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The Trump administration has turned litigation into a primary instrument of policy and political messaging. Rather than using courts solely for enforcement, the White House has targeted universities, media outlets, state governments, and technology companies in a broad campaign to enforce its ideological agenda and test executive power limits.
This approach has produced a historically low success rate when agency actions face court challenges. Data from the Institute for Policy Integrity at New York University School of Law shows the first Trump administration won only 23% of such challenges, compared to roughly 70% for previous administrations.
This pattern often stems from Administrative Procedure Act violations, suggesting a governance style that prioritizes swift action over procedural correctness.
In This Article
- The Trump administration used courts and regulatory power as tools to push its political agenda against universities, media, state governments, and Big Tech.
- Legal actions often targeted DEI programs, pro-Palestinian speech, and policies seen as hostile to federal priorities, using funding threats, investigations, and lawsuits.
- Media outlets faced defamation suits, access restrictions, and regulatory pressure, largely to burden and intimidate them.
- State and local policies, including sanctuary city laws, were challenged to assert federal supremacy.
So What?
- The strategy shifted policymaking from legislation to legal and administrative action.
- It created uncertainty and operational pressure for institutions and local governments.
- These tactics risk politicizing law enforcement and legal systems, blurring lines between law, policy, and partisan goals.
Universities Under Fire
The administration’s legal strategy against American universities reveals a coordinated effort to reshape higher education through two main approaches: dismantling diversity programs and suppressing pro-Palestinian viewpoints under the banner of fighting antisemitism.
Targeting Diversity Programs
The administration’s offensive on diversity initiatives began with sweeping executive orders designed to ban Diversity, Equity, and Inclusion programs on campuses nationwide. These orders weren’t limited to federally funded programs; they threatened to leverage billions in federal grants and contracts to compel universities to end all DEI-related activities.
This was part of a broader White House initiative to eliminate what it described as “radical,” “wasteful,” and illegally discriminatory DEI and environmental justice programs throughout the federal government.
The academic community responded immediately. Organizations, including the American Association of University Professors, filed suit, arguing the executive orders represented unconstitutional overreach that usurped Congressional authority and violated First and Fifth Amendment rights.
A federal court in Maryland agreed, granting a nationwide preliminary injunction against key parts of the orders. The court found the executive branch was punishing individuals and institutions for speech content and targeting disfavored viewpoints. The court also ruled that “‘equity-related’ grants or contracts” were unconstitutionally vague, inviting arbitrary enforcement.
The administration’s subsequent appeal and motion to stay the injunction were both rejected, keeping the DEI ban on hold.
Expanding Beyond College Admissions
The administration seized upon the Supreme Court’s landmark decision in SFFA v. Harvard, which ended race-conscious admissions, to dramatically expand its legal assault. Administration officials argued the ruling prohibited nearly any institutional effort to promote racial diversity, extending application far beyond college admissions to K-12 schools, faculty hiring, scholarships, student support programs, and virtually all other campus aspects.
This expansive interpretation was also blocked by a federal judge, though the Department of Justice continued issuing guidance reflecting this aggressive stance.
The administration then translated this legal theory into direct financial action by halting $350 million in federal grants for minority-serving institutions. This move cut vital funding streams, including over $250 million for Hispanic-Serving Institutions and millions more for colleges with significant Black, Asian American, Pacific Islander, or Native American student populations.
Funding for Historically Black Colleges and Universities was notably spared, as those institutions are legally open to all students regardless of race.
Education Secretary Linda McMahon defended the cuts, arguing that tying funding to ethnicity is unconstitutional and “reinforces stereotypes.” She pledged to work with Congress to redirect money toward institutions serving “underprepared or under-resourced” students.
This policy sharply reversed the Biden administration’s approach and was swiftly condemned by congressional Democrats and challenged in court by higher education advocates.
Antisemitism Investigations as Speech Control
The administration has used the Department of Education’s Office for Civil Rights to launch investigations into “alleged antisemitic incidents” at numerous universities, including Harvard, Columbia, and UC Berkeley. Critics view these investigations as part of a broader campaign to crack down on pro-Palestinian activism, which the administration frequently equates with antisemitism.
UC Berkeley provides a stark example of this strategy. In response to an OCR demand, the university provided names of 160 faculty, staff, and students connected to antisemitism complaints.
Targeted scholar Judith Butler, a prominent Jewish philosopher, likened the university’s compliance to a “practice from the McCarthy era.” While the university maintained it was fulfilling legal obligations, critics argued it should have resisted government demands to protect academic freedom and due process.
Affected individuals weren’t informed of specific allegations against them, nor given chances to respond before their names were sent to the federal government, raising serious constitutional concerns.
