a look. It looks really sleek and awesome. Also, oh, we have a 14 day free trial going so if you are interested in this kind of content ad free for the videos and all access to the newsletters. 14 free day trial. Just try to go to the subscribe button on the Bulwark and you'll get it. Ben, thanks for doing this buddy. Appreciate it.

[Ben Parker]

Thanks Sam.

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