Trump’s Legal House of Cards Collapses: Four Court Defeats in a Week Part 1

Courts across the country slam the brakes on Trump’s overreach; tariffs, deportations, work permits, and infrastructure meddling all struck down within days.

Jun 06, 2025

If Donald Trump thought his second term would sail smoothly under the banner of executive power, the judiciary just delivered a sharp reminder: the Constitution still matters. Within a span of days in late May, Trump’s administration was dealt a bruising four-part legal blow, each case dismantling a different pillar of his aggressive governance strategy.

This wasn’t just a bad day. It was a legal firewall reminding us that executive power, no matter how blustery, is not boundless.

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Case 1. Tariffs Declared Unconstitutional: The End of “Liberation Day” Economics

In a stinging rebuke on May 28th, the U.S. Court of International Trade invalidated Trump’s "Liberation Day" tariffs, ruling they were imposed under a legally indefensible emergency declaration. Trump had relied on the International Emergency Economic Powers Act (IEEPA)—typically used in times of war or extreme crisis—to sidestep Congress and unilaterally impose trade penalties.

The court's decision not only tossed the tariffs but also questioned the broader misuse of emergency powers. This ruling echoes growing concerns that Trump’s legal rationale was not about protecting national security, but about bulldozing economic checks and balances.

Legal impact: Future presidents may now face stricter judicial scrutiny if they attempt similar trade-based power grabs.

Case 2. Work Permit Blockade Thwarted in Boston

From trade to work permits, the Trump playbook of disruption and discretion hit another wall.

A federal judge in Massachusetts ordered the administration on May 28th to resume processing work permits for migrants in humanitarian parole programs. These included many who arrived under Biden-era relief efforts and were suddenly caught in Trump’s bureaucratic freeze.

Trump’s legal team argued that the president had "absolute discretion" to halt the process. The court disagreed forcefully. The ruling reaffirms that immigration policy must still respect procedural norms and cannot be weaponized through administrative sabotage.

Legal impact: Bolsters the legal foundation of Biden-era immigration programs and pushes back against executive attempts to dismantle them by neglect.

Case 3. Blocking NYC’s Congestion Pricing Was Illegal

Even outside immigration, the pattern held. In New York on May 27th, a federal judge ruled that Trump’s Department of Transportation had no legal authority to withhold federal funds from the city’s congestion pricing initiative.

The plan, designed to reduce traffic and fund public transportation, had become a political target, blocked not on legal grounds, but seemingly out of vindictiveness. The court struck the move down, underscoring that federal power doesn’t give the White House a veto over state-level progress.

Legal impact: Strengthens legal protections for climate-friendly transportation initiatives against federal sabotage.

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Pattern Recognition: A Presidency Built on Overreach

Taken together, the rulings paint a larger picture. Trump’s governance style isn’t just controversial; it’s structurally incompatible with the rule of law.

Whether it’s trade, labor rights, or infrastructure, Trump’s team has treated the law as a blunt instrument, one to be bent or bypassed. These decisions signal that courts are no longer willing to play along.

Crucially, these weren’t decisions made on ideology. They were grounded in precedent, process, and the simple demand for accountability. It turns out the judiciary remembers what the Constitution is for even when politicians forget.

What Comes Next?

Expect appeals. Trump’s legal team thrives on delay tactics and jurisdictional wrangling. However, these three decisions, taken together, expose the underlying fragility of his executive claims and the growing willingness of the judiciary to say enough.

As we edge closer to the 2026 midterms and the shadow of more Trump-led governance looms, these rulings are more than just courtroom victories. They are reminders that democracy has institutional memory and teeth.

Call to Action

The courts have spoken, but the fight isn’t over. Executive overreach thrives in silence, and silence isn’t an option.

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Educate others on what’s been ruled and why it matters.
Contact your representatives and demand support for judicial independence.

We can’t just count on judges. We have to be the guardrails, too.