Michael J. Gottlieb

Counting What Was Missing

The order that changed Freeman v. Giuliani begins by counting what was missing. After months of motions, hearings, extensions, and production orders, Rudolph Giuliani’s initial production amounted to 193 documents. The court described what the later effort produced: largely one page of communications, indecipherable data, a sliver of the required financial material, and stipulations offered in place of discovery. For Ruby Freeman and Shaye Moss, that absence bore directly on proof—how the accusations were spread, how far they traveled, what records remained, and what punitive damages could accomplish.

Gottlieb signed the plaintiffs’ sanctions reply. His declaration reported that, even after a court order, Giuliani had produced only two financial documents, both years old. He later signed the appellate brief asking the D.C. Circuit to affirm the judgment. Between those filings came a damages trial, final judgment, a follow-on injunction, bankruptcy litigation, and settlement enforcement. His work held the case together while its forum and remedy changed.

Gottlieb and the team remained in the case through preservation, discovery, trial, judgment, appeal, collection, and settlement. They traced falsehoods that spread through broadcasts, social platforms, fundraising, and private messages, then pursued damages, an injunction, and enforcement after Freeman and Moss received physical threats.

What Discovery Was Supposed to Prove

Freeman and Moss were Fulton County election workers. After the 2020 presidential election, Giuliani repeatedly accused them of manipulating ballots and participating in election fraud. The final judgment declared the actionable statements false, defamatory, made with actual malice, published without privilege, and harmful. Because liability was entered by default rather than decided by a merits jury, the central legal struggle concerned the integrity of the discovery process that should have produced a complete record.

The requested discovery went to the center of the case. Communications could show who developed and circulated the accusations. Electronic account data could reveal preservation and publication history. Audience information could measure reach. Financial records mattered to punitive damages. When a defendant controls those materials, delay and nonproduction can leave plaintiffs unable to reconstruct the private communications, decisions, and systems behind conduct that unfolded publicly.

Giuliani’s stipulations conceded factual elements of liability in this action while reserving arguments that his statements were protected, nonactionable opinion on appeal. His counsel also described the handling of data seized from electronic devices. Because default is an exceptional sanction, the court considered those explanations before finding the reservations inadequate, identifying inconsistencies in the account of what the discovery vendor held, and concluding that continued noncompliance had left no adequate lesser remedy.

When nonproduction becomes liability

Federal Rule of Civil Procedure 37 gives courts escalating tools when evidence is lost or orders are disobeyed. The August 2023 opinion applied two of its strongest provisions: Rule 37(e)(2)(C), addressing electronically stored information, and Rule 37(b)(2)(A)(vi), authorizing default for failure to obey discovery orders. The court found willful shirking of preservation and production duties and substantial prejudice to Freeman and Moss. It entered default on their claims for defamation, intentional infliction of emotional distress, and civil conspiracy, together with entitlement to seek punitive damages.

A discovery default prevents a party that withheld evidence from using the missing record as an advantage. It fixes liability without pretending the underlying record was complete. The court still required proof of damages, and Giuliani retained the ability to contest how much harm his conduct caused. That division preserved the jury’s role in assessing damages while curing the evidentiary prejudice the court attributed to him.

Gottlieb’s declaration gave the sanctions motion a concrete scale. The financial production, he stated, consisted of a 2018 tax return and a 2019 divorce-court transcript. His signature on the reply tied counsel’s argument to a sworn account of what had actually arrived. The court then tested the omissions against inventories, vendor representations, production logs, minute orders, and fee applications.

A jury measured the harm

The December 2023 trial began with liability already established. The jury’s task was damages. It awarded Freeman $16.171 million and Moss $16.998 million in defamation damages, $20 million to each woman for intentional infliction of emotional distress, and $75 million in punitive damages. The total verdict was $148,169,000.

Those categories separated injuries that public discussion often blends together. Defamation damages addressed injury to reputation. Emotional-distress damages addressed the personal consequences of being turned into the human target of an election conspiracy theory. Punitive damages addressed punishment and deterrence. The trial team presented each category separately while keeping Freeman and Moss’s experiences at the center of the damages evidence.

