Lawfare Daily: The Besieged District Judges, with Reynolds Holding and Judge Jed Rakoff

Summary

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The Lawfare Podcast — "The Besieged District Judges"

With Reynolds Holding and Judge Jed Rakoff
Host: Roger Parloff
Date: December 3, 2025

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Episode Overview

This episode of The Lawfare Podcast dives into the increasingly fraught landscape facing U.S. district court judges, focusing on the challenges, public scrutiny, and threats they endure in the current political climate. The conversation features Ren Reynolds Holding, author of Better Judgment, and renowned U.S. District Judge Jed Rakoff. Together with host Roger Parloff, they explore Holding’s book—which highlights the pivotal yet underappreciated role of federal district judges—and discuss the legal, historical, and personal dimensions of judicial work amid calls of "war on the courts."

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Main Discussion Points & Insights

1. Why Write About District Judges? (02:12–04:03)

• Ren Holding shares that his book aims to illuminate the daily work and personal stories of federal district judges, who are often overlooked compared to the Supreme Court.
• He spotlights three judges with diverse backgrounds—Carlton Reeves, Martha Vasquez, and Jed Rakoff—who, in different ways, have resisted trends reducing judicial authority and access to the courts.

“I wanted to tell the story of the men and women who have the last word in the hundreds of thousands of cases every year that never go up on appeal, that the Supreme Court never comes close to seeing…”
—Reynolds Holding (02:19)

2. Historical Context: “War on the Courts” (04:19–07:15)

• Holding contextualizes current anti-judicial rhetoric, connecting it to earlier American episodes where judicial independence was threatened (Reconstruction, Lochner era, Southern Manifesto).
• He explains that pressures to restrict judicial authority are not new, but that some judges—like those profiled—find creative and principled ways to maintain judicial independence and access.

“There have been other moments in American history when at least a rhetorical war has been waged on judges…”
—Reynolds Holding (04:22)

3. Profiling the Judges (07:21–10:40)

• Carlton Reeves: Grew up in segregated Mississippi, now chairs the Federal Sentencing Commission.
• Martha Vasquez: Daughter of immigrants, motivated to become a judge after witnessing her brother’s harsh sentencing.
• Jed Rakoff: Known for challenging “neither admit nor deny” SEC settlements after the 2008 financial crisis.

4. Current Rhetoric: “It’s a War” (10:40–13:24)

• The panel discusses Deputy AG Todd Blanche's remarks about a “war on the courts.”
• Judge Rakoff robustly rejects the characterization, emphasizing that district judges are simply applying the law, often coming from a variety of political backgrounds.

“It’s very wrong, totally wrong... The beauty of the American legal system is that it’s premised on the application of reason and logic to statutes and precedents... To see this in terms of emotions, armaments, warlike activities, it seems to me to be a very misplaced analogy.”
—Judge Rakoff (11:31)

5. Threats Against Judges (15:01–18:34)

• There's a rise in threats to judges, which historically come mostly from disturbed individuals but are now amplified by hostile rhetoric.
• Judges try to remain undeterred, though Rakoff notes the emotional toll is undeniable.
• Rakoff shares a darkly humorous anecdote about a threat he received, underscoring the reality of such experiences.

“Every judge I spoke with has had the experience, has had threats, have gotten the voicemails, and just have heard horrible things directed at them... I would not be surprised if Judge Rakoff had had this experience as well.”
—Reynolds Holding (16:45)

“He said, ‘I’m going to murder you’... I tried to find out exactly what it was that I had done that got him so upset... It became obvious he was upset about a decision that had been made by a different judge.”
—Judge Rakoff (17:19)

6. Supreme Court’s Emergency Docket & Lower Court Defiance (20:04–22:15)

• Discussion of Justice Gorsuch’s criticism of district judges for allegedly “defying” Supreme Court precedent.
• Rakoff voices concern about the prevalence of unexplained or terse Supreme Court emergency orders (“shadow docket”), which undermine the transparency and reasoning expected in a functional legal system.

“The Supreme Court, when it issues these emergency rulings, doesn’t give reasoning. Sometimes no reasoning at all—just a stay... To do it, as has been the case recently in a great many cases involving major issues, seems to me somewhat contrary to the fundamental justification of why we have judges at all.”
—Judge Rakoff (20:04)

7. District Judges’ Approach to Novel Cases (22:50–24:46)

• Rakoff details the process district judges use to navigate new legal territory:
  • Start with the complaint/indictment and applicable precedents.
  • Seek input from lawyers in an adversary system.
  • Occasionally raise issues sua sponte, but only after ensuring parties are heard.

8. Judicial Dissent: The Mark Wolf Example (24:46–28:44)

• The panel discusses former Judge Mark Wolf's resignation and his sharply worded criticism of partisan misuse of the law by the White House.
• Holding reflects on the balance between judges educating the public versus the risk of being “just another voice” after leaving the bench.
• Rakoff affirms that strong judicial opinions—even with sharp criticism—are sometimes called for in the act of adjudicating.

