Last Updated on July 22, 2025 by ThePublic
In April 2023, former President Donald Trump launched a $500 million lawsuit against his former attorney and fixer, Michael Cohen, alleging that Cohen violated attorney-client privilege and unjustly enriched himself through their relationship. The audacious claim, filed in a Florida federal court, was vintage Trump: a bold, headline-grabbing move aimed at punishing a disloyal ally turned critic. Yet, just six months later, in October 2023, Trump abruptly dropped the lawsuit, days before he was scheduled to be deposed under oath by Cohen’s legal team. For a man known for his litigious nature, with a track record of over 4,000 lawsuits, this retreat was stunning. What drove Trump to abandon a half-billion-dollar claim? The answer lies in a mix of legal peril, strategic backfiring, and the former president’s calculated instinct for self-preservation.
A Lawsuit Built on Shaky Ground
The lawsuit accused Cohen of breaching confidentiality by sharing details of his work for Trump in a tell-all book, Disloyal: A Memoir, and in public testimony before Congress. Trump claimed Cohen’s actions caused him reputational and financial harm, seeking a staggering $500 million in damages. Legal analysts, however, were skeptical from the start. Courts rarely award such sums for breaches of attorney-client privilege, especially when the client, Trump, had himself publicly discussed the matters in question, including the infamous Stormy Daniels hush money payments. Cohen’s attorneys argued that Trump had waived privilege long ago through his own statements on social media and in interviews, a point that weakened the case’s foundation.
Moreover, Cohen had already faced legal consequences for his role in Trump’s affairs, serving a three-year prison sentence for tax evasion, false statements, and campaign finance violations tied to the Daniels payments. His public disclosures, including testimony to Congress in 2019, were protected under whistleblower-like provisions, further undermining Trump’s claims. The $500 million figure seemed less a realistic demand and more a theatrical flourish, designed to intimidate Cohen and rally Trump’s base by painting him as a victim of betrayal.
The Deposition Dilemma
The turning point came in October 2023, when Trump’s legal team quietly filed to dismiss the lawsuit. The timing was no coincidence: Cohen’s lawyers were preparing to depose Trump under oath, a scenario the former president has spent decades avoiding. Depositions are a legal minefield, requiring sworn testimony that can be used in other cases or lead to perjury charges if false. For Trump, whose rhetorical style thrives on exaggeration and ambiguity, the prospect of being pinned down by Cohen’s attorneys was a clear danger.
Trump’s aversion to sworn testimony is well-documented. In the 2016 Trump University fraud case, he settled for $25 million just days before a scheduled court appearance. In the New York Attorney General’s investigation into the Trump Foundation, he paid $2 million and dissolved the charity, again, avoiding testimony. Most recently, in the New York civil fraud case against the Trump Organization, Trump invoked the Fifth Amendment over 400 times during a deposition, a stark contrast to his 2016 campaign rhetoric mocking others for taking the Fifth. “The mob takes the Fifth,” he said then. “If you’re innocent, why are you taking the Fifth Amendment?” The irony was not lost on observers when he employed the same tactic.
In the Cohen case, a deposition could have exposed Trump to questions not just about their attorney-client relationship but about broader issues: the hush money scheme, campaign finance violations, and internal Trump Organization practices. With multiple ongoing criminal and civil cases against him, including a Manhattan criminal trial where Cohen was a star witness—Trump likely saw the deposition as a Pandora’s box. Dropping the lawsuit was a strategic retreat to avoid opening it.
Discovery: A Double-Edged Sword
Beyond the deposition, the discovery process posed another threat. In civil lawsuits, both sides are entitled to request documents, emails, and communications relevant to the case. Cohen’s legal team could have demanded internal Trump Organization records, potentially uncovering evidence that could be used in other legal battles, such as the Manhattan hush money case or the New York AG’s fraud investigation. Trump, already under scrutiny for financial misconduct and election-related crimes, could ill afford to hand over such material. The risk of discovery likely outweighed any potential gain from pursuing the lawsuit.
A Failed Intimidation Tactic
The lawsuit’s collapse also reveals a broader pattern in Trump’s legal playbook: using litigation as a weapon to silence critics, only to back off when faced with real resistance. Trump has filed thousands of lawsuits over his career, from disputes with contractors to defamation claims against media outlets. Many are less about winning in court and more about generating headlines, intimidating opponents, or delaying accountability. The Cohen lawsuit fit this mold perfectly. By targeting Cohen, a key witness in the Manhattan criminal case, Trump may have hoped to discredit him or pressure him into silence. But Cohen, battle-hardened from his own legal woes and public feuds with Trump, refused to buckle. His legal team’s aggressive push for deposition signaled they were ready to fight, and Trump blinked.
This retreat mirrors other instances where Trump’s legal bluster has fizzled. In 2022, he sued CNN for defamation, seeking $475 million, only to drop the case a year later. In 2018, he threatened to sue The New York Times over a Pulitzer Prize-winning investigation into his family’s tax practices but never followed through. Each time, the pattern is clear: bold claims, media fanfare, and then a quiet withdrawal when the legal risks become too great.
The Political Calculus
The timing of the lawsuit’s dismissal also suggests a political dimension. In late 2023, Trump was gearing up for the 2024 presidential campaign, facing a crowded Republican primary field. A deposition in the Cohen case would have generated damaging headlines, especially if it touched on the Stormy Daniels scandal, which had already fueled his 2023 indictment in Manhattan. By dropping the lawsuit, Trump avoided a media circus that could have alienated voters or emboldened his rivals. Instead, he could focus on his narrative of being a victim of a “witch hunt,” a message that resonated with his base without the legal baggage of a deposition.
The Bigger Picture
The Trump-Cohen saga is more than a legal footnote; it’s a window into the former president’s approach to power, loyalty, and accountability. Cohen, once Trump’s loyal “fixer,” became a symbol of betrayal in Trump’s eyes, his public confessions and testimony a constant thorn. The lawsuit was an attempt to rewrite that narrative, casting Cohen as the villain and Trump as the wronged party. But when the legal realities set in, deposition risks, discovery threats, and a weak case, Trump did what he has done so often: he cut his losses and moved on.
Yet the story doesn’t end here. Cohen’s role as a witness in Trump’s criminal trials ensures their feud will remain in the spotlight. The dropped lawsuit, far from a resolution, is a chapter in an ongoing saga of legal chess, where every move is calculated for maximum leverage and minimum exposure. For Trump, the lesson is clear: lawsuits are a tool, but only until they become a liability. For Cohen, it’s a small victory in a long war, one he’s fighting not just in court, but in the court of public opinion.