Rudy Giuliani Confronts a Month Filled with Legal Challenges
Two judges are on the verge of deciding whether to sanction the former New York City mayor for disregarding their directives.
TroibNews 
**NEW YORK** — Rudy Giuliani is facing escalating legal troubles, as two federal judges are considering holding him in contempt, which could lead to jail time for defying court orders. Additionally, he is set to stand trial later this month over 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 currently under criminal indictment in both Arizona and Georgia due to his role in efforts to assist Donald Trump in overturning the 2020 election results. He has been disbarred in New York and Washington, D.C., but his most significant legal challenges have arisen from the civil judgment in the defamation case.
The plaintiffs, former election workers Ruby Freeman and Shaye Moss, have already taken possession of a substantial amount of Giuliani's property, which includes watches, a ring, and a vintage Mercedes-Benz convertible. The former mayor is also in the process of surrendering his Manhattan apartment. However, he continues to resist these collection efforts and has persisted in publicly disparaging Freeman and Moss.
Giuliani’s conduct has exasperated two federal judges, who have expressed their frustration at his noncompliance and now have the authority to impose sanctions—ranging from fines to imprisonment—to enforce legal compliance.
On Friday, a hearing is scheduled in federal court in Manhattan where Judge Lewis Liman will consider a request from Freeman and Moss to hold Giuliani in contempt and impose “severe” sanctions. The mother-daughter duo won the substantial defamation judgment after a jury concluded that Giuliani falsely accused them of election fraud post-2020 election. They allege that Giuliani has repeatedly obstructed Liman’s directives concerning the transfer of his assets necessary to satisfy the judgment.
They specifically contend that Giuliani has not complied with court orders requiring him to submit documents about his Palm Beach condo, which they are seeking to seize.
Giuliani is also preparing for another contempt hearing on January 10 in Washington, presided over by Judge Beryl Howell, who oversaw the December 2023 defamation trial. Freeman and Moss have requested that Howell hold Giuliani in contempt for violating an agreement prohibiting new defamatory remarks about them, claiming he made further false statements during two recent podcasts.
While Freeman and Moss have not explicitly sought jail time, they argue that fines would not suffice, asserting that Giuliani's debt to them greatly exceeds his available assets.
In Liman’s court, they called for “whatever coercive sanction” he deems fit. One sanction they proposed is for Liman to formally declare that Giuliani’s failure to produce condo-related documents signifies that he did not plan to reside there before claiming it as his primary residence. Such a determination would effectively resolve a key issue slated for a trial on January 16, potentially resulting in Giuliani having to forfeit the condo to the plaintiffs.
In written submissions, Liman has shown skepticism towards Giuliani’s reasoning for failing to provide the necessary documents, indicating that Friday’s contempt hearing may not favor Giuliani.
Giuliani has not endeared himself to Liman. At a November hearing, he confronted the judge after being questioned about his compliance regarding the transfer of property. His legal team even suggested in court filings that the judge might exhibit bias against Giuliani due to the opposition Liman faced during his confirmation.
On Thursday afternoon, Giuliani requested permission to attend the upcoming hearing virtually via Zoom, citing knee problems and a cough attributed to his presence at the World Trade Center site on September 11, 2001. Notably, he has made numerous media appearances recently, including an extensive discussion on Newsmax regarding a mass attack in New Orleans and a two-hour podcast on the same subject.
In an order issued Thursday, Liman mandated that Giuliani must appear in court in person if he wishes to testify.
Giuliani's troubles extend beyond the New York hearing; a week later, he faces another contempt hearing before Howell—a judge whom he has frequently criticized. He has accused her of bias based on her management of various cases related to the January 6, 2021, Capitol attack, claiming difficulties in securing legal representation in her courtroom.
Howell, appointed by former President Barack Obama, has admonished Giuliani multiple times over the past two years for ignoring her orders—a history that could significantly impact the upcoming contempt hearing.
Both contempt hearings may serve as precursors to Giuliani’s January 16 trial before Liman, which will determine the status of the Palm Beach condo and whether it qualifies for a “homestead” exemption from collection efforts.
The trial will also address the fate of Giuliani's New York Yankees World Series rings. He claims to have gifted these to his son, Andrew, years ago, positing that they are thus exempt from seizure by Freeman and Moss. He has provided photographs and text messages to support his assertion. The proceedings may require both Giuliani and his son to testify regarding the circumstances of the transfer.