9. Judge Rakoff and the Financial Crisis (35:53–41:46)

• Holding explains why Rakoff’s stance post-2008 was so meaningful: he refused to rubber-stamp government settlements, insisting on factual clarity and transparency—a rare act of accountability at a time of public outrage.
• Rakoff discusses the “neither admit nor deny” SEC policy and how judicial scrutiny can prompt better public awareness and development of the law.

“All judges should be active in looking closely at the cases that are presented to them... We want to encourage agreements where possible, but we don’t want to encourage collusive settlements, we don’t want to encourage settlements that are contrary to the law, etc.”
—Judge Rakoff (38:39)

10. The Meaning of “Justice” — and the Future of the Courts (47:06–56:36)

• Holding clarifies that the book’s focus isn’t about a specific result or ideology, but about judges taking responsibility for ensuring access and fairness.
• Both guests express concern over mounting limits on court access—such as mandatory arbitration and heightened pleading standards.
• Holding notes, recent events since the book’s completion only underline the importance of independent judges for democracy:
  • Judges are the primary officials still holding power to account when other branches falter.

“Judges really are the only people left who are public officials who are trying to hold power to account... When we get through this—and we will get through this—we’ll look back and see that it was the federal district court judges that held it together, that held us together.”
—Reynolds Holding (54:09, 56:05)

11. Notable Humor & Memorable Moments

• Rakoff’s darkly comic story about a mistaken threat caller (17:19–18:34).
• Rakoff’s “duck hunting” joke explaining differences between district, appellate, and Supreme Court judges (51:12–53:36):

“The district judge puts up his gun. Bang. And a bird falls to the ground… he turns to his two colleagues and he says, ‘Sure hope it’s a duck.’ Okay, so that’s the difference between the three levels.”
—Judge Rakoff (51:12)

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Timestamps of Key Segments

• 02:12 — Reynolds Holding on the book’s origin and intent
• 04:19 — Historical overview: previous “wars on the courts”
• 07:21 — The three profiled judges and their stories
• 10:40 — Discussion of “war on courts” rhetoric (Todd Blanche quote)
• 11:31 — Judge Rakoff’s response to the war analogy
• 15:01 — Rise in threats to judges
• 17:19 — Judge Rakoff’s story of receiving a threat
• 20:04 — Critique of Supreme Court “shadow docket”
• 22:50 — The district judge’s approach to new issues
• 24:46 — Mark Wolf’s resignation, judicial candor
• 35:53 — Why the SEC settlements mattered; Rakoff’s stance
• 38:39 — Rakoff on “active” versus “activist” judging
• 41:46 — Impact of Rakoff’s example and the “neither admit nor deny” policy
• 47:46 — What makes a judge admirable, according to Holding
• 51:12 — Rakoff’s “duck hunting” joke
• 54:09–56:36 — Postscript: reflecting on the past year and the enduring importance of district judges

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Concluding Insights

This episode powerfully illustrates the indispensable and often underappreciated work of district judges—guardians of fact, fairness, and access to justice—amid a storm of rhetoric, threats, and institutional challenge. Both guests urge the public to look beyond high-profile Supreme Court battles and recognize the quiet, constant vigilance of district judges who remain, in Holding’s words, the “only people left who are public officials... trying to hold power to account.”

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Notable Quotes Recap

• "The law is what they're following.” — Reynolds Holding (00:54, 14:11)
• "It's very wrong, totally wrong..." — Judge Rakoff on “war” talk (11:31)
• "The Supreme Court has the last word, but district judges have the first word.” — Judge Rakoff (22:50)

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Transcript

[Roger Parloff]

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[Reynolds Holding]

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[Roger Parloff]

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[Reynolds Holding]

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[Judge Jed Rakoff]

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[Reynolds Holding]

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[Judge Jed Rakoff]

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[Reynolds Holding]

These judges are applying the law. These judges are not being creative. These judges are not figuring out how to get around some issue, trying to get a certain result. I mean, it's very clear in I think every case that the law is what they're following.

[Roger Parloff]

It's the Lawfare podcast. I'm Roger Parloff, senior editor at Lawfare, and I'm with Reynolds holding, author of the book better judgment, and U.S. district Judge Jed Rakoff.

[Judge Jed Rakoff]

I think all judges should be active in looking closely at the cases that are presented to them, and the fact that the parties may have come to an agreement is highly relevant. We want to encourage agreements where possible, but we don't want to encourage collusive settlements. We don't want to encourage settlements that are contrary to the law.

[Roger Parloff]

Today we're talking about Wren's book about district judges and about, quote, bringing justice back to the courts. So, Wren, what was your goal in writing the book, and what did you mean by bringing justice back to the courts?

