Contempt Of Court

Legal Issues

from the playing-games-while-america-burns dept

I think lots of people know the kind of person who thinks they’re more clever than they really are. The kind of person who thinks that they can outwit the system by playing stupid games. The kind of person who thinks that this kind of beating the system is because they’re smart. This kind of person is usually viewed as a dipshit. Donald Trump’s DOJ seems to be, as a group, acting like just that kind of dipshit.

Like that overconfident student who thinks they’ve discovered one weird trick to beat the system, the DOJ keeps playing increasingly transparent games in court — making patently ridiculous arguments while acting shocked and offended when judges see right through their obvious nonsense.

It is a form of contempt. Not necessarily in the legal sense. But it is a kind of obvious contempt for the very systems and institutions of our judicial system that they are supposed to be protecting as a part of the constitutional order. And while judges are often willing to give great leeway to bad actors in their courtroom, at some point the outright contempt for the court can turn into something judges will start calling out.

I’m reminded of a college classmate who exemplified this mindset perfectly. He’d spend countless hours finding elaborate ways to game every assignment and test, devising increasingly convoluted schemes to avoid doing the actual work. The irony was that his schemes typically required far more effort than simply completing the assignments properly would have taken. But he sure was proud of the ways he believed he was beating the system.

That same misguided energy now permeates Trump’s DOJ (indeed, I just looked up on LinkedIn if that classmate might now work for the DOJ — thankfully he’s not there). These officials pour tremendous effort into crafting obviously laughable legal arguments, filing misleading declarations, and playing semantic games with court orders — all while seemingly convinced of their own clever brilliance. Just like my former classmate, they’re expending more energy trying to game the system than it would take to actually fulfill their constitutional duties and serve the American people. The result is a particularly toxic form of institutional contempt — not just disregard for the courts, but a sort of smirking certainty that they’re somehow outsmarting the entire judicial system.

It is nearly impossible to keep track of all of the various lawsuits that have been filed against the plethora of illegal actions taken by the Trump administration in the last two months since inauguration (though kudos to folks like Just Security who have been tracking them as best as they can).

The Boasberg case represents a critical escalation in this pattern of contempt. While legal scholars debate what precisely constitutes a constitutional crisis, Corbin Barthold makes a compelling case that we’ve now crossed that threshold. When a federal judge explicitly orders planes carrying deportees to return and the administration simply ignores that order, we’re witnessing something qualitatively different from their usual games.

THE LONG-AWAITED CONSTITUTIONAL CRISIS has now arrived. It is time for a court to say so.

On Saturday night, James Boasberg, a federal judge in the District of Columbia, issued a pair of emergency orders. The government, he had just been told at a hastily convened hearing, was removing from the country, without due process, more than a hundred alleged gang members. The planes, he learned, were already in the air. To justify this stunning move, President Trump had issued a proclamation invoking the Alien Enemies Act of 1798.

At around 6:45 p.m., Boasberg orally ordered the planes turned around. “Any plane containing these folks that is going to take off or is in the air needs to be returned to the United States,” he ruled from the bench. “This is something that you need to make sure is complied with immediately.”

At 7:26 p.m., he issued a brief written order barring the government from relying on the Alien Enemies Act to remove noncitizens from the country.

The government ignored both orders.

This outright defiance marks a subtle, but notable, departure from the administration’s playbook the past few months. Until now, they’ve preferred more smirking forms of contempt — slow-walking court orders, playing word games with compliance, or burying judges in misleading declarations. But each of these smaller acts of contempt has apparently emboldened them toward more brazen defiance.

Even in this case with Judge Boasberg, the White House has been trying to claim that it’s not ignoring his orders.

A second administration official said Trump was not defying the judge whose ruling came too late for the planes to change course: “Very important that people understand we are not actively defying court orders.”

This argument, that the order came too late, is nonsense. But it’s notable how the administration is trying to insist it’s actually obeying orders in court, while doing wink, wink, nod, nod stuff out of court.

