Michael J. Gottlieb

On December 14, 2023, closing for Ruby Freeman and Wandrea’ ArShaye “Shaye” Moss in the federal courthouse in Washington, Michael J. Gottlieb read Rudolph Giuliani’s memoir to the eight jurors who would decide what Giuliani owed the two women. “Never pick on someone smaller than you. Never be a bully,” the passage ran, a lesson Giuliani wrote that he had learned from his father. “Those are wise words,” Gottlieb said. “If only Mr. Giuliani had listened.” He played a video of Giuliani outside the same courthouse earlier that week repeating the accusations Judge Beryl A. Howell had already adjudged false. “Mr. Giuliani has shown over and over again he will not take our client’s names out of his mouth,” he told the jury. “Facts will not stop him. He says he isn’t sorry and he’s telegraphing he will do this again. Believe him.” “Day after day Mr. Giuliani reminds you who he is.”

Freeman and Moss, mother and daughter, had counted absentee ballots for Fulton County, Georgia on election night in 2020, and after the election Giuliani accused them, repeatedly and by name, of manipulating ballots and taking part in election fraud. The accusations upended two private lives, and the lawsuit they filed was built to restore them. Gottlieb, a litigation partner at Willkie Farr & Gallagher, represented them without charge, with his partners Meryl Governski, Kristin Bender and Aaron Nathan and the firm’s associates, alongside the nonprofit Protect Democracy, whose John Langford and Rachel Goodman worked the case through its Law for Truth project, and Von DuBose of DuBose Miller in Atlanta. The case ran through every phase a civil action can present: discovery sanctions that fixed Giuliani’s liability, a damages trial, a final judgment, a permanent injunction, his bankruptcy, an appeal to the D.C. Circuit, a settlement and, on February 24, 2025, a satisfaction of judgment that closed it with his clients’ names cleared and their protection in force. Gottlieb’s signature is on the sanctions reply and the sworn declaration about what Giuliani had produced, on the consent judgment that carried the injunction and on the appellate brief; he spoke in the opening at trial and gave the closing, and he remained counsel through the post-trial motions and the enforcement that followed.

State Farm Arena

Moss had worked for the Fulton County Department of Registration and Elections since September 2011, first as a temporary worker hired for that November’s election and from 2017 as a full-time employee, processing voter registrations and absentee ballot applications and helping tabulate ballots. In August 2020 she became registration supervisor, and in the November general election she oversaw the tabulation of absentee ballots. Her mother, known in her neighborhood as Lady Ruby, was hired that year as a temporary election worker under her supervision; her grandmother had retired from DeKalb County government. On the night of November 3, 2020 they worked at State Farm Arena in Atlanta, where the county’s tabulation center was, and after a supervisor’s instruction Moss and the remaining staff resumed scanning ballots later that evening. The Gateway Pundit published surveillance video from the arena, and the video became the raw material of the accusations. At a virtual hearing with Republican legislators in Georgia, Giuliani said the two women had pulled out suitcases of illegal ballots and had passed a thumb drive between them “like they were vials of heroin or cocaine.” “They should have been questioned already. Their places of work, their homes should have been searched,” he said. The FBI and the Georgia Bureau of Investigation found no evidence of wrongdoing by either woman, and the object in the video was a ginger mint.

On June 21, 2022 Moss testified before the House Select Committee on the January 6 attack. Representative Adam Schiff asked what her mother had actually handed her on the video. “A ginger mint,” she answered. “I don’t go to the grocery store at all. I haven’t been anywhere at all,” she said. The Facebook messages were “just a lot of horrible things,” and “A lot of them were racist”; one read, “Be glad its 2020 and not 1920.” People had gone to her grandmother’s house and tried to “burst down the door and conduct a citizen’s arrest of my mom and me.” “I felt it was my fault for putting my family in this situation,” she said. Freeman testified that she no longer introduced herself by name: “I’ve lost my name. I’ve lost my reputation. I’ve lost my sense of security.” Moss received the 2022 John F. Kennedy Profile in Courage Award that spring, and on January 6, 2023 President Biden presented both women with the Presidential Citizens Medal. “Ruby and Shaye, you don’t deserve what happened to you,” he said. “But you do deserve the nation’s eternal thanks for showing that dignity and grace of ‘We the People.’”

Freeman and Moss filed suit on December 23, 2021 in the United States District Court for the District of Columbia against Giuliani, Herring Networks, which operates One America News, Robert and Charles Herring and the OAN staffer Chanel Rion. The OAN defendants settled in April 2022, walking back the fraud claims as part of the settlement, and they were dropped from the case on May 10, 2022, when the amended complaint alleged that Giuliani had “knowingly and repeatedly disseminated false information” about the two women. Giuliani moved to dismiss in June, arguing that the claims were not pleaded in enough detail and that the First Amendment protected what he had said. On October 31, 2022 Chief Judge Howell denied the motion. The Trump campaign and its allies, including Giuliani, she wrote, had “engaged in a media offensive that at best questioned, and at worse condemned, their work,” and Giuliani had “persisted in pushing those very claims” and begun taking direct aim at the plaintiffs. The claims for defamation, intentional infliction of emotional distress and civil conspiracy all went into discovery. Gottlieb had come to the case through Protect Democracy, which had been in touch with the lawyer representing the women in Atlanta. “I’ve always despised bullies that pick on defenseless or seemingly defenseless people,” he said later. “There are so many ways to make your political points without endangering individual people’s lives.”