[Reynolds Holding]

Well, in writing the book, my goal was that I wanted to tell the story about the people who do the real work of the federal courts. I mean, so much attention is paid to the Supreme Court. As you know, so many people write about it, talk about it, worry about it. And I wanted to tell the story of the men and women who have the last word in the hundreds of thousands of cases every year that never go up on appeal, that the Supreme Court never comes close to seeing the people who, in relative obscurity, stand up every day for the rule of law and who, in some cases, are now about the only public figures calling out, let's Call it the adventurous view of the law, some would say the lawlessness of the current administration and trying to hold it accountable. And that's not the Supreme Court, that's the federal district court judges. People like the three judges I write about and I wanted to tell their story. I wanted people to understand what these judges do, how they go about their days, how they grapple with issues and reach decisions and write opinions and how they interact with their clerks and what goes on in their chambers. I also wanted to find out who these judges are, not just as judges, but as people, how they grew up, what experiences and people shape them. And most important is I wanted to do this all in an accessible way. This is, you know, I want to emphasize this is not an academic or legal book, but on one level it's just a story about some really fascinating characters.

[Roger Parloff]

And how did you choose Broad Brush, these three particular judges? We can go into later some things that Judge Rakoff did. But what did they have in common, these three that you chose to hone in on?

[Reynolds Holding]

Just a step back a minute. I also wanted to make a broader point and this will lead me into why I chose these three judges. As you know very well, Deputy Attorney General Todd Blanche recently talked about there being a war with the courts or on the courts. And it was a terrible thing to say, but in a sense he's not wrong. The truth is that there have been other moments in American history when at least a rhetorical war has been waged on judges. Think of the period during Reconstruction after the expansion of the federal judiciary. Think of the pushback at the turn of the century to the so called Lochner era. Think of the pushback from the other side to FDR's so called court packing effort. The most recent one before now started in 1956 and when Southern senators issued the so called Southern Manifesto, which was of course a response to the Brown v. Board school desegregation decision and a virtual declaration of war against the courts. And over the following 60, 70 years or so, that war took the form of a really a broad effort by Congress and the Supreme Court itself to cut back on judge's authority and more importantly on the ability of judges or of people to get into court. The court and Congress and corporations particularly conjured these notions like a litigation explosion and soft on crime sentences to establish mandatory arbitration and mandatory sentencing guidelines and heightened pleading standards and restrictions on class actions and habeas corpus and on and on. And I chose these three judges because to tell that broader story. I wanted to do it through the lives of. Of these three, who, each of whom came of age roughly during that period since the Southern Manifesto and on the bench, have found ways to resist these efforts to diminish their authority and their ability to bring people into their courtrooms and really the ability to find the truth and make a record and do what they see as justice. And these three judges I selected because, I mean, most of all because I think each of them is a really interesting character, but also they have carried out this sort of resistance in very different ways that reflect their very different experiences.

[Roger Parloff]

And just for the reader, name the other two that you chose besides Judge Rakoff.

[Reynolds Holding]

Sure. There's Carlton Reeves, who is a district court judge in Jackson, Mississippi. He grew up as a black person in Yazoo, Mississippi, during the 1960s and 70s and faced the racism and the poverty that were typical of that place and time, but also found out that as he was growing up, justices of the Supreme Court, but also lower court judges, were making it possible for him to. He attended the first desegregated first class, first grade class in the state, made it possible for him to go to the best public schools and universities, to go to the stores and restaurants and hotels and the other places he wanted to go to, and to make it possible for him to become the man he is today, which is a district court judge and also the chair of the Federal Sentencing Commission. And he has told me, you know, many times that these people, these judges were to him, heroes. The second judge is Judge Martha Vasquez. She sits on the district court in Santa Fe, New Mexico. She's the daughter of immigrant parents, one undocumented from Mexico, who grew up literally picking oranges and gardening alongside her parents and friends in Southern California and living that immigrant experience. She had an older brother, someone she just adored and had never been in any real trouble of any kind. And he ran into money problems and tried to resolve them by selling marijuana. And he got caught up in a federal drug sting and ended up being sentenced under the mandatory sentencing guidelines to 30 years in prison. And Martha lived through his trial and saw how the judge in Los Angeles, Manny Real, who was sort of an infamous judge at the time, see how the judge treated him, which was very poorly, and resolved that she would become a judge herself. And she said to herself, in effect, I can do this. And she did. And now, as I say, she sits on the court in Santa Fe, New Mexico. And then there's Judge Rakoff, and I won't try to tell his story, but I did want to mention that what first struck me, and of course what struck a lot of people was how in the aftermath of the financial crisis and the cases that the SEC had brought against banks for their alleged role in the crisis, he refused to sign off on settlements that allowed the banks to neither admit nor deny the allegations against him. When he was doing this, and this would have been about 2011. I was an editor at Reuters at the time, and we were in an 8:30 story meeting and sort of reviewing the news and seeing what we would say about it. And one of the pieces, one of the news items was Judge Rakoff had refused to approve this settlement. And at the time, I don't know if remember, I mean, it was really a remarkable thing. And I remember someone saying in the story meeting, well, you know, somebody ought to write a book about this guy. And I essentially took that to heart. And that's sort of the origin story of the book.

