With his attorney in tow, Rudy Giuliani traveled to Mar-a-Lago in recent months on a mission to make a personal and desperate appeal to former President Donald Trump to pay his legal bills. By going in person, a source familiar with the matter told CNN, Giuliani and his lawyer Robert Costello believed they could explain face-to-face why Trump needed to assist his former attorney with his ballooning legal bills.
Giuliani and Costello traveled to Florida in late April where they had two meetings with Trump to discuss Giuliani's seven-figure legal fees, making several pitches about how paying Giuliani's bills was ultimately in Trump's best interest.
But the former president, who is notoriously strict about dipping into his own coffers, didn't seem very interested. After Costello made his pitch, Trump verbally agreed to help with some of Giuliani's legal bills without committing to any specific amount or timeline.
Trump also agreed to stop by two fundraisers for Giuliani, a separate source said.
Another source told CNN that Trump only agreed to cover a small fee from a data vendor hosting Giuliani's records. And months later, Trump's Save America PAC paid $340,000 to that vendor, Trustpoint, federal campaign filings show. CNN has now confirmed the payment was intended to settle Giuliani's outstanding bill with the company.
Another attorney for Giuliani referenced that payment in court Wednesday, telling a New York state judge at a hearing that the former New York mayor does not have the money to pay additional legal costs to produce the records in a defamation lawsuit brought by voting technology company Smartmatic, claiming financial hardship.
The attorney also referenced the one-time payment from Trump's Save America PAC, and a source confirmed Giuliani has not received any additional payments since then. (Smartmatic has sued Giuliani over the 2020 election lies he peddled on Fox News and other right-wing networks.)
Giuliani's trip to Mar-a-Lago, which has not been previously reported, indicates the level of financial stress that he has been facing for months, as his legal troubles have continued to pile up.
But what has surprised those in Trump's inner circle is the former president's unwillingness to pay for Giuliani's bills, given Giuliani could find himself under intense pressure to cooperate with the federal and state prosecutors who have charged Trump. Giuliani sat down voluntarily with special counsel Jack Smith's investigators this summer, and he was indicted this week in Georgia by the Fulton County district attorney.
"It's not a smart idea" for Trump to refuse to pay Giuliani's legal fees, one person close to the situation told CNN, referencing how Trump's relationship with Michael Cohen famously deteriorated while he was investigated by special counsel Robert Mueller.
CNN reported on Tuesday that Giuliani is staring down hundreds of thousands of dollars in legal bills and sanctions amid numerous lawsuits tied to his false claims that the 2020 election was rigged.
His attorneys have said in court that these legal quagmires have left him effectively out of cash and that he "cannot afford" a potentially $15,000 to $23,000 bill to pay for more discovery-related document searches. He even appears to have responded to some of the money crunch by listing for sale a three-bedroom Manhattan apartment he owns for $6.5 million.
At the Wednesday court hearing in the Smartmatic case, Giuliani attorney Adam Katz said, "These are a lot of bills that he's not paying. I think this is very humbling for Mr. Giuliani."
The Georgia charges against Giuliani -- 13 in all -- includes violations of the state anti-racketeering law, soliciting a public officer to violate their oath, conspiracy to commit forgery, and making false statements.
He has said in post-indictment interviews that the charges are an "affront to American Democracy" that will create "irrevocable harm to our justice system."