UK attorney Mark Stephens delivered a striking assessment to media observers: Donald Trump has surpassed Prince Harry as the courts’ most prolific litigant among high-profile figures. While Harry has pursued privacy battles against British tabloids, Trump has launched an unprecedented legal assault on American media outlets, fundamentally reshaping how powerful individuals weaponize litigation.
The comparison highlights a significant shift in how influence operates within the legal system. Both men have filed lawsuits, but their strategies, objectives, and scale differ dramaticallyâand the implications for press freedom are profound.
Harry’s Privacy Battle
Prince Harry’s legal journey began in 2020 when he and Meghan Markle relocated to California and lost their taxpayer-funded police protection. Harry challenged the decision as discriminatory and a threat to his family’s safety, but the UK Court of Appeal rejected his case in May 2025. Undeterred, he pivoted to attacking the British tabloids he blamed for decades of harassment.
Harry joined six other prominent figuresâincluding Sir Elton John and actress Liz Hurleyâin suing Associated Newspapers Limited, publisher of the Daily Mail. The allegations are severe: private investigators allegedly planted listening devices, wiretapped phones, bribed police officers, and illegally accessed medical records spanning decades. A pre-trial hearing in late November set the stage for a trial in early 2026.
Associated Newspapers has vehemently denied all allegations, calling them “preposterous smears” lacking credible evidence. Complications have emerged, howeverâa private investigator’s confession of hacking may have been fabricated, potentially undermining key evidence and complicating what is already shaping up to be one of Britain’s most complex privacy trials.
Trump’s Media Offensive
Since 2024, President Trump has launched an aggressive legal campaign against major American media outlets, including ABC, CBS, The New York Times, and The Wall Street Journal. Media-law experts describe it as the most sustained legal offensive against the press by any sitting president in modern history.
In December 2024, ABC News settled Trump’s defamation lawsuit for $15 million after anchor George Stephanopoulos incorrectly stated Trump had been found liable for rape in an E. Jean Carroll case. ABC issued a statement of regret and covered $1 million in Trump’s legal fees. The settlement sent shockwaves through newsrooms, signaling that major networks might capitulate under legal pressure.
Months later, in July 2025, Paramount Global settled Trump’s lawsuit over a “60 Minutes” interview with then-Vice President Kamala Harris for $16 million. Trump accused CBS of deceptive editingâclaims the network disputed. The timing raised concerns: Paramount was simultaneously seeking FCC approval for an $8.4 billion merger with Skydance, a deal requiring Trump administration sign-off.
The Billion-Dollar Lawsuits
Trump’s ambitions extend far beyond these settlements. In September 2025, he filed a $15 billion lawsuit against The New York Times, alleging the paper acted as a “mouthpiece” for the Democratic Party and engaged in decades of defamatory coverage. A federal judge initially dismissed the complaint for procedural errors, but Trump’s legal team refiled an amended version in October 2025.
In July 2025, Trump filed a $10 billion lawsuit against The Wall Street Journal, claiming the paper defamed him by reporting on a birthday letter allegedly sent to convicted sex offender Jeffrey Epstein. Trump calls the letter “fake” and accuses The Journal and its owner, Rupert Murdoch, of ethical failures. The Journal has vowed to defend its reporting vigorously.
The Scorecard and Implications
Trump’s media lawsuits have already yielded $31 million in settlements, with $15 million from ABC and $16 million from CBS. His pending cases seek an additional $25 billion. If even a fraction of these cases succeed, Trump will have fundamentally altered how influential figures use litigation against the media.
The ABC and CBS settlements have triggered warnings of a “chilling effect” on press freedom. When major networks extract eight-figure payouts from influential figures, editorial decisions may begin prioritizing legal risk over newsworthiness. News organizations face a critical question: will they report aggressively on influential leaders, or will fear of bankrupting lawsuits force self-censorship?
Looking Forward
For Harry, the Daily Mail trial in early 2026 marks the culmination of years of legal warfare, representing his final major lawsuit against a British newspaper. For Trump, pending cases against The New York Times and Wall Street Journal could define his second term’s relationship with American media. Both men have proven willing to fight in court and reshape how power operates through litigation. Only one, however, has truly claimed dominance over the legal system itself.
Sources
ABC News settlement court filing and docket references confirming $15 million payment and $1 million in legal fees coverage.
Paramount Global/CBS settlement announcement and court dismissal filing confirming $16 million payment directed to Trump’s presidential library, with no apology.
Federal court docket for Trump v. New York Times Company (8:25-cv-02487, M.D. Fla.), including initial filing date and subsequent amended refiling entries.
Reuters filing on Trump’s $10 billion lawsuit against The Wall Street Journal over the Epstein letter report, confirming filing details and claimed damages.