193 Documents

Giuliani’s initial production in discovery consisted of 193 documents. The FBI had seized his electronic devices in April 2021 and returned them by August 19, 2022, and he claimed that they came back “wiped out.” His counsel described TrustPoint.One as an electronic discovery vendor holding data from those devices, and when the TrustPoint production was complete its 7,949 records consisted almost entirely of “nonusable, nonresponsive materials,” about 4,142 of them, more than half, indecipherable blobs; by the plaintiffs’ count fifty or fewer were directly relevant. On May 19, 2023 the court ordered Giuliani to produce his financial information, and on May 31 it ordered further production. The requested discovery went to the center of the case. Communications could show how the accusations were developed and circulated; electronic account data could establish preservation and publication history; audience information could measure reach; financial records bore on punitive damages. When a defendant controls those materials, delay and nonproduction alter the balance of proof: a plaintiff may know what happened in public while remaining unable to reconstruct the private machinery that made it happen. Freeman and Moss moved for sanctions on July 11, 2023, and the court issued a minute order cautioning Giuliani.

Giuliani answered with stipulations. On July 26, 2023 he filed one he had signed himself, unsworn, conceding the factual elements of the claims “for the purposes of this litigation” while preserving his argument that the statements were protected opinion and reserving his statute-of-limitations and other affirmative defenses. Judge Howell called those caveats “seemingly incongruous and certainly puzzling” and ordered a superseding stipulation or an explanation for declining one. The reply Gottlieb signed on August 1, with Langford, Goodman, Governski, Timothy Ryan, Tyler Knoblett, Annie Houghton-Larsen and DuBose, argued that a defaulting defendant admits the well-pleaded allegations, so that Giuliani’s concession of the “factual aspects of liability” let the court treat the amended complaint’s facts as admitted even on his reserved defenses; that the opinion defense had already been rejected on the motion to dismiss and the law of the case barred relitigating it; that the defamation claims were filed within the one-year limitations period and the emotional-distress and conspiracy claims within three years; that contesting causation conflicted with the stipulation; and that the stipulation still did not relieve him of producing the financial documents the court had ordered. The “nolo contendere” label was confusing in civil litigation, the reply added, and the stipulation was “not signed subject to penalty of perjury, which is contrary to the Local Rules.” Gottlieb’s declaration, filed with it, gave the motion its scale: “On May 19, 2023, the Court ordered Defendant Giuliani to produce his financial information to Plaintiffs.” “To date, Defendant Giuliani has produced a total of two documents in response to that order, which are from 2018 and 2019,” a 2018 tax return and a court transcript from his divorce proceedings dated December 10, 2019. His signature on the reply tied counsel’s argument to a sworn account of the records that had actually arrived. On August 8 Giuliani filed a superseding nolo contendere stipulation conceding liability, though not damages, on the defamation, emotional-distress and civil-conspiracy claims and on punitive damages, still reserving his legal defenses and his opinion argument for appeal. Gottlieb described the choice later: “He wasn’t interested in following the Court’s orders.” Rather than go back and do the work, Giuliani had decided, in Gottlieb’s rendering, “I’m just going to stipulate to liability.”

Judge Howell granted the motion on August 30, 2023. Rule 37 gives a court escalating tools when evidence is lost or orders are disobeyed, and she applied two of its strongest: Rule 37(e)(2)(C), for electronically stored information a party failed to preserve, and Rule 37(b)(2)(A)(vi), authorizing default for failure to obey discovery orders. “In this case, however, Giuliani has given only lip service to compliance with his discovery obligations and this Court’s orders by failing to take reasonable steps to preserve or produce his ESI,” she wrote. “Donning a cloak of victimization may play well on a public stage to certain audiences, but in a court of law this performance has served only to subvert the normal process of discovery in a straight-forward defamation case, with the concomitant necessity of repeated court intervention.” Giuliani had bemoaned the plaintiffs’ efforts to secure his compliance as “punishment by process.” Aside from the 193 documents, what discovery had produced “is largely a single page of communications, blobs of indecipherable data, a sliver of the financial documents required to be produced, and a declaration and two stipulations from Giuliani, who indicates in the latter stipulations his preference to concede plaintiffs’ claims rather than produce discovery in this case.” The sliver was his 2018 federal and New York tax returns and a settlement stipulation from his 2019 divorce proceeding. The court held that the reservations in his stipulations did not excuse compliance with the May 31 order, noted inconsistencies in the account of what TrustPoint held, since a declaration from his own counsel suggested the vendor had only a subset of the data, and emphasized that no professional verification supported the claim that the returned devices had been wiped. “The only reasonable explanation for Giuliani’s blatant disregard” of his preservation duties, she found, was that he had ignored them intentionally and willfully, and “Giuliani’s failure to preserve his ESI has significantly prejudiced plaintiffs’ abilities to prove their claims because circumstantial evidence of Giuliani’s knowledge of the falsity of his claims concerning plaintiffs likely would have existed in his lost ESI.” Default is an exceptional sanction, and the court concluded that continued noncompliance had left no adequate lesser remedy. It entered default judgment on the defamation, intentional-infliction-of-emotional-distress and civil-conspiracy claims, with entitlement to seek punitive damages, fixed the actionable statements as false and defamatory, and sent the case to a jury on damages alone. It ordered Giuliani to pay $89,172.50 in fees for the first motion to compel, with interest from July 25, 2023, and $43,684 on the motion against his businesses, with interest from September 20, 2023, plus the fees and costs of the sanctions motion; it set September 20 as the deadline for complete responses to the financial-records requests, for revenue and viewership records from the businesses and for Rule 30(b)(6) witnesses; and it warned that further noncompliance could bring adverse instructions and the exclusion of evidence at trial. On October 13 the court established adverse inferences and precluded certain evidence from trial, and on October 16 the plaintiffs filed a consent motion in limine with an appendix of Giuliani’s continued public statements. The sanction prevented the party who withheld the evidence from benefiting from his own noncompliance; it fixed liability and preserved a jury trial on damages, so that Freeman and Moss could present the full human and financial consequences of the defamatory campaign.

