No single number captures how many lawsuits Donald Trump has lost, because the cases fall into categories that were counted differently and often ended without a clean win-or-lose outcome. But the tracked data points in one direction. In his second term, the administration has lost roughly nine out of every ten cases decided on the merits in federal district court. In his first term, it won just 23 percent of challenges to its regulatory actions, compared with about 70 percent for prior administrations. Across 4,095 business lawsuits over three decades, a precise tally is impossible, though in the defamation subset he won only one case. The question of how many lawsuits Trump has lost is best answered term by term and category by category.
Second-Term Lawsuits Since January 2025
More than 750 lawsuits have been filed against the second Trump administration since January 20, 2025, according to a New York Times tracker.1The New York Times. Trump Administration Lawsuits The Just Security tracker at the Reiss Center on Law and Security counts 803.2Just Security. Tracker: Litigation and Legal Challenges to the Trump Administration
Of the 172 cases that have produced a final district court decision, the administration has won 7. Plaintiffs have won 67, 96 were dismissed, and 2 ended in mixed outcomes.1The New York Times. Trump Administration Lawsuits Setting aside dismissals, that is roughly a nine-to-one loss rate on the merits.
Broader counts that include preliminary rulings show similar patterns. The Just Security tracker records 262 plaintiff wins, counting temporary blocks and permanent orders, against 126 government wins.2Just Security. Tracker: Litigation and Legal Challenges to the Trump Administration Forbes, working from 191 rulings as of July 2025, put the administration’s overall success rate at 31 percent, with a 60 percent loss rate and 9 percent mixed. It also found a stark split by appointing president: the administration won 76 percent of rulings before Trump-appointed judges but just 14 percent before judges appointed by other presidents.3Forbes. Trump’s Success Rate in the Courts So Far: 31% A Stanford analysis found the administration lost 96 percent of federal district court rulings in May 2025 alone, including 72 percent from Republican-appointed judges and 80 percent from Democratic-appointed judges.4Democracy Docket. Trump Lower Court Streak Legal Losses
The Supreme Court Has Been Friendlier, With Notable Exceptions
The Supreme Court has ruled for the administration in 20 of 24 emergency docket cases in 2025, and the administration secured 22 total victories at the high court before that streak began to fracture in 2026.5SCOTUSblog. Looking Back at 2025: The Supreme Court and the Trump Administration6NBC News. Trump’s Winning Streak at Supreme Court Came to Abrupt End
The losses at the Supreme Court, though fewer in number, have been consequential. In a 7-2 vote, the Court blocked use of the Alien Enemies Act to deport Venezuelan nationals to a prison in El Salvador. A 6-3 ruling held that the president lacked authority to federalize the Illinois National Guard for immigration enforcement.5SCOTUSblog. Looking Back at 2025: The Supreme Court and the Trump Administration7Supreme Court of the United States. Trump v. Barbara8USA Today. Trump Supreme Court Cases: Immigration and Birthright Citizenship In consolidated tariff cases, the Court held that the International Emergency Economic Powers Act does not authorize the president to impose tariffs, noting that no president had used the statute for that purpose in its half-century of existence.9Supreme Court of the United States. Learning Resources, Inc. v. Trump
First-Term Lawsuits, 2017 to 2021
Trump’s first term produced one of the worst court records in modern presidential history. The Institute for Policy Integrity at NYU School of Law tracked legal challenges to the administration’s agency actions and found a win rate of just 23 percent, compared with roughly 70 percent for prior administrations going back decades.10NYU Law. Tired of Winning: Judicial Review of Regulatory Policy in the Trump Era
An NYU tracker that counted individual case outcomes found 54 successful results against 192 unsuccessful ones across 246 tracked outcomes.11NYU Institute for Policy Integrity. Trump Court Roundup The study concluded that judicial ideology did not explain the low win rate. Even Republican-appointed judges ruled against the administration frequently. The main reasons agencies lost: acting outside their statutory authority, failing to follow required procedures like notice-and-comment rulemaking, and failing to adequately explain reversals of prior policy.10NYU Law. Tired of Winning: Judicial Review of Regulatory Policy in the Trump Era
