We may be looking at nothing less than “the end of Rudy Giuliani,” according to Joseph Sibley, lawyer to the former New York City mayor and one-time personal attorney to Donald Trump.
That's because a federal jury ruled late last year that he owes nearly $150m to Georgia election workers Ruby Freeman and her daughter Shaye Moss after he defamed them, falsely claiming they had committed voter fraud to aid Joe Biden in the 2020 election.
The women described being harassed, receiving death threats and having to flee their homes due to the baseless conspiracy theories pushed by Mr Giuliani.
Before the ruling, Mr Sibley said awarding the women tens of millions of dollars in damages would be “the civil equivalence of a death penalty” for the man once hailed as “America’s mayor” for his response to the events of 9/11.
Since then, Mr Giuliani has filed for Chapter 11 bankruptcy and pleaded that creditors forcing him to sell his condo in Palm Beach, Florida, would leave him to “join the ranks of the homeless”. A judge has so far declined to rule on whether Mr Giuliani can be compelled to sell his Palm Beach property, but warned that “draconian requests” from the committee could ensue.
But how much is the former mayor actually worth?
“He has made it pretty clear that he doesn’t have the resources to handle litigation,” a source familiar with Mr Giuliani’s legal woes told ABC News late last year.
While there's no concrete number, there are some indicators as to how much Mr Giuliani has salted away.
The best current estimate is dated, but puts Mr Giuliani’s net worth at around $50m, with approximately $15m of that from his business activities, including his worth with his Giuliani Partners lobbying group, according to CNN.
At the time of the estimate – about 15 years ago – he was earning approximately $17m a year.
But that was more than a decade ago and a lot has changed for Mr Giuliani since then, not much of it good.
In addition to his present legal woes, the former attorney to Mr Trump has also had to deal with the financial fallout of a third divorce and been forced to turn to his 9/11 legacy to draw in cash, selling T-shirts commemorating the terror attack priced at $911.
He was also, at one point, selling Cameos on the personalised video website for $325 each, though his profile no longer appears to be accessible on the site, according to CBS News.
In addition to merchandise slinging, Mr Giuliani also earns approximately $400,000 a year from his radio show and has likely been able to monetise his podcast to some degree. But those earnings may be offset by the $3m in legal fees, according to The New York Times.
He also has some money tied up in major assets, like his $6.5m apartment, which was listed for sale in mid-December, according to Sotheby’s.
Unfortunately for Mr Giuliani, the defamation case isn’t his only concern: he has also been sued by two voting machine companies for claiming they too were involved in voter fraud in the 2020 election and is facing an unrelated sexual harassment suit seeking $10m brought by his former business associate.
He has “unequivocally” denied those allegations.
Mr Biden's son, Hunter Biden, has also sued Mr Giuliani for unspecified damages after accusing the ex-mayor of mishandling his personal data.
And perhaps most threatening to Mr Giuliani is his indictment in the criminal racketeering case being litigated in Fulton County, Georgia, regarding the 2020 election.
He is a co-defendant with Mr Trump and 17 others. Rather than fines, Mr Giuliani faces jail time if convicted in that case. He has pleaded not guilty there too.
Mr Giuliani’s filing for bankruptcy on 21 December came one day after the federal judge overseeing his defamation case ordered him to “immediately” pay Ms Freeman and Ms Moss, pointing to his history as an “uncooperative litigant” and concerns that he will try to “conceal his assets” during any appeals.
An eight-member jury unanimously agreed that Mr Giuliani owes Ms Freeman and Ms Moss $16.2m and $16.99m respectively in compensatory damages, an additional $20m each for intentional infliction of emotional distress and a further $75m in punitive damages.
His bankruptcy filing lists debts of as much as $500m and assets between $1m and $10m.
Asked in the filing about the nature of his debts, he simply wrote: “Lawsuits.”
In addition to the more than $148m owed to Ms Freeman and Ms Moss, Mr Giuliani owes roughly $1m in taxes and more than $3.5m to law firms.
“The filing should be a surprise to no one,” his spokesperson Ted Goodman said in a statement.
“No person could have reasonably believed that Mayor Rudy Giuliani would be able to pay such a high punitive amount,” he added.
“Chapter 11 will afford Mayor 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.”
In a federal court filing, the women asked the court to immediately enforce the verdict against Mr Giuliani, fearing he “will use whatever time he has to alienate or dissipate what assets are available to satisfy even a small portion” of the judgment awarded to them.
In her order, US district judge Beryl Howell – who has been repeatedly frustrated by Mr Giuliani’s attempts to evade evidence throughout the case – did just that.
Mr Giuliani’s claims that he has experienced “financial difficulties” are “difficult to square” against his hiring of a spokesperson “who accompanied him daily to trial,” the judge wrote.
Following the rulings, Mr Giuliani began hawking unapproved dietary supplements, The Daily Beast reported, showing his followers on livestreams how to create Christmas ornaments out of bottles of Balance of Nature dietary pills and asking them to buy the pills to help “fight the traitors”.
“Balance of Nature should be taken every single day to make sure you get your vegetables and your fruits,” he said.
“I expect you to have these in Christmas stockings for all those that you love, OK?”
The US Food and Drug Administration temporarily removed the supplements from the market in November, noting that they had been falsely promoted as battling cancer and Covid-19, a fact Mr Giuliani neglected to mention in his sales pitch.