Eight Jurors

Jury selection began on Monday, December 11, 2023, with liability already established and the jury’s task confined to damages. The plaintiffs had told the court they would seek “a sum ranging from $15.5 million to $43 million, inclusive of special damages.” Von DuBose opened by showing videos and playing audio of Giuliani repeating the false claims, played the voicemails the two women had received, and held up a ginger mint, the supposed USB drive. Gottlieb told the jurors that Giuliani’s accusations “had the most powerful amplifier on Earth: The social media accounts of Donald J. Trump,” and asked them to “consider a verdict that will send a message.” Joseph Sibley, Giuliani’s lawyer, called the request “the civil equivalent of the death penalty.” “They’re trying to end Mr. Giuliani,” he told the jury, while conceding the injury: “There’s really no question that these plaintiffs were harmed.” “They didn’t deserve what happened to them.” The harm, he argued, “involved a lot of people. It wasn’t just Rudy Giuliani.” When he invoked the Johnny Depp verdict, Judge Howell cut him off: “Mr. Sibley, let’s stick to this case.” Outside the courthouse Giuliani told reporters, “Of course I don’t regret it,” and “I told the truth. They were engaged in changing votes,” and that “everything I said about them is true.”

Moss testified on Tuesday. Her life had changed after Giuliani’s claims; she had left the job she loved and had received death threats; people had shown up at her family’s homes, including her grandmother’s, where one said he had authority to make a citizen’s arrest; her son, then fourteen, had heard messages calling for his mother and grandmother to be hanged; she had tried to change her appearance, seldom left home and suffered panic attacks and nightmares. “People are messaging me,” she said. “Calling, texting, online, saying that I need to die, they’re gonna kill me, they want to kill my mom,” and “they know where we are, they know where we sleep and we should die.” The jury heard the messages themselves: “You are dead,” one person had written. “Your family and you are now criminals and traitors to the union.” A voicemail ended, “Have a nice life. What’s left of it.” On Wednesday the plaintiffs called Ashlee Humphreys, a Northwestern University professor who studies consumer sentiment, whom the two women’s lawyers had retained. She examined sixteen statements at issue, estimated their impressions at 11 million on the low end and 250 million on the high end, counted more than 710,000 online mentions of the two women from November 2021 to May 2023 and more than 317,000 from May to August 2023, and priced a corrective advertising and social-media campaign at between $28,489,415 and $47,482,358, with the high end the more accurate. “False statements travel faster than truth,” she told the jury. “My model is tied directly to the impressions and damages for statements in this case.” Regina Scott, a researcher, had calculated the reach of the statements and testified as a lay witness. Giuliani offered no damages expert of his own. On cross-examination Sibley argued that “today’s misinformation is tomorrow’s truth” and asked whether converting election deniers would be a waste of time, comparing them to flat-earth believers; “I don’t offer an opinion on convincing flat earth people,” Humphreys answered, and Judge Howell sustained the objection: “I’m going to sustain the objection because I don’t know where you’re going with that.”

Freeman took the stand on Wednesday, the third day. “I took it as though they were going to hang me with their ropes on my street,” she testified. “I was scared. I didn’t know if they were coming to kill me.” “They started coming to the house with bullhorns.” The FBI told her she was not safe, and she left the home she had lived in; her online boutique filled with threatening messages. “It’s so scary, any time I go somewhere, if I have to use my name,” she said. “I miss my old neighborhood because I was me, I could introduce myself. Now I don’t have a name, really.” “I don’t have my name anymore,” she said through tears. “That’s the only thing in life, the only thing you have is your name.” “Giuliani just messed me up.” Sibley chose not to cross-examine her, and the plaintiffs rested. Giuliani had said repeatedly that he would testify and explain his claims; Judge Howell had barred him from asserting from the stand that his conspiracy theories were correct, and on Thursday morning the defense rested without calling a witness. Sibley said his client had declined to testify because the women had “been through enough.” “It matters that they took the stand under oath, right?” Gottlieb said afterward. “It matters they subjected themselves to cross examination.”

