Former New York mayor Rudy Giuliani, a lawyer for President Donald Trump, speaks during a news conference at Four Seasons Total Landscaping on legal challenges to vote counting in Pennsylvania, Nov. 7, 2020, in Philadelphia. A review panel says Giuliani should be disbarred in Washington for how he handled litigation challenging the 2020 election on behalf of then-President Donald Trump. The panel's report was released Friday, July 7, 2023. (AP Photo/John Minchillo, File)

Rudy Giuliani's legal woes do not appear to be waning after a stinging set of orders from the judge overseeing the defamation case against him by two election workers.

The one-time mayor of New York and stalwart Donald Trump supporter has been ordered by a federal judge to pay nearly $90,000 in attorneys' fees for refusing to provide discovery in the case against him by two Georgia election workers. Ruby Freeman and her daughter Wandrea "Shaye" Moss sued Giuliani in December 2021, alleging defamation and intentional infliction of emotional distress resulting from his accusations that the women were engaging in voter fraud during the 2020 presidential election.

According to U.S. District Judge Beryl Howell, Giuliani's apparent disregard for the discovery process will cost him.

"[D]efendant Giuliani is DIRECTED, by July 25, 2023, to reimburse plaintiffs $89,172.50 in attorneys' fees incurred for plaintiffs' Motion to Compel Discovery," wrote Howell, a Barack Obama appointee, in an order Thursday. As the judge notes, Giuliani had been "previously directed" to pay the fees by July 7, 2023, and "by that deadline[,] defendant Giuliani had neither objected to nor requested an extension of time to respond or contest the reasonableness of plaintiffs' requested attorneys' fees."

Giuliani has similarly failed to oppose a second motion to compel Giuliani's businesses — Giuliani Partners LLC and Giuliani Communications LLC, both named in the lawsuit — to respond to subpoenas and deposition orders. As such, Howell found, he essentially conceded to the factual truth of those motions.

"Given his clarification in a declaration that he is the sole owner of both Giuliani Partners LLC and Giuliani Communications LLC, he has no one to blame but himself for ignoring plaintiffs' pending motion to compel the Giuliani Businesses to comply with discovery obligations," the judge wrote (citations omitted). She has decided, however, to give Giuliani one more chance to answer for the failure to respond to discovery — he has until July 25 to make his case as to why that particular motion shouldn't be granted in favor of Freeman and Moss.

Howell also appears to acknowledge a recent motion for default judgment filed by Freeman and Moss over Giuliani's apparent recalcitrance in the case. As Law&Crime previously reported, the women say that Giuliani has all but refused to participate in discovery and has withheld key evidence and that he deserves to lose the case because of it.

In her order, Howell appeared to warn Giuliani that he is on thin ice.

According to a joint status report in which Giuliani is said to have "taken no steps to collect and search [digital data sources]," has produced no materials from his businesses, and only produced digital documents that "appear to consist almost exclusively of non-usable, non-readable raw data," Howell wrote, giving him a deadline of Aug. 4 to either comply or explain his failure to comply.

"Defendant Giuliani is CAUTIONED that failure to comply" with her previously-issued discovery order "may result in severe discovery sanctions," Howell wrote, specifically acknowledging default judgment as a potential penalty.

The warnings from Howell are the latest in an increasingly long line of reproach from judges for Giuliani's apparent disobedience. A panel of lawyers in Washington has recommended that he be blocked from practicing in the District of Columbia.

His license has been suspended in the district since July 2021 based on a New York court's finding that he made "demonstrably false and misleading" statements about alleged voter fraud in the election. He is also facing a sexual abuse lawsuit from a former employee and a defamation lawsuit by voting machine company Smartmatic.

Giuliani accused Freeman and Moss of, among other things, locking the doors to State Farm Arena in Atlanta, Georgia, to keep election observers out, passing each other a USB drive to manipulate the vote count, and hiding suitcases full of illegal ballots.

Multiple investigations yielded no proof to support these claims, and the Georgia Board of Elections recently — and unequivocally — cleared the women of any wrongdoing. What Giuliani claimed was a nefarious USB drive was a "ginger mint," as Moss testified before Congress.