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For a man who once parlayed his status as “America’s mayor” into an estimated $50 million fortune that consisted of a consulting business, major law firm and sprawling business interests, bankruptcy seemed an impossibility.

Yet, that is where Rudy Giuliani found himself Thursday, filing for Chapter 11 in the face of a crushing legal loss in which a judge ordered him to immediately pay $148 million to two Georgia election workers he had defamed during Donald Trump’s failed 2020 reelection campaign.

“The filing should be a surprise to no one,” Ted Goodman, a spokesman for the 79-year-old Giuliani, 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 bankruptcy proceeding will not absolve Giuliani of the debt, but will allow him time to pursue an appeal of the verdict.

The Chapter 11 filing represents the nadir of Giuliani’s once lofty fortune and reputation as the forceful leader who helped guide the Big Apple through the tragic aftermath of the Sept. 11 attacks in the waning days of his second term as the mayor of New York.

In the years after the 2001 terrorist attack that killed more than 2,600 people in lower Manhattan, Giuliani turned his post-political career into a lucrative consulting and lobbying business, raking in millions in fees.

The firm, called Giuliani Partners, made money advising high-end clients like insurer Aon and communications giant Nextel, to low-rent penny stock companies and offering security advice to governments in Qatar and Mexico. He also made millions in book deals and speaking fees. A major Texas law firm that had been around for more than 100 years, Bracewell & Patterson, brought in him on as a senior partner and changed its name to Bracewell & Giuliani.

In 2007, CNN estimated that Giuliani was worth $52.2 million. Now, according to his bankruptcy filing, the former federal prosecutor’s net worth lies somewhere between $1 million and $10 million. He estimated that his liabilities sit somewhere between $100 million and $500 million.

In between, Giuliani found his life and reputation enter a slow freefall as he moved through a bitterly-fought third divorce and as he became a top legal advisor to Donald Trump before, during and after his single, fitful term as president of the United States from 2016-2020.

Giuliani featured prominently in Trump’s first impeachment trial. While the president was acquitted by the senate, Giuliani was implicated in playing a key role in pressuring Ukraine into opening an investigation into Trump’s political rival Joe Biden’s son Hunter, under threat of losing vital military aid.

In the aftermath of Trump’s eventual electoral loss, Giuliani emerged as a kind of comic figure, making wild and unsubstantiated claims about voting fraud, including one memorable press conference in which he regaled the press in the parking lot of a Pennsylvania landscaping business with hair dye pouring down his face.  

Things took a more serious turn when Giuliani was indicted earlier this fall for allegedly taking part in a conspiracy to overturn election results in the state of Georgia by illegally appointing a false slate of electors favorable to Trump. Giuliani has pleaded not guilty in the case.

The defamation charges stem from those efforts in Georgia. In their suit, the two election workers accused Giuliani of falsely stating they had manipulated ballots in President Biden’s favor. The workers say Giuliani’s public statements triggered death threats against them. 

Among the other creditors listed in his bankruptcy filing, include lawyers suing him for unpaid bills, the Internal Revenue Service, and several voting machine companies that have sued him for defamation and Hunter Biden. Giuliani has denied any wrongdoing in those cases.

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