Rudy Giuliani: From 'America's Mayor' to facing financial ruin for trying to overturn the 2020 election

A jury's $148 million award against Rudy Giuliani for defaming two Georgia election workers is just the latest blow that took him from Gracie Mansion to the Oval Office – and a string of courtrooms as a defendant.

The former New York mayor spent the week inside a federal courthouse in Washington, DC as the jury considered a defamation claim by Ruby Freeman and Wandrea 'Shaye' Moss, who said he turned their lives 'upside down' with his false claims as part of his election overturn effort in Georgia.

That included the debunked assertion that they pulled 'suitcases' of ballots form under a table at the State Farm Arena in Atlanta during the 2020 election count, something a Georgia Secretary of State's investigation concluded didn't happen.

The financial penalty will be painful. Although his net worth climbed to $30 million as he raked in security consulting contracts after September 11th, Giuliani finds himself trying to unload his $65.5million Manhattan co-op, sued by his former lawyer, pressed for payments by his ex-wife, defending himself against conspiracy charges in Georgia, and defending himself against a suit by a former employee who claims he pressured her into having sex.

Below are some of the challenges and indignities Giuliani has encountered in recent years: 

Charged alongside Donald Trump in Georgia - and a humiliating mugshot

This summer, Giuliani found himself charged with racketeering as part of Donald Trump's election overturn effort in the state. 

Fulton County DA Fani Willis charged him under the same Racketeer Influenced and Corrupt Organizations laws that Giuliani once used to try to go after the mob as a federal prosecutor in New York City. He is accused as one of 18 people who operated as part of a 'criminal enterprise.' He has pleaded not guilty, as did his former client former President Donald Trump.

He surrendered to the Fulton County jail in August and had his mug shot taken.

Hair Dye incident that became the subject of internet ridicule 

Giuliani became a subject of Internet ridicule while promoting claims of election fraud during a November 2020 press conference at the Republican National Committee.

He was visibly sweating throughout the press conference, mopping his forehead and cheeks with a handkerchief. He appeared not to notice as thick streaks of brown hair dye ran down the sides of his face.

'This is real! It's not made up! There's nobody here who engages in fantasies,' Giuliani told an audience of reporters.

He stood alongside lawyer Sidney Powell, who apologized to the court in Fulton County Thursday, but who at the time described a conspiracy of 'massive influence of communist money through Venezuela, Cuba and likely China in the interference with our elections here in the United States' that was never substantiated.

Four Seasons Total Landscaping: The infamous press conference about election fraud 

The moment was on par with his appearance at Four Seasons Total Landscaping for an infamous press conference outside Philadelphia.

Trump had touted the event on Twitter, writing 'Big press conference today in Philadelphia at Four Seasons Total Landscaping — 11:30am!' But that came after he deleted a message promising a 'Lawyers Press Conference' at 'Four Seasons, Philadelphia,' suggesting the upscale hotel chain.

The outdoor venue was near a sex shop and a crematorium, and ended up going viral.

Financial woes 

In December 2022 he avoided jail time following a contempt order after a financial dispute over a divorce settlement with his third wife, Judith Giuliani. She had said her ex owed her $260,000. 

'I'm sad to know that the hero of 9/11 has become a liar,' she told the New York Times in 2019 amid their split.

Giuliani put his Manhattan co-op on the market for $6.5 million, and his former lawyer Robert Costello and his law firm sued him this fall alleging $1.4 million in unpaid bills stemming from multiple probes. 

'I can't express how personally hurt I am by what Bob Costello has done,' Giuliani said in a September statement. 'It's a real shame when lawyers do things like this, and all I will say is that their bill is way in excess to anything approaching legitimate fees.' 

Before the suit, Costello said Giuliani 'appears to be' the person referenced in Special Counsel Jack Smith's January 6 indictment as 'alleged co-conspirator No. 1.'

Borat movie - and THAT bed scene with an undercover actress 

Giuliani had a humiliating cameo in the 'Borat Subsequent Moviefilm,' where he sat for an interview with an actress posing as a journalist. 

A scene in the film captured by hidden camera featured the former prosecutor laying down on a bed in his hotel room and putting his hand down his pants after the actress offers to make him a drink and remove his microphone. Giuliani 

'is a complete fabrication,' insisting he was tucking his shirt in.

'At no time before, during, or after the interview was I ever inappropriate. If Sacha Baron Cohen implies otherwise he is a stone-cold liar.

(1) The Borat video is a complete fabrication. I was tucking in my shirt after taking off the recording equipment. At no time before, during, or after the interview was I ever inappropriate. If Sacha Baron Cohen implies otherwise he is a stone-cold liar. 

 Harassment and abuse allegations in lawsuit

Former employee Noelle Dunphy has sued Giuliani claiming harassment and abuse, in a case that brought stunning transcripts to light. She accuses him of 'sexual assault and harassment, wage theft, and other misconduct' and is seeking $10 million in damages.

Transcripts from the case have Giuliani commenting about her breasts.

'These breasts belong to me. Nobody else can get near these, okay? I don't care if they're flirting or they give you business cards. These are mine, you got it?' he said, according to the transcript.

'Yes,' she responds.

'Understand? I'm very f****ng possessive. I've gone easy on you,' Giuliani said. Giuliani's team has said it was a consensual relationship and is fighting the suit.