Kara Sears
Former US President Donald Trump has lost a number of high-profile lawsuits over the years, both as a private citizen and as a public official. In 1985, for example, New York City brought a lawsuit against Trump for allegedly using tactics to force out tenants of 100 Central Park South. In 1988, the Justice Department sued Trump for violating procedures related to public notifications when buying voting stock in a company related to his attempted takeovers of Holiday Corporation and Bally Manufacturing Corporation in 1986. Trump has also lost a number of cases involving federal agencies on deregulatory or policy issues during his presidency. In 2022, Trump lost a defamation lawsuit against Hillary Clinton, and in 2023, he lost a case in London against Orbis Business Intelligence, alleging that the company violated British data protection laws when compiling a 2016 dossier about him.
| Characteristics | Values |
|---|---|
| Win rate | 7.1% |
| Number of cases involving federal agencies on deregulatory or policy issues lost | 79 out of 85 |
| Number of cases lost | 93% |
| Number of judicial rulings that have at least temporarily paused the administration's initiatives | 180 |
| Number of lawsuits involving the removal of F-1 foreign student visa registration | Over 100 |
| Number of lawsuits in one week | 11 |
| Number of emergency appeals filed with the Supreme Court | Almost weekly |
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What You'll Learn
- Trump loses 93% of cases in court
- Trump's State Department changed its public charge policy
- Trump's administration has lost 79 of 85 cases involving federal agencies
- Trump's attack on judges is an attempt to undo the separation of powers
- Trump's lawyers file emergency appeals with the Supreme Court almost weekly
Trump loses 93% of cases in court
Former US President Donald Trump has lost 93% of cases brought against his administration in court, according to the Institute for Policy Integrity at the New York University School of Law. The Institute found that the Trump administration lost 79 out of 85 cases involving federal agencies on deregulatory or policy issues. This is a historically low 7.1% win rate, with most administrations achieving a 70% win rate.
Democracy Forward, a team of APA litigators and experts, has helped deliver legal blows to the Trump administration. These include successful challenges over Trump's unlawful halt of equal pay data collection, the illegal delay of e-cigarette regulation, the refusal of care rule, and the unexplained weakening of nutrition standards for school meals.
Trump's State Department also changed its public charge policy, denying immigrants entry into the US without providing advance notice or an opportunity to comment, and failing to provide an adequate explanation for the change. This was challenged in court by Democracy Forward, representing the City of Baltimore, and supported by the United States House of Representatives, 19 states, 17 cities and counties, 10 civil rights organizations, five Maryland immigrant advocacy organizations, and scholars of immigration law. The court rejected the administration's attempt to dismiss the case, and the lawsuit is now being litigated on its merits.
In another case, four federal courts ruled five consecutive times that the Trump administration's abrupt and unlawful attempt to cut off $200 million in grants to the Teen Pregnancy Prevention Program was unlawful. The program was reinstated in full.
Trump has also faced legal challenges regarding his personal conduct. In September 2020, government lawyers from the Department of Justice (DOJ) asserted that Trump had acted in his official capacity when responding to an accusation of sexual assault made by E. Jean Carroll. The DOJ's motion was rejected, with the judge ruling that the president is not a government employee and that Trump's comments were not related to his job.
Trump has also been involved in cases concerning tariffs, the removal of F-1 foreign student visa registrations, and the firing of Hampton Dellinger, the former head of the Office of Special Counsel.
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Trump's State Department changed its public charge policy
The public charge policy has had significant consequences for immigrants and their families. Being labelled as a public charge or potential public charge can result in denial of admission for immigrants or the inability to become lawful permanent residents. Many noncitizens responded to the tightening rules by reducing their use of benefits or services, even for their US-born children. This has led to major confusion and anxiety among immigrants, resulting in a "chilling effect" on the use of public benefits.
The Biden administration has since undone the deep restrictions imposed during the Trump era, reverting to the prior policy while developing a new final rule. However, despite the policy change, confusion and fear persist, and many immigrants remain reluctant to access benefits and services for which they are eligible. This has direct implications for public health, as individuals decline support and avoid disclosing personal information to government officials.
The Trump administration's public charge policy change is part of a broader pattern of unlawful policymaking. According to the Institute for Policy Integrity at the New York University School of Law, the administration has lost 79 out of 85 cases involving federal agencies on deregulatory or policy issues, a historically low 7.1% win rate.
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Trump's administration has lost 79 of 85 cases involving federal agencies
Former US President Donald Trump has had a tumultuous relationship with the law, with his administration losing 79 out of 85 cases involving federal agencies on deregulatory or policy issues. This is a historically low 7.1% win rate, with most administrations achieving a 70% win rate.
The Institute for Policy Integrity at the New York University School of Law found that the Trump administration's loss rate was due to its failure to follow the Administrative Procedure Act (APA). The APA ensures a transparent and public process for making rules and demands that agencies provide reasoned explanations for policy decisions.
Some of the cases lost by the Trump administration include:
- The Teen Pregnancy Prevention Program: Four federal courts ruled five consecutive times that the HHS's abrupt and unlawful attempt to cut off $200 million in grants to the evidence-based Teen Pregnancy Prevention Program was unlawful. The program was reinstated in full.
