A seismic shift has just rocked the American judicial system as the latest reports reveal that the Donald Trump administration is facing an unprecedented legal crisis. This is no longer a matter of isolated lawsuits; it is a systemic collapse, with Trump’s losing streak in court nearly doubling that of any predecessor. From conservative judges to the Supreme Court, a thunderous message is being sent: Presidential power is not above the Constitution.

1. The Numbers Behind a Systemic Collapse

According to assessments by Law 360 and Bloomberg, during the first year of his second term, the Trump administration has lost federal court cases at a frequency nearly twice the average of previous administrations.

• Over 600 Lawsuits: With hundreds of legal failures piling up, Trump’s ability to implement core policies is being stifled.

• Total Failure: This weakness spans every major sector—from immigration and election integrity to executive orders on education.

Legal experts, including Professor Kent Greenfield of Boston College, note they have never seen a Department of Justice (DOJ) lose so many cases so rapidly. The reason is simple: Their legal arguments are wrong—and obviously so.

2. The Backfire: Executive Orders Ruled “Unconstitutionally Retaliatory”

One of Trump’s most humiliating defeats involved his attempts to target top law firms like Covington & Burling and WilmerHale for representing his political opponents. Trump attempted to strip security clearances and pressure government agencies to terminate contracts with these firms.

However, Judge Richard Leon dealt a crushing blow by ruling that these orders must be completely vacated due to their unconstitutionally retaliatory nature. He wrote that upholding such orders would be a “betrayal of the vision of the Founding Fathers”. This was more than a technical ruling; it was a moral condemnation of the President’s conduct.

3. The Supreme Court “Turns Its Back”: The Limits of Loyalty

Even a Supreme Court with a conservative majority has refused to “save” Trump’s more extreme overreaches.

• A 6-3 Defeat: In December 2025, the Supreme Court rejected Trump’s demand to federalize and deploy the National Guard in Chicago.

  A Stern Ruling: Even the justices closest to him refused to support Trump’s attempt to exceed his constitutional authority by deploying the military into cities without proper authorization.

4. Political Consequences: Fear for the 2026 Midterms

These court defeats are not just paperwork; they have a direct impact on the balance of power for the 2026 midterm elections:

• Protecting Privacy and Voting Maps: Courts have struck down Trump’s efforts to force states to hand over sensitive voter data and have blocked plans to gerrymander electoral districts in California.

• Democratic Advantage: By upholding existing maps and regulations, the courts are protecting Democratic strongholds, effectively bankrupting Trump’s strategy to manipulate election laws.

5. Conclusion: Panic Among the Lawyers “Who Know the Outcome”

Why are Trump’s lawyers panicking? Because they are being forced to file legal theories that any competent attorney knows will fail. The departure of key attorneys like James Trusty and the constant reshuffling of the legal team point to a deep internal fracture.

A legal strategy built on retaliation and “obviously flawed” theories is turning Trump’s perceived strength into a fatal weakness. As judges—including conservatives—continuously say “No,” the vision of a high-powered term that Trump promised is slowly evaporating in the courtrooms.