(CNN) — Rudy Giuliani filed for bankruptcy in federal court in New York on Thursday, just days after a jury ordered him to pay nearly $150 million to two former Georgia election workers for defamation.

According to the filing, Giuliani listed debts between $100 million and $500 million, and assets worth up to $10 million.

The bankruptcy declaration is another setback for the former New York City mayor, federal prosecutor and one-time front-runner for the Republican presidential nomination, all stemming from his time as Donald Trump’s attorney after the 2020 presidential election.

Giuliani lists nearly $1 million in unpaid taxes among his liabilities as well as hundreds of thousands of dollars owed to lawyers and accountants.

He also lists pending lawsuits, including three defamation cases over his statements after the 2020 election that haven’t yet gone to trial and could add to his debt if he’s ordered to pay damages in those cases.

“The filing should be a surprise to no one,” Giuliani political adviser Ted Goodman said Thursday. “No person could have reasonably believed that Mayor Rudy Giuliani would be able to pay such a high punitive amount. 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.”

It comes a day after the federal judge who oversaw the blockbuster defamation case said the two plaintiffs – Ruby Freeman and Shaye Moss – can begin trying to collect from Giuliani immediately.

US District Judge Beryl Howell said in her order Wednesday that Giuliani had escaped revealing his worth by refusing to turn over evidence he had in the case before trial, never acknowledged previous court orders for him to reimburse the women for his attorneys’ fee and repeatedly claimed he’s broke and the verdict would severely hurt him.

During the trial, Giuliani attorney Joseph Sibley said Freeman and Moss were asking for “the civil equivalent of the death penalty.”

“They’re trying to end Mr. Giuliani,” Sibley said.

Giuliani may ask the bankruptcy court to excuse his debt to Moss and Freeman — in the same way Alex Jones tried and failed to do in his Sandy Hook defamation case.

But part of the final judgment in the 2020 election defamation case against Giuliani included his acknowledgement that he defamed them with malice, which will make it harder for him to escape his debt to them.

In the meantime, Moss and Freeman’s lawyers have indicated they would move quickly to ask for liens on Giuliani’s existing properties in New York and Florida and researching entities that may be providing money to him, such as Newsmax, where he has a show.

CNN’s Katelyn Polantz and Devan Cole contributed to this report.

This story has been updated with additional details.