The closing came on Thursday, December 14. Gottlieb read from Giuliani’s book and played the courthouse video, and he called Freeman and Moss “heroes”: “after everything they went through, they stood up and said, ‘no more.’” “Unlike some other people they testified here under oath,” he said, and Giuliani had let the accusations “rocket around the world millions and millions of times.” “The lies in this case became a sustained, deliberate, viral campaign, the purpose of which was to overturn an election.” He told the jury: “Rich famous people have valuable reputations, and ordinary people are irrelevant, replaceable, worthless.” “That is a fiction and it ends today.” “Facts matter. Truth is truth and you will be held accountable.” The plaintiffs asked for at least $24 million for each woman in defamation damages alone, plus damages for emotional harm and punitive damages. Sibley asked the jurors to “remember this is a great man” and to “send a message to America, we can come together in compassion and sympathy”; he argued that there was no evidence Giuliani had personally encouraged the harassment, that the Gateway Pundit had published the surveillance video first, and that although these things had happened, that did not make his client responsible for them. He conceded that Giuliani “hasn’t exactly helped himself with some of the things that happened in the past few days.”

The jury returned its verdict on Friday, December 15, after about ten hours of deliberation. It awarded Freeman $16,171,000 for defamation and Moss $16,998,000; $20,000,000 to each woman for intentional infliction of emotional distress; and $75,000,000 in punitive damages, $148,169,000 in all. The separate categories measured different legal injuries: defamation damages addressed reputation, emotional-distress damages the personal consequences of being made the human target of an election conspiracy theory, and punitive damages punishment and deterrence, and the trial record had translated the public accusations and their effects into those distinct measures without losing the two lives inside the numbers. When the foreperson read the $75 million figure there was an audible gasp in the courtroom; Giuliani showed no visible emotion, and after the jury left, Moss and Freeman hugged their lawyers. “My name is Lady Ruby,” Freeman said outside. “Today is a good day. A jury stood witness to what Mr. Giuliani did to me and my daughter and held him accountable.” “Money will never solve all my problems,” she told reporters. “I can never move back into the house that I call home.” “I miss my home.” “I miss my neighbors and I miss my name.” Moss: “The lies Rudy Giuliani told about me and my mommy after the 2020 presidential election have changed our lives.” “I know I won’t be able to retire from my job with the county like my grandmother did.” “We hope no one ever has to fight so hard just to get their name back.” Giuliani promised an appeal: “It will be reversed so quickly it will make your head spin.” Gottlieb, a few weeks later, put the award in his own terms: “So there was 16, 17 million dollars each in reputational damages alone,” and “the reputational worth of these civil servants is not tied to their income bracket.” The verdict’s significance, he said, lay in the message it sent to others, and “the significance of the verdict, and the size of the verdict, is not tied to how, what percentage of it they will collect.”

Three Days After the Verdict

Judge Howell entered final judgment on Monday, December 18, 2023. The parties had stipulated to a damages figure of $145,969,000, a reduction of a little more than $2 million that resolved a possible setoff claim tied to the 2022 settlement with the OAN defendants, and the judgment added the $237,113 in attorney’s fees Giuliani already owed under three discovery orders, the $89,172.50 and $43,684 of August 30 and $104,256.50 under a minute order of September 22, for a principal of $146,206,113, plus post-judgment interest at 5.01 percent on the damages and costs. The order converted the jury’s findings into an obligation enforceable through post-judgment proceedings. Under 28 U.S.C. § 2201(a) it also declared that the actionable statements in the amended complaint “are false,” “are defamatory and defamatory per se,” were “of and concerning plaintiffs,” were made “with actual malice,” were published to third parties “without privilege” and “caused plaintiffs harm”; that Giuliani “engaged in extreme and outrageous conduct” that “intentionally and maliciously” caused “severe emotional distress”; that on or before December 3, 2020 he had entered an agreement with named individuals and entities to defame the two women and inflict that distress; and that his conduct was “intentional, malicious, wanton, and willful, such that plaintiffs are entitled to punitive damages.” Those declarations fixed the findings supporting liability for defamation, intentional infliction of emotional distress and civil conspiracy in an authoritative legal record, the formal, public vindication Freeman and Moss had sought from the start.

