Even in bankruptcy, Rudy Giuliani keeps his financial picture hidden. Now he might lose control of it.

• Rudy Giuliani has delayed disclosing all of his finances even after declaring bankruptcy.
• Before he went bankrupt, lawyers accused him of hiding his finances in other civil lawsuits.
• A judge may soon appoint a trustee who would take over his entire financial life.

When Rudy Giuliani filed for bankruptcy late last year, it gave him some room to breathe.

A jury had ordered him to pay $148 million to two election workers he defamed. A sexual abuse lawsuit was creeping forward in court. And Smartmatic and Dominion Voting Systems — two election technology companies he falsely claimed rigged the 2020 election — were still going after him in court.

Declaring bankruptcy hit the pause button on all of those civil lawsuits. They all flowed into a federal bankruptcy court, where creditors could negotiate for whatever funds the aging former New York City mayor had left.

That relief may be about to run out. Sean H. Lane, the bankruptcy judge has expressed exasperation that Giuliani still hasn't managed to hire an accountant or bookkeeper to work for him. Lawyers for creditors seeking money from Giuliani have accused him of mismanaging his own finances, asking the judge to appoint a trustee to take over his assets.

"Throughout the bankruptcy case, the Debtor has made, at best, half-baked financial disclosures and prioritized delay over progress in his chapter 11 case," lawyers for creditors wrote in a recent court filing. "He files delinquent, inaccurate and incomplete monthly operating reports. He delayed for months the filing of an application to retain a broker to sell his New York City apartment. He continues to resist selling his Florida condominium, instead preferring to spend tens of thousands of dollars on maintenance fees."

A decision from Lane to appoint a trustee could come at any time.

Right now, the bankruptcy process allows the judge, a Justice Department trustee, and creditors to monitor Giuliani's finances closely.

But if the judge were to agree with the creditors and appoint a Chapter 11 bankruptcy trustee, Giuliani would lose control of his own financial life.

A bankruptcy trustee would control all of Giuliani's assets and would be able to sell his two homes unimpeded. His Upper East Side apartment is listed at $5.7 million and creditors value the Florida condo at $3.5 million.

The trustee would also be able to peer into Giuliani's phone and email records and may even waive attorney-client privilege between him and any of his lawyers, potentially exposing him to more criminal and civil cases.

"The trustee might conceivably try to waive the attorney-client privilege to see his interactions with his lawyers," Eric Snyder, the bankruptcy chair of Wilk Auslander LLP, told Business Insider. "To the extent that there's any concerns about fraud, that would make him very nervous as well."

Creditors have expressed frustration because, after months, they say they still don't have a full picture of Giuliani's finances.

They've accused him of "incompetence, at best, and fraud, at worst."

In recent weeks, court filings show, they were surprised to discover he struck a promotion deal with a coffee company and that a firm he owns has been receiving thousands of dollars a month from a 9/11 charity.

Giuliani's creditors have formed a supergroup to try to dig into his finances. Ruby Freeman and Shaye Moss, the two Georgia election workers to whom he owes $148 million in a defamation judgment; Noelle Dunphy, his sexual abuse accuser; and Dominion, the election technology company he falsely accused of rigging the election, all joined forces to scrape as much money as they can in the bankruptcy court.

Their lawyers, at the pricey firm Akin Gump, say Giuliani is being deceptive. He is funneling money to his business entities, they say, where the funds then go to his girlfriend and other supporters, as opposed to creditors who are owed.

A history of lying

There remains an enormous amount of mistrust from the creditors.

Despite losing a lawsuit and getting hit with a $148 million defamation judgment that forced him into bankruptcy in the first place, Giuliani continues to lie about Freeman and Moss. The two Georgia election workers have been the subjects of conspiracy theories that they manipulated ballots in the 2020 election, which now-President Joe Biden won.

Making things worse is that Giuliani has a history of hiding his finances. During the discovery phases for Freeman and Moss's defamation lawsuit, and in another defamation case from Smartmatic, Giuliani pleaded poverty. He claimed he didn't have the money to pay TrustPoint, his electronic discovery vendor, to search his own documents — an excuse that his legal opponents found difficult to believe.

"So far, Giuliani's financial position tends to be whatever is most convenient for Giuliani," Smartmatic's lawyers wrote in a scathing filing at the time. "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."