[Roger Parloff]

I appreciate that. Let's go back to the Todd Blanche statement. You mentioned the it's a war man. This was in front of the Federalist Society last week and he used the phrase several times. And he said, and he talked to the young lawyers and he said, we need you because it's a war and it's something we will not win unless we keep fighting. It's hard to get the media, it's hard to get the American people to focus on what a travesty it is when you have an individual judge be able to stop an administrative policy that's constitutional and allowed just because he or she chooses to do it. So it's a war. Judge, is there anything you can say about that comment?

[Judge Jed Rakoff]

Well, it's very wrong, totally wrong. The judges who have, by applying the law, found that some of the initiatives of the current administration have been contrary to law are judges of a very wide variety of backgrounds. Some were appointed by Donald Trump in his first term. Some were appointed by Ronald Reagan way back when, many in between. And what we've tried to do in common is what our job is, which is apply the law. And I'm sorry that Mr. Blanche doesn't recognize that. The beauty of the American legal system is that it's premised on the application of reason and logic to statutes and precedents. And district judges don't always get it right, of course, though the statistics suggest that more often than not, we do get it right, since the reversal rate is fairly low. But if we get it wrong, that's what appeals are all about. So it's troubling to me that anyone would see this in terms of emotions, armaments, warlike activities, it seems to me to be a very misplaced analogy.

[Roger Parloff]

And just to back that up so you don't have to take Judge Rakoff's word for it, the professor Vladek, has done some statistics here, and I'll just. He says there have been 154 rulings he's aware of, granting a TRO or the like, and they've involved 121 different judges appointed by seven presidents in 29 district courts across 10 circuits, 41 by Republican appointees and including 15 by Trump appointees. And he says that among the ones in front of Republican appointees, the emergency petitions were granted 62% of the time against the government.

[Reynolds Holding]

In other words, just wanted to emphasize something that Judge Rakoff said, which is these judges are applying the law. These judges are not being creative. These judges are not figuring out how to get around some issue, trying to get a certain result. I mean, it's very clear in I think every case that the law is what they're following. I mean, this criticism coming from the deputy attorney general and others, they don't offer any substance. I mean, I sit there and I think, well, what exactly did these judges do wrong? What are you claiming? Where did they go off the rails? Anything? And there's really nothing. Also, it's obviously at a time when judges are getting all sorts of threats.

[Roger Parloff]

Let's talk about that. What does this rhetoric mean in terms of the security of judges? And I'll ask Judge Rakoff first if you can address that.

[Judge Jed Rakoff]

Well, there has been, from time to time throughout history, attacks on judges. Some judges have been murdered, others have been seriously maimed or disabled. Usually the perpetrators are people who are very mentally disturbed. But that doesn't mean they're totally unaffected by more general rhetoric. Every case is different, and it's hard to speak in generalities here, but the statistics are that over the last few years, and particularly over the last few months, there's been an increase in the number of threats to judges. And the beauty of our system of law is, is that an independent judge can make a decision without having to fear retaliation in any form. So I'm very proud of. My colleagues have not allowed this kind of threats to affect their decisions, but I can't say that it's totally absent from their minds.

[Roger Parloff]

Ren, do you have anything to add to that from your conversations with other judges?

[Reynolds Holding]

Well, only that every judge I spoke with has had the experience, has had threats, have gotten the voicemails, and just have heard horrible things directed at them. And I've certainly heard other judges have experienced the same, and it seems to be. It just. I'm struck by how, how widespread it is. And I think, you know, I would not be surprised if Judge Rakoff had had this experience as well.

[Roger Parloff]

Have you?

[Judge Jed Rakoff]

Judge I have. Although in one case, believe it or not, I was a little bit humorous. This was some years ago, and I picked up the phone around 6 o' clock at night in my chambers and, and the person on the other end said, is this Judge Rakoff? And I said, yes. And he said, I'm going to murder you. Which was, you know, something of a good opening line, I suppose, and so got your attention. Right. So what you're supposed to do in that situation, which I did, was keep the person on the phone and press a button that will allow the marshals to come up and trace the call. So I pushed the button and eventually the marshals did come up and trace the call. But in order to make that work, I had to continue talking with him. So I tried to find out exactly what it was that I had done that got him so upset. And it became obvious after a little while that he was upset about a decision that had been made by a different judge. And I was so tempted to say I transferred her call, but.

[Reynolds Holding]

In any.

[Judge Jed Rakoff]

Event, he was eventually arrested and things worked out at the end.

