Alan Dershowitz Suggests Rosie O'Donnell Could Face Defamation Suit Over Trump-Epstein Allegations

Harvard Law Professor Emeritus Alan Dershowitz has suggested that comedian and actress Rosie O'Donnell may have opened herself to potential defamation litigation following her recent statements linking former President Donald Trump to the late financier Jeffrey Epstein. The comments, which aired in a podcast interview, reignited long-simmering debates over Trump's past association with Epstein and the limits of free speech protections in public discourse.

O'Donnell's Controversial Claims

In an appearance on journalist Jim Acosta’s podcast, Rosie O’Donnell alleged that Trump paid Epstein “a billion dollars” tied to their former friendship, insinuating that the money was intended to keep secrets. She also speculated on why Trump’s name appeared in Epstein’s contact lists and related documents.

The remarks were instantly polarizing. Critics argued that O’Donnell provided no verifiable evidence to support her claims, while her supporters contended that public figures, particularly former presidents, are subject to intense scrutiny given the gravity of their influence. The interview amplified ongoing public interest in the Epstein case, as Epstein’s connections with a wide array of political, financial, and cultural figures continue to fuel both legitimate inquiries and baseless conspiracy theories.

Dershowitz's Swift Response

Alan Dershowitz, himself a controversial figure in the Epstein saga due to prior associations, offered a blistering rebuttal. Speaking on the television program Sunday Agenda, Dershowitz called O’Donnell a “despicable liar and defamer of people.” He went further, stating he would provide pro bono legal support to Trump should the former president decide to pursue legal action.

According to Dershowitz, Trump and Epstein’s relationship was neither close nor long-lasting. He argued that the former president distanced himself from Epstein after a disagreement and that there are no official records showing Trump implicated in criminal activities tied to Epstein. Dershowitz emphasized that public figures retain legal recourse against false claims if malice can be proven in court.

Defamation Law and Public Figures

The legal principle at the heart of this clash is defamation law as it applies to celebrities and political leaders. In the United States, the bar for proving defamation against a public figure is set high. Established by the Supreme Court’s landmark 1964 ruling in New York Times v. Sullivan, plaintiffs must demonstrate “actual malice”—that is, that false statements were made either knowingly or with reckless disregard for the truth.

This heightened standard protects free speech but also makes successful lawsuits rare. High-profile cases, such as Sarah Palin’s failed defamation suit against The New York Times, highlight the difficulty of meeting the stringent criteria. Dershowitz, however, argued that O’Donnell’s comments fit the standard of malicious falsehood, characterizing them as accusations with no factual grounding.

The Long Shadow of Epstein's Legacy

The broader context to O’Donnell’s remarks is the enduring public fascination with Jeffrey Epstein’s ties to elite figures. Epstein’s 2019 arrest on federal sex trafficking charges, and his subsequent death in prison, left many questions unresolved. His social circle, which included Donald Trump, Bill Clinton, Prince Andrew, and others, has been a source of constant speculation and legal scrutiny.

Trump’s name appears in Epstein’s so-called “black book” and flight records from Epstein’s private jet, but these documents also contain hundreds of names ranging from academics and politicians to entertainers and business executives. Trump has acknowledged knowing Epstein socially and once described him as a “terrific guy” before later stating that the two had a falling out.

By invoking these associations, O’Donnell tapped into a complex web of half-truths, speculations, and documented fact that continues to draw public attention. Yet, without documentary evidence to back her explosive statement of a billion-dollar hush payment, legal experts warn her comments open the door to litigation.

Historical Context of Celebrity Legal Clashes

Clashes between celebrities over statements made in the public domain are not new. Hollywood has a long history of defamation lawsuits, from Shirley Temple’s family suing Graham Greene in the 1930s, to more modern legal disputes involving Johnny Depp, Amber Heard, and other high-profile cases.

In the political arena, lawsuits have surfaced over campaign ads, media commentary, and accusations made on social media. While some lawsuits have achieved success, more often they are dismissed, reflecting the judiciary’s consistent prioritization of free expression. Dershowitz’s intervention places O’Donnell’s remarks in this wider tradition of celebrity disputes escalating into legal battles.

Economic and Career Consequences

Beyond the courtroom, accusations of this magnitude can carry economic and reputational consequences. For O’Donnell, whose career has included stints as a talk show host, actress, and outspoken political commentator, backlash could come in the form of reduced opportunities in mainstream entertainment or advertising. Negative publicity tied to defamation claims has historically deterred sponsors, studios, and collaborators wary of brand damage.

For Trump, continued association with Epstein in public discourse has potential implications for business and political ventures. Even unfounded claims can shape public perception, complicating efforts to rehabilitate or advance post-presidency projects. Dershowitz highlighted these reputational stakes, arguing that truth-based protections must apply as vigorously to public figures as to private individuals.

Comparisons With Regional and Global Precedents

The question of defamation and freedom of speech takes different forms around the world. In the United Kingdom, libel laws are much stricter, often favoring plaintiffs. High-profile cases such as Meghan Markle’s legal battle against publishing outlets highlight the greater likelihood of claimants succeeding in UK courts.

In contrast, the United States’ reliance on the Sullivan standard reflects a cultural and judicial commitment to expansive free speech protections, even at the expense of a public figure’s reputation. Germany and France fall somewhere in between, affording individuals stronger privacy and defamation protections while still defending press freedom.

This global perspective underscores the uniquely challenging environment O’Donnell may face should litigation proceed under U.S. defamation law. The protection of sharp and even unfounded commentary remains a bedrock principle in American jurisprudence, but a case framed as intentional or reckless falsehood could still gain traction.

Public Reaction and Cultural Impact

Public response to the dispute underscores the division surrounding both Trump’s legacy and the Epstein scandal. On social media, supporters of O’Donnell praised her bravery in questioning Trump’s history, while detractors accused her of spreading baseless conspiracies. The incident also intensified broader debates about the role of celebrities in shaping political narratives and the line between commentary and misinformation.

For Dershowitz, stepping into the fray was also a reminder of his own history with Epstein allegations, which he strenuously denies and has fought in court. His willingness to go on the offensive against O’Donnell reflects his ongoing investment in defending both himself and those around him against what he sees as unfounded attacks.

What Happens Next

Whether Trump will seek to sue O’Donnell remains uncertain. Legal experts note that former presidents rarely file defamation suits, both because of the difficulty of proving malice and the risk of sustaining more public attention on the original claim. Yet Dershowitz’s offer to assist provides at least a theoretical framework for how litigation could proceed.

A lawsuit would require Trump’s legal team to demonstrate factual falsity in O’Donnell’s remarks about a billion-dollar payment, while also proving her intent or reckless disregard for the truth. If successful, damages could be awarded, and O’Donnell might face significant financial and reputational setbacks. If unsuccessful, however, the case could amplify her claims while reinforcing First Amendment protections for outspoken critics.

Conclusion

The O’Donnell-Dershowitz-Trump dispute encapsulates the enduring tension between personal reputation and the right to free expression in American public life. It is a case study in how high-profile figures, longstanding enmities, and unresolved scandals intersect in ways that reverberate well beyond the individuals involved. Whether or not a lawsuit materializes, the controversy has reignited cultural debates over responsibility, truth, and accountability in the age of celebrity politics.