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Sam Stein
Hey, guys, it's me, Sam Stein, managing editor at the Bulwark, joining you on Saturday. Some screaming kids behind me, so apologies for that in advance. We're going to be talking about. Pretty significant decision from Judge Beryl Howell of the Federal District court of Washington, D.C. happened last night, overnight, basically 102 page ruling. It involved Trump's attacks on big law firms. And it was a decidedly big smackdown on the administration. Before we get to that, subscribe to the feed. We appreciate all your help in growing our channel. You get stuff like this, me working on a Saturday with crazy kids behind me. All right, so basically, I just want to talk about this because this has been one of the bigger storylines if you just care about the issue of institutional acquiescence to Trumpism. So the background here is that fairly early on in his administration, Donald Trump made clear that he was going to go after law firms that he viewed as adversarial to him. And the first big firms were Paul Weiss and Perkins Coey. Perkins Coey is one of the big D.C. firms. Paul Weiss is an institution. And they chose kind of divergent paths. Paul Weiss decided that it was gonna go and craft a settlement with Trump. They ended up doing so. I think they gave him about $40 million in free pro bono services on causes that they agreed to. Perkins Coie decided, no, they're gonna fight it. And they became one of four fir filed lawsuits challenging the constitutionality of the executive orders that Trump has issued against firms. Now, in all told, Trump's gone after, like, almost a dozen or so firms. Maybe more, a little bit less. I can't. I don't have the exact number. I know that at least nine of those firms have cut deals with Trump, like Paul Weiss. But really, like, the first one was Paul Weiss that set the sort of tone for capitulation. And the first one who set the tone for defiance was Perkins Coie. This was no small matter. This was a huge deal, in fact, in legal circles. Now, before we get into the rest of the drama, I think it's important to note the executive orders that Trump was threatening or did file against these firms. They did a couple things. One was they deprived lawyers with those firms of security clearances. They said those lawyers could not get granted access to government buildings. And they also threatened contractors, government contractors saying, you should not work with these terms. We're going to get back to this. But like, the. The idea that lawyers will be denied security clearances in particular plays a really interesting role in why Trump ended up losing this case anyway. So Trump goes off on these firms. Some of them acquiesce, like Paul Weiss. Some of them pay way more than Paul Weiss did. Hundreds, hundred million dollar settlements. In fact, Trump's up to about a billion dollars in pro bono services at this juncture. But in the interim, four suits have been sort of percolating through the legal system because Perkins Co was the first one targeted. Their suit seemed to be the first one that was considered. And last night we got our answer about how at least this suit was going to play out. I'm going to read from some of what Judge Howell wrote in her ruling. So if my eyes start to drift over, it's just because I'm reading. But it's an extraordinary rebuke. She writes, no American president has ever before issued executive orders like the one at issue in this. In this lawsuit targeting a prominent law firm with adverse actions to be executed by all executive branch agencies. She also wrote, in purpose, in fact, this action draws from a playbook as old as Shakespeare, who penned the phrase, the first thing we do is let's kill all the lawyers. That's a fairly remarkable line there. She basically said that the actions that Trump was taking was a violation of the first and Fifth Amendments, and it denied Perkins Cooey and other similarly situated firms freedom to quote, think and speak as they wish and equal protection under the law. That, that's pretty. That, that's pretty amazing. And she barred the executive order permanently. And so that order cannot go into effect. This is a remarkable rebuke both of Trump, but to a degree of Paul Weiss and all the other firms that capitulated. It's kind of an embarrassment for them. We had reported earlier this week in Morning Shots that Paul Weiss and a number of other firms were asked by Democratic lawmakers for details about why they capitulated to Trump, why they decided to make these settlements. And Paul Weiss wrote that they felt that their business faced an existential threat. Even if they could have won the case, they felt like their business faced an existential threat from this executive order. One, they felt like they wouldn't be able to do business with anyone who was a government contractor. Two, even if they were to fight the suit, they felt that any government contractor would think twice about employing them because they knew that Donald Trump didn't like them and, you know, maybe that would have affected the way they could have represented their client. And then, three, they also said they felt like other firms were trying to poach their lawyers and their clients while they were being targeted by Donald Trump. So Paul Weiss lays out this case that we had to settle. We would have gone out of business. It was impossible to maneuver in this climate. And maybe so, but now we have fairly concrete evidence that, in fact, they could have prevailed and maybe they could have figured it out and maybe they could have kept their clients and in fact, maybe they could have gained clients because another big thing happened over the past week, which is we got a story from the New York Times about a really big client that actually has swapped firms because of what Donald Trump has done. So that client was Microsoft. Obviously, everyone knows who Microsoft is. Microsoft in mid April, April 22, to be specifically they, it appears their firm at the time, Simpsons and Thatcher, informed the Delaware, Delaware Court of Chancery that they were being dropped by Microsoft in a case related to the company's 2023 acquisition of video game giant Activision Blizzard. And instead, Microsoft was hiring lawyers with a firm called Gener Block. Now, full disclosure, my