Notable first-term losses included the Supreme Court’s 2020 ruling preserving DACA, a ruling that withholding federal funding from “sanctuary” jurisdictions was unconstitutional, and the Supreme Court’s 2021 decision preserving the Affordable Care Act.12Santa Barbara Independent. We Tracked California’s Lawsuits Against Donald Trump At the Supreme Court itself, Trump’s first-term win rate was approximately 47 percent, below the 65 to 67 percent typical for presidents from Roosevelt through Obama and below Reagan’s 75 percent high.13Washington University in St. Louis School of Law. Trump Has the Worst Record at the Supreme Court of Any Modern President
Business Lawsuits Over Three Decades
Before entering politics, Trump and his companies were involved in 4,095 lawsuits, according to a USA Today investigation. He was plaintiff in 2,121 of them and defendant in 1,919. The largest category was casino-related litigation at 1,863 cases, followed by personal injury claims at 697 and real estate disputes at 622.14USA Today. Trump Lawsuits
A precise win-loss count across all 4,095 cases does not exist. Many ended in settlements or dismissals where the resolution is unclear, and USA Today noted that “not all outcomes or information could be determined.” Within the defamation subset, the analysis found Trump won only one case, and that outcome was disputed.14USA Today. Trump Lawsuits
Trump’s Personal Criminal and Civil Cases
His personal cases have gone in different directions. In the New York hush money case, Trump was convicted on 34 felony counts of falsifying business records. On January 10, 2025, Judge Juan Merchan sentenced him to an unconditional discharge, meaning no prison time, probation, or fines, though the conviction remains on his record. The judge called it “the only lawful sentence that does not encroach on the office of the president.”15NPR. Trump Sentencing New York
The federal election interference case brought by Special Counsel Jack Smith was effectively shelved once Trump took office, consistent with Department of Justice policy against prosecuting a sitting president. The federal classified documents case was dismissed by Judge Aileen Cannon, and prosecutors withdrew their appeal after the inauguration.16ABC News. Trump’s Criminal Cases
In Georgia, District Attorney Fani Willis was disqualified by the Georgia Court of Appeals for a conflict of interest, and the Georgia Supreme Court declined to reverse that decision in a 4-3 ruling in September 2025.17The New York Times. Fani Willis Georgia Trump The case was handed to Pete Skandalakis of the Prosecuting Attorneys’ Council of Georgia, who moved to dismiss it entirely in November 2025.18NPR. Georgia Trump Election Case Dismissed
In the New York civil fraud case, a mid-level appeals court threw out the original financial penalty of approximately $464 million (over $500 million with interest), calling it “unlawfully excessive.” But the court upheld the underlying finding that Trump, his company, and two of his eldest sons are liable for fraud. A three-year ban on Trump serving as an officer of a New York company remains in place, along with an independent monitor overseeing the Trump Organization. Both sides have appealed to the state’s highest court.19BBC. New York Civil Fraud Penalty Thrown Out20The Hill. Trump Asks NY Court to Toss Remnants of Fraud Case
The Supreme Court declined to hear Trump’s personal appeal of a $5 million jury verdict finding him liable for sexual abuse and defamation in the E. Jean Carroll case, leaving that judgment intact. A separate $83.3 million defamation verdict in the same matter was upheld by a federal appeals court in September 2025 and remains subject to a possible Supreme Court petition.21The Guardian. Supreme Court Trump E. Jean Carroll
How the Record Compares Historically
By the measures researchers use to compare presidents, Trump’s court record is the worst in the modern era. The Institute for Policy Integrity’s data on major regulatory rules shows the Clinton administration winning 63 percent of the time. Trump’s rate was the lowest recorded, falling below Biden’s as well.22NYU Institute for Policy Integrity. Presidential Win Rates
At the Supreme Court, presidents from Roosevelt through Obama prevailed in roughly two-thirds of their cases. Obama’s 50.5 percent was the lowest in that dataset. Trump’s first-term Supreme Court win rate of 47 percent fell below even Obama’s mark.13Washington University in St. Louis School of Law. Trump Has the Worst Record at the Supreme Court of Any Modern President In the second term, heavy reliance on emergency applications has produced a stronger Supreme Court record on the emergency docket, but landmark losses on birthright citizenship, tariff authority, and the Alien Enemies Act have reshaped the boundaries of executive power all the same.