Giuliani contends with dual contempt hearings in bid to retain his condo
Two judges are poised to determine separately whether to impose penalties on the former New York City mayor for ignoring their directives.
TroibNews 
NEW YORK — Rudy Giuliani’s legal troubles are about to escalate.
Two federal judges are considering whether to hold him in contempt, a penalty that could potentially lead to incarceration, for violating court orders. Additionally, the former New York City mayor is set to face trial later this month regarding whether he must relinquish his Palm Beach condo to two Georgia women who secured a $148 million defamation judgment against him in 2023.
Giuliani is also under criminal indictment in Arizona and Georgia for his actions aimed at aiding Donald Trump in overturning the 2020 election results. He has been disbarred in New York and Washington, D.C. However, his most pressing legal challenges currently stem from the civil judgment in the defamation case.
The women who won that judgment—former election workers Ruby Freeman and Shaye Moss—have already taken possession of many of Giuliani's assets, including watches, a ring, and a vintage Mercedes-Benz convertible. He is in the process of handing over his Manhattan apartment as well but has vigorously fought against these collection efforts, continuing to insult Freeman and Moss.
This resistance has frustrated two federal judges, who have expressed irritation over his noncompliance and are now empowered to penalize him for his obstinacy through fines, jail time, or other measures to legally compel him to comply.
The first hearing is set for Friday in Manhattan federal court, where Judge Lewis Liman will consider a request from Freeman and Moss to find Giuliani in contempt and impose “severe” sanctions. The mother-daughter duo won the nine-figure defamation verdict after a jury concluded that Giuliani had falsely accused them of election fraud following the 2020 election. They argue that Giuliani has continuously impeded Liman’s orders concerning the transfer of his assets while they work to collect the judgment.
Specifically, they contend that he has failed to provide any documents in compliance with court orders requiring him to disclose details about his Palm Beach condo, which they are attempting to seize.
A second contempt hearing for Giuliani is scheduled on January 10—this time in Washington, D.C., before Judge Beryl Howell, who oversaw the defamation trial in December 2023. Freeman and Moss are requesting Howell to hold Giuliani in contempt for breaching an agreement not to make new defamatory statements about them. They allege that he has revived his false accusations during two recent podcast appearances.
While Freeman and Moss have not explicitly demanded jail time, they have indicated that any monetary fine would be inadequate as Giuliani’s debts to them already significantly surpass his assets.
In Liman's courtroom, they have urged the judge to impose “whatever coercive sanction” he “deems appropriate.” One punitive measure they suggested is that Liman formally rule Giuliani’s failure to produce the required documents about the Palm Beach condo serves as an admission that he never intended to live there full-time before asserting it as his primary residence. Such a ruling would effectively decide the key issue to be adjudicated in the trial set for January 16, potentially putting Giuliani at risk of having to forfeit the condo to the women.
Court filings suggest Liman has dismissed Giuliani’s justifications regarding his document submissions. The judge has already indicated that the upcoming contempt hearing may not favor Giuliani.
So far, Giuliani has done little to endear himself to Liman. During a court session in November, he lost his temper at Liman after the judge probed his efforts to submit the necessary property information. His legal team has implied in court documents that the judge—appointed by Trump—may be biased against Giuliani, highlighting that 29 GOP senators voted against Liman’s confirmation.
On Thursday afternoon, Giuliani requested permission to attend Friday’s hearing via Zoom due to knee issues and a cough stemming from his presence at the World Trade Center site on September 11, 2001.
Despite his health claims, Giuliani has participated in multiple television and podcast appearances recently, including an extended segment on Newsmax about a mass attack in New Orleans and a two-hour podcast on the same topic.
In a ruling on Thursday evening, Liman stated that Giuliani must appear in person if he intends to testify in the hearing.
Giuliani’s challenges won't conclude with the New York hearing. A week later, he is due for a contempt hearing before Howell, another judge he has repeatedly antagonized. He has criticized her as biased due to her handling of numerous cases related to the January 6, 2021, Capitol attack and claimed difficulty in finding legal representation willing to appear in her courtroom.
Howell, an appointee of former President Barack Obama, has reprimanded Giuliani multiple times over the past two years for disregarding her orders—a history that may play a significant role in the upcoming contempt hearing.
Both contempt hearings could lead up to Giuliani’s January 16 trial before Liman concerning the status of the Palm Beach condo and whether it qualifies for a “homestead” exemption against collection efforts.
The trial will also address the fate of his cherished World Series rings from the New York Yankees. Giuliani asserts that he gifted them to his son Andrew years ago, rendering them off-limits to Freeman and Moss. He has presented photos and text messages to support his claim, and the proceedings could require both Giuliani and his son to testify regarding the details of this transfer.