The same day, Freeman and Moss filed a second suit, No. 23-cv-3754, a 134-page complaint for a permanent injunction. During the trial week Giuliani had told Terry Moran of ABC News, outside the courthouse, that the women were “changing votes”; after the verdict he said he had “no doubt” his comments were “supportable,” and the next day he repeated the claims on Steve Bannon’s podcast. Giuliani “continues to spread the very same lies for which he has already been held liable,” the lawyers wrote, and they asked the court to bar him from “making or publishing, or causing to be made or published, further statements repeating any false claims” that the women “engaged in election fraud, illegal activity or misconduct of any kind.” In the first case they asked Judge Howell to “permit immediate enforcement” of the judgment rather than wait out the automatic thirty-day stay, warning of “a substantial risk” that Giuliani would try to avoid paying. On Wednesday, December 20 she agreed. His failure to pay the smaller fee awards “provides good cause to believe that he will seek to dissipate or conceal his assets during the 30-day period,” she wrote, and “Giuliani cannot and does not dispute that he has continued to disregard the Court’s orders”; his “persistent refusal” to turn over financial information undercut his claims of hardship. His lawyers had argued that the court should not “abnormally shorten” the stay. On December 21 he filed for Chapter 11 in the Southern District of New York, Case No. 23-12055, before Judge Sean H. Lane; in the bankruptcy he listed nearly $153 million in existing or potential debts, including almost $1 million in state and federal taxes, against assets he put at $1 million to $10 million. “We are going to work very, very hard to ensure that they see every bit of money,” Langford said. Gottlieb said in January that the debt was not dischargeable in bankruptcy and that Alex Jones had been trying the same course with the Sandy Hook families for some time: “He does have assets, you know, he doesn’t have 148 million dollars in assets, but he does have assets.”

Consent to a Permanent Injunction

The bankruptcy court lifted its automatic stay in February 2024 only far enough to let Giuliani file post-trial motions and an appeal, and the D.C. Circuit held the appeal in abeyance. On April 15, 2024, in forty-eight pages, Judge Howell denied his renewed motion for judgment as a matter of law under Rule 50(b) and his alternative requests for a new trial or an altered judgment under Rule 59. The standard asked whether the evidence was “so one-sided that reasonable men and women could not have reached a verdict in plaintiff’s favor,” and Rule 50(b) was not a vehicle “to rehash decisions that were made pre-trial.” His argument that the complaint failed to state a claim was barred by the law of the case; the default judgment had “established Giuliani’s liability for every well-pleaded allegation.” The statements he called unpleaded were properly admitted because they were his own or those of his stipulated co-conspirators. The emotional-distress claim “is subject to the same statute of limitation period as their defamation claim,” the court agreed, but Giuliani had “forfeited any affirmative defense presented in his Answer” by failing to participate meaningfully in discovery. Emotional distress needed no expert: “no expert is required, even if multiple factors may contribute to a plaintiff’s emotional distress.” The testimony of Scott and Humphreys had been properly admitted. The punitive award, the court observed, was “nearly equivalent to compensatory damages.”

Freeman and Moss had also sought relief preventing any repetition. On May 10, 2024 they opened an adversary proceeding in the bankruptcy court, No. 24-01355, and on May 21 the pieces came together in a single stipulation and agreed order, Doc. 229 in the Chapter 11 case, signed by Rachel C. Strickland of Willkie for the two women, Philip C. Dublin of Akin Gump for the official committee of unsecured creditors and Gary C. Fischoff for Giuliani, and so ordered by Judge Lane that day. It modified the automatic stay under 11 U.S.C. § 362(a) so that the plaintiffs could notify the Washington court, file the joint stipulation and consent judgment in the second case and enforce the injunction; “For the avoidance of doubt, the Automatic Stay shall not apply to” those proceedings or to any step taken to “otherwise secure the Debtor’s compliance with the Permanent Injunction.” Gottlieb signed the joint stipulation and consent to entry of final judgment for the plaintiffs. Its terms: “Mr. Giuliani is PERMANENTLY ENJOINED from publishing, causing others to publish, and/or assisting in others’ publication of” any statements suggesting that the plaintiffs, “whether mentioned directly, indirectly, or by implication,” “engaged in wrongdoing in connection with the 2020 presidential election,” or any of the actionable statements adjudged false and defamatory in the first case, “or any other statements conveying the same defamatory meaning,” the actionable statements being the list at pages 14 through 19 of the joint pretrial statement. The injunction supplied a prospective remedy distinct from the damages judgment. If Giuliani repeated the accusations, Freeman and Moss could bring him before the district court in Washington at once, and his bankruptcy would not stand in the way; the agreed order kept that nonmonetary protection alive while the fight over money and property went on in the other forum, so that both remedies stayed in force at the same time. “We are pleased that Mr. Giuliani has finally agreed to cease spreading lies about Ruby Freeman and Shaye Moss,” Gottlieb said. “Today ends his efforts to profit off of lies about these two heroes of American democracy.” Langford: “Even Rudy Giuliani knows the game is up.” “This victory sends yet another important message that our laws apply to everyone, no matter how powerful or famous.”

Giuliani tested the injunction within months. In November 2024 he returned to the subject on his podcasts, and on November 12 Freeman and Moss moved for civil contempt. “Mr. Giuliani started lying about Plaintiffs in December of 2020,” their lawyers wrote. At a hearing on January 10, 2025 Judge Howell held him in contempt. “This takes real chutzpah, Mr. Giuliani,” she said from the bench, and she called his suggestion that he had been treated unfairly “outrageous and shameful.” She ordered him to review the trial testimony and other case materials, set fines of $200 a day if he did not certify within ten days that he had complied, and warned that another violation could put him behind bars.