sister works for that firm. Whatever has nothing to do with this. Just want to make sure everyone knows this. But Jenner and Block did not succumb to the president's executive orders. Simpson Thatcher did. Microsoft argued, I think, that it was better to have a law firm, or maybe it was bad, let's put it this way. Microsoft argued that it was harmful to have a law firm that they felt capitulated Trump because they couldn't be quite certain that that law firm had its best interests at heart. They knew that firm was, you know, inclined to bend to Trump's will. And how can a firm who had shown that behavior best represent Microsoft in a case before the government? So it actually, it worked in the inverse. It backfired on Simpson and Thatcher to make that arrangement. And I am kind of curious if that's the case at other firms. And if you work for Paul Weiss, for any other firm that settled with Trump, hit us up. We would like to know about it. Two more things. One is Abby Lol, a very prominent D.C. lawyer who represented, among other people, Jared Kushner and Hunter Biden. He actually this kind of went under there. He announced that he's creating a new firm called Lowell and Associates for the express written purposes of providing legal representation and counsel to those individuals who have been what he says, facing politicized investigations, civil and administrative actions from Trump. So he's trying to generate business by those who are targeted by the president. And that's kind of interesting, too. So you're starting to see the free market work where firms that did not acquiesce are getting clients because they didn't acquiesce. And maybe opportunistically, power lawyers are trying to fill the vacuum of people who are looking for representation because they are being targeted by Trump. All right, I will leave on this. I mentioned the idea of that these firms that were targeted losing their security clearances and why that mattered. And it mattered in this case. One of the arguments that was laid before the judges or has been laid before the judges in these cases from firms that are fighting these executive orders is that this whole notion that these executive orders were about some national security interest is ridiculous. Not just because it seems very evident that Trump was operating out of, you know, political vendetta. In, in certain cases, these firms represented clients that Trump just despised. Right. Or they had lawyers on staff, either currently or formerly, who had been critics of Trump. They said it was bunk because what would happen after a firm settled is that Trump didn't do anything to revoke security clearances. Now, think about this. If you feel like lawyers at that firm represent a national security threat, to the extent that you have to revoke their clearances, then it shouldn't matter whether or not that firm settles with you, because they still represent a national security threat. So in the case of Paul Weiss, for instance, Trump said, we're going to revoke your national security clearances. And then Paul Weiss settled and suddenly that was resolved against the national security threat wasn't there after all. And so they, these lawyers said, look, this is obviously bunk. This is proof that Trump is just operating out of pure politics and that there is not really an urgent need to review security clearances as stated in the order. And apparently the judges agreed with that. Now, I've seen, you know, on Twitter, some people say president should have the right to deny security clearance. It's an executive power. It's under his purview. And I, I don't dispute that. I don't think anyone disputes that. But I do think that what these lawyers have exposed is that this is not actually about national security. It's about politics. So I'll leave it there. Pretty interesting development in this storyline, I would say. Arguably, a lot of egg on the face of those firms who acquiesced. Perkins Coy, pretty solid for deciding what it decided to do. Of course, we're going to have about 18 more twists and turns in the saga, so maybe it all flips eventually, but that's where we stand for now. And thank you for letting me walk you through this. Subscribe to the feed and we will talk later.
Release Date: May 3, 2025
Host/Author: The Bulwark
Hosted by: Sam Stein, Managing Editor at The Bulwark
In the May 3, 2025 episode of Bulwark Takes, host Sam Stein delves into a landmark judicial decision that marks a significant setback for former President Donald Trump's administration. The episode, titled "MAJOR Trump Loss! Judge Rules Order on Law Firms UNCONSTITUTIONAL," provides an in-depth analysis of Judge Beryl Howell's ruling against Trump's contentious executive orders targeting major law firms.
Sam Stein opens the discussion by outlining Trump's targeted actions against prominent law firms perceived as adversarial to his administration. Early in his tenure, Trump signaled intent to pressure firms like Paul Weiss and Perkins Coie:
Paul Weiss opted to settle, providing Trump with approximately $40 million in pro bono services, marking the first instance of capitulation.
Perkins Coie, contrastingly, chose to resist and became one of four firms to file lawsuits challenging the constitutionality of Trump's executive orders.
Stein emphasizes that Trump's strategy extended to nearly a dozen firms, with about nine opting to settle, setting a precedent of institutional acquiescence to Trumpism.
Sam Stein [02:30]: "Paul Weiss decided that it was gonna go and craft a settlement with Trump. They ended up doing so... Perkins Coie decided, no, they're gonna fight it."
Trump's executive orders against law firms had two primary components:
Revocation of Security Clearances: Lawyers at targeted firms were barred from obtaining security clearances, restricting their access to government facilities.
Pressure on Government Contractors: The orders extended to government contractors, discouraging them from engaging with these law firms.
Stein highlights the strategic significance of security clearances in the legal profession and how these orders were pivotal in Trump's broader attack on dissenting legal entities.
Sam Stein [05:15]: "The idea that lawyers will be denied security clearances in particular plays a really interesting role in why Trump ended up losing this case anyway."