These investigations are backed by explicit threats of cutting federal funding. This financial pressure has proven powerful, leading universities to agree to massive settlements to end federal probes.
Columbia University agreed to pay over $220 million, and Brown University settled for $50 million. A proposed $1 billion settlement with UCLA was rejected by California Governor Gavin Newsom, who called it an “extortion attempt.” A judge sided with Harvard after the university sued, claiming retaliation was behind a $2.2 billion cut in federal funding that the Trump administration claimed was the school’s failure to stem anti-Semitism.
This pattern of investigation followed by threats of severe financial penalties creates powerful incentives for universities to self-censor and comply with administration demands. By forcing institutions to choose between devastating financial losses and defending academic freedom, the administration fosters a chilling effect extending far beyond directly targeted individuals.
A rational university administrator, observing this pattern, would likely conclude that tolerating certain protests or academic inquiry carries existential financial risk, leading to pre-emptive speech restrictions to avoid becoming the next target.
On October 1, 2025, the Trump Administration attempted to codify its demands, circulating a Compact for Academic Excellence in Higher Education that outlined the connection between federal research funding and universities’ adherence to the administration’s ideology. None of the flagship institutions signed the compact, but New College of Florida did.
Immigration Enforcement on Campus
The administration’s strategy has extended to immigration enforcement. The Knight First Amendment Institute filed AAUP v. Rubio, challenging a policy of “ideological deportation” involving arresting, detaining, and deporting noncitizen students and faculty for participating in pro-Palestinian activism.
The lawsuit argues this policy violates the First Amendment by chilling protected speech and infringing on U.S. citizens’ rights to associate with and hear from their noncitizen colleagues.
Media as “Enemy of the People”
The administration has waged a comprehensive campaign to delegitimize the press, which President Trump frequently labels an “enemy of the people.” This campaign goes beyond rhetoric, employing high-stakes defamation lawsuits, regulatory pressure, and press access restrictions to punish unfavorable coverage and intimidate critics.
The lawsuits aren’t primarily designed to succeed on legal merits but to function as political theater, drain media resources, and create a chilling effect on journalism.
The Defamation Strategy
Unlike any previous president, Donald Trump has systematically wielded defamation lawsuits as a political weapon against media organizations. This strategy is characterized by sheer volume and astronomical damage sums sought.
In September 2025, the president filed a $15 billion lawsuit against The New York Times and several reporters, alleging a “decades-long ‘campaign of lies'” and “persistent election interference.”
The complaint, which legal experts described as “a press release masquerading as a lawsuit,” cited articles and a book, “Lucky Loser,” covering Trump’s finances, business career, and various scandals, claiming they were published with “actual malice” to damage his reputation and sabotage his 2024 candidacy.
The Times dismissed the suit as a meritless “attempt to stifle and discourage independent reporting.”
Two months earlier, Trump filed a $10 billion lawsuit against The Wall Street Journal and its owner, Rupert Murdoch. This suit stemmed from an article detailing a sexually suggestive letter, allegedly from Trump, contained in a 2003 birthday album for disgraced financier Jeffrey Epstein.
The lawsuit accused the paper of “knowingly and recklessly” publishing false statements and claimed the letter was a fabrication, while the Journal stood by its reporting accuracy.
While Trump has a poor record of winning such cases in court due to the high “actual malice” legal standard required for public figures established in New York Times Co. v. Sullivan, the strategy has successfully secured multi-million-dollar settlements.
Paramount, CBS News’s parent company, agreed to pay $16 million to settle a $20 billion lawsuit over what Trump alleged was a deceptively edited “60 Minutes” interview with then-Vice President Kamala Harris.
Similarly, ABC News paid $15 million to settle a suit after anchor George Stephanopoulos inaccurately stated on air that Trump had been found liable for “rape” in the E. Jean Carroll civil case; he was found liable for sexual abuse.
These settlements, often directed to Trump’s future presidential library, allow the administration to publicly claim victory and reinforce its narrative of media malfeasance without risking trial losses.
This tactic may erode Sullivan’s practical protections by making it cheaper for media companies to settle even meritless lawsuits than to endure costly legal battles against the president.
| Defendant | Lawsuit Amount | Status | Key Allegation |
|---|---|---|---|
| The New York Times | $15 billion | Active | “Campaign of lies” and election interference |
| The Wall Street Journal / News Corp | $10 billion | Active | False statements about Epstein ties |
| Paramount (CBS News) | $20 billion | Settled for $16M | Deceptively edited interview |
| ABC News / Disney | Unknown | Settled for $15M | Inaccurate rape liability statement |
| CNN | Various | Multiple active | Various coverage disputes |
Beyond Courts: Government Power Against Press
The administration’s media campaign extends beyond defamation suits to include direct government power use. The White House barred The Associated Press from the press pool and Air Force One travel after the news agency refused to comply with an executive order renaming the Gulf of Mexico to the “Gulf of America.”