White Plains

Giuliani’s Chapter 11 case created a separate forum for enforcement, with its own priorities and its own risk of delay. He asked at one point to convert the case to a Chapter 7 liquidation, then reversed himself. At a hybrid status hearing in White Plains on July 10, 2024, Strickland told Judge Lane: “The question here is always going to be the cat-and-mouse game of what dollar can be funneled outside of the estate.” The women’s lawyers called the bankruptcy a “bad-faith litigation tactic” and told the court that Giuliani “regards this court as a pause button on his woes while he continues to live his life unbothered by creditors.” Fischoff, for Giuliani, now favored dismissal too, arguing that liquidation fees would “consume if not 100%, a substantial portion of the assets”; Dublin, for the creditors’ committee, wanted the case kept alive with a trustee in control of the assets. “I’m leaning toward dismissal, frankly, because I’m concerned that the past is prologue,” Judge Lane said. On July 12, 2024 he dismissed the case and barred Giuliani from refiling for twelve months. “Transparency into Mr. Giuliani’s finances has proven to be an elusive goal,” he wrote, and he saw no evidence that this would change; of the failure to disclose sources of income, “Such a failure is a clear red flag.” The dismissal erased none of the debt. It freed Freeman and Moss to take collection back to the federal court in Washington and to the courts where his property sat, and it freed Giuliani to pursue his appeal. Gottlieb’s team had secured the dismissal of the bankruptcy, kept the judgment and the injunction intact through it and preserved the nonmonetary relief, and the AmLaw Litigation Daily gave the Willkie team a Litigator of the Week shout-out for the result.

Twenty-Six Watches

On August 30, 2024 Freeman and Moss moved in Washington to enforce the judgment and filed a complaint for a declaratory judgment on Giuliani’s claim that his Palm Beach condominium, worth more than $3 million, was an exempt Florida homestead; they held a lien on it. The collection fight moved to Manhattan, before Judge Lewis J. Liman of the Southern District of New York. On October 22, 2024 he ordered Giuliani to turn over within seven days his Upper East Side apartment, estimated at more than $5 million; his interest in about $2 million he said Donald Trump’s 2020 campaign owed him; a 1980 Mercedes-Benz SL 500 once owned by Lauren Bacall; a shirt signed by Joe DiMaggio, a picture signed by Reggie Jackson and a signed Yankee Stadium picture; a diamond ring and costume jewelry; and twenty-six watches, among them a Rolex, five Shinolas, two Bulovas and a Tiffany & Co. watch. Giuliani asked to keep a watch his grandfather had given him; an exemption was available if he proved it was worth less than $1,000, and he did not. “The Court also does not doubt that certain of the items may have sentimental value to Defendant,” Liman wrote. “But that does not entitle Defendant to continued enjoyment of the assets to the detriment of the Plaintiffs”; “no man should be permitted to live at the same time in luxury and in debt.” The women could sell what they received and “ensure that the liquidation of the transferred assets is accomplished quickly,” and Giuliani, who could have asked the Washington court for a stay and had not, got no bar on sales pending appeal. The condominium and the Yankees’ World Series rings, which his son Andrew claimed as gifts from 2018, were reserved for a later hearing, and Giuliani was barred from selling the condominium or diminishing its value. Until then he had paid the two women nothing. “We are proud that our clients will finally begin to receive some of the compensation to which they are entitled for Giuliani’s actions,” Aaron Nathan said. “This outcome should send a powerful message that there is a price to pay for those who choose to intentionally spread disinformation.” Giuliani’s lawyers, Kenneth Caruso and David Labkowski, answered: “Stay tuned. When the judgment is reversed in the Court of Appeals in Washington, D.C., these Plaintiffs will be required to return all this property to Mr. Giuliani.” He surrendered the apartment that fall, and in November 2024 Moss and Freeman began receiving his assets, the watch collection, jewelry and the car among them.

The appeal Giuliani had promised, D.C. Circuit No. 24-7021, was briefed in December. Gottlieb signed the brief for Freeman and Moss filed on December 16, 2024, with Governski, Nathan and Houghton-Larsen of Willkie, Langford and Goodman of Protect Democracy and DuBose. “This appeal involves egregious acts of defamation and intentional infliction of emotional distress,” it began. “All but one of Giuliani’s arguments on appeal are waived, forfeited, or otherwise beyond this Court’s power to review,” and “Giuliani’s only preserved argument challenges a supposed duplicative recovery for defamation and IIED.” To that the brief answered that the jury had received an anti-duplication instruction and that, as the district court had held, “IIED is a separate and distinct tort from defamation.” Giuliani had conceded below that the default sanction was appropriate; he had reserved in his stipulation “the right to contend on appeal that his statements constituted protected opinion,” an argument he then never raised; there was no “heightened foreseeability” requirement for proximate cause in an intentional tort; any error in instructing the jury on matters already decided “is harmless because the District Court also awarded and read to the jury adverse inferences” that conveyed the same information; his challenge to punitive damages was “waived and meritless”; and the size of the awards was unreviewable, since “none of them was raised in a post-verdict motion,” and in any event entitled to “overwhelming deference.” The brief carried the complete sanctions and damages record to the appellate court and asked it to “strictly enforce its waiver and forfeiture rules, reject Giuliani’s sole preserved challenge,” and “affirm without fanfare.” Its final request was direct: affirm.

