Giuliani's Legal Troubles: Breaking The Law?

Rudy Giuliani, the former mayor of New York and lawyer to Donald Trump, has been involved in several legal disputes in recent years, leading to questions about whether he has broken the law. Giuliani has been accused of defamation, held in contempt of court, and is facing criminal charges for his attempts to overturn the 2020 election. Giuliani has also been disbarred in New York and Washington, D.C., and is facing financial difficulties as a result of the legal cases against him.

Giuliani's Ukraine meetings

Rudy Giuliani, former New York mayor and personal lawyer to President Donald Trump, has been at the centre of a Ukraine controversy. Giuliani's eagerness to involve himself in US foreign policy has been scrutinised, particularly his meetings and communications with Ukrainian officials.

Giuliani's efforts in Ukraine were related to the push for the removal of the then-US Ambassador to Ukraine, Marie Yovanovitch. Giuliani's associates, Lev Parnas and Igor Fruman, have been indicted in a campaign finance case. They pleaded not guilty but it is alleged that they sought Yovanovitch's removal and encouraged Ukrainian officials to investigate Trump's political rival, Joe Biden, and his son, Hunter.

Giuliani's meetings in Ukraine were part of an effort to investigate Biden and his son, and these meetings were central to the Democratic impeachment inquiry into Trump. A call record released by the White House revealed that Trump asked Ukrainian President Volodymyr Zelensky to "look into" Biden and his son. Giuliani's role in this situation has been described as a direct conduit to Trump by Ukrainian officials.

The House Intelligence Committee subpoenaed Giuliani to provide documents, and he has been invited to testify before the Senate Judiciary Committee. Federal prosecutors are examining Giuliani's contacts in Ukraine, including with former Rep. Bob Livingston, who pushed for Yovanovitch's removal. Livingston denies any connection with Giuliani's efforts.

Giuliani's actions in Ukraine have had consequences for his personal life, as he has faced legal troubles and disbarment following his involvement in the controversy.

Giuliani's finances and medical history

Giuliani's Finances

Rudy Giuliani's finances have been the subject of much scrutiny in recent years, with questions arising over his consulting business and foreign clients. After leaving his position as mayor, Giuliani profited from book deals, high-priced speaking engagements, and consulting work for foreign governments and businesses. He has been criticised for potentially mixing his access to Trump with his personal business, blurring the lines between his role as a lawyer and security expert and his consulting work.

In 2018, Giuliani was making between $5 million and $10 million a year, enjoying a lavish lifestyle that included six homes, private jets, and multiple country club memberships. He has since declared bankruptcy, following a $148 million defamation lawsuit from Georgia election workers Ruby Freeman and Shaye Moss, who claimed he falsely accused them of committing election fraud. Giuliani has been accused of hiding assets and failing to comply with court orders to turn over financial information and assets to pay his debt.

Giuliani's Medical History

Giuliani has claimed to be suffering from various health issues, including knee, heart, and lung conditions. He has attempted to use his health as a reason to delay or avoid court appearances, citing "lung issues attributable to being at the World Trade Center on 9/11". However, his requests have been rejected by judges, who have demanded medical evidence and pointed out his ability to travel and appear in person at other events. Giuliani's lawyer has stated that his client is a healthy and thriving 80-year-old man with an incredibly sharp mind and quick wit.

Giuliani's contempt of court

Rudy Giuliani has been found in contempt of court twice in January 2025.

The first instance of contempt of court was ruled by Judge Lewis Liman in Manhattan federal court on January 6, 2025. Giuliani was found in contempt of court for failing to turn over information to lawyers representing Georgia election workers Ruby Freeman and her daughter, Shaye Moss. Freeman and Moss had won a $148 million defamation verdict against Giuliani, who had falsely accused them of attempting to steal the 2020 election in Georgia. Giuliani was accused of trying to "run out the clock" to avoid paying the $148 million, which may have cost him his $3.5 million Florida condo and his Yankees World Series rings.

The second instance of contempt of court was ruled by District Judge Beryl Howell on January 10, 2025. Giuliani was held in contempt for continuing to spread false statements about Freeman and Moss, in violation of court orders that prevented him from defaming the two women. Giuliani continued to make false insinuations about the two women, long after they won the defamation verdict against him. Judge Howell called Giuliani's actions outrageous and shameful and ordered him to swear in a statement that he has reviewed and acknowledges records showing there was no fraud in the 2020 election.

Giuliani's actions and the subsequent rulings by Judges Liman and Howell highlight the legal consequences he faces for his false statements and failure to comply with court orders.

Giuliani's defamation of Ruby Freeman and Shaye Moss

In 2023, Rudy Giuliani was ordered by a jury to pay $148.1 million to Ruby Freeman and her daughter Shaye Moss in compensatory and punitive damages. This was due to Giuliani's deliberate spreading of lies in an effort to undermine the results of the 2020 presidential election. Giuliani, a Trump ally and former mayor of New York City, falsely accused the women, who were Georgia election workers, of attempting to steal the election in Georgia.

Freeman and Moss filed a lawsuit in December 2021, claiming defamation, intentional infliction of emotional distress, and civil conspiracy. They were represented by Protect Democracy, through its Law for Truth project, in partnership with the law firms Willkie Farr & Gallagher LLP and DuBose Miller LLC. The lawsuit claimed that Giuliani's statements about the two women were made to intentionally undermine the results of the 2020 presidential election.

As a result of Giuliani's lies, Freeman and Moss experienced a devastating change in their lives, including their homes, family relationships, work, sense of safety, and mental health. They continue to work to rebuild their lives and seek justice, hoping that no one else will have to go through what they did.

Despite the ruling, Giuliani has shown little remorse for his actions and has continued to spread false statements about Freeman and Moss. He has been held in contempt of court multiple times for failing to cooperate in the handover of his personal assets and for continuing to defame the two women in violation of court orders. Giuliani's attorney, Ted Goodman, has claimed that the contempt ruling is an attempt to prevent Giuliani from exercising his constitutional rights and that the coverage of the case has been biased.

Giuliani's legal settlement with Freeman and Moss

In January 2025, Rudy Giuliani reached a tentative legal settlement with former election workers Wandrea "Shaye" Moss and her mother, Ruby Freeman, whom he had defamed by falsely accusing them of election fraud in the 2020 presidential election. The settlement allowed Giuliani to retain his New York and Florida homes and personal belongings, including his New York Yankees World Series rings, in exchange for compensation and a promise to refrain from making further defamatory statements about Moss and Freeman.

The settlement came after Giuliani was ordered by a jury to pay $148.1 million in damages to Moss and Freeman in 2023. The jury's award included $75 million in punitive damages, $33.169 million in defamation damages, and $40 million in damages for the infliction of emotional distress. The two women, who are Black, faced violent threats and harassment as a result of Giuliani's false accusations, forcing them into hiding.

Despite the settlement, Giuliani did not admit liability or wrongdoing. In a statement, he expressed satisfaction with the resolution and emphasised the negative impact the litigation had on all parties involved. Moss and Freeman also released a statement, describing the past four years as a "living nightmare" and expressing their relief at being able to move forward with their lives.

Giuliani, a former lawyer for President-elect Donald Trump, had attempted to delay the legal process by missing court appearances and failing to provide financial information. As a result, he was held in contempt of court twice in the weeks preceding the settlement.

Frequently asked questions