Rudy Giuliani asks bankruptcy judge to let him hire attorney for appeal of massive defamation judgment — and their connection runs deep

Former Mayor of New York Rudy Giuliani talks to reporters as he leaves after his defamation trial in Washington, Friday, Dec. 15, 2023. A jury awarded massive damages on Friday to two former Georgia election workers who sued Giuliani for defamation over lies he spread about them in 2020 that upended their lives with racist threats and harassment. (AP Photo/Jose Luis Magana, File)

Rudy Giuliani is requesting a new addition to his legal team while emphasizing it is “imperative” he has a successful appeal of the recently upheld $146 million Georgia election workers defamation judgment that sent him into Chapter 11 bankruptcy proceedings.

Giluani attorney Gary Fischoff filed an application with U.S. Bankruptcy Sean Lane on Wednesday seeking the court’s permission to hire Kenneth Caruso for a “flat fee” of $250,000 as “special litigation counsel,” starting on March 20. Fischoff explained that Caruso and his eponymous firm would be focusing on an appeal to the U.S. Court of Appeals for the D.C. Circuit, which Giuliani’s legal team hopes will end with him either having to pay Ruby Freeman and Shaye Moss a substantially lower amount or eliminating the judgment in its entirety — this after the number was slightly reduced from $148 million to $146 million as part of the final judgment .

Giuliani’s legal team has maintained that the “outsized judgment” was “ unreasonable on its face ” and presented an obstacle in making his other creditors whole.

“The Debtor believes the outsized judgment is unreasonable on its face and does not reflect the true damages, if any, suffered by Plaintiffs,” Fischoff said in January. “The Debtor expects to be successful in having the judgment modified or vacated. As such a substantial reduction in the Freeman claim would render a substantial benefit to the Debtor, his estate and his creditors.”

The Wednesday request for Caruso’s hire similarly called it “imperative” that Giuliani “succeed in an have excellent representation” in the appeal of the Freeman v. Giuliani judgment if bankruptcy “reorganization” proceedings are themselves to be successful.

The filing attached a declaration from Caruso that explained he and Giuliani have known each other since the 1970s and have been “personal friends and professional colleagues in both government service and private practice” in the decades since.

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A onetime “ special assistant ” to Giuliani, Caruso said he has “defended many defamation cases” and has the appellate seasoning to effectively represent Giuliani with a “fresh perspective.”

“In my experience, it is not uncommon for a party to change counsel when a case moves from a trial court to an appellate court,” Caruso’s declaration said. “Often, at the appellate stage, the party benefits from a new lawyer’s fresh perspective on the case, even a case that was very ably tried.”

“I respectfully submit that I will bring that fresh perspective to the Appeal, which, as this Court knows,” Caruso added, “is critically important to the Debtor’s successful reorganization, given the substantial damages awarded in the judgment challenged on the Appeal.”

The lawyer traced his and Giuliani’s history all the way back to 1977, just six years before Giuliani rose to become U.S. Attorney for the Southern District of New York. Their professional ties remained into Giuliani’s time as mayor of New York City, Caruso said.

“During his Mayoralty, he appointed me to positions of trust and confidence, such as membership on the Board of Director of the Metropolitan Transportation Authority, the New York City Charter Revision Commission, and the Mayor’s Appointments Committee,” the declaration continued.

Caruso, a former assistant U.S. Attorney in the Southern District of New York, pointed out that he and Giuliani were law partners together at Bracewell & Giuliani from 2005 to 2010. The lawyer further noted that he worked “[i]n recent years” as an attorney at the firm Mukasey Young LLP, where Marc Mukasey, the son of former U.S. Attorney General Michael Mukasey (Giuliani’s “ good friend “), is a founding partner. Like Caruso and Giuliani, Mukasey was himself a partner at Bracewell & Giuliani .

On Friday, lawyers for the Official Committee Of Unsecured Creditors separately filed a series of subpoena notices, including demands of Giuliani’s son Andrew Giuliani, the former mayor’s companies, and his legal defense funds to produce documents.

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