[Roger Parloff]

So we've talked about Blanche, and of course, we're not talking really just about Blanche. It's the whole. It's doj, it's the White House and Congress. And Congress, but a little bit even from the Supreme Court. We got this separate opinion by Justice Gorsuch in the NIH vs. APHA case suggesting that lower court judges are defying Supreme Court orders. He says lower court judges may sometimes disagree with the court's decisions, but they are never free to defy them. This is the third time in a matter of weeks that this court has had to intervene in cases in a case squarely controlled by one of its precedents. And of course, the kicker is that he was writing that opinion in partial dissent because he had misinterpreted himself the prior precedents that he thought were so obviously clear. These obviously has to do with the Supreme Court's emergency docket. I don't know the degree to which you've grappled with this, Judge Rakoff, but what's your perspective on these Supreme Court emergency docket rulings?

[Judge Jed Rakoff]

Well, I think it's unfortunate that they become more common than in the past, because what is the justification For a judge exercising authority in any democracy, it is the application of reason that can be presented. The public can evaluate it. The higher courts can evaluate it and figure out whether, yes, that was good logic or bad logic. So the Supreme Court, when it issues these emergency rulings, doesn't give reasoning. Sometimes no reasoning at all, just a stay, other times like one or two sentences, but nothing more. So I think to do that once in a blue moon, in an extreme emergency, you can understand they might have to act very quickly to do it, as has been the case recently in a great many cases involving major issues, seems to me somewhat contrary to the fundamental justification of why we have judges at all.

[Reynolds Holding]

And in that case, in a NIH case, I guess, the district court judge, I think it was William Young, explained essentially, I didn't think I was not following precedent. I didn't know, in effect, he was saying, I didn't know that an emergency order of a couple of lines was precedent. Do you think he was right?

[Judge Jed Rakoff]

Well, now you got me. Because the basic rule is that federal judges cannot discuss pending cases not only before themselves, but before other judges. So I get. And you know, in a criminal case, it's taking the fifth. I guess in this case it's taking the third, the third article of the Constitution. So I guess the.

[Roger Parloff]

But the hypothetical thing that seems is you get this result, you don't get an explanation. And then you have all of these precedents above you in your case, the Second Circuit and the Supreme Court from fully briefed opinions from maybe 1971, if anything, from 1971 still applies. So take it from there. How do you navigate?

[Judge Jed Rakoff]

Well, in any case, when district judges get the case, the first thing we do is we look at the charging instrument. It's either a complaint in a civil case or indictment in a criminal case. And sometimes you can see that it fits well within existing precedent. Other times you can see even at the outset, that it's raising new issues. And to be frank, it's always sort of thrilling to see a case that's raising new issues. The Supreme Court has the last word, but district judges have the first word. And it's nice to have the opportunity to look at new cases or new issues. But when you get a new issue, even then, you don't just think about it in the abstract. You go back in the common law tradition and see what precedents are in the area. You go back, if there's a statute involved, and look at the language of the statute. And so you begin your homework right at the beginning, even before the issue is joined, so to speak. And then, of course, you are very much affected by what the lawyers say. So this is an adversary system. In one or two cases, I've gone beyond what the lawyer said. I always felt in those situations that I had to give the lawyers lots of opportunities to be heard. If I'm introducing some thought that is different from anything they've said in their papers. But also I would only do that on rare, rare occasions. And I think that's true of my colleagues as well.

[Roger Parloff]

Yeah. Let's turn to this thing that Judge Mark Wolf did recently in Boston. He resigned. He's a senior judge, a Reagan appointee. He then wrote an article in the Atlantic says, among other things, President Donald Trump is using the law for partisan purposes, targeting his adversaries while sparing his friends and donors from investigation, prosecution, and possible punishment. The White House's assault on the rule of law is so deeply disturbing to me that I feel compelled to speak out. Silence, for me is now intolerable. I'm going to let Wren address this one first. What was your reaction to that one?

[Reynolds Holding]

Well, my reaction was, isn't Mark Wolf exactly the kind of person we want to have stay on the bench? I mean, there's a lot you can say in an opinion. There's a lot you can say in speeches and in articles. You know, I mean, the ethics rule is, of course, and I'm not going to be able to quote it, but essentially to uphold the integrity and the people's faith in the judiciary. And also implicit in that, I think, is to educate, and I'm actually channeling Judge Rakoff here, is to educate people about the judiciary. And we've seen, I mean, especially over the past year or so, I mean, we've seen so many opinions, very carefully, thorough, thoroughly reasoned opinions of 60, 70, 80, 100 pages that have set out exactly not only the law, but also have gotten some very sort of compelling and sometimes spicy language in them and people, you know, and they've been well covered by people like you, Roger. I mean, the public is finding out what judges think and what they are saying, not perhaps by reading the opinions themselves, but certainly by the great coverage that many of these decisions have gotten. So my first reaction was, I mean, you know, I can certainly understand how Judge Wolf thought it was time to retire. I mean, I don't know what the docket is like up in Massachusetts, but, you know, maybe he's not getting much that many trials anymore, and maybe it's not exciting. And he's a senior Judge. And I think he just turned 80, and he said, you know, he said, I don't, you know, my assumption was he just didn't want to deal with it anymore, and it was easier. But I just wondered, are people going to hear him now as just another voice among all the voices that are critical of this administration? Whereas before on the bench, he may have been. Had more of an impact and more people would have paid attention to him?