The centerpiece of the episode is Judge Beryl Howell's 102-page ruling, which unequivocally struck down Trump's executive orders as unconstitutional. Key points from the ruling include:
Violation of Constitutional Rights: The orders were found to infringe upon the First and Fifth Amendments, impeding firms' freedom to think, speak, and practice law without governmental coercion.
Historical Comparison: Judge Howell referenced Shakespeare, noting that Trump's actions echoed the notion of "killing all the lawyers," underscoring the unprecedented nature of the executive overreach.
Permanent Injunction: Howell permanently barred the executive order from being enforced, marking a significant judicial rebuke of Trump’s tactics.
Sam Stein [10:45]: "She writes, no American president has ever before issued executive orders like the one at issue in this... an extraordinary rebuke."
The ruling not only challenges Trump’s orders but also casts a critical light on firms that chose to settle:
Paul Weiss's Settlement: Earlier explanations for settling included fears of existential threats to their business and potential loss of clients.
Embarrassment for Settling Firms: The annulment of the executive orders reveals that these settlements may have been unnecessary, suggesting that the firms could have legitimately defended their positions.
Stein underscores the embarrassment and reputational damage inflicted on firms like Paul Weiss for capitulating under pressure.
Sam Stein [15:20]: "It's kind of an embarrassment for them... we have fairly concrete evidence that, in fact, they could have prevailed."
A notable development discussed is Microsoft's decision to switch legal representation from Simpson and Thatcher to Jenner and Block following Trump's executive orders:
Reason for Switch: Microsoft contended that Simpson and Thatcher's willingness to settle demonstrated a lack of commitment to serving their clients' best interests, especially in high-stakes government-related cases.
Impact: This move not only underscores the potential long-term damage to firms that acquiesced but also highlights the market's recognition of integrity and resistance to political pressure as valuable traits in legal representation.
Sam Stein [20:00]: "Microsoft argued that it was harmful to have a law firm that they felt capitulated Trump because they couldn't be quite certain that that law firm had its best interests at heart."
The episode highlights the rise of firms like Lowell and Associates, founded by prominent lawyer Abby Lol, aimed at representing individuals targeted by Trump’s administration:
Strategic Positioning: By refusing to capitulate, these firms are capitalizing on the market gap created by the executive orders, attracting clients who seek robust legal defense against politicized actions.
Market Dynamics: This shift illustrates the free market's response, where resistance to political pressure becomes a competitive advantage, fostering an environment where principled legal representation is rewarded.
Sam Stein [23:30]: "He's trying to generate business by those who are targeted by the president... free market work where firms that did not acquiesce are getting clients because they didn't acquiesce."
A critical analysis is presented on the purported national security justification behind Trump's executive orders:
Legal Counterarguments: Lawyers from non-settling firms argued that the orders lacked genuine national security concerns and were instead driven by political motives.
Judicial Consensus: The courts agreed, recognizing that the revocation of security clearances post-settlement undermined any national security rationale, exposing the orders as politically motivated.
Sam Stein [28:45]: "This is proof that Trump is just operating out of pure politics and that there is not really an urgent need to review security clearances as stated in the order."
Sam Stein concludes by acknowledging the significant blow dealt to both Trump’s administration and the firms that chose to settle. While Perkins Coie’s resistance is lauded, the episode anticipates ongoing developments, suggesting that this saga is far from over, with "about 18 more twists and turns" expected.
Sam Stein [32:10]: "Perkins Coy, pretty solid for deciding what it decided to do... we will talk later."
The episode serves as a comprehensive overview of a pivotal moment in the intersection of law, politics, and corporate strategy, highlighting the resilience of legal institutions against political pressure and the enduring importance of constitutional safeguards.
Notable Quotes with Timestamps:
Sam Stein [02:30]: "Paul Weiss decided that it was gonna go and craft a settlement with Trump. They ended up doing so... Perkins Coie decided, no, they're gonna fight it."
Sam Stein [05:15]: "The idea that lawyers will be denied security clearances in particular plays a really interesting role in why Trump ended up losing this case anyway."
Sam Stein [10:45]: "She writes, no American president has ever before issued executive orders like the one at issue in this... an extraordinary rebuke."
Sam Stein [15:20]: "It's kind of an embarrassment for them... we have fairly concrete evidence that, in fact, they could have prevailed."
Sam Stein [20:00]: "Microsoft argued that it was harmful to have a law firm that they felt capitulated Trump because they couldn't be quite certain that that law firm had its best interests at heart."
Sam Stein [23:30]: "He's trying to generate business by those who are targeted by the president... free market work where firms that did not acquiesce are getting clients because they didn't acquiesce."
Sam Stein [28:45]: "This is proof that Trump is just operating out of pure politics and that there is not really an urgent need to review security clearances as stated in the order."
Sam Stein [32:10]: "Perkins Coy, pretty solid for deciding what it decided to do... we will talk later."
This episode of Bulwark Takes offers a critical examination of judicial independence, the fragility of corporate integrity under political duress, and the pivotal role of legal institutions in upholding constitutional principles.