Orden reported from New York. Cheney reported from Washington.
Mathilde Moreau for TROIB News
Two federal judges are considering whether to hold him in contempt, a penalty that could potentially lead to incarceration, for violating court orders. Additionally, the former New York City mayor is set to face trial later this month regarding whether he must relinquish his Palm Beach condo to two Georgia women who secured a $148 million defamation judgment against him in 2023.
Giuliani is also under criminal indictment in Arizona and Georgia for his actions aimed at aiding Donald Trump in overturning the 2020 election results. He has been disbarred in New York and Washington, D.C. However, his most pressing legal challenges currently stem from the civil judgment in the defamation case.
The women who won that judgment—former election workers Ruby Freeman and Shaye Moss—have already taken possession of many of Giuliani's assets, including watches, a ring, and a vintage Mercedes-Benz convertible. He is in the process of handing over his Manhattan apartment as well but has vigorously fought against these collection efforts, continuing to insult Freeman and Moss.
This resistance has frustrated two federal judges, who have expressed irritation over his noncompliance and are now empowered to penalize him for his obstinacy through fines, jail time, or other measures to legally compel him to comply.
The first hearing is set for Friday in Manhattan federal court, where Judge Lewis Liman will consider a request from Freeman and Moss to find Giuliani in contempt and impose “severe” sanctions. The mother-daughter duo won the nine-figure defamation verdict after a jury concluded that Giuliani had falsely accused them of election fraud following the 2020 election. They argue that Giuliani has continuously impeded Liman’s orders concerning the transfer of his assets while they work to collect the judgment.
Specifically, they contend that he has failed to provide any documents in compliance with court orders requiring him to disclose details about his Palm Beach condo, which they are attempting to seize.
A second contempt hearing for Giuliani is scheduled on January 10—this time in Washington, D.C., before Judge Beryl Howell, who oversaw the defamation trial in December 2023. Freeman and Moss are requesting Howell to hold Giuliani in contempt for breaching an agreement not to make new defamatory statements about them. They allege that he has revived his false accusations during two recent podcast appearances.
While Freeman and Moss have not explicitly demanded jail time, they have indicated that any monetary fine would be inadequate as Giuliani’s debts to them already significantly surpass his assets.
In Liman's courtroom, they have urged the judge to impose “whatever coercive sanction” he “deems appropriate.” One punitive measure they suggested is that Liman formally rule Giuliani’s failure to produce the required documents about the Palm Beach condo serves as an admission that he never intended to live there full-time before asserting it as his primary residence. Such a ruling would effectively decide the key issue to be adjudicated in the trial set for January 16, potentially putting Giuliani at risk of having to forfeit the condo to the women.
Court filings suggest Liman has dismissed Giuliani’s justifications regarding his document submissions. The judge has already indicated that the upcoming contempt hearing may not favor Giuliani.
So far, Giuliani has done little to endear himself to Liman. During a court session in November, he lost his temper at Liman after the judge probed his efforts to submit the necessary property information. His legal team has implied in court documents that the judge—appointed by Trump—may be biased against Giuliani, highlighting that 29 GOP senators voted against Liman’s confirmation.
On Thursday afternoon, Giuliani requested permission to attend Friday’s hearing via Zoom due to knee issues and a cough stemming from his presence at the World Trade Center site on September 11, 2001.
Despite his health claims, Giuliani has participated in multiple television and podcast appearances recently, including an extended segment on Newsmax about a mass attack in New Orleans and a two-hour podcast on the same topic.
In a ruling on Thursday evening, Liman stated that Giuliani must appear in person if he intends to testify in the hearing.
Giuliani’s challenges won't conclude with the New York hearing. A week later, he is due for a contempt hearing before Howell, another judge he has repeatedly antagonized. He has criticized her as biased due to her handling of numerous cases related to the January 6, 2021, Capitol attack and claimed difficulty in finding legal representation willing to appear in her courtroom.
Howell, an appointee of former President Barack Obama, has reprimanded Giuliani multiple times over the past two years for disregarding her orders—a history that may play a significant role in the upcoming contempt hearing.
Both contempt hearings could lead up to Giuliani’s January 16 trial before Liman concerning the status of the Palm Beach condo and whether it qualifies for a “homestead” exemption against collection efforts.
The trial will also address the fate of his cherished World Series rings from the New York Yankees. Giuliani asserts that he gifted them to his son Andrew years ago, rendering them off-limits to Freeman and Moss. He has presented photos and text messages to support his claim, and the proceedings could require both Giuliani and his son to testify regarding the details of this transfer.
Orden reported from New York. Cheney reported from Washington.
Mathilde Moreau for TROIB News
