Rudy Giuliani, once hailed as “America’s Mayor” for his unwavering leadership during the 9/11 attacks, now faces mounting legal and financial challenges. On Monday, U.S. District Court Judge Lewis Liman—a Trump appointee with Democratic affiliations—found Giuliani in contempt of court for allegedly failing to comply with an order to transfer assets.
The case stems from a defamation lawsuit filed by Georgia election workers Ruby Freeman and Shaye Moss, who accuse Giuliani of spreading false claims about their involvement in election fraud during the 2020 presidential election.
The court’s decision highlights Giuliani’s ongoing struggle in what many view as a coordinated effort to punish Trump allies for questioning the 2020 election results. Ordered to pay $148 million in damages—a sum many critics argue is egregiously disproportionate—Giuliani’s defiance of the asset transfer order has now resulted in a contempt ruling.
Freeman and Moss became unlikely figures in the 2020 election saga after they were accused of mishandling ballots in Georgia. Giuliani, serving as Donald Trump’s attorney, voiced concerns about election irregularities, which led to claims that Freeman and Moss were involved in fraudulent activities. Despite video evidence fueling public skepticism, official investigations cleared the pair of any wrongdoing.
Freeman and Moss subsequently filed a defamation lawsuit, alleging that Giuliani’s comments put their lives at risk and caused emotional distress. A court sided with the plaintiffs, issuing a jaw-dropping $148 million judgment against Giuliani. Many legal experts have criticized the damages as excessive, arguing that the amount appears more punitive than compensatory.
Despite Giuliani’s attempts to comply with the court’s demands, his financial situation has reportedly made it impossible to satisfy the judgment. His failure to transfer assets by the court’s deadline resulted in Judge Liman declaring him in contempt, a ruling that could carry further penalties.
Giuliani’s career has taken a dramatic turn since his days as a celebrated mayor of New York City. Revered for his leadership during the aftermath of 9/11, he was once a symbol of resilience and patriotism. However, his alignment with Trump and his outspoken defense of election integrity have made him a prime target for legal and political attacks.
Critics argue that Giuliani is being unfairly punished for doing his job as Trump’s attorney. His willingness to challenge the 2020 election results—an action protected under the principles of advocacy—has subjected him to relentless lawsuits and professional sanctions. Last year, Giuliani was disbarred in Washington, D.C., over his public statements regarding election fraud, a decision many see as politically motivated.
“This isn’t about justice; it’s about sending a message,” said a close ally of Giuliani. “Rudy has become a scapegoat for those who want to delegitimize anyone who dared question the 2020 election.”
The involvement of Judge Lewis Liman, a Trump appointee with ties to the Democratic Party, has raised eyebrows among Giuliani’s supporters. While Liman’s appointment by Trump suggests impartiality, his rulings in politically charged cases have fueled concerns about judicial bias.
Legal analyst Mark Daniels questioned the proportionality of the damages awarded in the defamation case, calling it “an unprecedented judgment designed to bankrupt and humiliate a high-profile Trump ally.” Daniels added, “This contempt ruling is just the latest move in a broader campaign of lawfare against anyone who challenges the establishment narrative.”
Giuliani has faced significant financial difficulties in recent years, compounded by mounting legal bills and declining income. His struggles to meet the court’s demands are emblematic of the broader challenges faced by Trump allies caught in the crosshairs of litigation.
Despite the obstacles, Giuliani remains defiant. “I have always stood up for what I believe is right, no matter the cost,” Giuliani said in a recent interview. “This isn’t just about me—it’s about protecting the rights of every American to question and hold their government accountable.”
Giuliani’s legal team is expected to appeal the contempt ruling, arguing that his financial limitations were not adequately considered by the court. However, the path forward remains uncertain, with further legal proceedings looming.
Giuliani’s case is part of a broader trend of what many conservatives call “lawfare,” the weaponization of the legal system to target political opponents. While Freeman and Moss’s lawsuit has been framed as a quest for justice, the staggering damages and contempt ruling against Giuliani suggest a punitive motive aimed at silencing dissent.
For Giuliani’s supporters, his plight is a stark warning about the dangers of challenging the political status quo. As one ally put it, “If they can do this to Rudy Giuliani, what’s stopping them from coming after the rest of us?”
As Giuliani faces the fight of his life, his story underscores the growing polarization of the American legal system. Whether viewed as a cautionary tale or a miscarriage of justice, Giuliani’s case serves as a pivotal moment in the ongoing battle over free speech, advocacy, and accountability.
For now, “America’s Mayor” remains undeterred, vowing to continue his fight for justice—even as the odds seem increasingly stacked against him.
