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

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

The former New York mayor spent a week in a federal courthouse in Washington, D.C., while the jury considered a defamation lawsuit from Ruby Freeman and Wandrea “Shaye” Moss, who said he turned their lives “upside down” with his false claims as part of his election put an end to the efforts in Georgia.

That included the debunked claim that they pulled “suitcases” of ballots under a table at Atlanta's State Farm Arena during the 2020 election, something an investigation by Georgia's secretary of state found did not happen.

The financial penalty will be painful. Although his net worth rose to $30 million when he won security consulting contracts after September 11, Giuliani is trying to get rid of his $65.5 million Manhattan co-op, sued by his former lawyer, pressured for payments by his ex-wife, while saving himself defends. against conspiracy charges in Georgia, and defending herself against a lawsuit from a former employee who claims he pressured her to have sex.

Below are some of the challenges and humiliations Giuliani has faced in recent years:

Indicted in Georgia along with Donald Trump – and a humiliating mugshot

This summer, Giuliani was charged with racketeering as part of Donald Trump's election efforts in the state.

Fulton County District Attorney Fani Willis charged him under the same racketeering-influenced and corrupt organization laws that Giuliani once used to go after the mob as a federal prosecutor in New York City. He is accused of being one of 18 people who operated as part of a 'criminal enterprise'. He has pleaded not guilty, as has his former client, former President Donald Trump.

He surrendered to the Fulton County Jail in August and had his mugshot taken.

Hair dye incident that became the subject of internet ridicule

Giuliani became the subject of online ridicule when he promoted claims of election fraud during a November 2020 press conference at the Republican National Committee.

He was visibly sweating during the press conference and wiped his forehead and cheeks with a handkerchief. He didn't seem 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 is no one here who deals with fantasies,” Giuliani told an audience of reporters.

He stood next to attorney Sidney Powell, who apologized in court in Fulton County on Thursday but who at the time described a conspiracy of “tremendous influence of communist money through Venezuela, Cuba and probably China in interfering in our elections here in the United States . 'That has never been substantiated.

Four Seasons Total Landscaping: The infamous election fraud press conference

The moment was similar to his appearance at Four Seasons Total Landscaping for an infamous press conference outside Philadelphia.

Trump had touted the event on Twitter, writing: “Major press conference today in Philadelphia at Four Seasons Total Landscaping – 11:30am!” But that came after he deleted a post promising a “Lawyers Press Conference” at “Four Seasons, Philadelphia,” which suggested the luxury hotel chain.

The outdoor location was located near a sex shop and a crematorium and eventually went viral.

Financial problems

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

“I am saddened to know that the hero of September 11th has become a liar,” she told the New York Times in 2019 during their breakup.

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

“I cannot express how personally hurt I am by what Bob Costello did,” Giuliani said in a September statement. “It's a real shame when lawyers do this kind of thing, and all I'm saying is that their bill is way higher than anything even close to legitimate fees.”

Before the trial, Costello said Giuliani “appears to be the individual referred to in special counsel Jack Smith's Jan. 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.

In one scene in the film, captured on a hidden camera, the former prosecutor lay on a bed in his hotel room and put his hand down his pants after the actress offered to give him a drink and remove his microphone. Giuliani

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

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

(1) The Borat video is a complete fabrication. I tucked 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 suggests otherwise, he is a stone cold liar.

Allegations of harassment and abuse in the lawsuit

Former employee Noelle Dunphy has sued Giuliani for harassment and abuse, in a case that uncovered stunning transcripts. She accuses him of 'sexual assault and harassment, wage theft and other misconduct' and is seeking $!0 million in damages.

In transcripts of the case, Giuliani comments on her breasts.

'These breasts are mine. No one else can come near here, okay? I don't care if they flirt or give you business cards. These are mine, you know?' he said, according to the transcript.

“Yes,” she answers.

'To understand? I am very possessive. I made it easy for you,” Giuliani said. Giuliani's team has said the relationship was consensual and is fighting the lawsuit.