Rudy Giuliani, who used his career as a prosecutor to jumpstart a reputation as a tough-on-crime mayor, is now facing charges in one of the country’s most high-profile indictments.
Giuliani, who famously used the Racketeering Influenced and Corrupt Organizations Act (RICO) to crack down on the mob as a prosecutor, is being prosecuted on RICO charges himself in Georgia.
Once known as “America’s Mayor” for his response to the 9/11 terrorist attacks, Giuliani could be jailed over his efforts to keep former President Trump in power despite losing an election.
His surrender in Georgia last week on 13 charges over his efforts to overturn the state’s 2020 election results marks a new low for Giuliani, who has struggled to keep up with mounting legal bills.
It’s a dramatic fall for a man who was briefly a front-runner for the Republican presidential nomination in 2008 but has seen his reputation fall while aiding another GOP leader.
“America’s mayor should have been in the lede of his obituary, but instead it probably won’t appear until the fourth or fifth paragraph, and in an ironic juxtaposition,” said Ken Frydman, who served as Giuliani’s press secretary during his 1993 mayoral campaign.
“Rudy’s demise, given the peak that he reached — the abyss that he has fallen into is unimaginable,” Frydman said. “But here it is.”
The irony was not lost on Giuliani, who commented on the experience of surrendering to authorities in Georgia more like an onlooker rather than the man going through it.
“It was nothing. I did it on autopilot. Now I’m aware enough of human psychology to know that it was a tremendous attack on me. It had to be a terrible shock to me that I’m being mug-shotted and fingerprinted, when I probably prosecuted 6,000, 7,000 cases,” Giuliani said during an interview with Newsmax the night that Trump surrendered in the case.
“And here I am being treated like a common criminal. If I was a common criminal, I should get treated that way. If I was a lawyer honorably doing my job, for a client who is innocent, well that’s completely different. Then that’s an injustice.”
What Giuliani sees as the routine actions of a lawyer defending his client, the legal system has approached differently.
He’s facing proceedings in both New York and Washington, D.C., that would strip him of his law license.
Beyond the criminal charges in Georgia, he’s also facing three defamation suits, two from different voting equipment companies and a third from a mother-daughter duo of election workers he accused of manipulating ballots.
A D.C.-based judge found Giuliani liable Wednesday in the case from the election workers, moving the case to the next phase to determine whether he owes damages and how large they might be.
He was also ordered to pay more than $130,000 to the two women for legal fees they incurred in seeking to push him to turn over discovery in the case.
Giuliani is also facing a lawsuit from a former employee alleging sexual assault and harassment and wage theft who is seeking $10 million in damages.
The series of proceedings have already taken their toll on Giuliani’s finances.
Digital record-keeping to comply with evidence sharing is running into the thousands, and lawyers have told courts that Giuliani is struggling to pay his legal fees.
Giuliani has reportedly appealed to Trump for help with some of his legal bills, and Trump has since agreed to attend a $100,000-per-plate dinner fundraiser for his ally next month. But it’s not clear whether the former president plans to make any further contributions from his political action committees to aid in Giuliani’s defense.
After his own surrender in Georgia, Trump called Giuliani “the greatest mayor in the history” of New York City.
“Rudy shouldn’t be going through this,” Trump said on Newsmax. “He didn’t do anything wrong.”
Giuliani served as the U.S. Attorney for the Southern District of New York for six years, leaving a higher-ranking post at the Justice Department in favor of a high-profile role that left him bringing cases targeting drug dealers and other organized crime.
His mayoral bio bragged about his work reducing crime, proclaiming New York the safest large city in America.
His response to 9/11 thrust him further into the public spotlight, with Time magazine naming him “Person of the Year” at the close of 2001. A year later, he would be given an honorary knighthood by then-Queen Elizabeth.
But in recent years, Giuliani has been a presence in Trump’s biggest legal and political scandals, while raising questions over whether he is an asset or a liability.
He appeared on every major Sunday morning show in October 2016 to defend Trump in the aftermath of an “Access Hollywood” tape that featured Trump bragging about groping women without their consent.
His efforts to aid Trump amid questions over his dealings in Ukraine spurred a trip to the country to dig up dirt on Joe Biden that ultimately helped spark Trump’s first impeachment. During the visit, he sought to pressure numerous officials to investigate Biden and his son, Hunter, who worked on the board of a Ukrainian energy company — a dynamic central to an ongoing Republican investigation that has rehashed many of the same claims.
But it was Giuliani’s involvement in the post-2020 efforts that have proven the most personally damaging.
The former New York City mayor was at the heart of several notorious episodes after the 2020 election, including a press conference at Four Seasons Total Landscaping and another alongside Sidney Powell, Jenna Ellis and others in which hair dye appeared to streak down his face. He later told then-Arizona House Speaker Rusty Bowers (R) he had “theories” but no evidence to support his claims of widespread fraud in the state.
“Rudy fed into Donald’s worst instincts while he was the president,” said Sam Nunberg, who served as an adviser on Trump’s 2016 campaign.
“There was a seminal day in mid-November  where Donald was told by his campaign and lawyers what the reality of the situation was going to be,” Nunberg added. “And Rudy gave Donald happy-talk and made Donald believe that there could actually be a chance to overturn the election results.”
With Giuliani’s legal fate now closely intertwined with Trump’s in Georgia, there has been speculation about whether the former New York City mayor would ever flip on the former president to cut a deal with prosecutors.
Former Trump fixer Michael Cohen has suggested Trump could face consequences if he does not offer any assistance to Giuliani with his mounting legal bills, though Giuliani and Trump have publicly remained adamant that they did nothing wrong and have continued to stand with each other.
Ted Goodman, Giuliani’s political adviser, said on social media in July that any suggestions Giuliani had flipped on Trump were “false.”
Still, for those who have known Giuliani, like Frydman, they believe self-preservation will ultimately come first.
Frydman, who now runs Source Communications, noted Trump’s Save America PAC paid $340,000 to settle some of Giuliani’s legal bills, in addition to the fundraiser Trump will attend for the former mayor next month.
“Will that be enough to guarantee Rudy’s silence? Who knows,” Frydman said, adding, “Rudy Giuliani will not go to prison for Donald Trump.”
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