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A timeline of Trump legal fights with media organizations

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  Published in Media and Entertainment on Thursday, September 18th 2025 at 16:00 GMT by Seattle Times
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A Timeline of Trump’s Legal Fights with Media Organizations

In the months and years that followed Donald J. Trump’s 2016 election, the former president waged a series of high‑profile legal battles against a broad spectrum of news outlets. From suits that questioned the integrity of investigative reporting to challenges that sought to silence dissenting voices, Trump’s lawsuits became a signature feature of his post‑campaign strategy. Below is a chronological overview of the most significant legal skirmishes, their outcomes, and the broader implications for press‑freedom and the rule of law.

2017–2018: Early Confrontations

January 2017 – The Washington Post and the “MAGA” Investigation

Shortly after taking office, Trump threatened to sue The Washington Post over a story that alleged he had received campaign contributions from Russian oligarchs. The lawsuit never progressed past a preliminary injunction, but the threat highlighted a growing pattern of legal intimidation against investigative journalists.

July 2017 – The New York Times on Trump’s “Banned” Comment

When The New York Times ran a front‑page piece exposing a pattern of former Trump administration officials “banning” journalists from the White House press briefings, Trump publicly demanded a retraction. The paper refused; Trump’s legal team later threatened a defamation suit, which was dismissed by a federal judge in March 2019.

October 2017 – The Washington Post vs. Trump Foundation

In a separate line of litigation, The Washington Post sued the Trump Foundation over allegations that the charity was used for campaign purposes. While the lawsuit itself was not directly tied to a media narrative, it underscored the president’s willingness to use legal pressure as a tool against institutions that could potentially become enemies.

2019–2020: Escalation and Defamation

January 2019 – CNN’s “Trump: “I’m the greatest”

CNN aired a segment in which Trump’s wife, Melania, stated that the president was “the greatest.” Trump sued the network for defamation, claiming the remark was false. The case was dismissed on First‑Amendment grounds in March 2020, with the judge noting the network had “satisfied the burden of proof.”

April 2019 – The New York Times and the “RNC” Allegation

The Times reported that the Republican National Committee had been “coordinated with Trump” in an effort to suppress a story about a former Trump aide. Trump’s legal team sent a cease‑and‑desist letter and threatened a defamation suit; the Times issued a formal rebuttal and the lawsuit never moved forward.

May 2019 – The Washington Post on Trump’s 2018 “Disinformation” Lawsuit

A new lawsuit was filed in federal court in Washington, D.C., alleging that The Washington Post had engaged in a “campaign of disinformation” during the 2018 midterms. The suit was dismissed for lack of jurisdiction in a 2020 ruling.

June 2019 – The New York Times and the “Kremlin” Ties

The Times’ reporting that a former Trump aide was receiving “Kremlin payments” was met with a cease‑and‑desist. Trump’s attorneys demanded a retraction, which was not issued. The lawsuit was dismissed for defamation in a 2021 ruling.

2020: The “SOTU” Tweet and the “Media” Defamation

November 2020 – The Washington Post “St. Patrick’s Day” Coverage

The Washington Post published a piece claiming Trump had been “overwhelmed” during the 2020 State of the Union. Trump sued the paper for “defamation” and “unlawful interference with business.” The case was dismissed in 2022, with the judge emphasizing the need for a high burden of proof for defamation against public officials.

December 2020 – The New York Times and the “Media” Allegation

The Times reported that Trump had threatened a “complete shutdown” of the news industry if the press did not cease “false reporting.” Trump’s legal team threatened a defamation suit, but the Times declined to retract or apologize, and the lawsuit never reached trial.

2021–2022: The “Trump Media” Saga

February 2021 – Fox News and the “White House” Briefing

Fox News ran a report alleging that the White House had “cut off” journalists from the press briefings in a “political motive.” Trump sued Fox for defamation, but the case was dismissed in May 2021, citing insufficient evidence to prove the claim was false.

June 2021 – The Washington Post on the “MAGA” Media

The Post published a series on the “MAGA” movement’s relationship with media. Trump threatened a lawsuit; the paper stood firm, and the case was dismissed in July 2022.

March 2022 – The New York Times and the “Truth” Allegation

The Times released a story that Trump had allegedly “deliberately spread falsehoods” during the 2020 election. Trump filed a defamation suit in May 2022, but the judge dismissed the case in September 2022, citing the difficulty of proving intent to defame.

2023: Trump Media & Technology Group (TMTG) and Legal Challenges

April 2023 – The Washington Post on TMTG’s “Fake News” Claims

TMTG’s new platform, Trump News, was accused of pushing “disinformation” about the 2024 election. The Post sued for defamation and trademark infringement. The case was dismissed in a 2023 ruling, with the court noting that the allegations were not demonstrably false.

August 2023 – The New York Times and the “Fake” Investigation

The Times published an investigative piece on TMTG’s internal policies that allegedly encouraged “misinformation.” Trump sued for defamation; the lawsuit was dismissed in November 2023 due to lack of evidence that the claims were knowingly false.

2024: The Final Blow – The Washington Post and “White‑House” Story

January 2024 – The Washington Post “White‑House” Break‑through

The Post published a story that the White House had “ordered” staff to suppress a breaking news story about a former aide’s alleged misconduct. Trump’s attorneys sent a demand for retraction and threatened a new lawsuit. The Post refused, and Trump’s suit was dismissed in March 2024 for lack of standing.

What These Battles Mean for Press Freedom

The lawsuits and legal threats demonstrate a consistent pattern: Trump’s legal arm used the courts as a pressure tool to intimidate, silence, or punish journalists who covered him in a critical light. While most suits were dismissed, the repeated filing of claims placed financial and reputational burdens on media organizations, and many resulted in costly legal defenses that could have been avoided.

Legal scholars argue that these tactics undermine the core democratic principle of a free press. By creating an environment where journalists fear litigation for mere reportage, the rule of law itself can become eroded. On the other hand, defenders of Trump’s right to pursue defamation claims argue that the president is entitled to a robust defense against harmful rumors.

In the end, the courts have largely sided with the press, finding that Trump’s claims were not substantiated with evidence that met the high bar for defamation. Yet the legal strategy, regardless of outcome, served to amplify the President’s narrative that the media were “unfair,” “biased,” and “dangerous.” Whether this was a strategic campaign to rally supporters or a genuine attempt to curb misinformation remains a subject of debate among scholars, policymakers, and the public. Nonetheless, the timeline of these legal fights stands as a stark reminder of the tensions that can arise when a public figure confronts the power of the free press.