The last contest was set for Judge Liman’s courtroom on Thursday, January 16, 2025, a trial over the condominium and three World Series rings, with Giuliani as the first scheduled witness. The week before, Liman had held him in contempt for failing to turn over information about his assets and had barred him from using certain evidence, and Judge Howell had held him in contempt in Washington the same week. Giuliani never arrived at the courthouse. After three days of negotiation that ran, his lawyer Joseph Cammarata said, “into the wee hours of the night,” the parties settled that Thursday, resolving all of the litigation between them. Giuliani kept his homes and belongings, including the rings, in exchange for compensation whose amount was not disclosed and a promise never to defame the two women again, with no admission of liability. “The past four years have been a living nightmare,” Freeman and Moss said. “We have fought to clear our names, restore our reputations, and prove that we did nothing wrong.” “Today is a major milestone in our journey.” They had “agreed to allow Mr. Giuliani to retain his property in exchange for compensation and his promise not to ever defame us.” Giuliani’s statement: “No one deserves to be subjected to threats, harassment, or intimidation,” and “I and the Plaintiffs have agreed not to ever talk about each other in any defamatory manner, and I urge others to do the same.” On Monday, February 24, 2025 the satisfaction of judgment was filed in Liman’s court: the judgment had been “fully satisfied,” and the enforcement action was dismissed. The permanent injunction remained in force after the financial obligation was resolved. The Willkie team that carried the case to that point was Gottlieb, Governski, Bender and Nathan with associates Annie Houghton-Larsen, Tyler Knoblett, Tim Ryan, Logan Kenney, Maggie MacCurdy and Perri Haser, with Protect Democracy and DuBose Miller as co-counsel. Law.com had named the team Litigators of the Week after the verdict, on December 22, 2023, and in August 2024 Gottlieb and Governski were named finalists for a 2024 Winning Litigators Award. The Gateway Pundit, which had published the arena video, settled with the two women in 2024.

Comet Ping Pong and Aaron Rich

The Giuliani case was the third time Gottlieb had gone after a conspiracy theory that had attached itself to identifiable people. The first was Pizzagate, in 2016. Alex Jones and Infowars had spread the claim that Hillary Clinton and Democratic operatives ran a child sex-trafficking ring out of Comet Ping Pong, a pizzeria in Washington owned by James Alefantis, and in December 2016 a man who had been watching the Infowars episodes walked into the restaurant and fired a rifle; no one was hurt. Gottlieb represented Alefantis. Jones argued that the First Amendment protected what he had said; threatened with a lawsuit, he retracted the claims on the air in March 2017 and removed all of the Pizzagate content from the Infowars website and its social media, on confidential terms.

The second was the murder of Seth Rich, a Democratic National Committee staffer killed in a robbery in Washington in 2016, a killing that remains unsolved. Conspiracy theorists claimed that Rich had stolen the DNC’s emails for WikiLeaks, and his family was doxxed and harassed. In March 2018 the Washington Times ran a column asserting that it was well known in intelligence circles that Seth Rich and his brother Aaron had downloaded the DNC emails and that Aaron “was paid by Wikileaks for that information,” citing no evidence. Gottlieb, then a partner at Boies Schiller Flexner, sued that month in the District of Columbia for Aaron Rich, with Joshua Riley, against the newspaper, the businessman Ed Butowsky, the internet activist Matt Couch and Couch’s company, America First Media, for defamation, intentional infliction of emotional distress, false light, invasion of privacy and civil conspiracy. As Gottlieb put it, “you also can’t defame a dead person.” “Our constitutional system leaves wide room for debate on issues of public concern,” he wrote in the complaint; the work, he said, lay in “being able to isolate with precision false factual allegations that are actionable.” At the start of October 2018 the Times published a retraction and apology: the column included statements about Aaron Rich “that we now believe to be false,” “All online copies of the Column have been deleted,” and “The Washington Times apologizes to Mr. Rich and his family.” The “apology and retraction are robust,” Gottlieb said, “a significant step forward in clearing Aaron’s name.” The American Lawyer’s Litigation Daily named him and Riley Litigators of the Week. Butowsky and Couch fought on over personal jurisdiction before Judge Richard Leon, and in January 2021 they too settled, with retractions and apologies. “I take full responsibility for my comments and I apologize for any pain I have caused,” Butowsky said. Couch: “Today we retract and disavow our statements and we offer our apology to Mr. Rich and his family.” “The last two years have brought unimaginable pain and grief to my family and me,” Aaron Rich had said when the Times retracted. “I lost my only brother to a murder that to this date has not been solved, only to then have politically-motivated conspiracy theorists falsely accuse me of grotesque criminal acts.” “If this had happened to me or my brother or sister, and somebody was doing this to my parents, I would go ballistic,” Gottlieb said of the family. “And no one was helping them.” “Aaron is a decent and honorable American who has worked for the same defense contractor since he graduated from college,” he said in 2018, and of the firm’s reason for taking the case, “we felt compelled to defend a family that was being attacked after suffering a tragic loss”; “we do it because it is important and just.”