The AP sued, and a district court judge found the ban was likely unconstitutional viewpoint discrimination, stating, “if the Government opens its doors to some journalists… it cannot then shut those doors to other journalists because of their viewpoints.”
However, that ruling was later stayed by an appeals court.
The administration has also weaponized federal agencies. Following Trump’s return to office, the Federal Communications Commission reopened a “news distortion” investigation into CBS News concerning the same “60 Minutes” interview that was the settled lawsuit.
The Reporters Committee for Freedom of the Press subsequently sued the FCC under the Freedom of Information Act to obtain records related to the politically charged inquiry.
The president signed an executive order aiming to cancel federal funding for NPR and the Public Broadcasting Service, accusing them of producing “left-wing propaganda.” NPR sued, arguing the order was unconstitutional retaliation violating both the First Amendment and the separation of powers.
Federal Power vs. Local Control
The Trump administration has engaged in numerous legal battles with state and local governments, particularly Democratic-led ones. These lawsuits aren’t merely about policy disagreements but represent fundamental challenges to federalism principles and the separation of powers, as the administration uses courts to assert federal supremacy in traditional local control areas.
The Sanctuary City War
A central conflict front has been the administration’s war on “sanctuary cities.” The Department of Justice has filed lawsuits against multiple jurisdictions, including New York City, Boston, and Illinois, that have policies limiting local law enforcement cooperation with federal immigration agents.
The administration’s legal argument is that these local laws are preempted by federal immigration law and therefore violate the Constitution’s Supremacy Clause. The lawsuits claim that by obstructing information sharing and refusing to honor ICE detainer requests, these cities endanger public safety.
These legal challenges have been accompanied by intensified ground enforcement actions. In Boston, Immigration and Customs Enforcement launched an operation dubbed “Patriot 2.0,” targeting the city for a surge in “criminal illegal aliens” arrests.
Boston Mayor Michelle Wu condemned the crackdown as an administration attempt to “hide its own failures.”
The administration’s efforts have met significant court resistance. A federal judge dismissed the lawsuit against Illinois, ruling that forcing the state to enforce federal immigration law would violate the Tenth Amendment, which prohibits the federal government from “commandeering” state resources.
Local leaders in New York and elsewhere have vowed to fight the lawsuits, arguing that sanctuary policies actually enhance public safety by fostering trust between immigrant communities and local police, making residents more likely to report crimes without deportation fear.
California Climate Battles
California has been a primary target of the administration’s legal and regulatory actions, particularly concerning environmental policy. A major conflict point is the administration’s challenge to California’s long-standing authority to set its own vehicle emissions standards, which are stricter than federal requirements.
After President Trump signed resolutions declaring California’s rules “unlawful,” a group of truck manufacturers sued the state to block enforcement.
This lawsuit created a classic federalism dispute, with manufacturers caught between conflicting state and federal mandates. California, joined by ten other states, immediately countersued the Trump administration, accusing it of illegal interference in their ability to protect public health and the environment.
This legal battle is part of a broader campaign against California’s progressive policies. The administration has also cut federal funding for the state’s high-speed rail project and taken steps to roll back its first-in-the-nation rule banning new gasoline-powered car sales.
In response to these and other actions, California has sued the Trump administration 41 times on various issues.
Nationally, the administration has also shuttered the EPA’s environmental justice office and canceled related grants, linking these programs to the DEI initiatives it opposes.
Big Tech: Control vs. Competition
The administration’s legal agenda reveals a complex and sometimes contradictory approach to corporate power and online speech. While pursuing a landmark antitrust case to rein in Google’s market power, it has simultaneously issued executive orders aimed at dismantling the systems tech platforms use to moderate harmful content.
The Google Antitrust Victory
One of the most significant legal actions initiated during the Trump administration was the landmark antitrust lawsuit, United States v. Google LLC, filed in October 2020. The Department of Justice, joined by a bipartisan state coalition, alleged that Google violated the Sherman Antitrust Act by illegally monopolizing markets for online search and search advertising.
The government argued that Google used anticompetitive and exclusionary agreements with companies like Apple and mobile carriers to lock in its default search engine status on billions of devices, thereby stifling competition. A second lawsuit targeting Google’s digital advertising technology market dominance followed in 2023.
