Rudy Giuliani files for bankruptcy days after being ordered to pay $148 million in defamation case

Ted Goodman, a political adviser and spokesperson for Giuliani, said in a statement that Giuliani’s decision to seek bankruptcy protection “should be a surprise to no one” because “no person could have reasonably believed that Mayor Giuliani would be able to pay such a high punitive amount.”

The Chapter 11 filing will give Giuliani “the opportunity and time to pursue an appeal, while providing transparency for his finances under the supervision of the bankruptcy court, to ensure all creditors are treated equally and fairly throughout the process,” Goodman said.

But declaring bankruptcy likely won’t erase the $148 million verdict. Bankruptcy law doesn’t allow for the dissolution of debts that come from a “willful and malicious injury” inflicted on someone else. A judge said Wednesday that Freeman and Moss could start pursuing payment immediately, saying any delay could give Giuliani time to hide assets.

“This maneuver is unsurprising, and it will not succeed in discharging Mr. Giuliani’s debt to Ruby Freeman and Shaye Moss,” their lawyer, Michael Gottlieb, said.

After the verdict, Giuliani repeated his stolen election claims, insisted he did nothing wrong and suggested he’d keep pressing his claims even if it meant losing all his money or going to jail. His rhetoric prompted Freeman and Moss to sue him again this week.

The Dec. 15 verdict was the latest and costliest sign of the mounting financial toll incurred by the 79-year-old Giuliani, a one-time Republican presidential candidate and high-ranking Justice Department official once heralded as “America’s Mayor” for his calm and steady leadership after the terrorist attacks on Sept. 11, 2001.

Once swimming in cash as a globetrotting security consultant, Giuliani’s money woes intensified amid investigations, lawsuits, fines, sanctions, and damages related to his work helping Trump try to overturn the 2020 election.

Among his potential debts, he listed lawsuits brought by two voting machine manufacturers who say he and others defamed them with claims of a stolen election.

A lawyer for Giuliani, Adam Katz, suggested at an August court hearing in one of those cases that Giuliani was “close to broke,” and unable to pay a number of bills, including a $12,000 to $18,000 tab for a company to search through his electronic records for evidence.

In court papers rebuffing voting machine-maker Smartmatic’s demand for an accounting of his finances, Giuliani’s lawyers disclosed that he was so hard up for money that he solicited third-party donations to pay a prior $300,000 bill to the electronic discovery firm.

In September, Giuliani’s former lawyer Robert Costello sued him for nearly $1.4 million in unpaid legal bills. Giuliani claimed he never received them. The case is pending.

Costello represented Giuliani from November 2019 to this past July in matters ranging from an investigation into his business dealings in Ukraine, which resulted in an FBI raid on his home and office in April 2021, to investigations of his work in the wake of Trump’s 2020 election loss.

Investigators noted Giuliani’s dwindling finances in court papers unsealed this week from the 2021 raid, raising his need for money as possible motivation for his interest in aiding a Ukrainian official. Citing bank records and other information, they said Giuliani had gone from having about $1.2 million in the bank and $40,000 in credit card debt in January 2018 to about $288,000 in cash and $110,000 credit debt in February 2019. Giuliani was never charged with a crime as a result of that investigation.

Giuliani’s other lawsuits, which he listed as potential liabilities, include one brought against him by Biden’s son Hunter, who alleges Giuliani was responsible for the “total annihilation” of his digital privacy by accessing and sharing his personal data from his laptop computer.

Giuliani is also being sued by a woman who said she worked for him. She alleges he owed her nearly $2 million in unpaid wages and coerced her into sex. Another lawsuit involves a man who claims Giuliani defamed him after he slapped the ex-mayor on the back at a supermarket. Giuliani has denied the woman’s claims and has asked for the man’s lawsuit to be thrown out.

In August, Giuliani was indicted with Trump and others in Georgia on charges he acted as Trump’s chief co-conspirator in a plot to subvert Biden’s victory. He was also described as a co-conspirator but not charged in special counsel Jack Smith’s federal election interference case against Trump.

Giuliani’s bankruptcy filing did not detail his assets or add to what is already known about how he’s been making money in recent years.

Giuliani hosts a daily radio show in New York City and a nightly streaming show on social media. On social media, he’s pitched various products, including wares sold by election denier Mike Lindell. He also has hawked autographed 9/11 shirts for $911 dollars and has appeared on Cameo, a service where celebrities record short videos for profit. Giuliani was charging $325 for his greetings, though a recent check shows they’re “temporarily unavailable.”

After his Georgia indictment, he directed social media followers to the website of his legal defense fund. To save money, Giuliani has represented himself in some legal matters.

In July, Giuliani put his Manhattan apartment up for sale. He was initially asking $6.5 million for the three-bedroom residence a block from Central Park, but that might have proved a bit steep. Three months later, he trimmed his ask to $6.1 million. The apartment still hasn’t sold.

In September, Trump hosted a $100,000-a-plate fundraiser for Giuliani at his Bedminster, New Jersey, golf club. Giuliani’s son, Andrew, said the event was expected to raise more than $1 million for Giuliani’s legal bills.

Andrew Giuliani also said that Trump had committed to hosting a second fundraiser for the former mayor at his Mar-a-Lago club in Palm Beach, Florida, though that doesn’t appear to have happened.