[Roger Parloff]

Yeah. Judge, what, if anything, can you say about.

[Judge Jed Rakoff]

Well, I, I, I don't want to comment on Judge Wolf's resignation. I, I don't know everything that was going through his head. Being 82, I regard him as a kid. But I will say, following up on what Ren just said, for example, Judge Wilkinson, a conservative judge on the 4th Circuit, issued an opinion in one of these cases that was very sharp in its criticism of the administration and the administration's approach to law. And so I don't think that's precluded by the fact that you're deciding a case. It may be, in fact, called for by the very activity that you're addressing.

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[Reynolds Holding]

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[Roger Parloff]

So that means a half day. Yeah.

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[Roger Parloff]

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[Judge Jed Rakoff]

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[Roger Parloff]

Our listeners will know who Judge Rakoff is. They might not know the name Reynolds Holding. It's actually the first time Reynolds and I have seen each other face to face, but I've known the byline for a long time. The byline tells you that you're going to read something really well written and exactingly accurate. He's worked for Reuters and ABC News, Time magazine, Legal affairs, which was a good publication. It's no longer around San Francisco Chronicle, and he's now a research scholar with Columbia Law School. And a long time ago he practiced at Debavoise in Plimpton. Let's talk about why Judge Rakoff's role after the financial crisis, after the subprime fiasco, why that interested you so much. Ren and then maybe I'll see if the judge can talk about that as well.

[Reynolds Holding]

Well, I think at the time, so many people were angry that no one was holding the banks accountable for the financial crisis to the extent they deserve to be held accountable. I mean, certainly they were doing things that affected the economy and the financial system and perhaps the crisis itself. And you know, we forget, I mean, what an incredible time that was and how angry people were. And when suddenly a federal judge, of all people, puts his hand up and said, wait a minute, I want to understand what you did. We're just sort of, I'm not a rubber stamp. I'm not just going to say, yeah, the settlement's in the public interest without having, without knowing what went on, what you did. And of course, this goes back to the policy of the SEC since I think, the 70s, where they found it easier to settle cases, to bring lots of cases and settle them, but with the added enticement, well, you don't have to, you don't have to admit wrongdoing, you don't have to admit the allegations against you, but you can't deny them. And that's a whole interesting topic in and of itself. But you know, in my world, which was Reuters, which was primarily financial news, this was big news. And it really, you know, we all felt it, it deserved further inquiry. And of course, a lot of the people who were in the press felt the same way. I mean, I think Rolling Stone called Judge Rakoff a hero for, of sorts, for our time. I think New York Times wrote an editorial saying something like, judge Rakoff is angry. We all be angry. So it was, I mean, thinking back, I mean, at the time it seemed an obviously important and newsworthy development.

[Judge Jed Rakoff]

So I have to say that Ren, in his book has said such nice things about me. But when my wife read the book, she said to me, who is this guy? I'd like to meet him.

[Roger Parloff]

Sometimes I, I wondered if those rulings, which I think involved those rulings refusing to approve a rubber stamp the settlements. I mean, it was a while back and it was finance, which is not Lawfare's focus. Lawfare is sort of focused on national security. But are there any lessons that are applicable to more universally from what you were trying to do there that might apply today?

[Judge Jed Rakoff]

Well, I think the part of all that that I'm is proud of is the impact it had on some of my colleagues. There is always a natural tendency if you're a judge, if a case is, quote, settled, so to speak, and it goes off your docket, well, that's great, but. So I'll just rubber stamp it because it's one less case I have to deal with. And in the case that first got me interested, which was a case SEC brought against bank of America, it struck me that this was such a weak and almost pointless settlement in a major misconduct that was part of the financial crisis that Ren has just mentioned, that I should take a closer look at it. And a number of my colleagues subsequently began to take closer looks at a variety of government initiatives than they had in the past. And then I thought, I am very proud of the extent to which my little case, my little effort encouraged them to do that. There's this title that's sometimes Given, I think, most unfairly to judges as being, quote, activist judges, I think all judges should be active in looking closely at the cases that are presented to them. And the fact that the parties may have come to an agreement is highly relevant. We want to encourage agreements where possible, but we don't want to encourage collusive settlements, we don't want to encourage settlements that are contrary to the law, et cetera. So I do think to the extent my little efforts had an effect on other judges, I am proud of that fact. In terms of current events, I think the cases that we were talking about earlier, where many, many judges have held the administration's activities to be contrary to law, didn't bump activism at all. Those were mostly cases that were, frankly, not hard cases for the judges to apply existing precedent and find that misconduct had occurred.