The case, described as the most important high-tech antitrust trial since United States v. Microsoft Corp. in the 1990s, culminated in a major government victory. In August 2024, a federal judge ruled that Google had acted illegally to maintain its monopoly.
Following a remedies trial in May 2025, the court imposed significant restrictions, including prohibiting Google from entering exclusive distribution contracts and requiring it to make certain data available to rivals to help them compete.
Attorney General Pamela Bondi hailed the decision as “an important step forward in the Department of Justice’s ongoing fight to protect American consumers.”
Ending “Federal Censorship”
In stark contrast to its efforts to regulate Google’s market behavior, the administration has moved to deregulate content moderation. On his first day back in office, President Trump signed Executive Order 14149, titled “Restoring Freedom of Speech and Ending Federal Censorship.”
The order prohibits federal agencies from any form of “colluding” with social media companies to moderate, deplatform, or otherwise suppress speech, claiming that such coordination, under the guise of combating “misinformation,” unconstitutionally infringes on citizens’ rights.
The order was a direct repudiation of a June 2024 Supreme Court ruling that explicitly allowed the federal government to communicate with social media companies about removing misinformation. It fulfilled a key campaign promise to supporters who believe that tech platforms, in concert with Democrats, have systematically censored conservative viewpoints online.
However, disinformation experts have sharply criticized the order, warning it is a “direct assault on reality” that will cripple efforts to combat false information spread and will embolden foreign adversaries and domestic disinformation profiteers.
This reveals tension in the administration’s tech policy: one government arm is working to break up a corporate monopoly, while another is working to dismantle guardrails that prevent that monopoly’s platform from being overwhelmed by harmful content.
Civil Society Fights Back
The Trump administration’s aggressive use of executive and legal power has been met with equally robust and organized legal responses from civil society organizations. Groups like the American Civil Liberties Union, the Knight First Amendment Institute, and Democracy Forward have repeatedly challenged the administration’s actions in court, serving as a primary and often effective check on executive overreach.
The administration’s historically low win rate in cases challenging its agency actions is a direct result of this sustained legal opposition.
ACLU on Multiple Fronts
The ACLU has been one of the administration’s most prolific legal adversaries, filing over 430 legal actions during Trump’s first term and preparing a comprehensive strategy to counter the second term’s agenda, which it views as deeply intertwined with the Heritage Foundation’s “Project 2025” policy playbook.
The organization has been at the forefront of challenging the administration’s most controversial immigration policies. It filed a lawsuit over the administration’s use of the 1798 Alien Enemies Act, a wartime statute, to accelerate mass deportation of Venezuelan migrants, arguing it was an unlawful peacetime application of the act.
During the first Trump term, the ACLU also led successful legal challenges that enjoined the administration’s “Muslim Ban.”
The ACLU has also been a staunch defender of LGBTQ+ rights. It filed Orr v. Trump, a lawsuit challenging a new State Department policy that would require U.S. passports to reflect an individual’s sex “at conception.”
The suit argues the policy is arbitrary and violates the Constitution’s Due Process and Equal Protection clauses. A federal court granted a preliminary injunction, ordering the State Department to continue allowing individuals to self-select their gender marker on passport applications while litigation proceeds.
First Amendment Defense
The Knight First Amendment Institute at Columbia University has played a critical role in litigating key free speech issues. During the first term, it brought the landmark case Knight Institute v. Trump, successfully arguing that President Trump’s personal Twitter account, @realDonaldTrump, functioned as a “public forum” under the First Amendment and that he could not constitutionally block critics based on their viewpoints.
The U.S. Court of Appeals for the Second Circuit affirmed this ruling, establishing an important digital age precedent, though the Supreme Court later vacated the judgment as moot after Trump left office and was suspended from the platform.
More recently, the Knight Institute has taken the lead in fighting the administration’s “ideological deportation” policy, filing the AAUP v. Rubio lawsuit on behalf of academic organizations to protect noncitizen students and faculty from being targeted for their pro-Palestinian speech.
Legal Success Against Administrative Failures
The high volume and notable success of these lawsuits underscore the judiciary’s role as a crucial check on executive power. Many of the administration’s losses stem from its failure to adhere to the Administrative Procedure Act, which governs how federal agencies develop and issue regulations.
Courts have repeatedly struck down administration policies for being “arbitrary and capricious” or for being implemented without reasoned explanation or required public comment periods.
This pattern suggests that the administration’s focus on rapid, disruptive policy change often comes at the expense of legal and procedural diligence, leaving its actions vulnerable to effective challenges from well-prepared civil society.
The resistance efforts demonstrate how America’s system of checks and balances continues to function even under intense political pressure, with civil society organizations serving as crucial guardians of constitutional rights and democratic norms.
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