Donald Trump has lost a significant number of lawsuits in recent years, with the biggest defeats falling into three groups: the two E. Jean Carroll civil verdicts, which together total roughly $88 million; a run of defamation suits he filed against news organizations that judges have dismissed; and hundreds of court rulings blocking executive actions during his second term. He was also convicted on 34 felony counts in Manhattan in May 2024.
The E. Jean Carroll Verdicts
The largest courtroom losses Trump has sustained came in two civil trials brought by the writer E. Jean Carroll. In May 2023, a Manhattan federal jury found him liable for sexual abuse and defamation and awarded Carroll $5 million. In January 2024, a second jury awarded her $83.3 million in defamation damages over statements Trump made in 2019 calling her a liar and saying she was “not his type.”1ABC News. Appeals Court Upholds $83 Million Judgment Against Trump for Defaming Carroll
Trump appealed both, arguing chiefly that presidential immunity shielded him and that the United States should be substituted as defendant under the Westfall Act. The Second Circuit rejected the arguments in each case. On the $83.3 million judgment, a three-judge panel ruled in September 2025 that Trump “acted with, at a minimum, reckless disregard for the truth” and that the damages were not excessive, noting his attacks on Carroll reached an audience of up to 104 million people and produced hundreds of death threats against her.1ABC News. Appeals Court Upholds $83 Million Judgment Against Trump for Defaming Carroll On the $5 million verdict, a Second Circuit panel affirmed the trial court’s judgment on December 30, 2024.2Justia. Carroll v. Trump, No. 23-793
The full Second Circuit declined to rehear the $5 million appeal on June 13, 2025.3BBC. Court Declines to Rehear Trump Challenge to $5 Million Carroll Verdict It denied en banc review on the $83.3 million judgment on April 29, 2026, holding that presidential immunity is a waivable defense and that Trump waived it by waiting 15 months after trial to seek substitution.4Courthouse News Service. No En Banc in Trump Appeals of E. Jean Carroll Verdict, $83 Million Judgment
Trump has not paid either judgment. In May 2026, the Second Circuit paused the $83.3 million payment pending Supreme Court action but ordered Trump to increase his bond by $7.46 million to cover accruing interest, bringing the total to nearly $100 million.5The Guardian. Appeals Court Delays Trump Payment in E. Jean Carroll Case6NBC News. Appeals Court Pauses Trump $83 Million Payment to E. Jean Carroll His petition asking the Supreme Court to overturn the $5 million verdict has been rescheduled for conference at least eleven times without action.7SCOTUSblog. Court Puts Off Deciding Whether to Consider $5 Million Verdict Against Trump Yet Again
Defamation Suits Trump Filed and Lost
Trump has filed a series of high-dollar defamation cases against news organizations. Several have already been dismissed.
CNN and the “Big Lie”
Trump sued CNN in 2022 for $475 million, arguing the network’s use of “Big Lie” to describe his 2020 election fraud claims evoked Nazi comparisons. U.S. District Judge Raag Singhal dismissed the case in July 2023, ruling the phrase was protected opinion.8NPR. Federal Judge Dismisses Trump Defamation Case Against CNN Over Big Lie A unanimous three-judge panel of the Eleventh Circuit upheld the dismissal on November 18, 2025, calling Trump’s argument that the term was an unambiguous factual statement “untenable.” Two of the three judges were Trump appointees.9Politico. Court Rejects Trump Big Lie Defamation Lawsuit Trump’s legal team has said it intends to petition the Supreme Court.10National Law Journal. Trump to Ask Supreme Court to Revive CNN Lawsuit Over Phrase Big Lie
Bob Woodward and “The Trump Tapes”
Trump sued Bob Woodward, Simon & Schuster, and Paramount Global in January 2023 for nearly $50 million over the audiobook The Trump Tapes, which used recordings of 19 interviews. On July 18, 2025, U.S. District Judge Paul Gardephe dismissed the case in an 81-page ruling, finding Trump had not plausibly established any copyright interest in his interview responses or shown he was a joint author of the audiobook. The judge said it “appears unlikely” Trump could cure the deficiencies.11CNN. Trump Bob Woodward Simon Schuster Lawsuit Dismissed12NBC News. Judge Dismisses Trump Lawsuit Over Bob Woodward Audiobook
The New York Times and “Lucky Loser”
Trump’s $15 billion defamation suit against the New York Times, Penguin Random House, and several reporters, filed in September 2025, was struck four days later by U.S. District Judge Steven Merryday for violating Rule 8 of the Federal Rules of Civil Procedure. Merryday called the 85-page complaint “decidedly improper and impermissible” and described it as a “megaphone for public relations.”13CNN. Trump New York Times Lawsuit Dismissed14The Guardian. Trump New York Times Defamation Complaint15Civil Rights Litigation Clearinghouse. Trump v. New York Times
The Wall Street Journal and the Epstein Letter
Trump’s $10 billion suit against the Wall Street Journal, Dow Jones, Rupert Murdoch, and two reporters concerns a July 2025 article about a sexually suggestive letter allegedly bearing Trump’s signature in a 2003 birthday album for Jeffrey Epstein. Trump denies writing the letter. U.S. District Judge Darrin Gayles dismissed the complaint in April 2026, finding Trump failed to plausibly allege that the Journal published the story with “actual malice.”16NPR. Judge Dismisses Trump Lawsuit Over Epstein Letter WSJ Story Trump refiled an amended complaint on May 27, 2026, which is pending.17Politico. Trump Epstein Suit Wall Street Journal
