Conversations with Great Thinkers

Robes, Rules, and Rebellion: America's Judicial System on Trial

• Jim Lanshe • Season 1 • Episode 5

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The American judiciary faces a legitimacy crisis as procedural shortcuts threaten to undermine court authority in politically charged cases. Rule 65(c) of the Federal Rules of Civil Procedure, requiring injunction bonds, stands at the center of a constitutional standoff between the Trump administration and federal courts over deportations authorized under the Alien Enemies Act.

• Federal Judge James Boasberg issued a temporary restraining order blocking deportation flights without requiring the plaintiffs to post an injunction bond
• The Trump administration argued the order was void from inception due to the missing bond required by Rule 65(c)
• The Alien Enemies Act, dating to 1798, grants presidents broad authority to detain foreign nationals during wartime
• The administration cited cyber attacks and espionage as justification for using this rarely-invoked law
• Three potential outcomes exist: the court acknowledging procedural error, the administration complying under protest, or a constitutional crisis
• Federal circuits have consistently ruled that absence of a bond can invalidate an injunction
• The controversy raises fundamental questions about whether courts must follow procedural rules to maintain legitimacy

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Speaker 1:

Welcome to Conversations with Great Thinkers, where we explore the ideas shaping our world and we explore the people who champion them. I'm your host, jim Lanshey, and today we're diving into a conversation that strikes at the core of democracy and the rule of law, and that is the urgent need for judicial reform in these United States. And welcome to this particular series entitled Restoring Justice Rebuilding Trust in the American Judiciary, where we're discussing one of the most pressing questions of our time. Can the American people trust their courts to be neutral guardians of the law, or have our courts become mere extensions of the political branches they were originally designed to check? In today's expanded episode, judges or Politicians in Robes the Rise of Judicial Partisanship. We're going to dive into the legal and cultural forces transforming our courts, from ideological appointments to procedural overreach. This episode is going to combine two parallel stories one which is rooted in the legal technicalities of Rule 65 and federal injunctions, and the other in the growing perception of a politicized judiciary. Together, they paint a picture of a judicial system under a great deal of strain.

Speaker 1:

In early 2025, the Trump administration, amid rising national tensions, used the Alien Enemies Act to justify deportation flights of certain foreign nationals. But a federal judge James Boasberg of the United States District Court in Washington DC stepped in and issued a national temporary restraining order to halt those flights. At the heart of the controversy lies not just the immigration policy, but a forgotten legal safeguard, namely injunction bonds. But a forgotten legal safeguard, namely injunction bonds. Rule 65c of the Federal Rules of Civil Procedure requires that a party seeking an injunction put up a bond to cover potential damages. It's a rule meant to ensure responsibility and fairness, yet it's been routinely bypassed in politically charged cases like this one. So why has this basic rule of law been ignored? Why hasn't the Department of Justice challenged these injunctions when plaintiffs haven't posted a bond? And what does this say about the expanding reach of federal judges, who increasingly act as de facto policymakers? Act as de facto policymakers. In this episode, we'll explore how procedural tools like injunction bonds are really meant to check judicial overreach and how their neglect threatens the legitimacy of the courts. We'll also ask bigger questions, such as when judges wade into political waters, what happens to the delicate balance of powers between three branches of government that our Constitution demands? The heart of the administration's position in these particular cases is their belief that Judge Boasberg's order is invalid, and their argument Well what is it? Order is invalid. And their argument Well what is it? It centers on that small, overlooked procedural requirement buried in the federal rules of civil procedure. Their position, essentially, is that since there's no bond, or perhaps just a de minimis bond, therefore there is no valid order.

Speaker 1:

Let's take a little deeper dive into the Alien Enemies Act of 1789. It was one of four controversial Alien and Sedition Acts signed into law during the presidency of John Adams, a time when the young American Republic was still finding its footing, amid fears of war with France. Quoting amid fears of war with France. The Alien Enemies Act, in particular, granted the president sweeping authority to detain or remove foreign nationals from countries with which the United States was at war. It was a wartime tool rarely used but very powerful. Fast forward now to the 20th century and the act resurfaces again, this time under President Woodrow Wilson during World War I, and yet again later under President Franklin D Roosevelt during World War II. These uses included surveillance, internment and deportation of enemy aliens. In both wars, especially in World War II, the Act was part of the legal framework that justified the internment of Japanese, german and Italian nationals. Its legacy Well, that's complicated, powerful and obviously, at this point, pretty controversial. Now, in 2025, the act has been pulled off the legal shelf.

Speaker 1:

Yet once again, the Trump administration cited ongoing national security threats, this time involving state-sponsored cyber attacks, espionage concern. Espionage concern and what it labeled as growing hybrid war waged in the digital and intelligence arenas. The administration issued executive orders targeting nationals from a small number of adversarial states, countries suspected of harboring cyber operatives and intelligence agents engaged in hostile actions against the United States. Within days, immigration officials began detaining and preparing to deport hundreds of foreign nationals. Civil liberties groups were swift to respond. Organizations like the ACLU, human Rights First and National Immigration Law Center filed emergency lawsuits, arguing that the policy violated due process, was overly broad and amounted to racial and national origin discrimination.