Freeman and Moss framed the verdict as a step toward recovering their names. Gottlieb had helped secure liability when missing evidence threatened proof, helped take damages to a jury, and remained counsel through post-judgment motions and appeal. The judgment still had to survive those proceedings and later bankruptcy enforcement.

Why the verdict and judgment have different numbers

The jury’s $148.169 million verdict is the figure most often associated with the case. The final judgment, entered three days later, used a different measure. The parties stipulated to the amount of judgment, and the court ordered $145.969 million in damages. It then added three fee awards—$89,172.50, $43,684, and $104,256.50—for another $237,113. The resulting principal was $146,206,113, with interest accruing under the rates and dates specified in the judgment.

The judgment also supplied declaratory relief. It fixed, as between the parties, the falsity and defamatory character of the actionable statements, actual malice, publication without privilege, harm, outrageous conduct, emotional distress, and conspiracy findings. Those declarations carried the legal consequences of the default and final judgment without converting the damages jury into a liability jury.

The Permanent Injunction

The damages award addressed past harm. Freeman and Moss also sought an order stopping Giuliani from repeating the accusations. In a later action, he consented in May 2024 to a permanent injunction barring him from again accusing either woman of wrongdoing related to the 2020 election. If he violated the order, they could return promptly to the federal court in Washington.

Giuliani’s bankruptcy automatically stayed many lawsuits and collection efforts. Freeman, Moss, Giuliani, and the creditors’ committee therefore asked the bankruptcy court to lift the stay so the Washington court could enter and enforce the permanent injunction. The agreed order kept that injunction available while the dispute over money and property moved through bankruptcy.

Gottlieb marked the moment in terms of both cessation and motive: “Today ends his efforts to profit off of lies about these two heroes of American democracy.” The injunction prohibited further repetition rather than assigning additional damages for past conduct.

Bankruptcy, Appeal, and Satisfaction

Giuliani’s Chapter 11 case added another forum, another set of priorities, and another risk of delay. Willkie’s account states that the team secured dismissal of the bankruptcy case and continued enforcement. On appeal, Gottlieb signed a December 2024 brief defending the default, the damages trial, and the judgment. Its final request was direct: affirm.

The matter later settled. On February 24, 2025, a satisfaction of judgment was filed in federal court. Reuters reported that the terms were undisclosed and that Giuliani continued to promise he would not defame Freeman and Moss again. A satisfaction following settlement does not reveal that the face amount of the judgment was paid. It records the narrower legal fact that the judgment obligation is treated as fulfilled.

Each stage added a different form of relief. The verdict fixed damages, the judgment created an enforceable debt, and the injunction barred future accusations. Bankruptcy and appeal governed collection and review, while the satisfaction recorded that the financial obligation had been resolved. Gottlieb remained counsel throughout.

Gottlieb’s Public-Interest Litigation

Gottlieb is a Willkie litigation partner, a member of the firm’s Executive Committee, chair of its Crisis Management Group, co-chair of its Media & First Amendment practice, and a member of its Appeals & Strategic Motions practice. His work often combines defamation, constitutional law, emergency relief, appellate strategy, and public consequences.

His official record includes earlier representations arising from the Pizzagate conspiracy theory and from false claims surrounding the murder of Seth Rich. Freeman v. Giuliani extended that work into election administration. In each setting, a manufactured public narrative attached itself to identifiable people and produced consequences outside the screen. The legal response required defamation doctrine, emergency judgment, evidence discipline, and an understanding of how repetition changes risk.

Gottlieb served as associate counsel to President Barack Obama, an Assistant U.S. Attorney in the Central District of California, a Senate Judiciary Committee staffer, and deputy director of an international civil-military rule-of-law and anti-corruption task force in Afghanistan. He clerked for Justice John Paul Stevens and Judge Stephen Reinhardt. That experience now informs litigation involving government, public speech, constitutional rights, and reputational harm.

The Injunction Remained

The February 2025 satisfaction closed the financial judgment under undisclosed settlement terms. The permanent injunction remained enforceable, barring Giuliani from repeating the accusations against Freeman and Moss.