In two Florida federal suits, Donald J. Trump alleges that The New York Times Company and Penguin Random House ($15B) and Dow Jones ($10B) defamed him. Trump filed a second amended complaint against the Times on August 27, 2026, as the court ordered. A ruling is pending on Dow Jones’s motion to dismiss his amended Wall Street Journal complaint with prejudice.
Latest development Aug 27, 2026
On August 27, 2026, Trump filed a 62-page second amended complaint against The New York Times and Penguin Random House, as Judge Steven D. Merryday ordered on July 27, 2026. The complaint adds specific claims of inaccuracies and still seeks $15B.
Why it matters
The cases test whether a sitting president can plead actual malice under New York Times v. Sullivan against major newspapers. After settlements by ABC and Paramount (CBS), they also test the leverage that large damages claims give over the press.
Background
In July 2025, Donald J. Trump sued Dow Jones & Company, News Corp, and Rupert Murdoch for $10B in the U.S. District Court for the Southern District of Florida. The suit concerns a July 2025 Wall Street Journal story about an Epstein birthday letter. The story described a bawdy 2003 letter bearing Trump’s signature, which he denies writing. In September 2025, Trump sued The New York Times Company, four of its reporters, and book publisher Penguin Random House for $15B in the U.S. District Court for the Middle District of Florida. He tied the claim to Times reporting and to the book “Lucky Loser.”
On September 19, 2025, Judge Steven D. Merryday struck the 85-page Times complaint as an improper “public relations” document. The complaint did not reach its first defamation count until page 80. The court gave Trump leave to refile, and he filed a 40-page amended complaint on October 16, 2025. The amended complaint dropped the extensive political narrative.
On April 13, 2026, Judge Darrin P. Gayles dismissed the Dow Jones suit with leave to amend. He found that the complaint came “nowhere close” to plausibly pleading actual malice. In May 2026, the court denied Trump pre-complaint discovery into actual malice, and Trump filed an amended complaint on May 28, 2026. On June 10, 2026, Dow Jones moved to dismiss the amended complaint with prejudice. It argued that the complaint fails the actual-malice pleading standard and renewed its request for attorney fees under Florida’s anti-SLAPP statute.
On July 27, 2026, Judge Merryday deferred ruling on the Times’ motion to dismiss and ordered Trump to file another amended complaint by August 27, 2026. On August 5, 2026, Judge Gayles heard argument on the Dow Jones motion, did not rule from the bench, and stayed discovery pending his written ruling. On August 27, 2026, Trump filed a 62-page second amended complaint against the Times and Penguin Random House, still seeking $15B. In both cases, the central question is whether the actual-malice allegations are sufficient.
Timeline 10 events
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FilingTrump files second amended complaint against New York Times
Trump filed the 62-page complaint against the Times and Penguin Random House under Judge Merryday’s July 27 order. It added specific claims of inaccuracies and continued to seek $15B in damages.
Trump Updates Defamation Suit Against The New York TimesTrump Trollsuit Against New York Times Damages Trollsuit Against IRS
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HearingJudge Gayles hears argument on renewed WSJ motion, stays discovery
Judge Darrin P. Gayles held a roughly 90-minute hearing in Miami on the renewed Dow Jones motion to dismiss Trump’s amended $10B complaint with prejudice. He did not rule from the bench and indicated a written ruling would follow soon.
Judge jams Trump on Epstein birthday book lawsuit after WSJ pushes for dismissalJudge signals Trump's defamation lawsuit against Wall Street Journal may be dismissed againTrump's revived Wall Street Journal lawsuit meets more skepticism in court
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OrderMerryday defers NYT dismissal ruling, orders further amended complaint
Judge Steven D. Merryday declined to rule immediately on the Times’ motion to dismiss Trump’s $15B defamation suit. He ordered Trump to file another amended complaint by August 27, 2026.
Judge Doesn\u2019t Toss Trump\u2019s $15 Billion New York Times Lawsuit, But It Must Be AmendedJudge Allows Trump to Refile His $15 Billion New York Times Defamation Suit
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FilingDow Jones moves to dismiss Trump’s amended WSJ complaint with prejudice
The Wall Street Journal’s attorneys argued that the amended complaint fails to meet the actual-malice pleading standard. They also renewed a request for attorney fees under Florida’s anti-SLAPP statute.
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FilingTrump refiles amended $10B WSJ complaint after discovery denial
After the court refused pre-complaint discovery into actual malice, Trump filed an amended complaint against Dow Jones.
