The Trump Administration Is on a Legal Losing Streak

Summary

Podcast Summary: The Bulwark – "The Trump Administration Is on a Legal Losing Streak"
Date: July 23, 2026
Hosts: Sam Stein & Ben Parker

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Episode Overview

This episode explores the recent string of legal setbacks for the Trump administration, focusing on its aggressive but ultimately failed actions against journalists, academic institutions, and state election authorities. Hosts Sam Stein and Ben Parker analyze what these losses say about the administration's methods, legal strategy, and the state of checks and balances in contemporary American governance.

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Key Discussion Points & Insights

1. The New York Times Subpoena Withdrawal

• Background: The Trump administration attempted to subpoena New York Times reporters, and their family members, to testify about sources regarding lax security features on President Trump’s Qatari-gifted Air Force One.
• Key Info: The government abruptly withdrew the subpoenas following pushback in court and a "visibly irritated" Judge Aaron Submarine.
• Legal Norms: Usually, subpoenas against journalists are a last resort after other investigative avenues are exhausted, due to First Amendment concerns and the importance of press relations.
• Motives Analyzed:
  • Ben Parker (00:50): "Most of the time [the government would] rather have a good relationship with the press than like, constantly be hounding them with subpoenas and...criminal investigations and stuff."
  • Sam Stein (02:43): Notes that while the administration could try again, legal missteps undercut their aggressive intent: "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 careful with their procedure."
• Speculation on Goals:
  • Sam Stein (03:02): Suggests the action was more about intimidation: "Unless their goal was not to actually get the records, but to throw just a pitch, high and inside."
  • Ben Parker (03:20): Frames it as retribution: "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."

2. Political Timing & Optics

• White House Correspondents Makeup Dinner: The withdrawal occurred just before Trump was to speak at the rescheduled dinner, adding awkwardness given the administration's actions against the press.
  • Sam Stein (03:30): "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 (04:11): Ironically wonders if Trump will "praise the First Amendment."

3. Other Legal Defeats

• UPenn "List of Jews" Subpoena:

  • Background: The administration demanded that the University of Pennsylvania provide a list of Jewish faculty, students, and affiliated groups, under the pretext of investigating anti-Semitism.
  • UPenn’s Response: The university refused, and after a protracted legal battle, the administration dropped the request.
  • Ben Parker (04:34): Sarcastically: "Please give the government a list of your Jews. And the school, to its credit, said no."
  • Sam Stein (05:26): Reads a statement from UPenn affirming they never provided the requested information and remain committed to anti-discrimination.

• Blocked Voter Roll Requests:

  • Pattern: For the 19th time, courts (including Trump appointees) have ruled against the administration’s attempts to obtain states’ voter rolls.
  • Sam Stein (05:26): “For, I believe, the 19th time... A judge has ruled that the Trump administration cannot obtain a state's voter rules. This happened in Kentucky today. Notably, the judge in this case was a Trump appointee who said, no, you cannot.”

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Notable Quotes & Memorable Moments

• On Government’s Approach to the Press:
  • Ben Parker (00:50): “It’s got some First Amendment implications. The other one is...most of the time [the government would] rather have a good relationship with the press than like, constantly be hounding them with subpoenas.”
• On Subpoena Process:
  • Sam Stein (01:52): Reads Judge Submarine’s admonition: “Subpoenas are the last step. Not the first step, but the last step.”
• On Legal Incompetence:
  • Ben Parker (02:43): “The Trump administration could have done more damage if they'd been a little more competent...instead of going straight for the maximum amount of retribution against their enemies as quickly as possible.”
• On Retaliation Tactics:
  • Sam Stein (03:02): "Unless their goal was not to actually get the records, but to throw just a pitch, high and inside."
  • Ben Parker (03:20): "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."
• On the "List of Jews" Request:
  • Ben Parker (04:34): “[They] said, we’re investigating anti-Semitism. Would you please give us a list of all of your Jew[s]...Please give the government a list of your Jews. And the school, to its credit, said no.”
• On the White House Correspondents Dinner Irony:
  • Sam Stein (03:30): "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."

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Timestamps for Key Segments

• NYT Subpoena Case & Legal Context: 00:11 – 02:43
• Analysis of Administration’s Motives: 03:02 – 03:20
• Correspondents Dinner Discussion & Political Optics: 03:30 – 04:11
• UPenn/Jewish List Case: 04:34 – 05:26
• Blocked Voter Roll Requests: 05:26 – End

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Summary Takeaways

The episode paints a picture of an administration eager to punish perceived enemies but continually thwarted in court, often due to its own procedural overreach or disregard for legal norms. The string of legal losses is portrayed as emblematic of both the resilience of institutional checks and the limitations of heavy-handed executive tactics. Throughout, the hosts maintain a tone of incredulity and dark humor, highlighting the surreal and troubling nature of current events while emphasizing the rule of law.

Transcript

[A]

Hey, everybody, it's me, Sam Stein, agent at the Bork. I'm here. My partner in crime, Ben Parker. What's up, buddy?

[B]

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

[A]

Depends on the crime we're 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 lax security fee 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?

[B]

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, 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 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, right?

[A]

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 that come at a time when the Trump administration 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, an 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.

[B]

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.

[A]

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

[B]

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 brush back kind of thing. But if they. I think it's, I'm just speculating here.

[A]

You think it's retribution?

[B]

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.

[A]

Yeah, no, I, we got to put 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 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.

[B]

Yeah, I do wonder what he's gonna say, if he's gonna praise the First Amendment. Talk about how important it is, how

[A]

important you hold me to account and I appreciate that. No, that's definitely not gonna 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. Can you elaborate a little bit on that?

[B]

Yeah. The other one was again, another thing, the administration was forced, after a long legal battle, to quietly retract. You may remember this is 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 Jewish, cultural, religious, 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, Jesus.

[A]

So dark. I'll read the statement from UPENN 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 subpoen personal contact information was 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, as a, 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 rules. This happened in Kentucky today. Notably, the judge in this case was a Trump appointee who said, no, you cannot.