Rudy Giuliani will again square off in court against two Georgia election workers Thursday, this time seeking to keep his Florida condominium and other prized possessions from the women who won a $146 million defamation judgment against him. 

Giuliani faces trial in New York over whether his Palm Beach, Fla., condo, which he claims as his permanent residence, must be turned over to Ruby Freeman and Shaye Moss, who he has falsely asserted for years engaged in widespread 2020 election fraud.  

A federal judge will also weigh whether the ex-New York City mayor must cough up three New York Yankees World Series rings, which Giuliani says he gifted to his son, Andrew, and therefore are not his to give up. 

Giuliani, his son and two other witnesses could take to the stand during the bench trial, which could last three days. It comes after a more than yearlong effort by the two former election workers to collect their multimillion-dollar judgment.  

Though U.S. District Judge Lewis Liman already ordered Giuliani to turn over most of his assets, the judge has yet to decide the fate of the condo and rings. 

The upcoming trial over those assets caps a month of legal losses for Giuliani. He was held in contempt by two different courts last week in Manhattan for failing to turn over evidence about his assets, and in Washington for continuing to spread lies about the election workers.  

Giuliani’s contempt in New York set his defense back before the trial even began.  

Liman, who presides over both, ruled that he will draw an adverse inference against the former New York City mayor and prevent him from offering certain evidence at the trial. 

That evidence includes Giuliani’s change in service providers, like doctors and lawyers, when he purportedly moved his permanent residence to Florida, as well as texts or emails proving the move Giuliani failed to timely produce. 

Liman said he would take notice of the “gaps” caused by Giuliani’s failure. Giuliani’s attorney warned it would effectively be the death penalty in his fight to retain control of his roughly $3.5 million Florida condo, though Liman said the sanctions were “narrower.” 

The judge has also issued an order preventing Giuliani from calling as witnesses his longtime friend, Monsignor Alan Placa, and his spokesperson, Ted Goodman. 

The ex-mayor will be able to call Maria Ryan, another of his employees, to testify about his purported relocation from New York to Florida. If Giuliani successfully declares the condo his homestead, it would shield the property from being seized to satisfy a portion of the tens of millions of dollars he owes Freeman and Moss. 

Giuliani has asserted losing the condo effectively would make him homeless. 

He has already been forced to turn over his roughly $5 million Manhattan apartment, a Mercedes-Benz convertible and other prized possessions, like luxury watches. The election workers in recent weeks have said they’re still trying to secure some of the assets. 

World Series rings from 1996, 1999 and 2000, which Giuliani says he was gifted by former Yankees owner George Steinbrenner, are also in dispute at this week’s trial. 

However, Giuliani claims they were meant for his son, Andrew. The elder Giuliani testified during a Dec. 27 deposition he told Steinbrenner the rings would eventually be his son’s and that he made it official at a birthday celebration six or seven years ago. Court filings show a years-old photo of Giuliani’s son with the rings. 

“I made a little ceremony. I’d given it to him,” Giuliani said. “I said, ‘They are now yours. These are your rings. I don’t know what I’m keeping them for. They belong to you.’” 

Lawyers for Freeman and Moss argue the father-son duo have provided little evidence beyond the testimony and note the elder Giuliani listed the rings among his assets as part of his bankruptcy estate. 

The rings are currently in Andrew Giuliani’s possession, stored in the bedroom closet of his New York City apartment, according to his lawyers. Liman considered keeping the rings in the court’s possession. 

Andrew Giuliani could take the stand as well as a years-long acquaintance, Sean Kalin, he said will confirm the rings were gifted.

The elder Giuliani has repeatedly attacked the election workers’ legal team and his judges, portraying himself as the victim of political persecution. His attorney wrote in court filings this week that he is being treated differently because he “challenged the 2020 election.” 

The Hill requested comment from Goodman, Giuliani’s spokesperson. 

In particular, Giuliani has criticized the judge for refusing to delay Thursday’s trial until after Trump’s inauguration so Giuliani can attend. 

“The Court’s prejudicial actions is to deny Defendant a fair trial,” Giuliani’s lawyer wrote.