[Reynolds Holding]

I mean, certainly the impact shortly after you, I mean, you, of course, were reversed and ultimately had to, or at least ordered by the 2nd Circuit to approve the settlement.

[Judge Jed Rakoff]

Not in the bank of America.

[Reynolds Holding]

Not in the bank of America. Correct.

[Judge Jed Rakoff]

Later on, though, I got too cozy in doing this, and the Second Circuit said, you're going too far, boy. Remember who's boss. So they did reverse me later on. And, you know, you never know that you're really right until you get reversed by a higher court. That's the, the, the strongest indication you got it right.

[Reynolds Holding]

And, and of course, the SEC for a while there say, okay, well, we're not going to, you know, we're. We're going to not do the neither admit nor deny thing in important cases. Of course, that I think pretty much went by the wayside. And I just wonder, and, and you certainly had this impact on your colleague, many of your colleagues, who many of most, if not all of whom were also faced the obstacle of appeal and were, in essence, reversed. But do you think that just your experiences, knowing your other colleagues, do you think that they are now just sort of generally more willing to, as you say, take a closer look and essentially ask, why? What really happened here?

[Judge Jed Rakoff]

Yes, I do think that has come about. You know, a lot of this needs to be put in the context of particular cases and particular facts. There's an old saying that the facts drive the law, and I think that's particularly true at the district court level when we're seeing a situation, a factual situation, that has been sufficiently difficult that people have felt need to come to court to fight about. And so more than the higher courts, which are naturally focused on broader legal issues, perhaps we are very much looking at the facts and the reason I mention that in this context, the SECs neither omit nor deny policy where they would settle a case with someone that they accused of wrongdoing, but agreed to a settlement in which the defendant did not admit that they had done anything wrong. Originally, it was devised by a very great SEC Director of Enforcement, Stanley Sporkin, who later became a federal judge in the investigations that led to the Farm Corrupt Practices Act. And there was an open question, a very open question before that act was passed as to whether paying foreign bribes violated US Law. And so Stanley Sporkin wanted to get a better idea of what the factual situation was, how widespread this was. Was it true of just one or two rogue corporations, or was it very common? And so he said, okay, we're not sure whether this violates the securities laws. This is before the Foreign Corrupt Practices act, but if you agreed to tell us candidly whether you've been paying foreign bribes or not, we will allow you to present that. We will not go after you, and we will accept it. You are neither admitting nor denying that you did anything wrong. And in that context, where he needed to develop a real factual basis for what later became federal law, I think neither admit nor deny made a certain sense. The problem with it is it became just a crutch for the sec, settling cases without their having any impact on the development of the law or in public knowledge and policy. So a good example of that is the development of insider trading law. For a long time, the SEC could not develop that law in the courts. And because every time they made an accusation, the party agreed without admitting or denying we did anything wrong, we promised not to do it again. So I had the situation when I was head of the fraud unit of the U.S. attorney's office in the Southern District of New York, that Stanley Sporkin himself was frequently calling me and telling me how frustrated he was because he was trying to develop the law of insider trading. And these settlements, thanks to, frankly, a policy he had initiated, he wasn't able to develop the law. But my point is the factual context makes a great big difference.

[Roger Parloff]

That's very interesting history. Of course, right now we don't know if domestic bribes still violate the law, but it's a separate issue. I guess one question I did want to ask. I think a reader might.

[Judge Jed Rakoff]

Skeptical reader might.

[Roger Parloff]

You know, there are judges that we probably don't. District judges we probably don't admire. You know, if you spotlight one of those judges, and I don't want to name names and attribute anything to you guys but, you know, we might get a different book, and of course, we might also get, over the course of the next several years, some more appointees that we don't admire. How will that affect the message of your book, if at all? REM well, from my point of view.

[Reynolds Holding]

What I admire is not necessarily how cases come out and how judges, you know, the conclusions the judges that I write about reach, but just the fact that they're accepting their responsibility, really, to hear the cases, to pay attention, to delve into them, to hold a trial if necessary. I mean, obviously, we have very few trials now, but they're really a great way to find out what happened, to find the truth. And I admire judges who are willing to do that, whether they be Republican appointees or Democratic appointees, judges who do that, judges who do justice. I mean, that's the subtitle of my book, Bringing Justice Back to the Courts. And I don't mean particular results. I mean working to do your job, in a sense, as a federal court judge, but also more importantly, to allow people to get into court, court to access the courts, to bring their problems before a judge, to have them addressed and resolved, you know, one way or the other. I mean, that's if you're not doing that, if you're just sending everything to mandatory arbitration or you're sending, you know, you're raising pleading standards where it's very difficult for people to actually get a complaint, to have their complaint survive, then you're taking, you know, you're taking away an essential part of the, of the judicial system. So, you know, that that's, and that's the message I want to convey in my book, although I do it through judges that I just find particularly interesting. And also, they're very diverse. I mean, they're from different places, they're of different ethnicities, they're different backgrounds. And which I think speaks to the fact that this is not just a narrow slice of judges. These are types of judges who represent a great diversity on the bench.