Orden reported from New York. Cheney reported from Washington.
Lucas Dupont for TROIB News
Giuliani is currently under criminal indictment in both Arizona and Georgia due to his role in efforts to assist Donald Trump in overturning the 2020 election results. He has been disbarred in New York and Washington, D.C., but his most significant legal challenges have arisen from the civil judgment in the defamation case.
The plaintiffs, former election workers Ruby Freeman and Shaye Moss, have already taken possession of a substantial amount of Giuliani's property, which includes watches, a ring, and a vintage Mercedes-Benz convertible. The former mayor is also in the process of surrendering his Manhattan apartment. However, he continues to resist these collection efforts and has persisted in publicly disparaging Freeman and Moss.
Giuliani’s conduct has exasperated two federal judges, who have expressed their frustration at his noncompliance and now have the authority to impose sanctions—ranging from fines to imprisonment—to enforce legal compliance.
On Friday, a hearing is scheduled in federal court in Manhattan where Judge Lewis Liman will consider a request from Freeman and Moss to hold Giuliani in contempt and impose “severe” sanctions. The mother-daughter duo won the substantial defamation judgment after a jury concluded that Giuliani falsely accused them of election fraud post-2020 election. They allege that Giuliani has repeatedly obstructed Liman’s directives concerning the transfer of his assets necessary to satisfy the judgment.
They specifically contend that Giuliani has not complied with court orders requiring him to submit documents about his Palm Beach condo, which they are seeking to seize.
Giuliani is also preparing for another contempt hearing on January 10 in Washington, presided over by Judge Beryl Howell, who oversaw the December 2023 defamation trial. Freeman and Moss have requested that Howell hold Giuliani in contempt for violating an agreement prohibiting new defamatory remarks about them, claiming he made further false statements during two recent podcasts.
While Freeman and Moss have not explicitly sought jail time, they argue that fines would not suffice, asserting that Giuliani's debt to them greatly exceeds his available assets.
In Liman’s court, they called for “whatever coercive sanction” he deems fit. One sanction they proposed is for Liman to formally declare that Giuliani’s failure to produce condo-related documents signifies that he did not plan to reside there before claiming it as his primary residence. Such a determination would effectively resolve a key issue slated for a trial on January 16, potentially resulting in Giuliani having to forfeit the condo to the plaintiffs.
In written submissions, Liman has shown skepticism towards Giuliani’s reasoning for failing to provide the necessary documents, indicating that Friday’s contempt hearing may not favor Giuliani.
Giuliani has not endeared himself to Liman. At a November hearing, he confronted the judge after being questioned about his compliance regarding the transfer of property. His legal team even suggested in court filings that the judge might exhibit bias against Giuliani due to the opposition Liman faced during his confirmation.
On Thursday afternoon, Giuliani requested permission to attend the upcoming hearing virtually via Zoom, citing knee problems and a cough attributed to his presence at the World Trade Center site on September 11, 2001. Notably, he has made numerous media appearances recently, including an extensive discussion on Newsmax regarding a mass attack in New Orleans and a two-hour podcast on the same subject.
In an order issued Thursday, Liman mandated that Giuliani must appear in court in person if he wishes to testify.
Giuliani's troubles extend beyond the New York hearing; a week later, he faces another contempt hearing before Howell—a judge whom he has frequently criticized. He has accused her of bias based on her management of various cases related to the January 6, 2021, Capitol attack, claiming difficulties in securing legal representation in her courtroom.
Howell, appointed by former President Barack Obama, has admonished Giuliani multiple times over the past two years for ignoring her orders—a history that could significantly impact the upcoming contempt hearing.
Both contempt hearings may serve as precursors to Giuliani’s January 16 trial before Liman, which will determine the status of the Palm Beach condo and whether it qualifies for a “homestead” exemption from collection efforts.
The trial will also address the fate of Giuliani's New York Yankees World Series rings. He claims to have gifted these to his son, Andrew, years ago, positing that they are thus exempt from seizure by Freeman and Moss. He has provided photographs and text messages to support his assertion. The proceedings may require both Giuliani and his son to testify regarding the circumstances of the transfer.
Orden reported from New York. Cheney reported from Washington.
Lucas Dupont for TROIB News
