Giuliani Files for Bankruptcy Protection

Rudolph W. Giuliani filed for bankruptcy on Thursday, a day after a federal judge ordered him to start paying the $148 million in damages he owes to two former Georgia election workers for spreading lies that they had tried to steal the 2020 election from Donald J. Trump.

Mr. Giuliani also owes millions of dollars in legal fees as well as unpaid state and federal income taxes, according to the filing.

On Wednesday, the judge overseeing that case, Beryl A. Howell, ordered Mr. Giuliani to start paying the two women immediately out of concerns that he might “conceal his assets” if he were allowed to wait the typical 30 days.

“The filing should be a surprise to no one,” Mr. Giuliani’s political adviser, 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.”

The filing seeking protection from creditors under Chapter 11 of the bankruptcy code, he said, “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 total, Mr. Giuliani said in the filing, he owes creditors $152.7 million as well as other potential damages he faces in pending lawsuits.

The bankruptcy filing was the latest in a long line of woes that Mr. Giuliani, a former crusading federal prosecutor and mayor of New York, has suffered in the three years since he took the job as the lead lawyer helping Mr. Trump try to overturn his defeat in the 2020 election.

His legal work for the former president has led to his potential disbarment in Washington and to a lawsuit filed against him by Dominion Voting Systems for outlandish claims that the company helped to rig the presidential race against Mr. Trump.

Mr. Giuliani has been indicted in Georgia in a racketeering case with the former president on charges of tampering with that state’s election.

The bankruptcy filing also cited Mr. Giuliani’s involvement as a defendant in suits brought by Hunter Biden, President Biden’s son, and Smartmatic, another voting technology company that became ensnared in conspiracy theories related to Mr. Trump’s loss in the election.

Mr. Giuliani refused to turn over details about his finances in the defamation case brought by Ms. Freeman and Ms. Moss. Thursday’s bankruptcy filing was the clearest look yet at the extent of his often murky financial troubles.

Bankruptcy will not prevent Mr. Giuliani from paying damages to Ms. Freeman and Ms. Moss, because those damages are considered an “intentional tort,” lawyers said.

In October, the I.R.S. placed a lien on Mr. Giuliani’s property in Palm Beach, Fla., for his failure to pay more than $500,000 in income taxes. Mr. Giuliani and his ex-wife tried to sell it for $3.3 million in 2019 but did not find a buyer, The Palm Beach Daily News reported at the time.

Mr. Giuliani is also trying to sell his Upper East Side apartment in New York for $6.1 million.

Mr. Giuliani made millions of dollars a year in private law practice after he left public office. His divorce from his third wife exposed the couple’s once-lavish lifestyle with a $230,000-a-month spending habit, six houses and 11 country club memberships.

In May 2018, as he left his law firm to work with Mr. Trump, Mr. Giuliani had about $1.2 million in cash and about $40,000 in credit card debt, according to recently released documents that were part of a criminal investigation that never led to any charges. The documents show that by early 2019, Mr. Giuliani was down to $400,000 in cash and had up to $110,000 in credit card debt.

At the beginning of the federal trial to determine damages owed to Ms. Freeman and Ms. Moss, Mr. Giuliani’s lawyer, Joseph Sibley IV, warned that even $43 million would be the civil equivalent of the death penalty.

The women filed another defamation suit against him on Monday for continuing to spread the same lies about them.