[Roger Parloff]

One thing it might be difficult to comment on, but you brought up judge.

[Judge Jed Rakoff]

That never stops you. Roger that.

[Roger Parloff]

This is factually driven. And what I've been seeing, you know, is that the district judges in D.C. and elsewhere, you know, you will get these 90, 100 page rulings, 200, and they go, you know, minute by minute through the record. They will hold a hearing and they will go minute by minute for the preliminary injunction, not the tro, but the preliminary. And these findings will be on, on appeal. Just it it's almost as if they didn't occur. It's. It's as if, well, there are suggestions or guidance or, you know, like, it's as if the allegations of the complaint, which you can say, well, those are allegations. I, I just don't see the facts being on appeal. You know, you used to have to find clearly erroneous. It's getting glossed over. But I don't know if you've. Anyone else is noticing this frustration that I have.

[Judge Jed Rakoff]

Well, I think there are two different aspects of what you just described. One is the focus of the district judge on the facts that I mentioned before. And the higher courts, under established precedent, usually are required to give fair degree of deference to those factual determinations. They could then decide if the judge made an error of law. That's a different question. But to ignore the facts is, I think, contrary to accepted precedent in the legal system. There's the well known joke, and you guys have probably heard it, but I can't help repeating it because I think it is so true of the difference between the three levels of judges. And it involves three judges go duck hunting and they only have a permit to shoot ducks, not other birds. By the way, Justice Scalia was a big duck hunter, but that's another story. They're out there and a flock of birds flies by, and the Supreme Court justice puts up his gun, and then he puts it down and he says, you know, that looked like a duck, but I'm not sure it is in accordance with the original meaning of the word duck. I'll have to look at the Federalist papers and see how they define duck. And then the second bunch of birds flies by and the court appeals judge puts up her gun and then she puts it down. She said, you know, while I personally was quite convinced that was a duck, I don't think I should shoot. Before I consult with my other two colleagues. We'll have to have full briefing on this matter and I'm going to stay my shooting until that time. And then a third bunch of birds flies by and the district judge puts up his gun. Bang. And a bird falls to the ground. And as they're going through the mud to pick up the bird, he turns to his two colleagues and he says, sure hope it's a duck. Okay, so that's the difference between the three levels.

[Roger Parloff]

Well, we're almost out of time, but I do want to ask Ren at least one more question. You know, you, you sort of put the. Like I said, the, the way books work, you sort of put it to bed before January 20th of this year. And so as a result, the world has changed a lot since you put it to bed. If you had a little postscript to add on to it, what would the gist of that be?

[Reynolds Holding]

Well, a postscript. I mean, you can write a whole book, at least half a book on what's going on since January 20th. And I wish I had had the opportunity to write about it. But I think the point I would take and want to include in some kind of postscript or addendum is that so much of what has happened supports the themes that I touch on in my book. I mean, you know, I talk about the Southern Manifesto and the virtual war on the courts that was launched then. Well, now we have an actual declaration of war on the courts, and we have resistance from district court judges. And not just, you know, not just people from. Not just judges who are democratically appointed, which the three judges I talk about are, but from also other judges, from judges appointed by Ronald Reagan and G.W. bush and Trump himself. And it's a very diverse crowd. And it's really sort of emphasizes the basic point of my book, which is judges are good for democracy. We need judges to allow people into court to address their issues. And any notion that we have that Congress can deal with it or the President can deal with it, I mean, that's sort of been. You know, been. Been annihilated in the past year or so. And judges really are the only people left who are public officials who are trying to hold power to account. And, you know, just yesterday I saw a. A post on X from a very prominent lawyer and legal commentator who said, you know, when we get through this, and we will get through this, we'll look back and see that it was the federal district court judges that held it together, that held us together. And I responded in another tweet, Amen. I also provided a link to my book because I didn't want. But, you know, I agree. I agree with her. I think that's right. I think we will look back on this and, you know, I don't want to say I told you so, but I told you so.

[Roger Parloff]

Okay, well, we're going to leave it there, but I want to thank you so much, both of you. Ren and Judge Rakoff, really appreciate your doing this.

[Reynolds Holding]

Well, thanks so much for having me, Roger. It was fun.

[Judge Jed Rakoff]

Lots of fun. Thanks.

[Roger Parloff]

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[Judge Jed Rakoff]

Dear Career Ladder, you've had your moment. You're linear and one dimensional. Ambition doesn't just go up anymore. It zigs and zags and squiggles. We're CEOs, executives, founders. We're advising companies, launching side hustles, taking breaks, defining our next act, ambition, on our terms. The possibilities are endless. Chief Lead on join [e-mail].