No Discovery into Alleged ‘Actual Malice’ in Trump’s Lawsuit Against WSJ
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JudgmentJudge Gayles dismisses Dow Jones suit for failure to plead actual malice
The court found that the complaint came “nowhere close” to pleading actual malice and dismissed it with leave to amend.
No Discovery into Alleged ‘Actual Malice’ in Trump’s Lawsuit Against WSJ
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FilingTrump refiles a 40-page amended NYT complaint
The amended complaint dropped the extensive political narrative and stayed within the court’s page limit.
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JudgmentJudge Merryday strikes the NYT complaint as improper
The court called the 85-page filing an improper public-relations document and gave Trump leave to refile a 40-page complaint.
Federal judge tosses Trump’s $15B defamation lawsuit against New York Times
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FilingTrump sues The New York Times for $15B
The complaint named the Times, four reporters, and Penguin Random House, publisher of the book “Lucky Loser.”
Federal judge tosses Trump’s $15B defamation lawsuit against New York Times
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FilingTrump sues Dow Jones for $10B over WSJ Epstein-letter story
Trump sued Dow Jones, News Corp, and Rupert Murdoch over a Wall Street Journal report describing a 2003 birthday letter bearing his signature.
No Discovery into Alleged ‘Actual Malice’ in Trump’s Lawsuit Against WSJ
Experimental AI forecast
How it is madeHow will the Southern District of Florida rule on Dow Jones’s motion to dismiss Trump’s amended Wall Street Journal complaint with prejudice by March 31, 2027?
- WSJ suit dismissed with prejudice62%
- Still pending on March 31, 202715%
- Dismissed, Trump gets leave to amend again12%
- Trump’s WSJ claims survive dismissal7%
- Trump drops or settles WSJ suit4%
- Resolves by
- Mar 31, 2027in 5 months
- Record confidence
- Medium
The most likely result, at 62%, is that the Southern District of Florida dismisses Trump’s amended Wall Street Journal complaint with prejudice by March 31, 2027. The court already found the first complaint came “nowhere close” to pleading actual malice. It also denied pre-complaint discovery, so the amended pleading had no new evidence to draw on.
How it resolves. Resolved by the first written order on Dow Jones’s June 10, 2026, motion to dismiss in case 1:25-cv-23229 (S.D. Fla.), as shown on the public docket. “Dismissed with prejudice” means all claims against all defendants are dismissed and no further amendment is allowed. “Leave to amend again” means all claims are dismissed but Trump may file another complaint. “Claims survive” means at least one defamation claim against any defendant survives. “Drops or settles” means a voluntary dismissal or announced settlement before any ruling. The anti-SLAPP fee ruling does not affect resolution. If none of these has occurred by March 31, 2027, the result is “Still pending.”
Reasoning
Starting point. Renewed Rule 12(b)(6) motions in public-figure defamation suits after an earlier dismissal for failure to plead actual malice: Public-figure defamation claims are often dismissed at the pleading stage on actual malice. Roughly 60% to 75% of renewed motions after an earlier actual-malice dismissal are granted, and the Eleventh Circuit has affirmed such dismissals (Michel v. NYP Holdings).
Renewed motions to dismiss after a first actual-malice dismissal succeed in most public-figure cases, and courts rarely grant a third chance to plead. The April 13, 2026, order found the original complaint came “nowhere close” to the standard. The May 2026 denial of pre-complaint discovery left Trump to replead largely from the same public record. Those facts push dismissal with prejudice above the base rate. The main alternative to a merits loss is timing. The motion was argued on August 5, 2026, and a written ruling was said to follow soon, but district court opinions can take many months, so 15% is left for a still-pending docket. A further leave to amend remains possible if the amended complaint adds new factual allegations about the letter’s authenticity. Settlement or withdrawal is unlikely because Dow Jones has sought anti-SLAPP fees and has shown no public interest in settling. The Times case is not the focus here because the second amended complaint was filed only on August 27, 2026, and new briefing must follow before any ruling.
Prior order found actual malice “nowhere close” to pleaded · Court denied pre-complaint discovery into actual malice · Pace of a written ruling after August 5 hearing · Dow Jones pressing anti-SLAPP fees, not settlement · Courts rarely allow a third complaint after repeated failures
Generated automatically by Claude Opus 5.5 on Sep 24, 2026 from this case’s record on this site, and published without editorial review. The probabilities are the model’s judgment, not measured frequencies, and they are scored publicly as cases resolve. Not legal or investment advice. How the forecasts are made