As it turned out, some of Giuliani's legal expenses may have been funded by political donors supporting Donald Trump. After Trump's Saving America PAC disbursed hundreds of thousands to Trustpoint, Giuliani's lawyers told courts that a "third party" had helped pay some of the bills.

Giuliani's bankruptcy disputes reached a tipping point in recent weeks when he struck a deal to sell Rudy's Coffee.

The creditors said they learned about the deal from social media — a month after it was signed — rather than learning about the new income stream directly from Giuliani or his lawyers.

On top of that, creditors have expressed frustration that the Tunnel to Towers Foundation, a charity that supports 9/11 first responders, has sponsored Giuliani's social media videos by giving money to his communications company, rather than to Giuliani himself.

Both of those deals are structured so that money goes to Giuliani's businesses rather than to Giuliani himself, which allows the funds to flow to his girlfriend and undeserving employees rather than creditors, the lawyers say.

"At a minimum, if you enter into an agreement that brings money into the estate, and it's property of his estate — which it is — then the creditor should have been made aware of it," Snyder told Business Insider.

Maria Ryan, an employee of Giuliani who is widely reported to have been his romantic partner, recently jumped into the bankruptcy dispute herself.

In a court document earlier this month, she wrote she was filing a "motion" to have the creditors' lawyers "stop lying in their filings to the court."

She claimed payments to her often came in the form of reimbursements from Giuliani's retirement account, which he used as seed money for his media ventures and which is protected from the bankruptcy process. And she said she "personally coordinated" the Rudy's Coffee deal.

"Giuliani Communications, LLC is very proud of this quality coffee," she wrote. "In the future, the minute I do a business deal I will send to Mayor Rudy Giuliani's counsel."

Ryan couldn't be reached for comment.

Giuliani has also recently lost another major stream of income that could have gone to his creditors. In May, his show was canceled on WABC, a New York radio station owned by conservative billionaire John Catsimatidis, because he continued to lie about the 2020 election being stolen from Trump.

While in the bankruptcy process, Giuliani must file monthly financial statements. The numbers in them don't add up, the creditors' lawyers say. Account balances are inconsistent from month to month, and some statements from financial institutions appear to show the wrong dates.

A spokesperson for Giuliani directed Business Insider to his YouTube videos, where the former mayor rarely directly addresses the bankruptcy proceedings. In a recent episode of "America's Mayor Live," he said he is being targeted by President Biden.

"They want to destroy me, they want to bankrupt me, they want to take away everything I have, and they want to put me in jail for the rest of my life," Giuliani said the a recent video.

In his court filings, Giuliani has sought to lay the blame elsewhere. His longtime accountant declined to continue working for him, and his part-time bookkeeper is sick, his lawyers wrote in a recent filing. He hasn't yet been able to find new financial professionals to help him, they said. They also noted because Giuliani has had his law license suspended for lying about the 2020 election, he can't get work as a lawyer himself.

"Maybe the Committee also has a suggestion of who would employ an 80 year old disbarred attorney," they wrote in a recent filing.

The bankruptcy judge may not be convinced by Giuliani's explanations.

"There are lots of accountants out there," Snyder said. "He's a sophisticated businessman, so his inability to find accountants isn't going to work."

According to Snyder, the judge isn't supposed to consider Giuliani's history of lying about election workers or law license troubles while he considers whether Giuliani is too untrustworthy to remain in possession of his own finances. But the bankruptcy process itself has given the judge plenty to work with, Snyder said.

"He hasn't filed reports, he started a business without disclosing it, and he's paying the debts of third parties with the estate funds," he said. "Those three things are pretty big things."

While the bankruptcy has subsumed the civil lawsuits against Giuliani, he still has criminal indictments to contend with.

He is a codefendant, alongside Trump and over a dozen other allies, in Fulton County's criminal racketeering case over their efforts to overturn the 2020 election results in Georgia. That litigation was halted earlier in June as an appeals court weighs whether the top prosecutor can remain on the case.

Giuliani was also indicted in Arizona over his attempts to overturn the election in the state. In that case, he was forced to post a $10,000 bond — further depriving creditors of money they say should go to them.

He has pleaded not guilty in both cases.