By
Last month, as the special counsel's office inched closer to indicting Donald Trump for alleged election interference conspiracies involving Rudy Giuliani, among others, Giuliani himself was focused on another of his legal woes.
The former Trump attorney entered into a “nolo contendre stipulation” on July 25 in a civil lawsuit brought by a mother-daughter pair of Georgia election workers, Ruby Freeman and Shaye Moss, whom he falsely accused of election fraud.
In that filing, Giuliani basically agreed to all elements of liability on their claims, while attempting to carve out certain defenses, including the statute of limitations and his ability to characterize his statements as opinions, not facts. He also attempted to preserve his right to argue that Freeman and Moss suffered no damages, a steep proposition given their gut-wrenching testimony to the House Jan. 6 committee about the ways Giuliani and others' lies destroyed their privacy and threatened their security.
Howell explained why Giuliani's efforts to have his cake and eat it too, even if it seemed like a sacrifice, were deeply unsatisfying.
At the time, Giuliani and his legal team appear to have believed that the stipulation could transform the trial into little more than a damages case — but also had the advantage of relieving Giuliani from an automatic, or "default," judgment against him. More importantly, the stipulation would insulate Giuliani — who has claimed the discovery Freeman and Moss seek no longer exists — from further orders to produce what could be highly damaging evidence.
Yet not all legal observers saw the situation as Giuliani's counsel seem to have. One former prosecutor privately told me they believe U.S. District Judge Beryl Howell, who is overseeing Freeman and Moss' case in Washington, would never allow Giuliani to evade his discovery obligations without meaningful consequences, especially when the plaintiffs had shown how flagrant Giuliani’s non-compliance was. Indeed, the plaintiffs even accused him of destroying evidence. That prosecutor predicted Howell would see right through Giuliani’s apparent efforts to evade discovery by “not contesting” liability while attempting to preserve a bunch of defensive off-ramps.
My prosecutor friend was right. In an order last Friday, Howell explained why Giuliani's efforts to have his cake and eat it too, even if it seemed like a sacrifice, were deeply unsatisfying. If Giuliani is indeed conceding Freeman and Moss’ allegations are true, she reasoned, none of the affirmative defenses he has asserted previously have “continued viability.”
Noting the “seemingly incongruous and certainly puzzling caveats” in Giuliani’s stipulation as well as Freeman and Moss’ lawyers’ unsuccessful efforts to obtain clarification from the defense as to what it is and is not conceding, the judge then gave Giuliani a choice. By 4 p.m. ET on Tuesday, Giuliani could either:
- Submit a new stipulation conceding liability to the claims “all factual allegations ... as to his liability for plaintiffs’ defamation, intentional infliction of emotional distress, and civil conspiracy claims, and his liability as to plaintiffs’ claim for punitive damages” and that a default judgment as to his liability is appropriate, or
- Explain why he is declining to submit such a stipulation by clarifying “what precisely his original stipulation conceded regarding the plaintiffs’ factual allegations and legal claims.”
There was a third option, too — but it's not a good one. Should Giuliani fail to choose doors one or two, Howell made clear she'll convene an Aug. 15 hearing to determine how, if at all, he has complied with her prior order to search and produce all materials responsive to Freeman and Moss’ discovery requests “with the assistance of a professional vendor.”
Note that such discovery would not only hurt Giuliani in this lawsuit but it could also prove extremely damaging to him in special counsel Jack Smith's 2020 election probe if investigators do not already have those materials/data. (National security and legal blogger Marcy Wheeler has surmised that federal investigators long ago obtained evidence relevant to Giuliani's efforts to overturn the 2020 election through further, secret warrants to search the devices the Southern District of New York seized from Giuliani’s home and office in 2021 as part of its investigation into his Ukrainian business dealings.)
Last week, Freeman and Moss told the court that however Giuliani responds (or doesn't respond) on Tuesday, a default judgment is appropriate. That would leave for any future trial or other resolution only the amount of damages owed.
For his part, Giuliani did file a "superseding nolo contendre" on Tuesday. Yet it is almost as inconsistent as the first. On one hand, he acknowledges that his liability on plaintiffs' claims should be "treated as though there is default liability." On the other hand, he tries to preserve certain defenses for appeal.
Then again, Giuliani seems to understand he is in deep trouble, at least financially. Business Insider reported on Monday that his multi-million dollar Manhattan apartment went on the market the same week he submitted the initial stipulation. And especially given his too-cute-by-half filings, Giuliani's decision to sell his apartment sounds like the first smart move he's made in weeks.
CORRECTION (August 8, 2023, 9:12 p.m. ET): An earlier version of this article misstated the name of the judge overseeing the civil lawsuit brought by Shaye Moss and Ruby Freeman. The presiding judge is Beryl Howell, not Amy Berman Jackson.