Legal experts say it is highly unusual for Rudy Giuliani, once a top federal prosecutor, to be held in contempt of court by two judges in the same week as he defends cases brought by former Fulton County election workers.

Federal judges in New York and Washington, D.C., separately held Giuliani in civil contempt last week in cases stemming from the $148 million defamation verdict Ruby Freeman and Wandrea’ “Shaye” Moss won against him in 2023.

Giuliani, a now-disbarred attorney and former New York City mayor who served in the 1980s as the U.S. Associate Attorney General and U.S. Attorney for the Southern District of New York, was warned Friday by Judge Beryl Howell in D.C. that he could be jailed if he continues to defy her orders.

“There are people who have ignored court orders, but that’s certainly not a thing that happens regularly and you certainly would not expect it from a former U.S. Attorney,” said Florida lawyer Richard Serafini, who spent 11 years as a senior litigator in the U.S. Department of Justice’s criminal division. “I wouldn’t say this is run-of-the-mill type stuff.”

On Jan. 6, Judge Lewis Liman in New York held Giuliani in civil contempt for failing to comply with his orders requiring Giuliani to hand over documents requested by Moss and Freeman.

In the New York case, the Georgians are trying to obtain Giuliani’s Palm Beach condo and want evidence about his properties. Giuliani is fighting to keep his Florida condo under a homestead exemption, claiming it is his primary residence.

On Jan. 10, Giuliani was held in civil contempt by Howell, who presided over the defamation case. Howell found Giuliani had violated a May 2024 judgment barring him from continuing to allege that Moss and Freeman had engaged in wrongdoing in connection with the 2020 presidential election.

Giuliani’s public allegations against Moss and Freeman, including that they miscounted ballots, were debunked by Georgia and federal investigators.

A contempt ruling in a sophisticated civil case where the parties are represented by good lawyers is “incredibly rare,” said Atlanta litigator Kamal Ghali, a former federal prosecutor whose specialties include white collar criminal defense.

“Judges expect parties to follow their orders,” Ghali said. “Oftentimes courts will warn the parties before saying ‘If this happens again, I’ll hold you in contempt.’ It’s usually not a reaction of first resort.”

Giuliani faces fines, weakened defense at trial

In the D.C. case, Giuliani will be fined $200 for each day after Jan. 20 that he doesn’t comply with conditions imposed by Howell, including that he review large swathes of testimony from the defamation trial as well as the Georgia Secretary of State’s report on allegations of 2020 election fraud.

The contempt ruling in New York weakens Giuliani’s defense in a bench trial due to start Thursday. Liman, who will decide whether Giuliani’s condo can go to Moss and Freeman, limited Giuliani’s efforts to show he has had doctors and other professional service providers in Florida since January 2024. He also barred Giuliani from providing testimony about emails or text messages to show he primarily lives in Florida.

On Monday, Liman excluded two of Giuliani’s last-minute witnesses from trial and said Giuliani can’t rely on any document he did not previously give Moss and Freeman, saying the case had been “plagued” by Giuliani’s failure to respond to requests for information. Giuliani filed a same-day notice to appeal the order, stating the trial should be postponed until after former and future President Donald Trump’s inauguration on Jan. 20.

Civil versus criminal contempt

Because Giuliani was held in civil, and not criminal, contempt, any associated jail time would be an effort to force his compliance with a court order rather than punish him for defiance.

It means Giuliani, if jailed for continued noncompliance, could free himself by simply doing what the court had asked.

“In civil contempt, the view is that the defendant, or the person being held in contempt, holds the keys to the jailhouse door,” Serafini said. “As soon as they comply with the court’s order, the doors open and they’re out of jail.”

Contempt is the tool judges have to enforce their orders.

Ghali said civil contempt is “basically the court trying to coerce or force a party into complying with a court order,” whereas criminal contempt works to punish someone whose disobedience constitutes a crime.

A civil contempt ruling often imposes a penalty until the order in question is complied with, giving the recipient an opportunity to purge themselves of contempt. It does not require proof beyond a reasonable doubt or trigger a jury trial, unlike criminal contempt.

The U.S. Department of Justice says civil contempt is “designed to compel future compliance with a court order” and is “avoidable through obedience.”

A person charged with criminal contempt has the usual protections afforded to any criminal defendant, such as the right to have a lawyer and present a defense.

“It’s prosecuted like any other crime,” Serafini said.