The administration’s attempts to characterize this as a routine “deportation” matter represent perhaps their most cynical wordplay yet (and one the media should stop repeating, though that’s a different issue). Deportation is a legal process with established due process rights. What happened here was something far darker: the US government engaging in what amounts to human trafficking, shipping people to El Salvador as forced labor without any due process. The mask slipped entirely when El Salvador’s President tweeted “Oopsie… too late” in response to Judge Boasberg’s order — a tweet that Secretary of State Marco Rubio and Elon Musk both found amusing enough to amplify:

The full scope of what’s happening deserves to be called out directly. Start with the legal sleight-of-hand: The administration has resurrected the Alien Enemies Act, a widely disparaged authoritarian relic that only applies during “a declared war” or “invasion” — neither of which exists. They’re wielding this zombie legislation to deny basic due process rights to people on American soil, shipping them to El Salvador (not even their country of origin) to become literal slave labor — all funded by US taxpayers.

The contempt deepens with their public justification. Without due process requirements, they don’t actually have to prove their claims that these people are gang members. And they can’t — because the claims are false for many of those shipped out. Reports show that many of the deportees have no gang connections at all. Any competent law enforcement official would recognize these allegations as nonsense.

But the most chilling display comes in their response to judicial oversight: when a federal judge attempts to restore basic due process rights, the administration not only ignores his order, but the Secretary of State publicly mocks it while coordinating with their partner in human trafficking. This isn’t just contempt of court — it’s contempt for the entire concept of legal constraints on executive power.

The administration’s response to Judge Boasberg perfectly encapsulates their broader strategy: when the facts aren’t on your side, attack the judge. Their characterization of Boasberg as a “radical left lunatic partisan” would be merely laughable if it weren’t so deliberately misleading. This is the same conservative judge who repeatedly ruled in Trump’s favor in other cases — ordering Hillary Clinton’s emails released, blocking the release of Trump’s tax returns, and limiting disclosures from both the Mueller investigation and the classified documents grand jury.

The contempt here operates on multiple levels: there’s the surface-level dishonesty of painting a conservative judge as a radical leftist, but more insidiously, there’s the implicit message that any judge who dares enforce the law against Trump must be acting from partisan motives. This fits a broader pattern where the administration’s lawyers aren’t just playing games with legal arguments — they’re actively working to undermine the legitimacy of judicial oversight itself.

The Boasberg case may be the most brazen example, but it’s far from isolated. Across multiple courts, judges are increasingly witnessing this administration’s attempts to treat the judicial system like a game they can cleverly exploit. Their contempt generally takes three forms, each more concerning than the last:

First, there’s the malicious compliance playbook — taking court orders so literally they become absurd. The Social Security Administration exemplifies this approach. When Judge Ellen Hollander blocked DOGE from accessing records, interim SSA head Lee Dudek responded by threatening to shut down the entire Social Security system, claiming his entire IT staff were somehow “DOGE affiliates.” This led to an increasingly furious series of clarifications from the judge, culminating in her observation that either Dudek was lying or the DOJ lawyers were.

Second, there’s the strategy of procedural manipulation — exploiting court customs and courtesy to gain tactical advantages. Take the EPA case, where officials used procedural games to try to circumvent judicial oversight. They asked for a routine 24-hour extension on a hearing (which opposing counsel typically grant as a professional courtesy), then used that delay to sneak in actions that would have been prevented by the pending TRO:

Third, we’re seeing increasingly more open defiance of court orders, coupled with attempts to delegitimize any judge who rules against them. The Perkins Coie case perfectly demonstrates this escalation. When Judge Beryl Howell issued a TRO blocking an obviously unconstitutional executive order targeting the law firm for representing Democratic interests, Attorney General Pam Bondi and OMB Director Russell Vought responded with explicit defiance:

The Executive Branch’s position is that Executive Order 14230 is permissible, and that the Court’s order was erroneous. The government reserves the right to take all necessary and legal actions in response to the “dishonest and dangerous” conduct of Perkins Coie LLP, as set forth in Executive Order 14230.

