Rudy Giuliani keeps telling judges he's broke, but won't share financial statements and took a private jet to his Georgia booking

• Rudy Giuliani keeps saying he's broke and can't pay legal bills.
• But he's scrupulously avoided actually showing financial statements in court.
• He blames an earlier FBI raid for disorganizing his documents — an excuse blasted by a federal judge.

Rudy Giuliani wants you to know he can't pay his bills.

But he won't tell anyone how much money he has — even if he has to face down sanctions to avoid it.

This past week, a federal judge handed Giuliani an automatic loss in a defamation lawsuit brought by two Georgia poll workers who say Giuliani falsely accused them of manipulating ballots in the 2020 election. The ruling came with an order for Giuliani to pay a whopping $132,000 in his opponents' legal fees.

Giuliani, US District Judge Beryl Howell wrote, provided only "a sliver of the financial documents required to be produced" for the lawsuit. His excuses for withholding them, Howell wrote, didn't make any sense.

The disgraced attorney will be on the hook for even more in fines if he doesn't produce the material by later this month. A jury, Howell ruled, can skip the step of determining whether Giuliani did anything wrong and move straight to deciding how much he should pay in damages.

In her ruling, Howell recognized an odd dynamic that has played out in numerous ongoing lawsuits Giuliani is involved in.

On one hand, Giuliani claims he is "having financial difficulties" and can't pay for adequate legal preparation, the judge wrote. On the other hand, he has taken great risks to avoid proving it.

Giuliani has neglected to go through the proper channels of filing motions to delay fees until the case is resolved, "let alone provided any evidence about his inability to reimburse plaintiffs," Howell wrote.

There are signs that Giuliani is indeed bleeding financially.

In early August, he put up his Manhattan apartment for sale. If he finds a buyer, he can spare himself the $10,719 monthly maintenance fee and use the funds from its $6.5 million asking price toward legal bills.

Giuliani is a defendant in several civil lawsuits. In some of them — like one brought by a woman accusing him of sexual misconduct and another from a grocery store worker who claims the ex-mayor had him wrongly arrested — he's partially representing himself instead of hiring a large legal team.

His prestigious resume — once the top federal prosecutor in Manhattan, New York City mayor, and president's personal lawyer — has become a measure of how far he has fallen. Because of his attempts to overturn the 2020 election results, he is on the verge of losing his ability to practice law and is under criminal indictment in Georgia, a serious and embarrassing charge that he will be sure to rack up more bills defending. Former President Donald Trump has announced a $100,000-per-plate fundraising event to help pay his legal tab.

But there are also indications that Giuliani seems to be doing OK.

He took a private jet to his jail booking in Atlanta. He still owns a Hamptons house and two Palm Beach condos, according to the New York Times. He still has a daily radio show in New York on a channel owned by a billionaire Republican donor. And, as Howell noted in her ruling, he has a large monetizable audience for his daily podcast.

Rudy is pleading poverty over his failure to hand over records in another suit

Giuliani's mysterious financial situation has come under scrutiny in another lawsuit he's defending.

In a lawsuit brought by Smartmatic, an election technology company he falsely accused of flipping votes from Trump to now-President Joe Biden in 2020, he hasn't handed over any of the discovery material that he's required to — and he's blaming his bank account.

Giuliani has "produced no documents" and "located two publicly available Tweets," Smartmatic's lawyers wrote in a scathing August filing asking for sanctions.

"'The dog ate my homework.' 'I have to wash my hair.' 'I can't go out, I'm sick.' Since the dawn of time, people have made up excuses to avoid doing things they do not want to do," Smartmatic's lawyers wrote. "This is exactly what Giuliani has done here. For months, Giuliani has made up excuses to get out of his discovery obligations to Smartmatic and to violate orders from this Court."

Giuliani's electronic files are hosted by a company called Trustpoint, which can search them and provide the documents Smartmatic needs for the lawsuit.

But Giuliani hasn't paid Trustpoint the fees it needs to run those searches, Smartmatic's lawyers say. According to Smartmatic, Giuliani has provided shifting and slippery answers to questions about whether he can afford them.

"From the start of discovery through today, Giuliani and his counsel regularly flipped position on whether or not Giuliani could afford to search for and produce documents stored by his e-discovery vendor," Smartmatic's lawyers wrote. "And, even when Giuliani agreed to provide information or documents to Smartmatic, he ultimately failed to uphold his side of the agreement without any believable explanation."

Smartmatic's attorneys have asked the judge to order Giuliani to provide a sworn statement about his financial status, calling his bluff.

Giuliani blames the FBI

If Giuliani is asked to swear under oath that he doesn't have the money, he'll probably find a way to come up with it instead of risking perjury charges, Smartmatic says.

The company noted that Trump's Save America PAC paid $340,000 to Trustpoint earlier this year, according to public filings — at which point Giuliani was able to produce discovery material in a separate lawsuit.

"So far, Giuliani's financial position tends to be whatever is most convenient for Giuliani," Smartmatic's lawyers wrote. "Whenever he is ordered to do something, he lacks the money to pay for it. But, when told he must submit a declaration showing he lacks funds, somehow the previously unavailable money appears. It's a miracle."

A spokesperson for Giuliani didn't respond to questions about his finances. In court filings, his attorneys have pointed to media reports indicating he's having money troubles, but they have not included any financial statements that show his net worth, asset value, or income streams as exhibits.

Giuliani has blamed his failure to provide financial records on the April 2021 FBI raid on his Manhattan home and office. The seizure of his documents and electronic devices, his lawyers have said, means his financial records have become disorganized and hard to access.

"Mayor Giuliani is wrongly accused of not preserving electronic evidence that was seized and held by the FBI," his spokesperson Ted Goodman said following last week's sanctions ruling.

Howell tore apart that excuse in her ruling, writing that it demonstrated he failed to take the necessary steps to preserve ESI — or electronically stored information — even though he knew he would be sued as far back as late 2020. "The government is not Giuliani's ESI preservation team," Howell wrote.

"Given Giuliani's much-vaunted experience as an attorney, he plainly should have known better, and had he taken the proper steps prior to or even after the FBI's seizure of his devices, his potentially relevant ESI could have been preserved," Howell wrote.