Speaker 1:

Now that's when Judge Boasberg stepped in. Judge Boasberg, a former presiding judge of the US Foreign Intelligence Surveillance Court, commonly known as the FISA Court, issued a temporary restraining order that blocked the deportation flights pending judicial review that blocked the deportation flights pending judicial review. The order cited concerns about the constitutionality of the executive actions and the potential harm to individuals with no proven links to hostile activities. That ruling was immediate and controversial. Cable news split along predictable lines. Conservative commentators decried the ruling as judicial activism, while liberal analysts praised it as a necessary check on executive overreach. But behind the headlines, a far quieter, more technical issue emerged.

Speaker 1:

The administration claimed that Judge Boasberg's order was void from the start, not because of its logic or its language, but because the plaintiffs failed to post a bond and, as previously noted, under Rule 65C of the Federal Rules of Civil Procedure, that failure could prove decisive, because injunctions stop people from acting. It turns out that if the injunction was wrongly issued, the defendant, which is often the government, could suffer real financial or operational harm. So these bonds deter frivolous or overly aggressive litigation, and they also give the defendant recourse if they are harmed by a legally flawed injunction. The only exception to these bonds is when the government itself is seeking an injunction. But in this case it was the government that was being enjoined, not doing the enjoining. So the Trump administration argued that, since no bond was posted, the injunction or more properly, the temporary restraining order never had any legal effect. And here's where the argument finds surprising legal strength. Under well-established federal case law, rule 65C has been interpreted as mandatory, that is, unless the court expressly waives or sets the bond at zero, and even then the justification has to be made clear. Failure to post any bond at all can void the injunction.

Speaker 1:

The government's refusal to comply wasn't a blanket rejection of judicial authority. It was a procedural objection rooted in the rules of civil litigation. Supporters called it defensive constitutionalism, refusing to recognize judicial orders that exceed the bounds of procedural legitimacy, while critics called it executive defiance. But, as the administration's legal counsel explained, when a court steps outside the procedural boundaries established by Congress and the rules of civil procedure, it forfeits its authority to enforce. Rule 65C is not window dressing, it's the price of halting government action.

Speaker 1:

So where does all this go from here? Well, there are three possible scenarios. The first is that the court backs down and acknowledges procedural error and vacates the temporary restraining order. The second is that, if the administration complies, under protests challenging the order on appeal. And the third is a constitutional standoff, with the judge issuing contempt and the administration refusing enforcement. Each path carries enormous stakes for the rule of law, for the legitimacy of the courts and for how future administrations respond to rulings that they don't like. That they don't like. Now let's take a moment to look at precedent.

Speaker 1:

In several federal circuits, courts have ruled that the absence of a bond can be fatal to an injunction. For example, the Ninth Circuit in Nintendo of America versus Louis Globe Toys, a case decided in 1994,. That case emphasized that the bond requirement is not optional unless the trial court expressly rules that that is so. Likewise, the DC Circuit rules that that is so. Likewise, the DC Circuit the very jurisdiction in which Judge Boasberg sits has recognized the seriousness of failing to observe Rule 65C. So what happens when a court skips this requirement? Well, according to the Department of Justice, the answer is clear the court's order is legally defective. The administration therefore believed it was not in violation of a lawful court order, but in compliance with a superior legal rule that invalidated the court's order. As one administration official put it, you wouldn't obey a warrant without a judge's signature. So why should we obey an injunction without a bond?

Speaker 1:

This framing gave the administration a constitutional high ground, at least in their view. It wasn't about ignoring the courts. It was about defending the integrity of law against procedural shortcuts. Judge Boasport, for his part, threatened contempt proceedings. But that raised another critical question Can a judge enforce an order that is, by law, procedurally invalid? Legal scholars remain divided. Some argue that procedural defects do not strip a federal court of jurisdiction. Others insist that due process for the enjoined party in this instance the government requires strict compliance with Rule 65C. And here's the bigger issue If the courts begin to ignore the procedural safeguards in the names of urgency or public interest, they risk undermining the very legitimacy they seek to preserve. So while it may seem like legal hair-splitting, the absence of a bond in this case touched off a profound constitutional debate.

Speaker 1:

We began this episode with a paradox, a technical rule with sweeping consequences. But this episode is much more than just a discussion of Rule 65C. It's about whether the judiciary can still command respect not just from citizens, but from the other branches of government as well. Because when court orders become suggestions, when compliance becomes conditional and when legal form matters more than legal authority, we risk losing something very fundamental to our form of government not just procedural integrity, but the public trust in justice itself.

Speaker 1:

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