With 119 court defeats, Trump’s legally dubious second term agenda is focused on dictatorship

Six months into his unprecedented second term, the administration of President Donald Trump is embroiled in an escalating conflict with the federal judiciary, facing an unprecedented wave of legal defeats and accusations of systematic lawlessness that legal scholars warn is pushing the nation toward a constitutional breakdown.

A comprehensive review of federal court records reveals a staggering pattern of judicial pushback.

To date, at least 119 separate court rulings have blocked, temporarily halted, or suspended pending appeal a wide array of illegal executive actions and administrative policies.

This judicial losing streak spans the ideological spectrum, involving judges appointed by both Republican and Democratic presidents, and targets policies reaching into nearly every facet of American life, from immigration and healthcare to environmental protection and government transparency.

The standoff has moved beyond legal disputes into a direct institutional confrontation.

The administration has taken the extraordinary step of suing an entire federal district court and filing misconduct complaints against sitting judges, tactics described by legal experts as attempts to intimidate and delegitimize the judicial branch.

“They are trying to intimidate, threaten and just run over the courts in ways that we have never seen,” said a retired federal judge, who spoke anonymously given the climate of harassment the Trump administration has created.

A Campaign of Legal Resistance

The 119 successful challenges, tracked by legal experts, paint a picture of an administration operating with a brazen disregard for legal and constitutional boundaries. The cases cover a breathtaking scope of policy:

• Immigration and Citizenship: Over 40 cases have thwarted aggressive immigration measures, including attempts to use the Alien Enemies Act to conduct mass removals to third countries like El Salvador, efforts to end birthright citizenship, and policies restricting asylum access. Cases like Abrego Garcia v. Noem (D. Md.) and J.G.G. v. Trump (D.D.C.) have repeatedly found administration actions unlawful.
• Civil Rights and Liberties: Dozens of rulings have blocked executive orders targeting LGBTQ+ Americans, including bans on gender-affirming care for minors and restrictions on transgender inmates and passport holders. Cases such as State of Washington et al. v. Donald J. Trump et al. (W.D. Wash.) and PFLAG, Inc. v. Trump (D. Md.) have served as a legal bulwark against these policies.
• Government Structure and Grants: Courts have halted the systematic dismantling of federal agencies, including the attempted restructuring of the Department of Education (State of New York v. McMahon), the defunding of AmeriCorps (San Francisco Unified School District v. AmeriCorps), and the wholesale termination of grants to nonprofits and universities (National Council of Nonprofits v. Office of Management and Budget).

An Administration at War with the Bench

The judicial response has been met with unprecedented retaliation from the executive branch.

This summer, the Justice Department sued the entire U.S. District Court for the District of Maryland after its chief judge temporarily blocked immigration removals.

It also filed a judicial misconduct complaint against Chief Judge James “Jeb” Boasberg, the chief judge of the United States District Court for the District of Columbia.

After Trump called Boasberg a “radical left lunatic” and “Obama-appointed” judge, Supreme Court Chief Justice John Roberts issued a rare and highly unusual public rebuke.

The administration’s posture was crystallized by whistleblower allegations against then-top DOJ official Emil Bove, who was accused of telling attorneys they may need to ignore court orders and “consider telling the courts ‘f*** you.’”

Despite these allegations, grandstanding by Senator Cory Booker, and Democrats walking out of a Judiciary Committee vote in protest of the unjustifiably rushed process, Bove was later confirmed to a lifetime seat on the 3rd Circuit Court of Appeals.

“The truth is we are at the mercy of the executive branch,” said one former federal appellate judge, noting that courts lack their own enforcement mechanisms. “At the end of the day, courts are helpless.”

The Tools of Judicial Pushback

Faced with administration intransigence, judges have begun exploring their options to enforce compliance.

Judges Boasberg and Paula Xinis in Maryland have moved toward sanctions or contempt proceedings against officials for disobeying orders related to migrant detainees.

“The more egregious the contemptible behavior, the more speedy the judge will probably move, and the heavier weapons they’ll use,” said a former federal district court judge.

In a Rhode Island case, even a Trump-appointed judge, Mary McElroy, chastised the Department of Housing and Urban Development for its “inaction” as a potential “serious violation of the Court’s Order” after it failed to pay out $760 million in grants for affordable housing as mandated.

A Nation Veering Toward Crisis

Legal experts argue that the sheer volume of legal losses, combined with the administration’s retaliatory tactics, reveals a government engaging in rampant law-breaking.

“None of these developments are a constitutional crisis unto themselves,” said Steve Vladeck, a law professor at Georgetown University. “But they all reflect efforts to undermine the power and prestige of the federal courts for if and when that day comes.”

He added, “The problem is that too many people are waiting for a crossing-the-Rubicon moment, when what we’ve seen to date is the Trump administration finding lots of other ways to try to sneak into Rome.”

The judiciary’s ability to serve as a check on executive power has been further complicated by the Supreme Court’s conservative majority, which has frequently sided with the administration in emergency disputes, and by the fact that many of the legal challenges remain mired in slow-moving appeals processes.

In a stark warning, conservative 4th Circuit Judge J. Harvie Wilkinson III, a Reagan appointee, recently invoked President Eisenhower’s enforcement of school desegregation to urge compliance with court orders.

He wrote that the branches are nearing a conflict that “promises to diminish both,” warning that “The Executive may succeed for a time in weakening the courts, but over time history will script the tragic gap between what was and all that might have been, and law in time will sign its epitaph.”

With 119 court rulings serving as a testament to its legally dubious agenda, the Trump administration’s second term appears less focused on governing within the framework of law and more on testing whether the foundations of American constitutional democracy can withstand an outright assault from within.