Those matters, and Freeman v. Giuliani after them, required defamation law, evidence preservation, emergency litigation judgment and remedies directed at false public narratives affecting identifiable people, and Gottlieb has developed that work into a recognized discipline. He arrived at it by accident, he has said, after litigation around the 2016 election exposed him to disinformation aimed at polling places; in law school he had been interested in the law of democracy and political law. He and his team call the cases a “hobby,” and he does not mind how others square them with his commercial practice: “However people want to think about it and look at it is sort of fine with me.”

Joint Task Force 435

Gottlieb graduated from Northwestern University in 1999, where he twice won the National Debate Tournament, and from Harvard Law School in 2003, where he won the Sears Prize and edited the Harvard Law Review. He clerked for Judge Stephen Reinhardt of the Ninth Circuit and for Justice John Paul Stevens. His government service ran through the staff of the Senate Judiciary Committee, the United States Attorney’s office for the Central District of California, where he was an Assistant U.S. Attorney, and the Obama White House, where he was Special Assistant to the President and Associate White House Counsel, associate counsel to President Barack Obama. In Afghanistan he was the senior civilian of Joint Task Force 435, the international civil-military task force for rule-of-law development, serving as deputy director of its rule-of-law and anti-corruption work, experience in building legal institutions under pressure that later informed his courtroom work defending individuals against coordinated falsehoods. At Boies Schiller Flexner he argued Animal Science Products, Inc. v. Hebei Welcome Pharmaceutical Co. in the Supreme Court on April 24, 2018, for the petitioners in a transnational antitrust class action, with the United States as amicus on his side and the Chinese Ministry of Commerce as amicus on the other. “The question in this case is whether a district court is bound to accept a foreign sovereign’s statement of foreign law in the unusual case in which the court has concerns about the statement’s clarity, its completeness, or its consistency,” he told the Court. “The answer to that question is no.” The Court agreed unanimously.

He joined Willkie Farr & Gallagher’s Washington office on January 22, 2019 as a litigation partner and leader of its crisis management practice. “Today’s enterprise-threatening matters are rarely confined within a single court or agency,” he said then. He is now 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, working from Los Angeles and Washington and admitted in the District of Columbia, New York and California. Law360 named him an MVP and The National Law Journal honored him as one of the profession’s outstanding young lawyers; he was nominated for The American Lawyer’s Attorney of the Year in 2023; he is a fellow at George Mason University’s National Security Institute and a former term member of the Council on Foreign Relations. His other work includes a $455 million award against Iran under the Foreign Sovereign Immunities Act for American servicemembers and civilians harmed in terrorist attacks in Iraq; the representation of PDV Holding, the U.S. subsidiary of PDVSA, in litigation over $1.9 billion in bonds, and a Delaware Chancery ruling affirming the boards of PDVSA’s American subsidiaries; CITGO Petroleum’s federal suits against former contractors over fraud and corruption; Steven A. Cohen, who avoided a potential lifetime ban on managing client money; LifeLock in Federal Trade Commission litigation and consumer class actions, resolved by settlement; and Sony Pictures Entertainment after the data breach tied to The Interview. For William Browder he defeated, on December 23, 2024, the defamation claims the Russian lobbyist Rinat Akhmetshin had filed in 2018 over Browder’s linking him to Russian intelligence, after a 2019 dismissal on personal jurisdiction, several rounds in the D.C. Circuit, a certified question that produced a new rule of District of Columbia personal-jurisdiction law and revived the complaint, and a second motion to dismiss, more than six years in all, with Aaron Nathan leading alongside him; the Litigation Daily gave that team a shout-out too. For Blake Lively he and Governski, Bender and Nathan, with Manatt as co-counsel, moved against the $400 million countersuit that Justin Baldoni, the director and co-star of It Ends With Us, brought against Lively, Ryan Reynolds, Leslie Sloane, Vision PR and The New York Times after Lively filed a complaint with the California Civil Rights Department about his conduct during and after the production. Judge Liman dismissed the entire suit in June 2025 in a 132-page opinion, holding that Lively’s providing her complaint to the Times was protected by the litigation privilege and the fair report privilege, and the Litigation Daily made the team a Litigator of the Week runner-up. “The ultimate moment for a plaintiff’s story to be told is at trial,” Gottlieb had said that May, when asked whether Lively would testify. “You can’t just go around subpoenaing people because they’re famous and you think it will generate a bunch of headlines.” “And the federal courts don’t tolerate that kind of behavior.” The case settled on May 4, 2026, two weeks before a trial set for May 18; the joint statement said the “concerns raised by Ms. Lively deserved to be heard.”

In March 2024, at forty-seven, Gottlieb described the two sides of his practice from his K Street office. “I feel fortunate to have had a career where I’ve had a wide variety of cases,” he said. On what defamation law can and cannot do, he had been precise a few weeks after the Giuliani verdict: it is “a limited tool.” “It’s a tool that protects individuals. It is a tool that can be really effective at protecting individuals.” He did not think the right answer to disinformation was “to sue any news organization that runs a story.” “What it can’t do is it can’t stop the spread of disinformation in political discourse or policy debate.”