- Refusal of Care Rule: A federal court found that the Trump administration violated the APA by creating a rule that would have allowed healthcare workers' personal beliefs to dictate patient care. The rule was struck down entirely.
- E-Cigarette Regulation: A judge ruled that the Trump administration unlawfully delayed regulation of e-cigarettes as required by Congress. The Fourth Circuit sealed the victory by rejecting an appeal, forcing the agency to regulate e-cigarettes.
- School Nutrition Standards: A federal court ruled that the USDA violated the APA by making changes without seeking feedback, including gutting sodium and whole-grain requirements. The Obama-era standards were restored, and the administration decided not to appeal.
- Equal Pay: A federal judge ruled that the Trump administration violated the APA with its "arbitrary and capricious" rollback of a critical equal pay protection.
Trump has also faced legal challenges regarding his personal conduct, including the well-known E. Jean Carroll case, where she accused him of sexual assault and defamation. In addition, Trump has been criticised for his attacks on the judiciary, with some arguing that he attempted to undermine the separation of powers and expand the powers of the presidency.
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Trump's attack on judges is an attempt to undo the separation of powers
Since his return to power, Donald Trump has carried out a series of attacks on the country's rule of law, including gutting federal agencies, deporting immigrants without due process, firing thousands of federal workers, and ordering an end to birthright citizenship. In response, federal district court judges have issued over 190 orders blocking or temporarily pausing Trump's actions, which they considered illegal.
Trump has displayed a pattern of attacking judges and the courts for rulings he disagrees with. This pattern began during his presidential campaign and has continued into his presidency. He has attacked judges who have ruled against him, such as Judge William Alsup, who blocked the Trump administration from ending the Deferred Action for Childhood Arrivals (DACA) program. Trump has also questioned the impartiality of the Ninth Circuit Court of Appeals, despite Chief Justice John Roberts' assertion that the judiciary is independent.
Trump's attacks on judges have been interpreted as an attempt to undo the separation of powers. Ty Cobb, a lawyer who defended Trump in a special counsel investigation during his first term, stated that Trump's actions are an attempt to "take what is three coequal branches and make it one dominant branch." J. Michael Luttig, a conservative retired federal appeals court judge, echoed this sentiment, stating that Trump has consistently sought to undermine respect for judges because he knows he is trying to push the powers of the presidency beyond the limits set by Congress or the Constitution.
Trump's administration has lost 79 out of 85 cases involving federal agencies on deregulatory or policy issues, a historically low 7.1% win rate. Judges have ruled against the Trump administration on various issues, including school nutrition standards, equal pay, and the Teen Pregnancy Prevention Program. These rulings have prevented Trump from implementing policies that violate statutes or exceed his constitutional authority.
In conclusion, Trump's attacks on judges are indicative of his authoritarian tendencies and his disregard for the rule of law. By undermining the judiciary, Trump seeks to consolidate power and evade accountability for his illegal actions. The separation of powers, as intended by the Constitution, acts as a crucial check on Trump's excesses, highlighting the importance of an independent judiciary in preserving American democracy.
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Trump's lawyers file emergency appeals with the Supreme Court almost weekly
Since the start of his second term, Trump's lawyers have been filing emergency appeals with the Supreme Court almost weekly. These appeals come about when a lower court judge blocks a part of Trump's agenda, an appellate panel refuses to put the order on hold, and the Justice Department turns to the Supreme Court. The Supreme Court is not being asked to render a final decision but rather to set the rules while the case makes its way through the courts.
The most recent emergency filing, as of June 2025, asked the Supreme Court to halt an order by U.S. District Judge Brian Murphy in Boston. Murphy found that the White House had violated his earlier order with a deportation flight bound for an African nation carrying convicted criminals from other countries. Trump's top Supreme Court lawyer, Solicitor General D. John Sauer, asked for an immediate high court order that would allow the third-country deportations to resume. Murphy has stalled efforts to carry out deportations of migrants who can't be returned to their home countries.
In another case, Citizens for Responsibility and Ethics in Washington (CREW) argued in a lawsuit that DOGE, which has been central to Trump's push to remake the government, is a federal agency and must be subject to the Freedom of Information Act. The administration appealed, and Chief Justice John Roberts agreed to temporarily pause the orders pending additional word from the Supreme Court.
In May 2025, the justices took the rare step of hearing arguments in an emergency appeal. The court seemed intent on keeping the changes on hold while looking for a way to scale back nationwide court orders. One possibility advanced by some justices was to find a different legal mechanism, perhaps a class action, to accomplish the same thing as the nationwide injunctions blocking Trump's citizenship order.
Trump's lawyers have also been dealing with lawsuits on other fronts. For example, in December 2024, Trump settled a defamation case with ABC News after anchor George Stephanopoulos incorrectly stated that a jury found Trump liable for rape. ABC News agreed to pay $15 million to Trump's presidential library and $1 million for his legal fees, as well as issue a public apology. In another case, E. Jean Carroll sued Trump for defamation after he published a lengthy post against her on Truth Social, to which he attached a photograph of her. Carroll successfully claimed that this post was defamatory.
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