Suits Still in Progress
Several other Trump-filed cases have not been decided and are not defeats yet. A $10 billion suit against the BBC over the edited Panorama documentary is at the motion-to-dismiss stage.18Politico. BBC Lawsuit Donald Trump A suit against the Des Moines Register and pollster J. Ann Selzer over a November 2024 Iowa Poll is pending in Polk County District Court.19Des Moines Register. Judge to Rule on Trump Lawsuit Against Des Moines Register Over Iowa Poll A 2022 libel suit against the Pulitzer Prize Board survived a motion to dismiss and is in discovery.20Bloomberg Law. Mueller Report, Trump Russia Evidence Demanded in Pulitzer Suit
The ABC and Paramount Settlements Are Not Losses
Two media cases ended with payments to Trump, and they are often described as wins for him rather than losses. ABC News settled a defamation suit in December 2024, agreeing to pay $15 million to Trump’s presidential library and $1 million in legal fees, after George Stephanopoulos said on air that Trump had been “found liable for rape.” The Carroll jury had found Trump liable for sexual abuse, not “rape” under New York’s narrow penal-code definition. The settlement was reached the same day a federal magistrate ordered depositions of both Trump and Stephanopoulos.21NPR. ABC E. Jean Carroll Trump George Stephanopoulos22The New York Times. Trump ABC Settlement
Paramount settled a separate suit over a 60 Minutes interview with Kamala Harris in July 2025, agreeing to pay $16 million to Trump’s presidential library. CBS had released the full unedited transcript in February 2025 and maintained the editing followed standard broadcast practice. Legal experts widely called the underlying suit “frivolous and unwinnable” under the First Amendment. CBS News CEO Wendy McMahon and 60 Minutes executive producer Bill Owens resigned over the settlement, and Democratic senators called the payment a “bribe” tied to regulatory approval of Paramount’s merger with Skydance Media.23AP. Paramount Will Pay $16 Million in Settlement With Trump Over 60 Minutes Interview24The New York Times. Trump Paramount CBS 60 Minutes Lawsuit
Losses on Executive Actions
The Trump administration has faced more than 750 lawsuits during the second term. Courts have partially or fully blocked policies in over 150 cases, and among cases that have reached a final decision, plaintiffs have won 67 while the administration has won 7.25The New York Times. Trump Administration Lawsuits
Notable defeats include rulings against executive orders sanctioning law firms that opposed Trump. In May 2025, Judge Beryl Howell held that an order targeting Perkins Coie violated the First, Fifth, and Sixth Amendments and permanently blocked its enforcement. Weeks later, Judge John Bates declared a similar order against Jenner & Block “null and void” on First Amendment grounds. The appeals were consolidated at the D.C. Circuit.26Just Security. Tracker: Litigation and Legal Challenges to the Trump Administration
The Supreme Court delivered several losses on its emergency docket in 2025. In an apparent 7-2 vote, it stopped the administration from using the Alien Enemies Act of 1798 to deport Venezuelan nationals to a prison in El Salvador. In a 6-3 decision, it ruled Trump lacked authority to federalize the Illinois National Guard. In a 5-4 vote, it declined to halt a district court order requiring the administration to pay nearly $2 billion in foreign assistance reimbursements.27SCOTUSblog. Looking Back at 2025: The Supreme Court and the Trump Administration
Lower courts have ruled against the administration on immigration detention (roughly 225 judges found a mandatory detention policy likely violated due process), F-1 student visa cancellations (reversed after more than 100 lawsuits), the exclusion of the Associated Press from events over its use of “Gulf of Mexico,” and attempts to condition disaster relief and transportation grants on immigration compliance.25The New York Times. Trump Administration Lawsuits26Just Security. Tracker: Litigation and Legal Challenges to the Trump Administration
The Manhattan Criminal Conviction
In May 2024, a Manhattan jury convicted Trump on 34 felony counts of falsifying business records tied to hush-money payments during his 2016 campaign. Judge Juan Merchan sentenced him on January 10, 2025, to an unconditional discharge, the lightest sentence available under New York law. It carries no jail time, probation, or fine, but the conviction stands.28ABC News. Trump Formally Appeals New York Hush Money Conviction
Trump’s lawyers at Sullivan & Cromwell filed a formal appeal with New York’s Appellate Division on October 27, 2025, arguing the trial improperly included evidence of official presidential acts, that Merchan should have recused over $35 in political donations, and that prosecutors improperly elevated time-barred misdemeanors into felonies.29The Hill. Trump Hush Money Conviction Appeal A parallel petition to transfer the case to federal court on presidential immunity grounds was still pending as of late October 2025.30NBC New York. Donald Trump Hush Money Appeal
The two federal criminal cases against Trump, over classified documents and the January 6 investigation, were dropped by the Justice Department in November 2024 after his election victory. The Georgia election interference case is indefinitely paused pending a ruling on whether the Fulton County district attorney should be disqualified.31CNN. Trump Indictments Criminal Cases