At the same time, the DOJ is trying to disqualify Judge Howell for… “hostility” towards the President, again setting up the idea that any judicial action holding them to account is driven by bias, rather than an actual respect for the Constitution.

The pattern of contempt continues across other cases, each fitting into these three categories of increasingly brazen defiance:

More malicious compliance games appear in the DOGE leadership saga, where pretend DOGE boss Amy Gleason filed a declaration claiming to run the agency even as Trump himself said in his address to Congress that Elon Musk runs it. When called on this discrepancy, Gleason’s response dripped with technically-accurate-but-misleading wordplay: “Elon Musk does not work at USDS. I do not report to him, and he does not report to me. To my knowledge, he is a Senior Advisor to the White House.” The contempt deepened when it emerged that Gleason was simultaneously appointed as an HHS consultant a week after being named DOGE head.

The EPA case shows how procedural games escalate to outright dishonesty. EPA boss Lee Zeldin, fixated on a deceptively edited Project Veritas video, illegally froze a Citibank account, and attempted to launch a grand jury investigation. When challenged in court, DOJ lawyers told Judge Tanya Chutkan they couldn’t provide evidence of any criminal violation because “this Court is not in a position to rule upon whether or not this termination was consistent with the contracts.”

Perhaps most telling is the transgender military ban case, where the administration’s contempt for judicial oversight is laid bare. The DOJ keeps insisting to the judge that there is no ban on transgender service members, while Secretary of Defense Pete Hegseth openly declares exactly the opposite:

These examples paint a clear picture of an administration that, like my college classmate from years ago, believes it’s brilliantly outsmarting the system while actually just making itself look increasingly desperate to avoid any accountability. But unlike that student’s academic games, these legal shenanigans carry profound constitutional implications.

What started as wannabe-clever-but-obvious attempts to circumvent court orders has evolved into something far more dangerous: a systematic effort to delegitimize judicial oversight itself. Each time they respond to a court order with malicious compliance, procedural manipulation, or outright defiance, they’re not just showing contempt for individual judges — they’re undermining the very concept of judicial review.

The progression is clear: first came the word games and barely-technically-accurate-but-misleading declarations, then the exploitation of court procedures and customs, and now increasingly open defiance coupled with attempts to paint any judge who enforces the law as politically biased. This is how institutional guardrails get dismantled — not through dramatic confrontation, but through a thousand small acts of contempt that gradually normalize the idea that court orders are merely suggestions to be cleverly evaded.

Trump has already effectively neutered congressional oversight. Now his DOJ appears determined to do the same to the judiciary, treating federal judges like frustrated professors whose rules are just obstacles to be gamed. But unlike my former classmate’s academic adventures, the stakes here aren’t just a passing grade — they’re the continued functioning of our constitutional system of checks and balances.

Judges are starting to catch on, calling out these games with increasing fury. But judicial anger alone won’t be enough. An administration that responds to court orders with winks, nods, and “technically accurate” lies isn’t demonstrating clever lawyering — it’s showing fundamental contempt for constitutional governance itself. Those who shrug this off as mere legal gamesmanship are missing the escalating danger: when government lawyers treat the judicial branch as a system to be cleverly gamed rather than an essential check on power, they’re not just failing their professional obligations. They’re actively participating in the dismantling of judicial review itself.

These officials seem convinced they can keep playing these games forever — or at least until there’s no independent judiciary left to play games with. At some point, judges need to stop writing angry opinions and start issuing contempt charges. And Congress needs to wake the fuck up before it’s too late.

Filed Under: alien enemies act, amy gleason, beryl howell, constitutional crisis, contempt of court, dod, doge, doj, donald trump, el salvador, ellen hollander, elon musk, epa, james boasberg, lee zeldin, marco rubio, nayib bukele, pam bondi, pete hegseth, russ vought, tanya chutkan, usds